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Pseudoephedrine (PSE) is a
sympathomimetic Sympathomimetic drugs (also known as adrenergic drugs and adrenergic amines) are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in hea ...
drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...
of the
phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amin ...
and
amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...
chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classificat ...
es. It may be used as a nasal/sinus decongestant, as a
stimulant Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
, or as a
wakefulness-promoting agent Eugeroics (originally "eugrégorique" or "eugregoric"), also known as wakefulness-promoting agents and wakefulness-promoting drugs, are a class of drugs that promote wakefulness and alertness. They are medically indicated for the treatment of cer ...
in higher doses. It was first characterized in 1889 by the German chemists
Ladenburg Ladenburg is a town in northwestern Baden-Württemberg, Germany. It lies on the right bank of the river Neckar, northwest of Heidelberg and east of Mannheim. The town's history goes back to the Celtic and Roman Ages, when it was called Lopo ...
and Oelschlägel, who used a sample that had been isolated from ''
Ephedra vulgaris ''Ephedra distachya'' is a shrub in the family Ephedraceae that stands about 25 cm to 50 cm high. The shrub grows in many parts of the world, including southern and central Europe and western and central Asia. Its local names include '' ...
'' by the Merck pharmaceutical corporation of Darmstadt, Germany. The
salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively cha ...
pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many
over-the-counter Over-the-counter (OTC) drugs are medicines sold directly to a consumer without a requirement for a prescription from a healthcare professional, as opposed to prescription drugs, which may be supplied only to consumers possessing a valid prescr ...
preparations ''Preparations'' is a studio album by Prefuse 73. It was released on Warp Records Warp Records (or simply Warp) is a British independent record label founded in Sheffield in 1989 by record store employees Steve Beckett and Rob Mitchell and r ...
, either as a single ingredient or (more commonly) in a fixed-dose combination with one or more additional active ingredients such as
antihistamine Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic (not patented) drug that can be bought without a prescription and provid ...
s, guaifenesin,
dextromethorphan Dextromethorphan (DXM) is a medication most often used as a cough suppressant in over-the-counter cold and cough medicines. It is sold in syrup, tablet, spray, and lozenge forms. In 2022, the FDA approved a formulation of it combined with bu ...
,
paracetamol Paracetamol, also known as acetaminophen, is a medication used to treat fever and mild to moderate pain. Common brand names include Tylenol and Panadol. At a standard dose, paracetamol only slightly decreases body temperature; it is inferior ...
(acetaminophen) or an
NSAID Non-steroidal anti-inflammatory drugs (NSAID) are members of a therapeutic drug class which reduces pain, decreases inflammation, decreases fever, and prevents blood clots. Side effects depend on the specific drug, its dose and duration of ...
(such as
aspirin Aspirin, also known as acetylsalicylic acid (ASA), is a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and/or inflammation, and as an antithrombotic. Specific inflammatory conditions which aspirin is used to treat inc ...
or
ibuprofen Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus arte ...
).


Medical uses

Pseudoephedrine is a
stimulant Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
, but it is well known for shrinking swollen nasal mucous membranes, so it is often used as a
decongestant A decongestant, or nasal decongestant, is a type of pharmaceutical drug that is used to relieve nasal congestion in the upper respiratory tract. The active ingredient in most decongestants is either pseudoephedrine or phenylephrine (the latter ...
. It reduces tissue
hyperemia Hyperaemia (also hyperemia) is the increase of blood flow to different tissues in the body. It can have medical implications but is also a regulatory response, allowing change in blood supply to different tissues through vasodilation. Clinically, ...
,
edema Edema, also spelled oedema, and also known as fluid retention, dropsy, hydropsy and swelling, is the build-up of fluid in the body's Tissue (biology), tissue. Most commonly, the legs or arms are affected. Symptoms may include skin which feels t ...
, and
nasal congestion Nasal congestion is the blockage of nasal breathing usually due to membranes lining the nose becoming swollen from inflamed blood vessels. Background In about 85% of cases, nasal congestion leads to mouth breathing rather than nasal breathing. ...
commonly associated with
colds The common cold or the cold is a viral infectious disease of the upper respiratory tract that primarily affects the respiratory mucosa of the nose, throat, sinuses, and larynx. Signs and symptoms may appear fewer than two days after exposu ...
or
allergies Allergies, also known as allergic diseases, refer a number of conditions caused by the hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic derma ...
. Other beneficial effects may include increasing the drainage of
sinus Sinus may refer to: Anatomy * Sinus (anatomy), a sac or cavity in any organ or tissue ** Paranasal sinuses, air cavities in the cranial bones, especially those near the nose, including: *** Maxillary sinus, is the largest of the paranasal sinuses, ...
secretions, and opening of obstructed
Eustachian tube In anatomy, the Eustachian tube, also known as the auditory tube or pharyngotympanic tube, is a tube that links the nasopharynx to the middle ear, of which it is also a part. In adult humans, the Eustachian tube is approximately long and in d ...
s. The same
vasoconstriction Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels, in particular the large arteries and small arterioles. The process is the opposite of vasodilation, the widening of blood vessel ...
action can also result in
hypertension Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high bl ...
, which is a noted side effect of pseudoephedrine. Pseudoephedrine can be used either as oral or as
topical decongestant Topical decongestants are decongestants applied directly to the nasal cavity. Their effectiveness by themselves in the common cold appears to have a small benefit in adults. Topical decongestants should only be used by patients for a maximum of 5� ...
. Due to its stimulating qualities, however, the oral preparation is more likely to cause adverse effects, including
urinary retention Urinary retention is an inability to completely empty the bladder. Onset can be sudden or gradual. When of sudden onset, symptoms include an inability to urinate and lower abdominal pain. When of gradual onset, symptoms may include loss of bladd ...
. According to one study, pseudoephedrine may show effectiveness as an
antitussive Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including ...
drug (suppression of
cough A cough is a sudden expulsion of air through the large breathing passages that can help clear them of fluids, irritants, foreign particles and microbes. As a protective reflex, coughing can be repetitive with the cough reflex following three pha ...
). Pseudoephedrine is indicated for the treatment of nasal congestion, sinus congestion and Eustachian tube congestion.Bicopoulos D, editor. AusDI: Drug information for the healthcare professional, 2nd edition. Castle Hill: Pharmaceutical Care Information Services; 2002. Pseudoephedrine is also indicated for
vasomotor rhinitis Nonallergic rhinitis is rhinitis—inflammation of the inner part of the nose—not caused by an allergy. Nonallergic rhinitis displays symptoms including chronic sneezing or having a congested, drippy nose, without an identified allergic reaction ...
, and as an adjunct to other agents in the optimum treatment of
allergic rhinitis Allergic rhinitis, of which the seasonal type is called hay fever, is a type of inflammation in the nose that occurs when the immune system overreacts to allergens in the air. Signs and symptoms include a runny or stuffy nose, sneezing, red, i ...
,
croup Croup, also known as laryngotracheobronchitis, is a type of respiratory infection that is usually caused by a virus. The infection leads to swelling inside the trachea, which interferes with normal breathing and produces the classic symptoms o ...
,
sinusitis Sinusitis, also known as rhinosinusitis, is inflammation of the nasal mucosa, mucous membranes that line the paranasal sinuses, sinuses resulting in symptoms that may include thick Mucus#Respiratory system, nasal mucus, a nasal congestion, plugg ...
,
otitis media Otitis media is a group of inflammatory diseases of the middle ear. One of the two main types is acute otitis media (AOM), an infection of rapid onset that usually presents with ear pain. In young children this may result in pulling at the ear, ...
, and
tracheobronchitis Tracheobronchitis is inflammation of the trachea and bronchi. It is characterised by a cough, fever, and purulent (containing pus) sputum and is therefore suggestive of pneumonia. It is classified as a respiratory tract infection. Tracheobronchitis ...
. Pseudoephedrine is also used as a first-line prophylactic for recurrent
priapism Priapism is a condition in which a penis remains erect for hours in the absence of stimulation or after stimulation has ended. There are three types: ischemic (low-flow), nonischemic (high-flow), and recurrent ischemic (intermittent). Most cases ...
.
Erection An erection (clinically: penile erection or penile tumescence) is a physiological phenomenon in which the penis becomes firm, engorged, and enlarged. Penile erection is the result of a complex interaction of psychological, neural, vascular, ...
is largely a
parasympathetic The parasympathetic nervous system (PSNS) is one of the three divisions of the autonomic nervous system, the others being the sympathetic nervous system and the enteric nervous system. The enteric nervous system is sometimes considered part of t ...
response, so the sympathetic action of pseudoephedrine may serve to relieve this condition. Treatment for
urinary incontinence Urinary incontinence (UI), also known as involuntary urination, is any uncontrolled leakage of urine. It is a common and distressing problem, which may have a large impact on quality of life. It has been identified as an important issue in geria ...
is an
off-label use Off-label use is the use of pharmaceutical drugs for an unapproved indication (medicine), indication or in an unapproved age group, dose (biochemistry), dosage, or route of administration. Both prescription drugs and over-the-counter drugs (OTCs) ...
("unlabeled use") for these medications.


Adverse effects

Common adverse drug reactions (ADRs) associated with pseudoephedrine therapy include
central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all par ...
stimulation, insomnia, nervousness, excitability, dizziness and anxiety. Infrequent ADRs include
tachycardia Tachycardia, also called tachyarrhythmia, is a heart rate that exceeds the normal resting rate. In general, a resting heart rate over 100 beats per minute is accepted as tachycardia in adults. Heart rates above the resting rate may be normal (su ...
or
palpitation Palpitations are perceived abnormalities of the heartbeat characterized by awareness of cardiac muscle contractions in the chest, which is further characterized by the hard, fast and/or irregular beatings of the heart. Symptoms include a rapi ...
s. Rarely, pseudoephedrine therapy may be associated with
mydriasis Mydriasis is the dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, trauma, or the use of certain types of drugs. Normally, as ...
(dilated pupils),
hallucination A hallucination is a perception in the absence of an external stimulus that has the qualities of a real perception. Hallucinations are vivid, substantial, and are perceived to be located in external objective space. Hallucination is a combinatio ...
s,
arrhythmia Arrhythmias, also known as cardiac arrhythmias, heart arrhythmias, or dysrhythmias, are irregularities in the heartbeat, including when it is too fast or too slow. A resting heart rate that is too fast – above 100 beats per minute in adults ...
s,
hypertension Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high bl ...
, seizures and ischemic colitis;Rossi S, editor.
Australian Medicines Handbook Australian Medicines Handbook (AMH) is a peer-reviewed medicines prescribing guide for Australian health professionals. The handbook is available in paper and digital formats and is supplemented by the ''AMH Aged Care Companion'' and the ''AMH C ...
2006. Adelaide: Australian Medicines Handbook; 2006.
as well as severe skin reactions known as recurrent pseudo-scarlatina, systemic contact dermatitis, and nonpigmenting
fixed drug eruption Fixed drug reactions, are common and so named because they recur at the same site with each exposure to a particular medication. Medications inducing fixed drug eruptions are usually those taken intermittently. Signs and symptoms A painful and it ...
. Pseudoephedrine, particularly when combined with other drugs including narcotics, may also play a role in the precipitation of episodes of paranoid
psychosis Psychosis is a condition of the mind that results in difficulties determining what is real and what is not real. Symptoms may include delusions and hallucinations, among other features. Additional symptoms are incoherent speech and behavior ...
. It has also been reported that pseudoephedrine, among other
sympathomimetic Sympathomimetic drugs (also known as adrenergic drugs and adrenergic amines) are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in hea ...
agents, may be associated with the occurrence of
stroke A stroke is a medical condition in which poor blood flow to the brain causes cell death. There are two main types of stroke: ischemic, due to lack of blood flow, and hemorrhagic, due to bleeding. Both cause parts of the brain to stop functionin ...
.


Precautions and contraindications

Pseudoephedrine is contraindicated in patients with
diabetes mellitus Diabetes, also known as diabetes mellitus, is a group of metabolic disorders characterized by a high blood sugar level ( hyperglycemia) over a prolonged period of time. Symptoms often include frequent urination, increased thirst and increased ap ...
,
cardiovascular disease Cardiovascular disease (CVD) is a class of diseases that involve the heart or blood vessels. CVD includes coronary artery diseases (CAD) such as angina and myocardial infarction (commonly known as a heart attack). Other CVDs include stroke, h ...
, severe or uncontrolled
hypertension Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high bl ...
, severe
coronary artery disease Coronary artery disease (CAD), also called coronary heart disease (CHD), ischemic heart disease (IHD), myocardial ischemia, or simply heart disease, involves the reduction of blood flow to the heart muscle due to build-up of atherosclerotic pla ...
,
prostatic hypertrophy Benign prostatic hyperplasia (BPH), also called prostate enlargement, is a noncancerous increase in size of the prostate gland. Symptoms may include frequent urination, trouble starting to urinate, weak stream, inability to urinate, or loss o ...
,
hyperthyroidism Hyperthyroidism is the condition that occurs due to excessive production of thyroid hormones by the thyroid gland. Thyrotoxicosis is the condition that occurs due to excessive thyroid hormone of any cause and therefore includes hyperthyroidism ...
, closed angle glaucoma, or by pregnant women. The safety and effectiveness of nasal decongestant use in children is unclear.


Interactions

Concomitant or recent (previous fourteen days)
monoamine oxidase inhibitor Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, espe ...
use can lead to hypertensive reactions, including
hypertensive crises Severely elevated blood pressure (equal to or greater than a systolic 180 or diastolic of 120—sometimes termed malignant or accelerated hypertension) is referred to as a hypertensive crisis, as blood pressure at this level confers a high risk ...
. The antihypertensive effects of
methyldopa Methyldopa, sold under the brand name Aldomet among others, is a medication used for high blood pressure. It is one of the preferred treatments for high blood pressure in pregnancy. For other types of high blood pressure including hypertensive e ...
,
mecamylamine Mecamylamine ( INN, BAN; or mecamylamine hydrochloride (USAN); brand names Inversine, Vecamyl) is a non-selective, non-competitive antagonist of the nicotinic acetylcholine receptors (nAChRs) that was introduced in the 1950s as an antihypertensi ...
,
reserpine Reserpine is a drug that is used for the treatment of high blood pressure, usually in combination with a thiazide diuretic or vasodilator. Large clinical trials have shown that combined treatment with reserpine plus a thiazide diuretic reduces m ...
and
veratrum alkaloids ''Veratrum'' is a genus of flowering plants in the family Melanthiaceae. It occurs in damp habitats across much of temperate and subarctic Europe, Asia, and North America. ''Veratrum'' species are vigorous herbaceous perennials with highly poiso ...
may be reduced by sympathomimetics.
Beta-adrenergic antagonist Beta blockers, also spelled β-blockers, are a class of medications that are predominantly used to manage abnormal heart rhythms, and to protect the heart from a second heart attack after a first heart attack (secondary prevention). They are al ...
s may also interact with sympathomimetics. Increase of ectopic pacemaker activity can occur when pseudoephedrine is used concomitantly with
digitalis ''Digitalis'' ( or ) is a genus of about 20 species of herbaceous perennial plants, shrubs, and biennials, commonly called foxgloves. ''Digitalis'' is native to Europe, western Asia, and northwestern Africa. The flowers are tubular in sha ...
.
Antacids An antacid is a substance which neutralizes stomach acidity and is used to relieve heartburn, indigestion or an upset stomach. Some antacids have been used in the treatment of constipation and diarrhea. Marketed antacids contain salts of alu ...
increase the rate of pseudoephedrine absorption, while
kaolin Kaolinite ( ) is a clay mineral, with the chemical composition Al2 Si2 O5( OH)4. It is an important industrial mineral. It is a layered silicate mineral, with one tetrahedral sheet of silica () linked through oxygen atoms to one octahedral ...
decreases it.


Mechanism of action

Pseudoephedrine is a sympathomimetic
amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...
. Its principal mechanism of action relies on its direct action on the
adrenergic receptor The adrenergic receptors or adrenoceptors are a class of G protein-coupled receptors that are targets of many catecholamines like norepinephrine (noradrenaline) and epinephrine (adrenaline) produced by the body, but also many medications like beta ...
system. The
vasoconstriction Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels, in particular the large arteries and small arterioles. The process is the opposite of vasodilation, the widening of blood vessel ...
that pseudoephedrine produces is believed to be principally an α-adrenergic receptor response. Pseudoephedrine acts on α- and β2-adrenergic receptors, to cause vasoconstriction and relaxation of smooth muscle in the bronchi, respectively. α-Adrenergic receptors are located on the muscles lining the walls of blood vessels. When these receptors are activated, the muscles contract, causing the blood vessels to constrict (vasoconstriction). The constricted blood vessels now allow less fluid to leave the blood vessels and enter the nose, throat and sinus linings, which results in decreased inflammation of nasal membranes, as well as decreased mucus production. Thus, by constriction of blood vessels, mainly those located in the nasal passages, pseudoephedrine causes a decrease in the symptoms of nasal congestion. Activation of β2-adrenergic receptors produces relaxation of smooth muscle of the bronchi, causing bronchial dilation and in turn decreasing congestion (although not fluid) and difficulty breathing.


Other uses

There have been reports of off-label uses of pseudoephedrine for its stimulant properties. Long-distance truck drivers and athletes, for example, have reportedly used pseudoephedrine as a stimulant to increase their state of alertness/awareness. A study has also found that pseudoephedrine can reduce milk production in breastfeeding women.


Manufacture of amphetamines

Its membership in the
amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...
class has made pseudoephedrine a sought-after chemical precursor in the illicit manufacture of
methamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity. Methamph ...
and
methcathinone Methcathinone (α-methylamino-propiophenone or ephedrone) (sometimes called "cat" or "jeff" or "catnip" or "M-Kat" or "kat" or "intash" ) is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational ...
. As a result of the increasing regulatory restrictions on the sale and distribution of pseudoephedrine, many pharmaceutical firms have reformulated, or are in the process of reformulating medications to use alternative, but less effective, decongestants, such as
phenylephrine Phenylephrine is a medication primarily used as a decongestant, to dilate the pupil, to increase blood pressure, and to relieve hemorrhoids. In the United States, it was previously used orally as an over-the-counter decongestant to relieve nas ...
. In the United States, federal laws control the sale of pseudoephedrine-containing products. Many retailers in the US have created corporate policies restricting the sale of pseudoephedrine-containing products. Their policies restrict sales by limiting purchase quantities and requiring a minimum age and government issued photographic identification. These requirements are similar to and sometimes more stringent than existing law. Internationally, pseudoephedrine is listed as a Table I precursor under the
United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances The United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances of 1988 is one of three major drug control treaties currently in force. It provides additional legal mechanisms for enforcing the 1961 Single Con ...
.


Sports

Pseudoephedrine was on the International Olympic Committee's (IOC) banned substances list until 2004, when the
World Anti-Doping Agency The World Anti-Doping Agency (WADA; french: Agence mondiale antidopage, AMA) is a foundation initiated by the International Olympic Committee based in Canada to promote, coordinate, and monitor the fight against drugs in sports. The agency's key ...
(WADA) list replaced the IOC list. Although WADA initially only ''monitored'' pseudoephedrine, it went back onto the "banned" list on January 1, 2010. Pseudoephedrine is excreted through urine, and concentration in urine of this drug shows a large inter-individual spread; that is, the same dose can give a vast difference in urine concentration for different individuals. Pseudoephedrine is approved to be taken up to 240 mg per day. In seven healthy male subjects this dose yielded a urine concentration range of 62.8 to 294.4 microgram per milliliter (µg/mL) with mean ± standard deviation 149 ± 72 µg/mL. Thus, normal dosage of 240 mg pseudoephedrine per day can result in urine concentration levels exceeding the limit of 150 µg/mL set by WADA for about half of all users. Furthermore, hydration status does not affect urinary concentration of pseudoephedrine. Canadian rower
Silken Laumann Silken Suzette Laumann, (born November 14, 1964) is a Canadian champion rower. Life and career Laumann was born in Toronto Township, Ontario, now Mississauga. Starting in 1976, Laumann won a number of awards, including a gold medal in quadr ...
was stripped of her 1995 Pan American Games team gold medal after testing positive for pseudoephedrine. In February 2000,
Elena Berezhnaya Elena Viktorovna Berezhnaya (russian: Елена Викторовна Бережная, born 11 October 1977) is a Russian former pair skater. With partner Anton Sikharulidze, she is the 1998 and 1999 World champion, 1998 Olympic silver medali ...
and
Anton Sikharulidze Anton Tarielyevich Sikharulidze (russian: link=no, Антон Тариэльевич Сихарулидзе, born 25 October 1976) is a Russian former pair skater. With Elena Berezhnaya, he is the 1998 and 1999 World champion, 1998 Olympic sil ...
won gold at the
2000 European Figure Skating Championships The 2000 European Figure Skating Championships was a senior international figure skating competition in the 1999–2000 season. Medals were awarded in the disciplines of men's singles, ladies' singles, pair skating, and ice dancing. The event w ...
but were stripped of their medals after Berezhnaya tested positive. This resulted in a three-month disqualification from the date of the test, and the medal being stripped. She stated that she had taken cold medication approved by a doctor but had failed to inform the ISU as required. The pair missed the World Championships that year as a result of the disqualification. Romanian gymnast
Andreea Răducan Andreea Mădălina Răducan (; born 30 September 1983) is a retired gymnast from Bârlad, Romania. She currently works as a sports announcer and journalist. Răducan began competing in gymnastics at a young age and was training at the Romanian j ...
was stripped of her gold medal at the 2000 Summer Olympic Games after testing positive. She took two pills given to her by the team coach for a cold. Although she was stripped of the overall gold medal, she kept her other medals, and, unlike in most other doping cases, was not banned from competing again; only the team doctor was banned for a number of years.
Ion Ţiriac An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conven ...
, the president of the Romanian Olympic Committee, resigned over the scandal. In the 2010 Winter Olympic Games, the IOC issued a reprimand against the Slovak
ice hockey Ice hockey (or simply hockey) is a team sport played on ice skates, usually on an ice skating rink with lines and markings specific to the sport. It belongs to a family of sports called hockey. In ice hockey, two opposing teams use ice hock ...
player Lubomir Visnovsky for usage of pseudoephedrine. In the
2014 Winter Olympic Games , ''Zharkie. Zimnie. Tvoi'') , nations = 88 , events = 98 in 7 sports (15 disciplines) , athletes = 2,873 , opening = 7 February 2014 , closing = 23 February 2014 , opened_by = President Vladimir Putin , cauldron = , stadium = Fisht Olympic ...
Team Sweden and
Washington Capitals The Washington Capitals (colloquially known as the Caps) are a professional ice hockey team based in Washington, D.C. The team competes in the National Hockey League (NHL) as a member of the Metropolitan Division in the Eastern Conference (NHL) ...
ice hockey player
Nicklas Bäckström Nicklas Bäckström (; born 23 November 1987) is a Swedish professional ice hockey centre and alternate captain for the Washington Capitals of the National Hockey League (NHL). Bäckström was selected fourth overall by the Capitals at the 2006 ...
was prevented from playing in the final for usage of pseudoephedrine. Bäckström claimed he was using it as allergy medication. In March 2014, the IOC Disciplinary Commission decided that Bäckström would be awarded the silver medal. In January 2015 Bäckström, the IOC, WADA and the
IIHF The International Ice Hockey Federation (IIHF; french: Fédération internationale de hockey sur glace; german: Internationale Eishockey-Föderation) is a worldwide governing body for ice hockey. It is based in Zurich, Switzerland, and has 83 m ...
agreed to a settlement in which he accepted a reprimand but was cleared of attempting to enhance his performance.


Detection of use

Pseudoephedrine may be quantified in blood, plasma, or urine to monitor any possible performance-enhancing use by athletes, confirm a diagnosis of poisoning, or to assist in a medicolegal death investigation. Many commercial
immunoassay An immunoassay (IA) is a biochemical test that measures the presence or concentration of a macromolecule or a small molecule in a solution through the use of an antibody (usually) or an antigen (sometimes). The molecule detected by the immunoass ...
screening tests directed at the amphetamines cross-react appreciably with pseudoephedrine, but
chromatographic In chemical analysis, chromatography is a laboratory technique for the separation of a mixture into its components. The mixture is dissolved in a fluid solvent (gas or liquid) called the ''mobile phase'', which carries it through a system (a ...
techniques can easily distinguish pseudoephedrine from other phenethylamine derivatives. Blood or plasma pseudoephedrine concentrations are typically in the 50–300 µg/L range in persons taking the drug therapeutically, 500–3000 µg/L in people with substance use disorder involving pseudoephedrine, or poisoned patients and 10–70 mg/L in cases of acute fatal overdose.


Chemistry

Pseudoephedrine is a
diastereomer In stereochemistry, diastereomers (sometimes called diastereoisomers) are a type of stereoisomer. Diastereomers are defined as non-mirror image, non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have di ...
of
ephedrine Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in ...
and is readily reduced into
methamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity. Methamph ...
or
oxidized Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...
into
methcathinone Methcathinone (α-methylamino-propiophenone or ephedrone) (sometimes called "cat" or "jeff" or "catnip" or "M-Kat" or "kat" or "intash" ) is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational ...
.


Nomenclatures

The
dextrorotary Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain materials. Circul ...
(+)- or d-
enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...
is (1''S'',2''S'')-pseudoephedrine, whereas the levorotating (−)- or l- form is (1''R'',2''R'')-pseudoephedrine. In the outdated system (+)-pseudoephedrine is also referred to as pseudoephedrine and (−)-pseudoephedrine as pseudoephedrine (in the
Fisher projection In chemistry, the Fischer projection, devised by Emil Fischer in 1891, is a two-dimensional representation of a three-dimensional organic molecule by projection. Fischer projections were originally proposed for the depiction of carbohydrates a ...
then the phenyl ring is drawn at bottom). Often the system (with
small caps In typography, small caps (short for "small capitals") are characters typeset with glyphs that resemble uppercase letters (capitals) but reduced in height and weight close to the surrounding lowercase letters or text figures. This is technicall ...
) and the d/l system (with
lower-case Letter case is the distinction between the letters that are in larger uppercase or capitals (or more formally ''majuscule'') and smaller lowercase (or more formally ''minuscule'') in the written representation of certain languages. The writing ...
) are confused. The result is that the dextrorotary d-pseudoephedrine is wrongly named pseudoephedrine and the levorotary l-ephedrine (the diastereomer) wrongly ephedrine. The IUPAC names of the two enantiomers are (1''S'',2''S'')- respectively (1''R'',2''R'')-2-methylamino-1-phenylpropan-1-ol. Synonyms for both are ''psi''-ephedrine and ''threo''-ephedrine. Pseudoephedrine is the International Nonproprietary Name of the (+)-form, when used as pharmaceutical substance.


Society and culture


Brand names

The following is a list of consumer medicines that either contain pseudoephedrine or have switched to a less-regulated alternative such as
phenylephrine Phenylephrine is a medication primarily used as a decongestant, to dilate the pupil, to increase blood pressure, and to relieve hemorrhoids. In the United States, it was previously used orally as an over-the-counter decongestant to relieve nas ...
. *
Actifed Actifed is a registered trademark for a combination antihistamine and nasal decongestant medication used for cold and allergy symptoms. Actifed was developed in 1958 by Burroughs Wellcome & Company (now part of GlaxoSmithKline), later Haleon. 200 ...
(made by
GlaxoSmithKline GSK plc, formerly GlaxoSmithKline plc, is a British multinational pharmaceutical and biotechnology company with global headquarters in London, England. Established in 2000 by a merger of Glaxo Wellcome and SmithKline Beecham. GSK is the ten ...
) — contains 60 mg pseudoephedrine and 2.5 mg
triprolidine Triprolidine is an over-the-counter antihistamine with anticholinergic properties. It is used to combat the symptoms associated with allergies and is sometimes combined with other cold medications designed to provide general relief for flu-like ...
in certain countries. *Advil Cold & Sinus (made by Pfizer Canada Inc.) — contains 30 mg pseudoephedrine
hydrochloride In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (e.g. an amine). An alternative name is chlorhydrate, which comes from French. An archaic alternative n ...
and 200 mg Ibuprofen. * Aleve-D Sinus & Cold (made by
Bayer Healthcare Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of business include pharmaceutica ...
) — contains 120 mg pseudoephedrine
hydrochloride In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (e.g. an amine). An alternative name is chlorhydrate, which comes from French. An archaic alternative n ...
(also 220 mg
naproxen Naproxen is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulati ...
). * Allegra-D (made by
Sanofi Aventis Sanofi S.A. is a French multinational pharmaceutical and healthcare company headquartered in Paris, France. Originally, the corporation was established in 1973 and merged with Synthélabo in 1999 to form Sanofi-Synthélabo. In 2004, Sanofi-Syn ...
) — contains 120 mg of pseudoephedrine hydrochloride (also 60 mg of
fexofenadine Fexofenadine, sold under the brand name Allegra among others, is an antihistamine pharmaceutical drug used in the treatment of allergy symptoms, such as hay fever and urticaria. Therapeutically, fexofenadine is a selective peripheral H1 block ...
). * Allerclear-D (made by
Kirkland Signature Costco Wholesale Corporation (doing business as Costco Wholesale and also known simply as Costco) is an American multinational corporation which operates a chain of membership-only big-box retail stores (warehouse club). As of 2022, Costco i ...
) — contains 240 mg of pseudoephedrine sulfate (also 10 mg of
loratadine Loratadine, sold under the brand name Claritin among others, is a medication used to treat allergies. This includes allergic rhinitis (hay fever) and hives. It is also available in combination with pseudoephedrine, a decongestant, known as lora ...
). *
Benadryl Benadryl is a brand of various antihistamine medications used to stop allergies, whose content varies in different countries, but which includes some combination of diphenhydramine, acrivastine, and/or cetirizine. It is sold by Johnson & Joh ...
Plus (made by
McNeil Consumer Healthcare McNeil Consumer Healthcare is an American medicals products company belonging to the Johnson & Johnson Health care, healthcare products group. It primarily sells fast-moving consumer goods such as Over-the-counter drug, over-the-counter drugs. ...
, a
Johnson & Johnson Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
company) — contains 60 mg pseudoephedrine hydrochloride (also 8 mg
acrivastine Acrivastine is a medication used for the treatment of allergies and hay fever. It is a second-generation H1-receptor antagonist antihistamine (like its base molecule triprolidine) and works by blocking histamine H1 receptors. This non-sedating a ...
) *
Cirrus Cirrus may refer to: Science *Cirrus (biology), any of various thin, thread-like structures on the body of an animal *Cirrus (botany), a tendril * Infrared cirrus, in astronomy, filamentary structures seen in infrared light *Cirrus cloud, a typ ...
(made by UCB) — contains 120 mg pseudoephedrine hydrochloride (also 5 mg
cetirizine Cetirizine, sold under the brand name Zyrtec among others, is a second-generation antihistamine used to treat allergic rhinitis (hay fever), dermatitis, and urticaria (hives). It is taken by mouth. Effects generally begin within thirty minutes a ...
). * Claritin-D (made by
Bayer Healthcare Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of business include pharmaceutica ...
) — contains 120 mg of pseudoephedrine sulfate (also 5 mg of
loratadine Loratadine, sold under the brand name Claritin among others, is a medication used to treat allergies. This includes allergic rhinitis (hay fever) and hives. It is also available in combination with pseudoephedrine, a decongestant, known as lora ...
). * Claritin-D 24 Hour (made by
Bayer Healthcare Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of business include pharmaceutica ...
) — contains 240 mg of pseudoephedrine sulfate (also 10 mg of
loratadine Loratadine, sold under the brand name Claritin among others, is a medication used to treat allergies. This includes allergic rhinitis (hay fever) and hives. It is also available in combination with pseudoephedrine, a decongestant, known as lora ...
). *
Codral Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including ...
(made by
Asia-Pacific Asia-Pacific (APAC) is the part of the world near the western Pacific Ocean. The Asia-Pacific region varies in area depending on context, but it generally includes East Asia, Russian Far East, South Asia, Southeast Asia, Australia and Pacific Isla ...
subsidiary of
Johnson & Johnson Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
) — Codral Original contains pseudoephedrine, Codral New Formula substitutes phenylephrine for pseudoephedrine. * Congestal (made by
SIGMA Pharmaceutical Industries Sigma (; uppercase Σ, lowercase σ, lowercase in word-final position ς; grc-gre, σίγμα) is the eighteenth letter of the Greek alphabet. In the system of Greek numerals, it has a value of 200. In general mathematics, uppercase Σ is used as ...
) — contains 60 mg pseudoephedrine hydrochloride (also 650 mg
paracetamol Paracetamol, also known as acetaminophen, is a medication used to treat fever and mild to moderate pain. Common brand names include Tylenol and Panadol. At a standard dose, paracetamol only slightly decreases body temperature; it is inferior ...
and 4 mg
chlorpheniramine Chlorphenamine (CP, CPM), also known as chlorpheniramine, is an antihistamine used to treat the symptoms of allergic conditions such as allergic rhinitis (hay fever). It is taken by mouth. The medication takes effect within two hours and las ...
). *
Contac Pseudoephedrine (PSE) is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant, as a stimulant, or as a wakefulness-promoting agent in higher doses. It was first chara ...
(made by
GlaxoSmithKline GSK plc, formerly GlaxoSmithKline plc, is a British multinational pharmaceutical and biotechnology company with global headquarters in London, England. Established in 2000 by a merger of Glaxo Wellcome and SmithKline Beecham. GSK is the ten ...
) — previously contained pseudoephedrine, now contains phenylephrine. As at Nov 2014 UK version still contains 30 mg pseudoephedrine hydrochloride per tablet. * Demazin (made by
Bayer Healthcare Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of business include pharmaceutica ...
) — contains pseudoephedrine sulfate and chlorpheniramine maleate * Eltor (made by
Sanofi Aventis Sanofi S.A. is a French multinational pharmaceutical and healthcare company headquartered in Paris, France. Originally, the corporation was established in 1973 and merged with Synthélabo in 1999 to form Sanofi-Synthélabo. In 2004, Sanofi-Syn ...
) — contains pseudoephedrine hydrochloride. *
Mucinex Guaifenesin, also known as glyceryl guaiacolate, is an expectorant medication that aids in the elimination of sputum from the respiratory tract. Chemically it is an ether of guaiacol and glycerine. It is often used in combination with other m ...
D (made by
Reckitt Benckiser Reckitt Benckiser Group plc, trading as Reckitt, is a British multinational consumer goods company headquartered in Slough, England. It is a producer of health, hygiene and nutrition products. The company was formed in March 1999 by the merg ...
) — contains 60 mg pseudoephedrine hydrochloride (also 1200 mg guaifenesin). *
Nexafed Nexafed is a formulation of pseudoephedrine developed by Acura Pharmaceuticals used to deter the use of the pseudoephedrine contained in the product for illicit methamphetamine synthesis. Nexafed uses a polymer matrix that forms a thick gel when ...
(made by Acura Pharmaceuticals) — contains 30 mg pseudoephedrine per tablet, formulated with Impede Meth-Deterrent technology. *
Nurofen Nurofen is a brand name range of pain-relief medication containing ibuprofen made by the British multinational Reckitt. Introduced in 1983, the Nurofen brand was acquired following Reckitt Benckiser's acquisition of Boots (company), Boots in 200 ...
Cold & Flu (made by
Reckitt Benckiser Reckitt Benckiser Group plc, trading as Reckitt, is a British multinational consumer goods company headquartered in Slough, England. It is a producer of health, hygiene and nutrition products. The company was formed in March 1999 by the merg ...
) — contains 30 mg pseudoephedrine hydrochloride (also 200 mg
ibuprofen Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus arte ...
). *Respidina – contains 120 mg of pseudoephedrine in the form of extended release tablets. * Rhinex Flash (made by
Pharma Product Manufacturing Pharma may be an abbreviation for: Drugs * Pharmaceutical drug * Pharmaceutical industry * Pharmaceutical Research and Manufacturers of America (PhRMA) * Pharmacology Pharmacology is a branch of medicine, biology and pharmaceutical sciences co ...
, Cambodia) — contains pseudoephedrine combined with
paracetamol Paracetamol, also known as acetaminophen, is a medication used to treat fever and mild to moderate pain. Common brand names include Tylenol and Panadol. At a standard dose, paracetamol only slightly decreases body temperature; it is inferior ...
and
triprolidine Triprolidine is an over-the-counter antihistamine with anticholinergic properties. It is used to combat the symptoms associated with allergies and is sometimes combined with other cold medications designed to provide general relief for flu-like ...
. * Rhinos SR (made by Dexa Medica) — contains 120 mg of pseudoephedrine hydrochloride (also 5 mg loratadine). *Rino-Ebastel (made by
Almirall Almirall, S.A. is a Spanish pharmaceutical company, with headquarters in Barcelona, founded in 1943. In 2016, it generated total revenue of €859.3 million and became the leading pharmaceutical company in R&D investment in Spain. With over ...
) – contains 120 mg of pseudoephedrine hydrochloride (also 10 mg
ebastine Ebastine is a H1 antihistamine with low potential for causing drowsiness. It does not penetrate the blood–brain barrier to a significant amount and thus combines an effective block of the histamine H1 receptor, H1 receptor in peripheral bio ...
). * Sinufed (made by Trima) — contains 60 mg pseudoephedrine hydrochloride. * Sinutab (made by
McNeil Consumer Healthcare McNeil Consumer Healthcare is an American medicals products company belonging to the Johnson & Johnson Health care, healthcare products group. It primarily sells fast-moving consumer goods such as Over-the-counter drug, over-the-counter drugs. ...
, a
Johnson & Johnson Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
company) — contains 500 mg paracetamol and 30 mg pseudoephedrine hydrochloride. *
Sudafed Pseudoephedrine (PSE) is a sympathomimetic drug of the substituted phenethylamine, phenethylamine and substituted amphetamine, amphetamine chemical classes. It may be used as a decongestant, nasal/sinus decongestant, as a stimulant, or as a wake ...
Decongestant (made by
McNeil Consumer Healthcare McNeil Consumer Healthcare is an American medicals products company belonging to the Johnson & Johnson Health care, healthcare products group. It primarily sells fast-moving consumer goods such as Over-the-counter drug, over-the-counter drugs. ...
, a
Johnson & Johnson Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
company) — contains 60 mg of pseudoephedrine hydrochloride. * Theraflu (made by
Novartis Novartis AG is a Swiss-American multinational pharmaceutical corporation based in Basel, Switzerland and Cambridge, Massachusetts, United States (global research).name="novartis.com">https://www.novartis.com/research-development/research-loc ...
) — previously contained pseudoephedrine, now contains
phenylephrine Phenylephrine is a medication primarily used as a decongestant, to dilate the pupil, to increase blood pressure, and to relieve hemorrhoids. In the United States, it was previously used orally as an over-the-counter decongestant to relieve nas ...
. * Unifed (made by
United Pharmaceutical Manufacturer United may refer to: Places * United, Pennsylvania, an unincorporated community * United, West Virginia, an unincorporated community Arts and entertainment Films * ''United'' (2003 film), a Norwegian film * ''United'' (2011 film), a BBC Two f ...
, Jordan) — contains pseudoephedrine hydrochloride (also
triprolidine Triprolidine is an over-the-counter antihistamine with anticholinergic properties. It is used to combat the symptoms associated with allergies and is sometimes combined with other cold medications designed to provide general relief for flu-like ...
and guaifenesin). * Zyrtec-D 12 Hour (made by
McNeil Consumer Healthcare McNeil Consumer Healthcare is an American medicals products company belonging to the Johnson & Johnson Health care, healthcare products group. It primarily sells fast-moving consumer goods such as Over-the-counter drug, over-the-counter drugs. ...
, a
Johnson & Johnson Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
company) — contains 120 mg pseudoephedrine hydrochloride (also 5 mg of
cetirizine Cetirizine, sold under the brand name Zyrtec among others, is a second-generation antihistamine used to treat allergic rhinitis (hay fever), dermatitis, and urticaria (hives). It is taken by mouth. Effects generally begin within thirty minutes a ...
). *Zephrex-D (made by
Westport Pharmaceuticals Westport is the name of several communities around the world. Canada *Westport, Nova Scotia *Westport, Ontario **Westport Rideaus, local junior "B" ice hockey team ** Westport/Rideau Lakes Airport * Westport, Newfoundland and Labrador Ireland * ...
) – a special meth-resistant form of pseudoephedrine that becomes gooey when heated


Legal status


Australia

Illicit diversion of pseudoephedrine in Australia has caused significant changes to the way the products are regulated. , all products containing pseudoephedrine have been rescheduled as either "Pharmacist Only Medicines" (Schedule 3) or "Prescription Only Medicines" (Schedule 4), depending on the amount of pseudoephedrine in the product. A Pharmacist Only Medicine may only be sold to the public if a pharmacist is directly involved in the transaction. These medicines must be kept behind the counter, away from public access. Pharmacists are also encouraged (and in some states required) to log purchases with the online database Project STOP. This system aims to prevent individuals from purchasing small quantities of pseudoephedrine from many different pharmacies. As a result, many pharmacies no longer stock Sudafed, the common brand of pseudoephedrine cold/sinus tablets, opting instead to sell Sudafed PE, a
phenylephrine Phenylephrine is a medication primarily used as a decongestant, to dilate the pupil, to increase blood pressure, and to relieve hemorrhoids. In the United States, it was previously used orally as an over-the-counter decongestant to relieve nas ...
product that has not been proven effective in clinical trials.


Canada

Health Canada Health Canada (HC; french: Santé Canada, SC)Health Canada is the applied title under the Federal Identity Program; the legal title is Department of Health (). is the Structure of the Canadian federal government#Departments, with subsidiary unit ...
has investigated the risks and benefits of pseudoephedrine and
ephedrine Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in ...
/
Ephedra Ephedra may refer to: * Ephedra (medicine), a medicinal preparation from the plant ''Ephedra sinica'' * ''Ephedra'' (plant), genus of gymnosperm shrubs See also * Ephedrine Ephedrine is a central nervous system (CNS) stimulant that is of ...
. Near the end of the study, Health Canada issued a warning on their website stating that those who are under the age of 12, or who have heart disease and may have strokes, should avoid taking pseudoephedrine and ephedrine. Also, they warned that everyone should avoid taking ephedrine or pseudoephrine with other stimulants like
caffeine Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class. It is mainly used recreationally as a cognitive enhancer, increasing alertness and attentional performance. Caffeine acts by blocking binding of adenosine t ...
. They also banned all products that contain both ephedrine (or pseudoephedrine) and caffeine. Products whose only medicinal ingredient is pseudoephedrine must be kept behind the pharmacy counter. Products containing pseudoephedrine along with other medicinal ingredients may be displayed on store shelves but may be sold only in a pharmacy when a pharmacist is present.


Colombia

The Colombian government prohibited the trade of pseudoephedrine in 2010.


Japan

Medications that contain more than 10% pseudoephedrine are prohibited under the Stimulants Control Law in Japan.


Mexico

On 23 November 2007, the use and trade of pseudoephedrine in Mexico was made illegal as it was argued that it was extremely popular as a precursor in the synthesis of methamphetamine.


Netherlands

Pseudoephedrine was withdrawn from sale in 1989 due to concerns about adverse cardiac side effects.


New Zealand

In New Zealand, pseudoephedrine is currently classified as a Class B Part II controlled drug in the
Misuse of Drugs Act 1975 The Misuse of Drugs Act 1975 is a New Zealand drug control law that classifies drugs into three classes, or schedules, purportedly based on their projected risk of serious harm. However, in reality, classification of drugs outside of passing law ...
, making it illegal to supply or possess except on prescription. Pseudoephedrine, ephedrine, and any product containing these substances, e.g. cold and flu medicines, were first classified in October 2004 as Class C Part III (partially exempted) controlled drugs, due to being the principal ingredient in methamphetamine. New Zealand Customs and police officers continued to make large interceptions of precursor substances believed to be destined for
methamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity. Methamph ...
production. On 9 October 2009, Prime Minister
John Key Sir John Phillip Key (born 9 August 1961) is a New Zealand retired politician who served as the 38th Prime Minister of New Zealand from 2008 to 2016 and as Leader of the New Zealand National Party from 2006 to 2016. After resigning from bo ...
announced pseudoephedrine-based cold and flu tablets would become prescription-only drugs and reclassified as a class B2 drug. The law was amended by The Misuse of Drugs Amendment Bill 2010, which passed in August 2011.


Turkey

In
Turkey Turkey ( tr, Türkiye ), officially the Republic of Türkiye ( tr, Türkiye Cumhuriyeti, links=no ), is a list of transcontinental countries, transcontinental country located mainly on the Anatolia, Anatolian Peninsula in Western Asia, with ...
, medications containing pseudoephedrine are available with prescription only.


United Kingdom

In the UK, pseudoephedrine is available over the counter under the supervision of a qualified pharmacist, or on prescription. In 2007, the MHRA reacted to concerns over diversion of ephedrine and pseudoephedrine for the illicit manufacture of methamphetamine by introducing voluntary restrictions limiting over the counter sales to one box containing no more than 720 mg of pseudoephedrine in total per transaction. These restrictions became law in April 2008. No form of ID is required.


United States


=Federal

= The
United States Congress The United States Congress is the legislature of the federal government of the United States. It is bicameral, composed of a lower body, the House of Representatives, and an upper body, the Senate. It meets in the U.S. Capitol in Washing ...
has recognized that pseudoephedrine is used in the illegal manufacture of methamphetamine. In 2005, the
Committee on Education and the Workforce The Committee on Education and Labor is a standing committee of the United States House of Representatives. There are 50 members in this committee. Since 2019, the chair of the Education and Labor committee is Robert Cortez Scott of Virginia. Hi ...
heard testimony concerning education programs and state legislation designed to curb this illegal practice. Attempts to control the sale of the drug date back to 1986, when federal officials at the
Drug Enforcement Administration The Drug Enforcement Administration (DEA; ) is a Federal law enforcement in the United States, United States federal law enforcement agency under the U.S. Department of Justice tasked with combating drug trafficking and distribution within th ...
(DEA) first drafted legislation, later proposed by Senator Bob Dole, that would have placed a number of chemicals used in the manufacture of illicit drugs under the
Controlled Substances Act The Controlled Substances Act (CSA) is the statute establishing federal government of the United States, federal drug policy of the United States, U.S. drug policy under which the manufacture, importation, possession, use, and distribution of ...
. The bill would have required each transaction involving pseudoephedrine to be reported to the government, and federal approval of all imports and exports. Fearing this would limit legitimate use of the drug, lobbyists from over the counter drug manufacturing associations sought to stop this legislation from moving forward, and were successful in exempting from the regulations all chemicals that had been turned into a legal final product, such as Sudafed. Prior to the passage of the
Combat Methamphetamine Epidemic Act of 2005 The Combat Methamphetamine Epidemic Act of 2005 (CMEA) is federal legislation enacted in the United States on March 9, 2006, to regulate, among other things, retail over-the-counter sales of following products because of their use in the manufactu ...
, sales of the drug became increasingly regulated, as DEA regulators and pharmaceutical companies continued to fight for their respective positions. The DEA continued to make greater progress in their attempts to control pseudoephedrine as methamphetamine production skyrocketed, becoming a serious problem in the western United States. When purity dropped, so did the number of people in rehab and people admitted to emergency rooms with methamphetamine in their systems. This reduction in purity was usually short lived, however, as methamphetamine producers eventually found a way around the new regulations. Congress passed the ''
Combat Methamphetamine Epidemic Act of 2005 The Combat Methamphetamine Epidemic Act of 2005 (CMEA) is federal legislation enacted in the United States on March 9, 2006, to regulate, among other things, retail over-the-counter sales of following products because of their use in the manufactu ...
'' ("CMEA") as an amendment to the renewal of the
USA Patriot Act The USA PATRIOT Act (commonly known as the Patriot Act) was a landmark Act of Congress, Act of the United States Congress, signed into law by President of the United States, President George W. Bush. The formal name of the statute is the Uniti ...
. Signed into law by president
George W. Bush George Walker Bush (born July 6, 1946) is an American politician who served as the 43rd president of the United States from 2001 to 2009. A member of the Republican Party, Bush family, and son of the 41st president George H. W. Bush, he ...
on March 6, 2006, the act amended , concerning the sale of pseudoephedrine-containing products. The law mandated two phases, the first needing to be implemented by April 8, 2006, and the second to be completed by September 30, 2006. The first phase dealt primarily with implementing the new buying restrictions based on amount, while the second phase encompassed the requirements of storage, employee training, and record keeping. Though the law was mainly directed at pseudoephedrine products it also applies to all over-the-counter products containing ephedrine, pseudoephedrine, and phenylpropanolamine, their salts, optical isomers, and salts of optical isomers. Pseudoephedrine was defined as a " scheduled listed chemical product" under (45(A)). The act included the following requirements for merchants ("regulated sellers") who sell such products: * Required a retrievable record of all purchases, identifying the name and address of each party, to be kept for two years * Required verification of proof of identity of all purchasers * Required protection and disclosure methods in the collection of personal information * Required reports to the
Attorney General In most common law jurisdictions, the attorney general or attorney-general (sometimes abbreviated AG or Atty.-Gen) is the main legal advisor to the government. The plural is attorneys general. In some jurisdictions, attorneys general also have exec ...
of any suspicious payments or disappearances of the regulated products * Required training of employees with regard to the requirements of the CMEA. Retailers must self-certify as to training and compliance. * The non-liquid dose form of regulated products may only be sold in unit dose blister packs * Regulated products must be stored behind the counter or in a locked cabinet in such a way as to restrict public access * Sales limits (per customer): ** Daily sales limit—must not exceed 3.6 grams of pseudoephedrine base without regard to the number of transactions ** 30-day (not monthly) sales limit—must not exceed 7.5 grams of pseudoephedrine base if sold by mail order or "mobile retail vendor" ** 30-day purchase limit—must not exceed 9 grams of pseudoephedrine base. (A misdemeanor possession offense under for the person who buys it.) In regards to the identification that may be used by an individual buying pseudoephedrine products the following constitute acceptable forms of identification: * US passport * Alien registration or permanent resident card * Unexpired foreign passport with temporary I-551 stamp * Unexpired Employment Authorization Document * Driver's License or Government issued identification card (including Canadian driver's license) * School ID with picture * Voter's Registration card * US Military Card * Native American tribal documents The requirements were revised in the Methamphetamine Production Prevention Act of 2008 to require that a regulated seller of scheduled listed chemical products may not sell such a product unless the purchaser: * Presents a government issued photographic identification; and * Signs the written logbook with their name, address, and time and date of the sale


=State

= Most states also have laws regulating pseudoephedrine. The states of Alabama, Arizona, Arkansas, California, Colorado, Delaware, Florida, Georgia, Hawaii () Idaho, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana (), Massachusetts, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska, Nevada, New Jersey, North Carolina, Ohio, Oklahoma, Oregon, Pennsylvania, South Dakota, Tennessee, Texas, Utah, Vermont, Virginia, Washington, West Virginia and Wisconsin have laws requiring pharmacies to sell pseudoephedrine "behind the counter". Though the drug can be purchased without a prescription, states can limit the number of units sold and can collect personal information from purchasers.'' The states of Oregon and Mississippi previously required a prescription for the purchase of products containing pseudoephedrine. However as of January 1, 2022 these restrictions have been repealed The state of Oregon reduced the number of methamphetamine lab seizures from 467 in 2004 (the final full year before implementation of the prescription only law) to a new low of 12 in 2009. The decrease in
meth lab A rolling meth lab is a transportable laboratory that is used to illegally produce methamphetamine.Staff writerMethamphetamine, meth-lab assessment and clean-up" ''Forensic Applications Consulting Technologies Inc.'' Retrieved on 2009-02-14. Ro ...
incidents in Oregon occurred largely before the prescription-only law took effect, according to a NAMSDL report titled ''Pseudoephedrine Prescription Laws in Oregon and Mississippi''. The report posits that the decline in meth lab incidents in both states may be due to other factors: "Mexican traffickers may have contributed to the decline in meth labs in Mississippi and Oregon (and surrounding states) as they were able to provide ample supply of equal or greater quality meth at competitive prices". Additionally, similar decreases in meth lab incidents were seen in surrounding states, according to the report, and meth-related deaths in Oregon have dramatically risen since 2007. Some municipalities in Missouri have enacted similar ordinances, including
Washington Washington commonly refers to: * Washington (state), United States * Washington, D.C., the capital of the United States ** A metonym for the federal government of the United States ** Washington metropolitan area, the metropolitan area centered o ...
,
Union Union commonly refers to: * Trade union, an organization of workers * Union (set theory), in mathematics, a fundamental operation on sets Union may also refer to: Arts and entertainment Music * Union (band), an American rock group ** ''Un ...
,
New Haven New Haven is a city in the U.S. state of Connecticut. It is located on New Haven Harbor on the northern shore of Long Island Sound in New Haven County, Connecticut and is part of the New York City metropolitan area. With a population of 134,02 ...
,
Cape Girardeau Cape Girardeau ( , french: Cap-Girardeau ; colloquially referred to as "Cape") is a city in Cape Girardeau and Scott Counties in the U.S. state of Missouri. At the 2020 census, the population was 39,540. The city is one of two principal citi ...
and
Ozark The Ozarks, also known as the Ozark Mountains, Ozark Highlands or Ozark Plateau, is a physiographic region in the U.S. states of Missouri, Arkansas, Oklahoma and the extreme southeastern corner of Kansas. The Ozarks cover a significant portio ...
. Certain pharmacies in
Terre Haute, Indiana Terre Haute ( ) is a city in and the county seat of Vigo County, Indiana, United States, about 5 miles east of the state's western border with Illinois. As of the 2010 census, the city had a population of 60,785 and its metropolitan area had a ...
do so as well. Another approach to controlling the drug on the state level mandated by some state governments to control the purchases of their citizens is the use of electronic tracking systems, which require the electronic submission of specified purchaser information by all retailers who sell pseudoephedrine. Thirty-two states now require the National Precursor Log Exchange (NPLEx) to be used for every pseudoephedrine and ephedrine OTC purchase, and ten of the eleven largest pharmacy chains in the US voluntarily contribute all of their similar transactions to NPLEx. These states have seen dramatic results in reducing the number of methamphetamine laboratory seizures. Prior to implementation of the system in Tennessee in 2005, methamphetamine laboratory seizures totaled 1,497 in 2004, but were reduced to 955 in 2005, and 589 in 2009. Kentucky's program was implemented statewide in 2008, and since statewide implementation, the number of laboratory seizures has significantly decreased. Oklahoma initially experienced success with their tracking system after implementation in 2006, as the number of seizures dropped in that year and again in 2007. In 2008, however, seizures began rising again, and have continued to rise in 2009. Nonetheless, when Oklahoma adopted NPLEx, their lab seizures also dropped significantly. NPLEx appears to be successful by requiring the real-time submission of transactions, thereby enabling the relevant laws to be enforced at the point of sale. By creating a multi-state database and the ability to compare all transactions quickly, NPLEx enables pharmacies to deny purchases that would be illegal based on gram limits, age, or even to convicted meth offenders in some states. NPLEx also enforces the federal gram limits across state lines, which was impossible with state-operated systems. Access to the records is by law enforcement agencies only, through an online secure portal.


In popular culture

In the pilot episode of ''Breaking Bad'', Walter White first synthesizes methamphetamine through the Nagai route, using
red phosphorus Elemental phosphorus can exist in several allotropes, the most common of which are white and red solids. Solid violet and black allotropes are also known. Gaseous phosphorus exists as diphosphorus and atomic phosphorus. White phosphorus White ...
and
iodine Iodine is a chemical element with the symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , and boils to a vi ...
to reduce pseudoephedrine. In the episode "
Vitamin D Vitamin D is a group of fat-soluble secosteroids responsible for increasing intestinal absorption of calcium, magnesium, and phosphate, and many other biological effects. In humans, the most important compounds in this group are vitamin D3 (c ...
" of ''
Glee Glee means delight, a form of happiness. Glee may also refer to: * Glee (music), a type of English choral music * ''Glee'' (TV series), an American musical comedy-drama TV series, and related media created by Ryan Murphy * ''Glee'' (Bran Van 30 ...
'',
Terri Terri is an alternative spelling of Terry. It is a common feminine given name and is also a diminutive for Teresa. Notable people with the name include: * Terri Allard (born 1962), American country/folk singer/songwriter * Terri S. Armstrong, Am ...
takes a job as the school nurse to stop her husband,
Will Schuester William Michael Schuester, often referred to as Mr. Schue, is a fictional teacher character and one of the two main protagonists from the Fox musical comedy-drama series ''Glee'', alongside his student Rachel Berry. He has appeared in ''Glee'' ...
, from becoming closer to
guidance counsellor A school counselor is a professional who works in primary (elementary and middle) schools or secondary schools to provide academic, career, college access/affordability/admission, and social-emotional competencies to all students through a school ...
Emma Pillsbury Emma Pillsbury Schuester (previously Pillsbury-Howell) is a fictional character from the Fox musical comedy-drama series '' Glee''. Portrayed by actress Jayma Mays, Emma has appeared in ''Glee'' from its pilot episode, first broadcast on May 1 ...
(
Jayma Mays Jamia Suzette "Jayma" Mays is an American actress. She is known for playing Emma Pillsbury in the Fox musical series '' Glee'' (2009–2015) and for her starring roles in the films ''Red Eye'' (2005), '' Paul Blart: Mall Cop'' (2009) and ''Th ...
), but is fired after giving the students performance-enhancing pseudoephedrine tablets. In her 2013 single " Avant Gardener", Australian rock musician
Courtney Barnett Courtney Melba Barnett (born 3 November 1987) is an Australian singer, songwriter, and musician. Known for her deadpan singing style and witty, rambling lyrics, she attracted attention with the release of her debut EP ''I've Got a Friend Call ...
refers to the effects of pseudoephedrine: "Reminds me of the time / When I was really sick and I / Had too much pseudoephedrine and I / Couldn't sleep at night". In her 2017 album ''
Melodrama A modern melodrama is a dramatic work in which the plot, typically sensationalized and for a strong emotional appeal, takes precedence over detailed characterization. Melodramas typically concentrate on dialogue that is often bombastic or exces ...
'', pop artist
Lorde Ella Marija Lani Yelich-O'Connor (born 7 November 1996), known professionally as Lorde ( ), is a New Zealand singer-songwriter. Taking inspiration from aristocracy for her stage name, she is known for her unconventional musical styles and i ...
references pseudoephedrine on the song "
Writer in the Dark "Writer in the Dark" is a song recorded by New Zealand singer-songwriter Lorde for her second album '' Melodrama'' (2017). She co-wrote and co-produced the track with Jack Antonoff. It is a piano ballad with sparse production and an outro. It ...
". The lyric reads: "I still feel you, now and then / Slow like pseudoephedrine / When you see me, will you say I've changed?"


Synthesis

Although pseudoephedrine occurs naturally as an
alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...
in certain plant species (for example, as a constituent of extracts from the ''
Ephedra Ephedra may refer to: * Ephedra (medicine), a medicinal preparation from the plant ''Ephedra sinica'' * ''Ephedra'' (plant), genus of gymnosperm shrubs See also * Ephedrine Ephedrine is a central nervous system (CNS) stimulant that is of ...
'' species, also known as ''ma huang'', in which it occurs together with other isomers of
ephedrine Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in ...
), the majority of pseudoephedrine produced for commercial use is derived from
yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constitut ...
fermentation Fermentation is a metabolic process that produces chemical changes in organic substrates through the action of enzymes. In biochemistry, it is narrowly defined as the extraction of energy from carbohydrates in the absence of oxygen. In food ...
of dextrose in the presence of benzaldehyde. In this process, specialized strains of yeast (typically a variety of ''
Candida utilis Torula (''Cyberlindnera jadinii'') is a species of yeast. Use Torula, in its inactive form (usually labeled as torula yeast), is widely used as a flavoring in processed foods and pet foods. It is often grown on wood liquor, a byproduct of paper ...
'' or ''
Saccharomyces cerevisiae ''Saccharomyces cerevisiae'' () (brewer's yeast or baker's yeast) is a species of yeast (single-celled fungus microorganisms). The species has been instrumental in winemaking, baking, and brewing since ancient times. It is believed to have been o ...
'') are added to large vats containing water, dextrose and the enzyme pyruvate decarboxylase (such as found in
beet The beetroot is the taproot portion of a beet plant, usually known in North America as beets while the vegetable is referred to as beetroot in British English, and also known as the table beet, garden beet, red beet, dinner beet or golden beet ...
s and other plants). After the yeast has begun fermenting the dextrose, the benzaldehyde is added to the vats, and in this environment the yeast converts the ingredients to the precursor
l-phenylacetylcarbinol Phenylacetylcarbinol (PAC) is an organic compound that has two enantiomers, one with R- and one with S-configuration. (R)-PAC, which is commonly called -PAC, is known as a precursor in the synthesis of pharmaceuticals such as ephedrine and pse ...
(L-PAC). L-PAC is then chemically converted to pseudoephedrine via
reductive amination Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is considered ...
. The bulk of pseudoephedrine is produced by commercial
pharmaceutical manufacturers The pharmaceutical industry discovers, develops, produces, and markets drugs or pharmaceutical drugs for use as medications to be administered to patients (or self-administered), with the aim to cure them, vaccinate them, or alleviate symptoms. ...
in
India India, officially the Republic of India (Hindi: ), is a country in South Asia. It is the seventh-largest country by area, the second-most populous country, and the most populous democracy in the world. Bounded by the Indian Ocean on the so ...
and
China China, officially the People's Republic of China (PRC), is a country in East Asia. It is the world's most populous country, with a population exceeding 1.4 billion, slightly ahead of India. China spans the equivalent of five time zones and ...
, where economic and industrial conditions favor its mass production for export.Suo, Steve. Clamp down on shipments of raw ingredients. The Oregonian; 6 October 2004. From a version reprinted on a U.S
congressional caucus
website.


See also

*
Amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...
*
Carbinoxamine/pseudoephedrine Carbinoxamine/pseudoephedrine is an antihistamine and decongestant combination, marketed as Rondec, Ceron and Coldec. It contains two active ingredients: carbinoxamine and pseudoephedrine Pseudoephedrine (PSE) is a sympathomimetic drug of th ...
*
Ephedrine Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in ...
*
Methamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity. Methamph ...
* ''N''-Methylpseudoephedrine *
Phenylephrine Phenylephrine is a medication primarily used as a decongestant, to dilate the pupil, to increase blood pressure, and to relieve hemorrhoids. In the United States, it was previously used orally as an over-the-counter decongestant to relieve nas ...
*
Phenylpropanolamine Phenylpropanolamine (PPA) is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was commonly used in prescription and over-the-counter cough and cold preparations. In veterinary medicine, it is used to contr ...
* Thomas Latham, sponsor of the "Angie Fatino Save the Children from Meth Act"


References


External links

* {{Portal bar , Medicine Amphetamine alkaloids Decongestants Methamphetamine Norepinephrine releasing agents Phenylethanolamines