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''para''-Methoxy-''N''-methylamphetamine (also known as PMMA, Red Mitsubishi), chemically known as methyl-MA, 4-methoxy-''N''-methylamphetamine, 4-MMA) or (4-PMDA, as listed to its original physical name) 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 ...
and
psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science o ...
closely related to 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
serotonergic Serotonergic () or serotoninergic () means "pertaining to or affecting serotonin". Serotonin is a neurotransmitter. A synapse is serotonergic if it uses serotonin as its neurotransmitter. A serotonergic neuron ''produces'' serotonin. A substance is ...
drug ''para''-methoxyamphetamine (PMA). PMMA is the 4-
methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position as ...
analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...
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 ...
. Little is known about the
pharmacological Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which exerts a biochemica ...
properties,
metabolism Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...
, and
toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...
of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug
MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in Tablet (pharmacy), tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for Recreational dru ...
were linked to misrepresented tablets and capsules of PMMA. Its effects in humans are reputedly similar to those of PMA, but slightly more empathogenic in nature. It has a reduced tendency to produce severe
hyperthermia Hyperthermia, also known simply as overheating, is a condition in which an individual's body temperature is elevated beyond normal due to failed thermoregulation. The person's body produces or absorbs more heat than it dissipates. When extreme ...
at low dosages, but at higher dosages side effects and risk of death become similar to those of PMA. The synthesis and effects of PMMA were described by American experimental chemist
Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamph ...
in his book '' PiHKAL'', where it is referred to by the name "methyl-MA", as the ''N''-methylated form of 4-MA (PMA). Shulgin reported that PMMA produces an increase in
blood pressure Blood pressure (BP) is the pressure of circulating blood against the walls of blood vessels. Most of this pressure results from the heart pumping blood through the circulatory system. When used without qualification, the term "blood pressure" r ...
and in
heart rate Heart rate (or pulse rate) is the frequency of the heartbeat measured by the number of contractions (beats) of the heart per minute (bpm). The heart rate can vary according to the body's physical needs, including the need to absorb oxygen and excr ...
, at doses above 100 mg, but causes no
psychoactive A psychoactive drug, psychopharmaceutical, psychoactive agent or psychotropic drug is a chemical substance, that changes functions of the nervous system, and results in alterations in perception, mood, consciousness, cognition or behavior. Th ...
effects at these levels.


Recreational use

PMMA has been found in tablets and capsules of the
MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in Tablet (pharmacy), tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for Recreational dru ...
sold as "ecstasy". A number of deaths have been attributed to tablets sold as ecstasy that contained other substances, such as PMMA's structural analog, PMA. Death can occur when an ecstasy user believes they are consuming recreational doses of MDMA, when they are in fact consuming a lethal dose of another substance with similar effects. PMA is of particular concern because it not only causes a release of serotonin but also acts as a monoamine oxidase inhibitor (MAOI); if it is used in combination with MDMA or another MDMA-like substance,
serotonin syndrome Serotonin syndrome (SS) is a group of symptoms that may occur with the use of certain serotonergic medications or drugs. The degree of symptoms can range from mild to severe, including a potentiality of death. Symptoms in mild cases include high ...
can result. PMMA can be detected with
reagent testing Reagent testing is one of the processes used to identify substances contained within a pill, usually illicit substances. With the increased prevalence of drugs being available in their pure forms, the terms "drug checking" or "pill testing" may a ...
kits.


Deaths

In January 2011, the
Norwegian Broadcasting Corporation NRK, an abbreviation of the Norwegian ''Norsk Rikskringkasting AS'', generally expressed in English as the Norwegian Broadcasting Corporation, is the Norwegian government-owned radio and television public broadcasting company, and the largest ...
reported that Norway had seen 12 deaths related to PMMA over the course of six months. In March 2011,
Dutch Dutch commonly refers to: * Something of, from, or related to the Netherlands * Dutch people () * Dutch language () Dutch may also refer to: Places * Dutch, West Virginia, a community in the United States * Pennsylvania Dutch Country People E ...
media reported that there had been four deaths in the province of
Limburg Limburg or Limbourg may refer to: Regions * Limburg (Belgium), a province since 1839 in the Flanders region of Belgium * Limburg (Netherlands), a province since 1839 in the south of the Netherlands * Diocese of Limburg, Roman Catholic Diocese in ...
since November 2010. In April 2011,
Iceland Iceland ( is, Ísland; ) is a Nordic island country in the North Atlantic Ocean and in the Arctic Ocean. Iceland is the most sparsely populated country in Europe. Iceland's capital and largest city is Reykjavík, which (along with its s ...
ic media reported the death of a young woman that may have been connected to PMMA. In 2011, four deaths were recorded in Scotland as a result of ecstasy tablets which also contained PMMA. In January 2012, a number of ecstasy-related deaths in
Canada Canada is a country in North America. Its ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, covering over , making it the world's second-largest country by tot ...
in the previous year were linked to PMMA overdoses. In the single year, approximately 45 exposures occurred, resulting in 21 deaths. Cases were centred primarily in Calgary and Vancouver. In September 2012, the deaths of two men in
County Cork County Cork ( ga, Contae Chorcaí) is the largest and the southernmost county of Ireland, named after the city of Cork, the state's second-largest city. It is in the province of Munster and the Southern Region. Its largest market towns are ...
,
Ireland Ireland ( ; ga, Éire ; Ulster Scots dialect, Ulster-Scots: ) is an island in the Atlantic Ocean, North Atlantic Ocean, in Northwestern Europe, north-western Europe. It is separated from Great Britain to its east by the North Channel (Grea ...
, have been linked to PMMA overdoses. In the same month, the death of a man in Queensland, Australia was attributed to PMMA. In June 2013 a PMMA-related death occurred in the Dutch city of
's-Hertogenbosch s-Hertogenbosch (), colloquially known as Den Bosch (), is a city and municipality in the Netherlands with a population of 157,486. It is the capital of the province of North Brabant and its fourth largest by population. The city is south of th ...
. Two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town of
Sliedrecht Sliedrecht () is a town and municipality in the western Netherlands, in the province of South Holland. The municipality covers an area of of which is covered by water. Sliedrecht is known for the many large dredging companies (including Boskal ...
. In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA. In the same month, in Sweden, another man died from ecstasy laced with PMMA. In May 2015 a young woman died in
Dublin Dublin (; , or ) is the capital and largest city of Republic of Ireland, Ireland. On a bay at the mouth of the River Liffey, it is in the Provinces of Ireland, province of Leinster, bordered on the south by the Dublin Mountains, a part of th ...
, Ireland, after taking what is suspected to be PMMA. In April 2016 four young
Argentines Argentines (mistakenly translated Argentineans in the past; in Spanish (masculine) or (feminine)) are people identified with the country of Argentina. This connection may be residential, legal, historical or cultural. For most Argentines, s ...
and one
Uruguay Uruguay (; ), officially the Oriental Republic of Uruguay ( es, República Oriental del Uruguay), is a country in South America. It shares borders with Argentina to its west and southwest and Brazil to its north and northeast; while bordering ...
an died during a massive rave called "Time Warp" in
Buenos Aires Buenos Aires ( or ; ), officially the Autonomous City of Buenos Aires ( es, link=no, Ciudad Autónoma de Buenos Aires), is the capital and primate city of Argentina. The city is located on the western shore of the Río de la Plata, on South ...
and five more were hospitalized. PMMA was found in their bodies.


Legal status


United States

On June 25, 2021 the DEA finalized a rule placing PMMA on the Controlled Substance Act federal Schedule as a Schedule I substance effective July 26, 2021.


United Kingdom

PMMA is controlled as a Schedule 1,
Class A drug These drugs are known in the UK as ''controlled drugs'', because this is the term by which the act itself refers to them. In more general terms, however, many of these drugs are also controlled by the Medicines Act 1968, there are many other dru ...
in the UK.


See also

* ''para''-Methoxyamphetamine (PMA) * 2-Methoxymethamphetamine (Methoxyphenamine) *
3-Methoxymethamphetamine 3-Methoxymethamphetamine (also known as ''meta''-methoxymethamphetamine or MMMA), which is most closely related to 3-methoxyamphetamine and PMMA and shares similar monoamine releasing effects, although its effects have not been studied so extensi ...
(MMMA) * 4-Fluoromethamphetamine (4-FMA) * 4-Methylmethamphetamine (4-MMA) * 4-Methoxymethcathinone (bk-PMMA) *
Venlafaxine Venlafaxine, sold under the brand name Effexor among others, is an antidepressant medication of the serotonin-norepinephrine reuptake inhibitor (SNRI) class. It is used to treat major depressive disorder, generalized anxiety disorder, panic di ...


References


External links


Methyl-MA entry in PiHKAL

Methyl-MA entry in PiHKAL • info

Dutch article by TRIMBOS institute from 31-03-2011

Icelandic arictle by Mbl news(Mbl.is) from 30-04-2011
{{DEFAULTSORT:Methoxy-N-methylamphetamine, para- Monoamine oxidase inhibitors Phenol ethers Designer drugs Serotonin releasing agents Methamphetamines