Aminophenazone (or aminopyrine, amidopyrine, Pyramidon) is a non-narcotic

analgesic An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...

substance. It is a

pyrazolone Pyrazolone is 5-membered heterocycle containing two adjacent nitrogen atoms. It can be viewed as a derivative of pyrazole possessing an additional ketone, carbonyl (C=O) group. Compounds containing this functional group are useful commercially in ...

and a derivative of

phenazone Phenazone (International Nonproprietary Name, INN and British Approved Name, BAN; also known as phenazon, antipyrine (United States Adopted Name, USAN), antipyrin, or analgesine) is an analgesic (pain reducing), antipyretic (fever reducing) and an ...

, which also has anti-inflammatory and

antipyretic An antipyretic (, from ''anti-'' 'against' and ' 'feverish') is a substance that reduces fever. Antipyretics cause the hypothalamus to override a prostaglandin-induced increase in temperature. The body then works to lower the temperature, which r ...

properties. While inexpensive and effective, especially in the treatment of

rheumatism Rheumatism or rheumatic disorders are conditions causing chronic, often intermittent pain affecting the joints or connective tissue. Rheumatism does not designate any specific disorder, but covers at least 200 different conditions, including a ...

, the drug carries a serious risk of severe and sometimes fatal side-effects, including

agranulocytosis Agranulocytosis, also known as agranulosis or granulopenia, is an acute condition involving a severe and dangerous lowered white blood cell count (leukopenia, most commonly of neutrophils) and thus causing neutropenia in the circulating blood. I ...

. While its production and use have been banned in many countries, including France, Thailand, India and Japan, it is still sometimes used in the developing world. A breath test with ¹³C-labeled aminopyrine has been used as a non-invasive measure of

cytochrome Cytochromes are redox-active proteins containing a heme, with a central iron (Fe) atom at its core, as a cofactor. They are involved in the electron transport chain and redox catalysis. They are classified according to the type of heme and its ...

P-450 metabolic activity in liver-function tests. It is also used in measuring the total body water in the human body system.

History

Aminophenazone was first synthesized by Friedrich Stolz and

Ludwig Knorr Ludwig Knorr (2 December 1859 – 4 June 1921) was a German chemist. Together with Carl Paal, he discovered the Paal–Knorr synthesis, and the Knorr quinoline synthesis and Knorr pyrrole synthesis are also named after him. The synthesis in 1883 ...

in the late nineteenth century, and sold as an anti-fever medicine known as Pyramidon by

Hoechst AG Hoechst AG () was a German chemicals, later life sciences, company that became Aventis Deutschland after its merger with France's Rhône-Poulenc S.A. in 1999. With the new company's 2004 merger with Sanofi-Synthélabo, it became a subsidiar ...

from 1897 until its eventual replacement by the safer propyphenazone molecule.

Symptoms

Symptoms of exposure to this compound include: * allergic reactions * strong spasmolytic effect on smooth muscle of peripheral blood vessels * irritability *

palsy Palsy is a medical term which refers to various types of paralysisDan Agin, ''More Than Genes: What Science Can Tell Us About Toxic Chemicals, Development, and the Risk to Our Children'' (2009), p. 172. or paresis, often accompanied by weakness and ...

* copious sweating * dilated pupils * sharp drop then rise in body temperature *

dysuria Dysuria refers to painful or uncomfortable urination. It is one of a constellation of ''irritative'' bladder symptoms (also sometimes referred to as lower urinary tract symptoms), which includes nocturia and urinary frequency. Diagnosis The cl ...

dyspnea Shortness of breath (SOB), known as dyspnea (in AmE) or dyspnoea (in BrE), is an uncomfortable feeling of not being able to breathe well enough. The American Thoracic Society defines it as "a subjective experience of breathing discomfort that ...

anxiety Anxiety is an emotion characterised by an unpleasant state of inner wikt:turmoil, turmoil and includes feelings of dread over Anticipation, anticipated events. Anxiety is different from fear in that fear is defined as the emotional response ...

* rectal tenesmus * urinary frequency * intermittent fever * fatty infiltration of the liver * heart muscle degeneration * death due to circulatory failure following cardiovascular collapse

Agranulocytosis Agranulocytosis, also known as agranulosis or granulopenia, is an acute condition involving a severe and dangerous lowered white blood cell count (leukopenia, most commonly of neutrophils) and thus causing neutropenia in the circulating blood. I ...

often occurs. Ingestion may cause central nervous system stimulation, vomiting, convulsions,

cyanosis Cyanosis is the change of Tissue (biology), tissue color to a bluish-purple hue, as a result of decrease in the amount of oxygen bound to the hemoglobin in the red blood cells of the capillary bed. Cyanosis is apparent usually in the Tissue (bi ...

tinnitus Tinnitus is a condition when a person hears a ringing sound or a different variety of sound when no corresponding external sound is present and other people cannot hear it. Nearly everyone experiences faint "normal tinnitus" in a completely ...

leukopenia Leukopenia () is a decrease in the number of white blood cells (leukocytes). It places individuals at increased risk of infection as white blood cells are the body's primary defense against infections. Signs and symptoms Symptoms may include: * s ...

, kidney damage and coma. Ingestion may also lead to nausea, mental disturbances,

methemoglobinemia Methemoglobinemia, or methaemoglobinaemia, is a condition of elevated methemoglobin in the blood. Symptoms may include headache, dizziness, shortness of breath, nausea, poor muscle coordination, and blue-colored skin (cyanosis). Complications ma ...

, chocolate-colored blood, dizziness, epigastric pain, difficulty in hearing, thready pulse and liver damage. Other symptoms reported via ingestion include

hemolytic anemia Hemolytic anemia or haemolytic anaemia is a form of anemia due to hemolysis, the abnormal breakdown of red blood cells (RBCs), either in the blood vessels (intravascular hemolysis) or elsewhere in the human body (extravascular). This most commonl ...

porphyria Porphyria ( or ) is a group of disorders in which substances called porphyrins build up in the body, adversely affecting the skin or nervous system. The types that affect the nervous system are also known as Porphyria#Acute porphyrias, acute p ...

and severe gastrointestinal bleeding. Bone marrow depression also occurs. Rare eye effects include acute transient myopia. Chronic symptoms include: *

anorexia Anorexia nervosa (AN), often referred to simply as anorexia, is an eating disorder characterized by Calorie restriction, food restriction, body image disturbance, fear of gaining weight, and an overpowering desire to be thin. Individuals wit ...

edema Edema (American English), also spelled oedema (British English), and also known as fluid retention, swelling, dropsy and hydropsy, is the build-up of fluid in the body's tissue (biology), tissue. Most commonly, the legs or arms are affected. S ...

oliguria Oliguria or hypouresis is the low output of urine specifically more than 80 ml/day but less than 400ml/day. The decreased output of urine may be a sign of dehydration, kidney failure, hypovolemic shock, hyperosmolar Hyperglycemic Nonketotic Syndro ...

urticaria Hives, also known as urticaria, is a kind of skin rash with red or flesh-colored, raised, itchy bumps. Hives may burn or sting. The patches of rash may appear on different body parts, with variable duration from minutes to days, and typically ...

* hypersensitivity *

aplastic anemia Aplastic anemia (AA) is a severe hematologic condition in which the body fails to make blood cells in sufficient numbers. Normally, blood cells are produced in the bone marrow by stem cells that reside there, but patients with aplastic anemia ...

* sore throat * fever * pharyngeal membrane * jaundice enlargement of the liver and spleen * exfoliative dermatitis * gastric or duodenal erosion with perforation or bleeding * adrenal

necrosis Necrosis () is a form of cell injury which results in the premature death of cells in living tissue by autolysis. The term "necrosis" came about in the mid-19th century and is commonly attributed to German pathologist Rudolf Virchow, who i ...

* thrombocytopenic purpura * acute

leukemia Leukemia ( also spelled leukaemia; pronounced ) is a group of blood cancers that usually begin in the bone marrow and produce high numbers of abnormal blood cells. These blood cells are not fully developed and are called ''blasts'' or '' ...

When heated to decomposition this compound emits toxic fumes of

nitrogen oxide Nitrogen oxide may refer to a binary compound of oxygen and nitrogen, or a mixture of such compounds: Charge-neutral *Nitric oxide (NO), nitrogen(II) oxide, or nitrogen monoxide * Nitrogen dioxide (), nitrogen(IV) oxide * Nitrogen trioxide (), o ...

Metabolism

Amidopyrine is metabolized by demethylation and acetylation. Amidopirina metabolites are 4-aminoantipyrine, metilaminoantipirin, rubazonovaya and metilrubazonovaya acid. These acids have a reddish color. At high amidopirine doses, urine can have a reddish brown coloration, due to the presence in the urine of these acid markers.

In popular culture

Hospital Universitario Ramón y Cajal The Hospital Universitario Ramón y Cajal is a public general hospital located in the Valverde neighborhood, in Madrid, Spain, part of the hospital network of the Servicio Madrileño de Salud. It is one of the healthcare institutions associated ...

in Madrid, Spain was built as a center for specialized surgery, a

panacea In Greek mythology and religion, Panacea (Greek ''Πανάκεια'', Panakeia), a goddess of universal remedy, was the daughter of Asclepius and Epione. Mythology Panacea and her four sisters each performed a facet of Apollo's art: * Panac ...

for the ills of the health system in Madrid. Locals hence nicknamed it .

References

Pyrazolones Antipyretics Nonsteroidal anti-inflammatory drugs Dimethylamino compounds {{analgesic-stub