''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 and psychedelic drug closely related to the amphetamine-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 a ...

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. 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 c ...

, 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 subs ...

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 form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for recreational purposes. The desire ...

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 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 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 effects at these levels.

Recreational use

PMMA has been found in tablets and capsules of the

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 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 a ...

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 Bosk ...

. 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 Ireland. On a bay at the mouth of the River Liffey, it is in the province of Leinster, bordered on the south by the Dublin Mountains, a part of the Wicklow Mountains range. At the 2016 c ...

, 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, ...

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.

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