PMA

Effects

Shulgin notes

These figures come from the Shulgins' own small trials, published decades ago. They are history, not a dosing guide: they were never checked the way a harm reduction dose table is, and batches, purity and people differ.

Book

PiHKAL (1991), entry #97

Dose listed

50–80 mg orally WP

Duration listed

“Short” WP

In Shulgin's words

Wikipedia's article on this compound, quoting Shulgin.

According to Alexander Shulgin in PiHKAL (Phenethylamines I Have Known and Loved), the effects of PMA at doses of 50 to 80 mg orally included hypertension, diethyltryptamine (DET)-reminiscent effects, distinct after-images, and some paresthesia, "intoxication" or alcohol-like intoxication, and no psychedelic effects. WP

Read entry #97 in Erowid's online library

From PiHKAL and TiHKAL by Alexander and Ann Shulgin, as tabulated in Wikipedia's articles on the books (CC BY-SA 4.0). The books' text belongs to the Shulgins, so only the listed figures and a link are given here. Synthesis details are never shown on this site.

Overview

para-Methoxyamphetamine (also known as 4-methoxyamphetamine, 4-MeOA, inaccurately as 4-MA (which should be reserved for 4-MA (4-MeA) instead) and more commonly as PMA) is a potent hallucinogen substance of the amphetamine class. PMA belongs to a family of substances known as the substituted amphetamines. However, unlike other substituted amphetamines, PMA does not produce stimulant or entactogen effects, nor euphoria. It is not taken on its own but is instead found as an ingredient in tablets of "Ecstasy" as a false substitute for MDMA. PW

An empathogen with a slow onset and very strong serotonin release. This, combined with its lack of dopamine release, often leads users to dose more for the pleasurable effects which never come, leading to hospitalisations and deaths. Sometimes mis-sold as MDMA. TS

para-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogenic effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.[1–7] WP

PMA has been found in black market tablets sold as MDMA (ecstasy) although its effects are markedly different compared to those of MDMA. The consequences of such deception have often included hospitalization and death for unwitting users. PMA is commonly synthesized from anethole, the essential oil of anise and fennel, mainly because the starting material for MDMA and MDA, safrole (a major component of the essential oil of sassafras), has become less available due to increasing government controls, causing illicit drug manufacturers to make PMA as an alternative.[8–12] WP

History

History

PMA was first described in the scientific literature by T. Patrick and colleagues by 1946. It first came into circulation as a recreational drug in the early 1970s, where it was used intentionally as a substitute for the psychedelic drug LSD. The drug went by the street names of "Chicken Powder" and "Chicken Yellow" and was found to be the cause of a number of drug overdose deaths (the doses taken being in the range of hundreds of milligrams) in the United States and Canada from that time. Between 1974 and the mid-1990s, there appear to have been no known fatalities from PMA.[1][2][13][14] WP

Several deaths reported as MDMA-induced in Australia in the mid-1990s are now considered to have been caused by PMA, the users unaware that they were ingesting PMA and not MDMA as they had intended. There have been a number of PMA-induced deaths around the world since then.[11][15][16] WP

In July 2013, seven deaths in Scotland were linked to tablets containing PMA that had been mis-sold as ecstasy and which had the Rolex crown logo on them. Several deaths in Northern Ireland, Particularly East Belfast, were also linked to "Green Rolex" pills during that month.[9][17] WP

In 2014, 2015, and early 2016, PMA sold as ecstasy was the cause of more deaths in the United States, United Kingdom, Netherlands, and Argentina. The pills containing the drug were reported to be red triangular tablets with a "Superman" logo.[10][18][19][20] WP

The Red Ferarri pills are a new press of the Superman logo tablets that were reported to be found in Germany and Norway from 2016 to 2017.[21] WP

Legal status

• Internationally, PMA is a Schedule I substance under the Convention on Psychotropic Substances.[22] PW
• Austria: PMA is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich) |[23] PW
• Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[24] PW
• Canada: PMA is a Schedule I substance.[25] PW
• France: PMA is scheduled as a "stupéfiant", i.e. a recognized drug of abuse. It is illegal to possess, buy, sell or manufacture.[26] PW
• Germany: PMA is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of September 1, 1984. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[27][28][29] PW
• Russia: PMA is classed as a Schedule I substance.[30] PW
• Switzerland: PMA is a controlled substance specifically named under Verzeichnis D.[31] PW
• United Kingdom: PMA is a Class A drug. PW⚠ PsychonautWiki itself has flagged this text: citation needed.
• United States: PMA is a Schedule I substance.[32] PW

International

PMA is a Schedule I drug under the Convention on Psychotropic Substances.[22] WP

Australia

PMA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[33] WP

Canada

PMA is a Schedule I controlled substance in Canada.[34] WP

Finland

Substance is scheduled in decree of the substances, preparations and plants considered to be narcotic drugs.[35][36] WP

Germany

PMA is part of the Appendix 1 of the Betäubungsmittelgesetz. Therefore, owning and distribution of PMA is illegal. WP

Netherlands

On 13 June 2012 Edith Schippers, Dutch Minister of Health, Welfare and Sport, revoked the legality of PMA in the Netherlands after five deaths were reported in that year.[37] WP

United kingdom

PMA is a Class A drug in the UK.[38] WP

United states

PMA is classified as a Schedule I hallucinogen under the Controlled Substances Act in the United States.[39] WP

Distribution

Because PMA is given out through the same venues and distribution channels that MDMA tablets are, the risk of being severely injured, hospitalized or even dying from use of ecstasy increases significantly when a batch of ecstasy pills containing PMA starts to be sold in a particular area. PMA pills could be a variety of colours or imprints, and there is no way of knowing just from the appearance of a pill what drug(s) it might contain. Notable batches of pills containing PMA have included Louis Vuitton, Mitsubishi Turbo, Blue Transformers, Red/Blue Mitsubishi and Yellow Euro pills. Also PMA has been found in powder form.[40–44] WP

Analogues

Four analogues of PMA have been reported to be sold on the black market, including PMMA, PMEA, 4-ETA and 4-MTA. These are the N-methyl, N-ethyl, 4-ethoxy and 4-methylthio analogues of PMA, respectively. PMMA and PMEA are anecdotally weaker, more "ecstasy-like" and somewhat less dangerous than PMA itself, but can still produce nausea and hyperthermia similar to that produced by PMA, albeit at slightly higher doses. 4-EtOA was briefly sold in Canada in the 1970s, but little is known about it. 4-MTA, however, is even more dangerous than PMA and produces strong serotonergic effects and intense hyperthermia, but with little to no euphoria, and was implicated in several deaths in the late 1990s.[2][45] WP

Drug test false positives

PMA is formed as a metabolite by mebeverine and can result in false positives on drug tests for "ecstasy".[46] WP

Pharmacology

Actions

PMA acts as a selective serotonin releasing agent (SSRA) with weak effects on dopamine and norepinephrine transporters. Its EC₅₀ (half-maximal effective concentration) values for induction of monoamine release are 166 nM for dopamine and 867 nM for norepinephrine in rat brain synaptosomes, whereas serotonin was not reported. The drug has been found to robustly increase brain serotonin levels and to weakly increase brain dopamine levels in rodents in vivo. Relative to MDMA, PMA appears to be considerably less effective as a releaser of serotonin, with properties more akin to a serotonin reuptake inhibitor in comparison.[47–54] WP

PMA has also been shown to act as a potent monoamine oxidase inhibitor (MAOI), specifically as a reversible inhibitor of the enzyme monoamine oxidase A (MAO-A) with no significant effects on monoamine oxidase B (MAO-B). The IC₅₀ (half-maximal inhibitory concentration) of PMA for MAO-A inhibition has been reported to be 300 to 600 nM.[55][56][57] WP

PMA shows very low affinities for the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors. Its affinities (Kᵢ) for these receptors have been reported to be >20,000 nM, 11,200 nM, and >13,000 nM, respectively. In another earlier study, PMA similarly showed very weak affinity for serotonin receptors, including the serotonin 5-HT₁ and 5-HT₂ receptors (Kᵢ = 79,400 nM and 33,600 nM, respectively). On the other hand, PMA shows much higher affinities for the mouse and rat trace amine-associated receptor 1 (TAAR1).[50][58][59] WP

Chemistry

Formula

C10H15NO PC

CAS number

64-13-1 PC

Molar mass (g/mol)

165.23 PC

IUPAC name (computed by PubChem)

1-(4-methoxyphenyl)propan-2-amine PC

SMILES

CC(CC1=CC=C(C=C1)OC)N PC

InChIKey

NEGYEDYHPHMHGK-UHFFFAOYSA-N PC

PubChem CID

31721

Pop culture

No references added yet.

References

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