PMMA

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 #130

Dose listed

>100 mg orally WP

Duration listed

“Short” WP

Read entry #130 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-Methoxymethamphetamine (also known as 4-methoxymethamphetamine, 4-MeOMA, inaccurately as "4-MMA" (which should instead be reserved for 4-MMA (4-MeMA) instead) and more commonly as PMMA) is a highly dangerous and toxic synthetic substance of the amphetamine class that is closely related to PMA. Like PMA, it is known for producing extremely dangerous, life-threatening side effects. At lower dosages, its effects are somewhat different from PMA, with reduced tendency to cause severe hyperthermia while producing more entactogenic effects that can be mistaken for MDMA (although at higher dosages it does have the same risk as PMA). Its history of use is unknown, but it has appeared more frequently in the 2000s and 2010s. It is generally less potent than PMA. PW

para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy analogue of methamphetamine.[1][2] WP

Little is known about the pharmacological properties, metabolism, and toxicity 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 (ecstasy) were linked to misrepresented tablets and capsules of PMMA.[3][4] WP

PMMA is a serotonin–norepinephrine releasing agent (SNRA) as well as potent monoamine oxidase inhibitor (MAOI). It has a reduced tendency to produce severe hyperthermia at low doses compared to PMA, but at higher doses, side effects and risk of death become similar to those of PMA.[5–12] WP

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).[1] WP

History

History

PMMA was first described in the scientific literature by at least 1984.[13] WP

Legal status

• In February 2002, the European Council decided that PMMA shall be subjected by the Member States to control measures and criminal penalties within three months.[14] PW
• Austria: PMMA is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich). PW⚠ PsychonautWiki itself has flagged this text: citation needed.
• Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[15] PW
• Canada: PMMA is a Schedule I substance. PW⚠ PsychonautWiki itself has flagged this text: citation needed.
• France: PMMA is scheduled as a "stupéfiant", i.e. a recognized drug of abuse. It is illegal to possess, buy, sell or manufacture.[16] PW
• Germany: PMMA is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of October 10, 2000. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[17][18][19] PW
• Switzerland: PMMA is a controlled substance specifically named under Verzeichnis D.[20] PW
• United Kingdom: PMMA is a Class A drug. PW⚠ PsychonautWiki itself has flagged this text: citation needed.
• United States: PMMA is a Schedule I drug as of July 26th, 2021.[21] PW

United kingdom

PMMA is controlled as a Schedule 1, Class A drug in the UK. WP⚠ Wikipedia itself has flagged this text: citation needed.

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.[21] WP

Pharmacology

Pharmacodynamics

PMMA is a monoamine releasing agent (MRA). The drug's EC₅₀ (half-maximal effective concentration) values for induction of monoamine release in rat brain synaptosomes have been reported for the individual enantiomers of PMMA. In the case of (S)-PMMA, they were 41 nM for serotonin, 147 nM for norepinephrine, and 1,000 nM for dopamine, whereas for (R)-PMMA, they were 134 nM for serotonin, >14,000 nM for norepinephrine, and 1,600 nM for dopamine. Hence, PMMA appears to be a serotonin–norepinephrine releasing agent (SNRA) with weak effects on dopamine release. The drug has been found to strongly release serotonin and to weakly release dopamine in the brain in rodents in vivo.[5–8] WP

In addition to its MRA activity, PMMA is a potent monoamine oxidase A (MAO-A) inhibitor. Its IC₅₀ (half-maximal inhibitory concentration) for MAO-A inhibition has been reported to be 1,700 nM. This is several-fold less potent than the related agents para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA).[9] WP

PMMA is said to lack affinity for the serotonin 5-HT2A receptor. In one study, its affinities were >20,000 nM for the serotonin 5-HT1A receptor, 13,600 nM for the serotonin 5-HT2A receptor, and >13,000 nM for the serotonin 5-HT2C receptor. On the other hand, PMMA shows much higher affinities for the mouse and rat trace amine-associated receptor 1 (TAAR1).[5][22] WP

In rodents, PMMA produces hyperlocomotion, no changes in locomotor activity, and/or catatonia, and has effects that are said to differ from those of amphetamine-like stimulants. It has been said not to have amphetamine-like properties in rodents even at high doses. Similarly, PMMA did not substitute for the psychedelic DOM. On the other hand, in contrast to PMA, PMMA fully substituted for MDMA in drug discrimination tests in rodents, despite not having MDMA-like psychoactive effects in humans. In any case, PMMA is said to lack the amphetamine- or stimulant-like properties of MDMA.[1][2][5][23] WP⚠ A table follows this text in the source and is not copied here. Open the source to see it.

Detection

PMMA can be detected with reagent testing kits. WP⚠ Wikipedia itself has flagged this text: citation needed.

Chemistry

Formula

C11H17NO PC

CAS number

22331-70-0 PC

Molar mass (g/mol)

179.26 PC

IUPAC name (computed by PubChem)

1-(4-methoxyphenyl)-N-methylpropan-2-amine PC

SMILES

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

InChIKey

UGFMBZYKVQSQFX-UHFFFAOYSA-N PC

PubChem CID

90766

Pop culture

No references added yet.

References

1. Other CitePiHKAL
2. Other Shulgin A, Manning T, Daley P. The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 2011
3. Journal / agency Becker J, Neis P, Röhrich J, Zörntlein S. A fatal paramethoxymethamphetamine intoxication. Legal Medicine. March 2003. doi:10.1016/s1344-6223(02)00096-2 · PMID 12935573
4. Other Five B.C. deaths linked to lethal chemical PMMA. 10 January 2012
5. Journal / agency Glennon RA. The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse. J Med Chem. April 2017. doi:10.1021/acs.jmedchem.7b00085 · PMID 28244748 · PMC5824997
6. Journal / agency Glennon RA, Young R. Drug Discrimination. 5 August 2011. doi:10.1002/9781118023150.ch6
7. Journal / agency Vekariya R. Towards Understanding the Mechanism of Action of Abused Cathinones. 2012. doi:10.25772/AR93-7024
8. Journal / agency Matsumoto T, Maeno Y, Kato H, Seko-Nakamura Y, Monma-Ohtaki J, Ishiba A, Nagao M, Aoki Y. 5-hydroxytryptamine- and dopamine-releasing effects of ring-substituted amphetamines on rat brain: a comparative study using in vivo microdialysis. Eur Neuropsychopharmacol. August 2014. doi:10.1016/j.euroneuro.2014.04.009 · PMID 24862256
9. Journal / agency Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK. Amphetamine Derivatives as Monoamine Oxidase Inhibitors. Front Pharmacol. 2019. doi:10.3389/fphar.2019.01590 · PMID 32038257 · PMC6989591
10. Journal / agency Glennon RA, Young R, Dukat M, Cheng Y. Initial characterization of PMMA as a discriminative stimulus. Pharmacology, Biochemistry, and Behavior. 1997. doi:10.1016/S0091-3057(96)00306-1 · PMID 9164566
11. Journal / agency Rangisetty JB, Bondarev ML, Chang-Fong J, Young R, Glennon RA. PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA. Pharmacology, Biochemistry, and Behavior. 2001. doi:10.1016/S0091-3057(01)00530-5 · PMID 11420094
12. Journal / agency Johansen SS, Hansen AC, Müller IB, Lundemose JB, Franzmann MB. Three fatal cases of PMA and PMMA poisoning in Denmark. Journal of Analytical Toxicology. 2003. doi:10.1093/jat/27.4.253 · PMID 12820749
13. Journal / agency Clark, Cc. The Identification of Methoxy- N -Methylamphetamines. Journal of Forensic Sciences. 1 October 1984. doi:10.1520/JFS11772J
14. Other Council Decision concerning control measures and criminal sanctions in respect of the new synthetic drug PMMA. February 28, 2002
15. Other http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
16. Other Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants
17. Other Vierzehnte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften
18. Other Anlage I BtMG
19. Other § 29 BtMG
20. Other Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien
21. Other https://www.federalregister.gov/documents/2021/06/25/2021-13460/schedules-of-controlled-substances-placement-of-para-methoxymethamphetamine-pmma-in-schedule-i
22. Journal / agency Simmler LD, Rickli A, Hoener MC, Liechti ME. Monoamine transporter and receptor interaction profiles of a new series of designer cathinones. Neuropharmacology. April 2014. doi:10.1016/j.neuropharm.2013.11.008 · PMID 24275046
23. Journal / agency Glennon RA. Arylalkylamine drugs of abuse: an overview of drug discrimination studies. Pharmacol Biochem Behav. October 1999. doi:10.1016/s0091-3057(99)00045-3 · PMID 10515299

Text and values on this page are quoted from PsychonautWiki (CC BY-SA 4.0), Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.