para-Methoxymethamphetamine

*para*-Methoxymethamphetamine
Clinical data
Other names	PMMA; p-Methoxymethamphetamine; para-Methoxy-N-methylamphetamine; 4-Methoxy-N-methylamphetamine; 4-MMA; Methyl-MA; 4-PMDA
Drug class	Serotonin–norepinephrine releasing agent; Monoamine oxidase inhibitor
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule 1;
Identifiers
	IUPAC name 1-(4-Methoxyphenyl)-N-methylpropan-2-amine;
CAS Number	22331-70-0 ;
PubChem CID	90766;
ChemSpider	81951;
UNII	037U5SR9KL;
KEGG	C22810 ;
CompTox Dashboard (EPA)	DTXSID30874251 ;
ECHA InfoCard	100.040.818
Chemical and physical data
Formula	C11H17NO
Molar mass	179.263 g·mol−1
3D model (JSmol)	Interactive image; Interactive image;
	SMILES CC(CC1=CC=C(C=C1)OC)NC; ; C1=CC(=CC=C1CC(C)NC)OC;
	InChI InChI=1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3; Key:UGFMBZYKVQSQFX-UHFFFAOYSA-N;
	(verify)

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. 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.^[2] In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.^[3]

PMMA is a serotonin–norepinephrine releasing agent (SNRA)^[4]^[5]^[6]^[7] as well as potent monoamine oxidase inhibitor (MAOI).^[8] 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 at low dosages,^[9]^[10] but at higher dosages side effects and risk of death become similar to those of PMA.^[11]

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).^[12]

^ Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
^ Becker J, Neis P, Röhrich J, Zörntlein S (March 2003). "A fatal paramethoxymethamphetamine intoxication". Legal Medicine. 5. 5 (Suppl 1): S138-41. doi:10.1016/s1344-6223(02)00096-2. PMID 12935573.
^ "Five B.C. deaths linked to lethal chemical PMMA". vancouversun. Vancouver Sun. 10 January 2012.
^ Cite error: The named reference Glennon2017 was invoked but never defined (see the help page).
^ Cite error: The named reference GlennonYoung2011 was invoked but never defined (see the help page).
^ Cite error: The named reference Vekariya2012 was invoked but never defined (see the help page).
^ Cite error: The named reference MatsumotoMaenoKato2014 was invoked but never defined (see the help page).
^ Cite error: The named reference Reyes-ParadaIturriaga-VasquezCassels2019 was invoked but never defined (see the help page).
^ Glennon RA, Young R, Dukat M, Cheng Y (1997). "Initial characterization of PMMA as a discriminative stimulus". Pharmacology, Biochemistry, and Behavior. 57 (1–2): 151–8. doi:10.1016/S0091-3057(96)00306-1. PMID 9164566. S2CID 28758326.
^ Rangisetty JB, Bondarev ML, Chang-Fong J, Young R, Glennon RA (2001). "PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA". Pharmacology, Biochemistry, and Behavior. 69 (1–2): 261–7. doi:10.1016/S0091-3057(01)00530-5. PMID 11420094. S2CID 41953749.
^ Johansen SS, Hansen AC, Müller IB, Lundemose JB, Franzmann MB (2003). "Three fatal cases of PMA and PMMA poisoning in Denmark". Journal of Analytical Toxicology. 27 (4): 253–6. doi:10.1093/jat/27.4.253. PMID 12820749. S2CID 42519181.
^ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

[1] Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.

[2] Becker J, Neis P, Röhrich J, Zörntlein S (March 2003). "A fatal paramethoxymethamphetamine intoxication". Legal Medicine. 5. 5 (Suppl 1): S138-41. doi:10.1016/s1344-6223(02)00096-2. PMID 12935573.

[3] "Five B.C. deaths linked to lethal chemical PMMA". vancouversun. Vancouver Sun. 10 January 2012.

[Glennon2017-4] Cite error: The named reference Glennon2017 was invoked but never defined (see the help page).

[GlennonYoung2011-5] Cite error: The named reference GlennonYoung2011 was invoked but never defined (see the help page).

[Vekariya2012-6] Cite error: The named reference Vekariya2012 was invoked but never defined (see the help page).

[MatsumotoMaenoKato2014-7] Cite error: The named reference MatsumotoMaenoKato2014 was invoked but never defined (see the help page).

[Reyes-ParadaIturriaga-VasquezCassels2019-8] Cite error: The named reference Reyes-ParadaIturriaga-VasquezCassels2019 was invoked but never defined (see the help page).

[9] Glennon RA, Young R, Dukat M, Cheng Y (1997). "Initial characterization of PMMA as a discriminative stimulus". Pharmacology, Biochemistry, and Behavior. 57 (1–2): 151–8. doi:10.1016/S0091-3057(96)00306-1. PMID 9164566. S2CID 28758326.

[10] Rangisetty JB, Bondarev ML, Chang-Fong J, Young R, Glennon RA (2001). "PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA". Pharmacology, Biochemistry, and Behavior. 69 (1–2): 261–7. doi:10.1016/S0091-3057(01)00530-5. PMID 11420094. S2CID 41953749.

[11] Johansen SS, Hansen AC, Müller IB, Lundemose JB, Franzmann MB (2003). "Three fatal cases of PMA and PMMA poisoning in Denmark". Journal of Analytical Toxicology. 27 (4): 253–6. doi:10.1093/jat/27.4.253. PMID 12820749. S2CID 42519181.

[PiHKAL-12] Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

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