Back 4-Methoxymethamphetamin German Parametoximetanfetamina Spanish 4-methoxymethamfetamine Dutch Пара-Метоксиметамфетамин Russian Para-Metoksi-N-metilamfetamin Serbo-Croatian Para-Metoksi-N-metilamfetamin Serbian Para-Metoxi-N-metylamfetamin Swedish 对甲氧基甲基安非他命 Chinese

Para-Methoxymethamphetamine

para-Methoxymethamphetamine
Clinical data
Other namesPMMA; p-Methoxymethamphetamine; para-Methoxy-N-methylamphetamine; 4-Methoxy-N-methylamphetamine; 4-MMA; Methyl-MA; 4-PMDA
Drug classSerotonin–norepinephrine releasing agent; Monoamine oxidase inhibitor
Legal status
Legal status
Identifiers
  • 1-(4-Methoxyphenyl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.040.818 Edit this at Wikidata
Chemical and physical data
FormulaC11H17NO
Molar mass179.263 g·mol−1
3D model (JSmol)
  • CC(CC1=CC=C(C=C1)OC)NC

  • C1=CC(=CC=C1CC(C)NC)OC
  • 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.[medical citation needed] 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). Shulgin reported that PMMA produces an increase in blood pressure and in heart rate, at doses above 100 mg, but causes no psychoactive effects at these levels.

  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". Vancouver Sun. 10 January 2012.
  4. ^ Cite error: The named reference Glennon2017 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference GlennonYoung2011 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Vekariya2012 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference MatsumotoMaenoKato2014 was invoked but never defined (see the help page).
  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.
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