Chemistry:4T-MMDA-2

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4T-MMDA-2, also known as 3,4-methylenethiooxy-6-methoxyamphetamine or as 2-methoxy-4,5-methylenethiooxyamphetamine, is a psychoactive drug of the phenethylamine and amphetamine families related to 3,4-methylenedioxyamphetamine (MDA).[1][2][3] It is the analogue of MMDA-2 (6-methoxy-MDA) in which one of the oxygen atoms of the methylenedioxy ring, specifically the 4-position oxygen, has been replaced with a sulfur atom.[1][2][3]

According to Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved), a 4T-MMDA-2 dose of 25 mg orally might be a threshold dose and the active dose is listed as greater than 25 mg.[1][2][3] The effects at this "inactive" dose included possible mild exhiliration and a hint of tremor and teeth clenching 3 hours after administration.[1][3] Higher doses were not explored and the duration is unknown.[1][2][3] For comparison, MMDA-2 has a dose of 25 to 50 mg and a duration of 8 to 12 hours.[1][2][3]

The effects of 4T-MMDA-2 and various analogues on serotonin and dopamine release in rat brain synaptosomes in vitro were studied by Dennis McKenna and Shulgin and colleagues.[4] 4T-MMDA-2 and MMDA-2 showed essentially abolished monoamine release, in contrast to other related drugs like MDA, MDMA, and MMDA (5-methoxy-MDA), suggesting that 4T-MMDA-2 would not have entactogenic or stimulant effects.[4] The chemical synthesis of 4T-MMDA-2 has been described.[1]

4T-MMDA-2 was first described in the scientific literature by Alexander Shulgin and colleagues in PiHKAL and in a journal article by 1991.[1][2][4][3] It was first tested by Shulgin in 1977.[5]

See also

  • Substituted methylenedioxyphenethylamine § Related compounds
  • 2T-MMDA-3a

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml.  https://erowid.org/library/books_online/pihkal/pihkal167.shtml
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 828–829. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. "Two of the methylenedioxyamphetamine compounds have also been similarly modified. The 2-methoxy group of MMDA-3a is replaced with a methylthio group giving 3.4-methylenedioxy-2-methylthioamphetamine, or 2T-MMDA-3a. It is not active at a dosage of 12mg. The second analogue has one of the oxygens of the methylenedioxy group changed to a sulfur. This is 6-(2-aminopropyl)-5-methoxy-l,3-benzoxathiol (4-T-MMDA-2) and it shows no activity at 25mg orally." 
  4. ↑ 4.0 4.1 4.2 "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacol Biochem Behav 38 (3): 505–512. March 1991. doi:10.1016/0091-3057(91)90005-m. PMID 1829838. 
  5. ↑ https://isomerdesign.com/pihkal/notebooks/transcripts/p2/p2.240.pdf



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