4T-MMDA-2

Last updated
4T-MMDA-2
4T-MMDA-2 structure.png
Clinical data
Other names4-T-MMDA-2; 2-Methoxy-4,5-methylenethiooxyamphetamine; 6-(2-Aminopropyl)-5-methoxy-1,3-benzoxathiol; 4,5-Thiomethyleneoxy-2-methoxyamphetamine; 4-Thio-MMDA-2
Routes of
administration 		Oral [1]
Drug class Psychoactive drug
ATC code
  • None
Pharmacokinetic data
Duration of action Unknown [1]
Identifiers
  • 1-(5-methoxy-1,3-benzoxathiol-6-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C11H15NO2S
Molar mass 225.31 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1OC)SCO2)N
  • InChI=1S/C11H15NO2S/c1-7(12)3-8-4-10-11(15-6-14-10)5-9(8)13-2/h4-5,7H,3,6,12H2,1-2H3
  • Key:NCUQXFZYILOELC-UHFFFAOYSA-N

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]

Contents

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

References

  1. 1 2 3 4 5 6 7 8 9 10 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. https://erowid.org/library/books_online/pihkal/pihkal167.shtml
  2. 1 2 3 4 5 6 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 828–829. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  3. 1 2 3 4 5 6 7 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN   978-0-12-433951-4. Archived from the original on 13 July 2025. 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. 1 2 3 McKenna DJ, Guan XM, Shulgin AT (March 1991). "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. 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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