| Width | 250px |
|---|---|
| Routes of administration | Oral[1] |
| Class | Psychoactive drug |
| Atc prefix | None |
| Duration of action | Unknown[1] |
| Cas number | 133787-69-6 |
| Pubchem | 44719663 |
| Chemspiderid | 23553180 |
| Unii | NF243AEE6J |
| Synonyms | 4-T-MMDA-2; 3,4-Methyleneoxythio-6-methoxyamphetamine; 2-Methoxy-4,5-methylenethiooxyamphetamine; 6-(2-Aminopropyl)-5-methoxy-1,3-benzoxathiol; 4,5-Thiomethyleneoxy-2-methoxyamphetamine; 4-Thio-MMDA-2 |
| Iupac name | 1-(5-methoxy-1,3-benzoxathiol-6-yl)propan-2-amine |
| C | 11 |
| H | 15 |
| N | 1 |
| O | 2 |
| S | 1 |
| Smiles | CC(CC1=CC2=C(C=C1OC)SCO2)N |
| Stdinchi | 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 |
| Stdinchikey | NCUQXFZYILOELC-UHFFFAOYSA-N |
4T-MMDA-2, also known as 3,4-methyleneoxythio-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
- SDA (3T-MDA) and SDMA (3T-MDMA)
References
- ^ https://erowid.org/library/books_online/pihkal/pihkal167.shtml
- ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function] (in German). Nachtschatten-Science. 1 ed. Solothurn: Nachtschatten-Verlag. pp. 828–829. ISBN 978-3-03788-700-4. OCLC 858805226. Archived 21 August 2025 at the Wayback Machine.
- ^ Shulgin AT (2003). "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived 13 July 2025 at the Wayback Machine.
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.
- ^ 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
- ^ "4-thio-MMDA-2"