4T-MMDA-2

Not to be confused with 4C-T-2.

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]

4T-MMDA-2

Clinical data
Other names	4-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
IUPAC name 1-(5-methoxy-1,3-benzoxathiol-6-yl)propan-2-amine
CAS Number	133787-69-6
PubChem CID	44719663
ChemSpider	23553180
UNII	NF243AEE6J
Chemical and physical data
Formula	C11H15NO2S
Molar mass	225.31 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC2=C(C=C1OC)SCO2)N
InChI 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

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