MDMAT

MDMAT
Clinical data
ATC code	none;
Legal status
Legal status	US: Uncontrolled; May fall under the Federal Analogue Act;
Identifiers
	IUPAC name N-Methyl-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxol-6-amine;
CAS Number	34620-52-5 ;
PubChem CID	23324601;
ChemSpider	14921388 ;
UNII	JV4FSP6YL3;
CompTox Dashboard (EPA)	DTXSID80632929 ;
Chemical and physical data
Formula	C12H15NO2
Molar mass	205.257 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C3c1cc2OCOc2cc1CCC3NC;
	InChI InChI=1S/C12H15NO2/c1-13-10-3-2-8-5-11-12(15-7-14-11)6-9(8)4-10/h5-6,10,13H,2-4,7H2,1H3 ; Key:MTRLJTZQUZHTJI-UHFFFAOYSA-N ;
	(what is this?) (verify)

MDMAT (6,7-methylenedioxy-N-methyl-2-aminotetralin) is a selective serotonin releasing agent (SSRA) and entactogen drug. It is the N-methylated derivative of MDAT, similarly to the relationship of MDMA to MDA.^[2]^[3] It has been theorized to have less long-term neurotoxicity and less hallucinogenic effects than other MDxx derivatives,^[4] but no formal scientific research has been conducted specifically on MDMAT.

There is a lack of research on MDMAT in general, with much of the research and citation in literature being in reference to the wider pharmalogical/chemical class as a whole.

Chemistry

MDMAT is a substituted methylenedioxyphenethylamine, having structural similarities to MDMA and MDA.

References

^ "Controlled Substances - Alphabetical Order -" (PDF). Controlled Substances - Alphabetical Order - DEA Diversion Control Division. US Drug Enforcement Agency. Retrieved Aug 17, 2024.
^ Violland R, Violland-Duperret N, Pacheco H, Trouiller G, Lebland A (1971). "Potential psychotropic compounds. VIII. Synthesis and pharmacological activity of 2-aminotetralins related to psychomimetics". Chimica Therapeutica. 6 (3): 196.
^ Malmusi L, Dukat M, Young R, Teitler M, Darmani NA, Ahmad B, et al. (January 1996). "1,2,3,4-Tetrahydroisoquinoline and related analogs of the phenylalkylamine designer drug MDMA". Medicinal Chemistry Research. 6 (6): 412–26m.
^ Nichols DE, Brewster WK, Johnson MP, Oberlender R, Riggs RM (February 1990). "Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry. 33 (2): 703–710. doi:10.1021/jm00164a037. PMID 1967651.

[1] "Controlled Substances - Alphabetical Order -" (PDF). Controlled Substances - Alphabetical Order - DEA Diversion Control Division. US Drug Enforcement Agency. Retrieved Aug 17, 2024.

[2] Violland R, Violland-Duperret N, Pacheco H, Trouiller G, Lebland A (1971). "Potential psychotropic compounds. VIII. Synthesis and pharmacological activity of 2-aminotetralins related to psychomimetics". Chimica Therapeutica. 6 (3): 196.

[3] Malmusi L, Dukat M, Young R, Teitler M, Darmani NA, Ahmad B, et al. (January 1996). "1,2,3,4-Tetrahydroisoquinoline and related analogs of the phenylalkylamine designer drug MDMA". Medicinal Chemistry Research. 6 (6): 412–26m.

[4] Nichols DE, Brewster WK, Johnson MP, Oberlender R, Riggs RM (February 1990). "Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry. 33 (2): 703–710. doi:10.1021/jm00164a037. PMID 1967651.

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v t e Empathogens/entactogens
Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 3-CMA 4-CAB 4-FA 4-MA 4-MMA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA mMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA DMMDA DMMDA-2 EIDA Lys-MDA MDEA MDMA (midomafetamine) (R)-MDMA MDMOH MDOH MMDA MMDA-2 MMDMA N-t-BOC-MDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MAPBT 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB IBF5MAP Indanes: 5-APDI 5-MAPDI Indoles: 5-IT 6-API Naphthalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI BFAI ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-CMC 3-MMC 4-EMC BK-5-MAPB Brephedrone Butylone Dimethylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

Chemistry

See also

References