MDMAT - Misplaced Pages

(Redirected from 6,7-methylenedioxy-N-methyl-2-aminotetralin) Selective serotonin releasing agent and psychoactive drug

Pharmaceutical compound

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-tetrahydrobenzobenzodioxol-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
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
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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. It has been theorized to have less long-term neurotoxicity and less hallucinogenic effects than other MDxx derivatives, 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.

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

Monoamine releasing agents

DRAsTooltip Dopamine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP MDBZP MeOPP oMPP
Others: 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine

NRAsTooltip Norepinephrine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) Iofetamine (123I) Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine Selegiline (also D-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP
Others: 2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine Tuaminoheptane

SRAsTooltip Serotonin releasing agents

Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI
Aminotetralins: 6-CAT 8-OH-DPAT MDAT MDMAT
Oxazolines: 4-Methylaminorex Aminorex Clominorex Fluminorex
Phenethylamines: 2-Methyl-MDA 4-CAB 4-FA 4-FMA 4-HA 4-MTA 5-APDB 5-Methyl-MDA 6-APDB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP Iofetamine Levofenfluramine Lophophine MBDB MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA TAP
Piperazines: 2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP
Tryptamines: 4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine
Others: Indeloxazine Viqualine

Others

DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041

Adrenergic release blockers: Bethanidine
Bretylium
Guanadrel
Guanazodine
Guanethidine
Guanoxan

See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

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