2-Methyl-MDA

2-Methyl-MDA
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries);
Identifiers
	IUPAC name 1-(4-methyl-1,3-benzodioxol-5-yl)propan-2-amine;
CAS Number	691876-73-0 ; 204916-87-0 (HCl);
PubChem CID	10104064;
ChemSpider	8279591 ;
ChEMBL	ChEMBL6391 ;
CompTox Dashboard (EPA)	DTXSID10435622 ;
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.246 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O2COc1c2ccc(c1C)CC(C)N;
	InChI InChI=1S/C11H15NO2/c1-7(12)5-9-3-4-10-11(8(9)2)14-6-13-10/h3-4,7H,5-6,12H2,1-2H3 ; Key:WVACHJAKQMSYSU-UHFFFAOYSA-N ;
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2-Methyl-3,4-methylenedioxyamphetamine (2-methyl-MDA) is an entactogen-related drug of the amphetamine class. It acts as a selective serotonin releasing agent (SSRA), with IC₅₀ values of 93nM, 12,000nM, and 1,937nM for serotonin, dopamine, and norepinephrine efflux.^[1] 2-Methyl-MDA is more potent than MDA and 5-methyl-MDA.^[1] However, it is slightly more selective for serotonin over dopamine and norepinephrine release in comparison to 5-methyl-MDA.^[1]

References

^ ^a ^b ^c Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE (March 1998). "Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry. 41 (6): 1001–5. CiteSeerX 10.1.1.688.9559. doi:10.1021/jm9705925. PMID 9526575.

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v t e Entactogens
Phenethylamines	Unfused benzene ring: 3-CMA 4-CAB 4-FA 4-MA 4-MMA 4-FMA 4-MTA 4,4'-DMAR Metaescaline MMA PMA PMEA PMMA mMMA Benzodioxines: EDA 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 } Phenylisobutylamines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans: 2-MAPB 5-APB 5-EAPB 5-MAPB 5-MBPB (5-MABB) 6-APB 6-EAPB 6-MAPB 6-MBPB (6-MABB) Dihydrobenzofurans: 5-APDB 5-MAPDB 6-APDB 6-MAPDB IBF5MAP Benzothiophenes: 5-APBT 5-MAPBT 6-APBT 6-MAPBT Indanes: 5-APDI 5-MAPDI Indoles: 5-IT 6-API Naphthalenes: Methamnetamine Naphthylaminopropane Tetralins: 6-APT Cathinones: 3-CMC 3-MMC 4-EMC BK-5-MAPB Brephedrone Butylone Dimethylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Cyclized phenethylamines	Aminoindanes: 5-IAI AMMI BFAI ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Tryptamines	α-Alkyltryptamines: 4-Methyl-αET αET αMT 5-Chloro-αMT 5-Fluoro-AMT β-Ketotryptamines: BK-NM-AMT BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT
See also: Stimulants Psychedelics Phenethylamines Tryptamines