en MDMAI

5,6-Methylenedioxy-N-methyl-2-aminoindane
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine;
CAS Number	132741-82-3 ;
PubChem CID	125559;
ChemSpider	111695 ;
UNII	5N88M9ZTD8;
CompTox Dashboard (EPA)	DTXSID20157742 ;
Chemical and physical data
Formula	C11H13NO2
Molar mass	191.230 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C3c2cc1OCOc1cc2CC3NC;
	InChI InChI=1S/C11H13NO2/c1-12-9-2-7-4-10-11(14-6-13-10)5-8(7)3-9/h4-5,9,12H,2-3,6H2,1H3 ; Key:KNZKMFXEUONVMF-UHFFFAOYSA-N ;
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5,6-Methylenedioxy-N-methyl-2-aminoindane (MDMAI), is a drug of the 2-aminoindane group developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in animals and a putative entactogen in humans.^[1]

Chemistry

MDMAI can be thought of as a cyclised analogue of MDMA where the alpha-methyl carbon of the alkylamino side chain has been joined back round to the 6-position of the aromatic ring to form an indane ring system. This changes the core structure of the molecule from phenethylamine to aminoindane, and causes the pharmacological properties of the two compounds to be substantially different.^[1]

References

^ ^a ^b Oberlender R, Nichols DE (1990). "(+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxy-methamphetamine-like behavioral activity". J Pharmacol Exp Ther. 255 (3): 1098–1106. PMID 1979813.

[pmid1979813-1] Oberlender R, Nichols DE (1990). "(+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxy-methamphetamine-like behavioral activity". J Pharmacol Exp Ther. 255 (3): 1098–1106. PMID 1979813.

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