MDMAI

5,6-Methylenedioxy-N-methyl-2-aminoindane

Systematic (IUPAC) name
N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
Clinical data
Routes of administration	Oral
Legal status	Uncontrolled
Identifiers
CAS Number	132741-82-3
ATC code	none
PubChem	CID 125559
ChemSpider	111695
UNII	5N88M9ZTD8
Chemical data
Formula	C11H13NO2
Molar mass	191.226 g/mol
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 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]

See also

• MDAI
• MMAI
• MDAT
• NM-2-AI

References

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.