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

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5,6-Methylenedioxy-N-methyl-2-aminoindane
MDMAI.svg
Systematic (IUPAC) name
N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
Clinical data
Legal status Uncontrolled
Routes Oral
Identifiers
CAS number 132741-82-3 N
ATC code None
PubChem CID 125559
ChemSpider 111695 YesY
Chemical data
Formula C11H13NO2 
Mol. mass 191.226 g/mol
 N (what is this?)  (verify)

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[edit]

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[edit]

References[edit]

  1. ^ 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.