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Open Access Articles- Top Results for 5,6-Methylenedioxy-N-methyl-2-aminoindane

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

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5,6-Methylenedioxy-N-methyl-2-aminoindane
Structural formula of MDMAI
Ball-and-stick model of the MDMAI molecule
Systematic (IUPAC) name
N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
Clinical data
  • Uncontrolled
Oral
Identifiers
132741-82-3 7pxN
None
PubChem CID 125559
ChemSpider 111695 7pxY
Chemical data
Formula C11H13NO2
191.226 g/mol
 14pxN (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

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

References

  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.