MDMAI

MDMAI
Structural formula of MDMAI
Ball-and-stick model of the MDMAI molecule
Clinical data
Other names5,6-Methylenedioxy-N-methyl-2-aminoindane; MDMAI
Routes of
administration		Oral
Drug classSerotonin releasing agent; Entactogen
ATC code
  • None
Legal status
Legal status
Identifiers
IUPAC name
  • N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13NO2
Molar mass191.230 g·mol−1
3D model (JSmol)
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 checkY
  • Key:KNZKMFXEUONVMF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 serotonin releasing agent in animals and is a putative entactogen in humans.[1]

Interactions

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. 1 2 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. doi:10.1016/S0022-3565(25)22947-0. PMID 1979813.
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