MDMAI

Last updated
MDMAI
MDMAI.svg
MDMAI 3D ball.png
Clinical data
Other names5,6-Methylenedioxy-N-methyl-2-aminoindane; MDMAI
Routes of
administration 		Oral
Drug class Serotonin releasing agent; Entactogen
ATC code
  • None
Legal status
Legal status
Identifiers
  • 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
Formula C11H13NO2
Molar mass 191.230 g·mol−1
3D model (JSmol)
  • C3c2cc1OCOc1cc2CC3NC
  • 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 Yes check.svgY
  • Key:KNZKMFXEUONVMF-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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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