This article relies largely or entirely on a single source. Relevant discussion may be found on the talk page. Please help improve this article by introducing citations to additional sources.Find sources: "MDMAI" – news · newspapers · books · scholar · JSTOR (October 2014)
Structural formula of MDMAI
Ball-and-stick model of the MDMAI molecule
Clinical data
Routes of
ATC code
  • none
Legal status
Legal status
  • N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
Molar mass191.230 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 checkY
 ☒NcheckY (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]


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]


  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.