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MDMAI

MDMAI, also known as 5,6-methylenedioxy-N-methyl-2-aminoindane, is a drug of the 2-aminoindane family developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic serotonin releasing agent (SRA) in animals and is a putative entactogen in humans.

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MDMAI
Structural formula of MDMAI
Ball-and-stick model of the MDMAI molecule
Clinical data
Other names5,6-Methylenedioxy-N-methyl-2-aminoindane; MDMAI
Drug classSerotonin 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
FormulaC11H13NO2
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
  • Key:KNZKMFXEUONVMF-UHFFFAOYSA-N checkY
 X markNcheckY (what is this?)  (verify)

MDMAI, also known as 5,6-methylenedioxy-N-methyl-2-aminoindane, is a drug of the 2-aminoindane family developed in the 1990s by a team led by David E. Nichols at Purdue University.12 It acts as a non-neurotoxic serotonin releasing agent (SRA) in animals and is a putative entactogen in humans.12

Interactions

History

MDMAI was first described in the scientific literature by David E. Nichols and colleagues in 1990.12

Chemistry

MDMAI can be thought of as a cyclized analogue of MDMA where the α-methyl group 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 2-aminoindane, and causes the pharmacological properties of the two compounds to be substantially different.2

See also

See also

References

References

  1. Sainsbury PD, Kicman AT, Archer RP, King LA, Braithwaite RA (2011). "Aminoindanes--the next wave of 'legal highs'?". Drug Test Anal. 3 (7–8): 479–482. doi:10.1002/dta.318. PMID 21748859.
  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.
External links