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MDMAI

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
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
 ☒NcheckY (what is this?)  (verify)

MDMAI, also known as5,6-methylenedioxy-N-methyl-2-aminoindane, is adrug of the2-aminoindane family developed in the 1990s by a team led byDavid E. Nichols atPurdue University.[1][2] It acts as a non-neurotoxicserotonin releasing agent (SRA) in animals and is a putativeentactogen in humans.[1][2]

Interactions

[edit]
See also:MDMA § Interactions

History

[edit]

MDMAI was first described in thescientific literature byDavid E. Nichols and colleagues in 1990.[1][2]

Chemistry

[edit]

MDMAI can be thought of as acyclizedanalogue ofMDMA 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 anindane ring system. This changes the core structure of the molecule fromphenethylamine to2-aminoindane, and causes the pharmacological properties of the two compounds to be substantially different.[2]

See also

[edit]

References

[edit]
  1. ^abcSainsbury 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. ^abcdOberlender 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

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