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MDMAI

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(Redirected from 5,6-Methylenedioxy-N-methyl-2-aminoindane) Chemical compound
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Find sources: "MDMAI" – news · newspapers · books · scholar · JSTOR (October 2014)
Pharmaceutical compound
5,6-Methylenedioxy-N-methyl-2-aminoindane
Structural formula of MDMAI
Ball-and-stick model of the MDMAI molecule
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • N-methyl-6,7-dihydro-5H-cyclopentabenzodioxol-6-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13NO2
Molar mass191.230 g·mol
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
  • Key:KNZKMFXEUONVMF-UHFFFAOYSA-N
  (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 and highly selective serotonin releasing agent (SSRA) in animals and a putative entactogen in humans.

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.

References

  1. ^ 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.
Empathogens/entactogens
Phenylalkyl-
amines

(other than
cathinones)
Cyclized phenyl-
alkylamines
Cathinones
Tryptamines
Chemical classes
Monoamine releasing agents
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
See also: Receptor/signaling modulatorsMonoamine reuptake inhibitorsAdrenergicsDopaminergicsSerotonergicsMonoamine metabolism modulatorsMonoamine neurotoxins
Categories:
MDMAI Add topic