MDMAI

Chemical compound From Wikipedia, the free encyclopedia

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.[1][2] It acts as a non-neurotoxic serotonin releasing agent (SRA) in animals and is a putative entactogen in humans.[1][2]

Other names5,6-Methylenedioxy-N-methyl-2-aminoindane; MDMAI
ATC code
  • None
Legal status
Quick facts Clinical data, Other names ...
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
 ☒NcheckY (what is this?)  (verify)
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Interactions

History

MDMAI was first described in the scientific literature by David E. Nichols and colleagues in 1990.[1][2]

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

References

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