5,6-Methylenedioxy-N-methyl-2-aminoindane

5,6-Methylenedioxy-N-methyl-2-aminoindane

Systematic (IUPAC) name
N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled
Routes	Oral
Identifiers
CAS number	132741-82-3
ATC code	None
PubChem	CID 125559
ChemSpider	111695 Y
Chemical data
Formula	C11H13NO2
Mol. mass	191.226 g/mol
SMILES	eMolecules & PubChem
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 Y Key:KNZKMFXEUONVMF-UHFFFAOYSA-N Y
Y (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]

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.^[1]

See also

• MDAI
• MMAI
• MDAT

References