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Methylenedioxymethylaminoindane: Wikis

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5,6-Methylenedioxy-N-methyl-2-aminoindane
Systematic (IUPAC) name
N-methyl-6,7-dihydro-5H-cyclopenta[ f][1,3]benzodioxol-6-amine
Identifiers
CAS number 132741-82-3
ATC code  ?
PubChem 125559
Chemical data
Formula C 11H13NO2  
Mol. mass 191.226 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status legal
Routes  ?

5,6-Methylenedioxy-N-methyl-2-aminoindane (MDMAI), is a drug and research chemical 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 empathogen in humans.[1] It is closely related to MDAI, MMAI, and MDAT.

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]

References

  1. ^ a b 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.  
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5,6-Methylenedioxy-N-methyl-2-aminoindane
Systematic (IUPAC) name
N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
Identifiers
CAS number 132741-82-3
ATC code None
PubChem CID 125559
ChemSpider 111695
Chemical data
Formula C11H13NO2 
Mol. mass 191.226 g/mol
SMILES eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Oral

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

References

  1. ^ a b Oberlender R, Nichols DE. (1990). [Expression error: Unexpected < operator "(+)-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. 

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