MDMAI

MDMAI
Clinical data
Other names	5,6-Methylenedioxy-N-methyl-2-aminoindane; MDMAI
Drug class	Serotonin releasing agent; Entactogen
ATC code	None;
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine;
CAS Number	132741-82-3 ;
PubChem CID	125559;
ChemSpider	111695 ;
UNII	5N88M9ZTD8;
CompTox Dashboard (EPA)	DTXSID20157742 ;
Chemical and physical data
Formula	C11H13NO2
Molar mass	191.230 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
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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]

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]

References

^ ^a ^b ^c Sainsbury 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.
^ ^a ^b ^c ^d 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. doi:10.1016/S0022-3565(25)22947-0. PMID 1979813.

External links

MDMAI - Isomer Design

[SainsburyKicmanArcher2011-1] Sainsbury 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.

[pmid1979813-2] 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. doi:10.1016/S0022-3565(25)22947-0. PMID 1979813.

[1]

[2]

Interactions

History

Chemistry

See also

References

External links