MDMAI

5,6-Methylenedioxy-N-methyl-2-aminoindane
Clinical data
Routes of; administration	Oral
ATC code	none
Legal status
Legal status	Uncontrolled;
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
Chemical and physical data
Formula	C11H13NO2
Molar mass	191.226 g/mol
3D model (Jmol)	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 ;
(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[edit]

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[edit]

^ ^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.

[pmid1979813-1] 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.

[1]

v t e Empathogens/entactogens (category)

Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 4-CAB 4-FA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA 5-Methyl-MDA 6-Methyl-MDA DiFMDA DMMDA DMMDA-2 EIDA MDEA MDMA MDMOH MDOH MMDA MMDA-2 MMDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans and dihidrobenzofurans: 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB Indanes: 5-APDI 5-MAPDI Indole: 6-API Naphtalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT

Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT

Cathinones	3-MMC 4-EMC Brephedrone Butylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone Pentylone

Tryptamines	4-Methyl-αET αET αMT

Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

MDMAI

Chemistry[edit]

References[edit]

Navigation menu

Personal tools

Namespaces

Variants

Views

More

Search

Navigation

Interaction

Tools

Print/export

Languages

Clinical data


Routes of administration	Oral
ATC code	none
Legal status
Legal status	Uncontrolled
Identifiers
IUPAC name N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
CAS Number	132741-82-3^N
PubChem (CID)	125559
ChemSpider	111695^Y
UNII	5N88M9ZTD8^Y
Chemical and physical data
Formula	C₁₁H₁₃NO₂
Molar mass	191.226 g/mol
3D model (Jmol)	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^Y Key:KNZKMFXEUONVMF-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)