MMAI

MMAI
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 5-Methoxy-6-methyl-2,3-dihydro-1H-inden-2-amine;
CAS Number	132980-16-6;
PubChem CID	131575;
ChemSpider	116274;
UNII	JF10U4I82P;
Chemical and physical data
Formula	C11H15NO
Molar mass	177.242 g/mol
3D model (Jmol)	Interactive image;
	SMILES Cc1cc2CC(N)Cc2cc1OC ;
	InChI InChI=1S/C11H15NO/c1-7-3-8-4-10(12)5-9(8)6-11(7)13-2/h3,6,10H,4-5,12H2,1-2H3 ; Key:JLESVLCTIOAHPT-UHFFFAOYSA-N ;

5-Methoxy-6-methyl-2-aminoindane (MMAI), is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University.^[1] It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogen effects in humans.^[1]^[2]^[3] It has been sold as a designer drug and research chemical online since 2010.

MMAI has been shown to relieve stress-induced depression in rats more robustly than sertraline,^[4] and as a result it has been suggested that SSRAs like MMAI and 4-MTA could be developed as novel antidepressants with a faster onset of therapeutic action and superior efficacy to current antidepressants such as the selective serotonin reuptake inhibitors (SSRIs).^[5]

References[edit]

^ ^a ^b Marona-Lewicka D, Nichols DE (1994). "Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan". Eur J Pharmacol. 258 (1-2): 1–13. doi:10.1016/0014-2999(94)90051-5. PMID 7925587.
^ Li Q, Murakami I, Stall S, Levy AD, Brownfield MS, Nichols DE, Van de Kar LD (1996). "Neuroendocrine pharmacology of three serotonin releasers: 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (MBDB), 5-methoxy-6-methyl-2-aminoindan (MMAi) and p-methylthioamphetamine (MTA)". J Pharmacol Exp Ther. 279 (3): 1261–1267. PMID 8968349.
^ Rudnick G, Wall SC (1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Mol Pharmacol. 43 (2): 271–276. PMID 8429828.
^ Marona-Lewicka D, Nichols DE (1997). "The Effect of Selective Serotonin Releasing Agents in the Chronic Mild Stress Model of Depression in Rats". Stress. 2 (2): 91–100. doi:10.3109/10253899709014740. PMID 9787258.
^ Neuropharmacology; Silveira, R; Nichols, DE; Reyes-Parada, M (1999). "Effects of 5-HT-releasing agents on the extracellullar hippocampal 5-HT of rats. Implications for the development of novel antidepressants with a short onset of action". Neuropharmacology. 38 (7): 1055–1061. doi:10.1016/S0028-3908(99)00023-4. PMID 10428424.

[pmid7925587-1] Marona-Lewicka D, Nichols DE (1994). "Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan". Eur J Pharmacol. 258 (1-2): 1–13. doi:10.1016/0014-2999(94)90051-5. PMID 7925587.

[pmid8968349-2] Li Q, Murakami I, Stall S, Levy AD, Brownfield MS, Nichols DE, Van de Kar LD (1996). "Neuroendocrine pharmacology of three serotonin releasers: 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (MBDB), 5-methoxy-6-methyl-2-aminoindan (MMAi) and p-methylthioamphetamine (MTA)". J Pharmacol Exp Ther. 279 (3): 1261–1267. PMID 8968349.

[pmid8429828-3] Rudnick G, Wall SC (1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Mol Pharmacol. 43 (2): 271–276. PMID 8429828.

[pmid9787258-4] Marona-Lewicka D, Nichols DE (1997). "The Effect of Selective Serotonin Releasing Agents in the Chronic Mild Stress Model of Depression in Rats". Stress. 2 (2): 91–100. doi:10.3109/10253899709014740. PMID 9787258.

[pmid10428424-5] Neuropharmacology; Silveira, R; Nichols, DE; Reyes-Parada, M (1999). "Effects of 5-HT-releasing agents on the extracellullar hippocampal 5-HT of rats. Implications for the development of novel antidepressants with a short onset of action". Neuropharmacology. 38 (7): 1055–1061. doi:10.1016/S0028-3908(99)00023-4. PMID 10428424.

[1]

[2]

[3]

[4]

[5]

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

MMAI

References[edit]

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Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 5-Methoxy-6-methyl-2,3-dihydro-1H-inden-2-amine
CAS Number	132980-16-6
PubChem CID	131575
ChemSpider	116274
UNII	JF10U4I82P
Chemical and physical data
Formula	C₁₁H₁₅NO
Molar mass	177.242 g/mol
3D model (Jmol)	Interactive image
SMILES Cc1cc2CC(N)Cc2cc1OC
InChI InChI=1S/C11H15NO/c1-7-3-8-4-10(12)5-9(8)6-11(7)13-2/h3,6,10H,4-5,12H2,1-2H3 Key:JLESVLCTIOAHPT-UHFFFAOYSA-N