Jump to content

Main menu Navigation ●Main page ●Contents ●Current events ●Random article ●About Wikipedia ●Contact us ●Donate Contribute ●Help ●Learn to edit ●Community portal ●Recent changes ●Upload file

●Create account ●Log in ●Create account ● Log in Pages for logged out editors learn more ●Contributions ●Talk

(Top) 1 References

MMAI

●日本語 ●Српски / srpski ●Srpskohrvatski / српскохрватски Edit links ●Article ●Talk ●Read ●Edit ●View history Tools Actions ●Read ●Edit ●View history General ●What links here ●Related changes ●Upload file ●Special pages ●Permanent link ●Page information ●Cite this page ●Get shortened URL ●Download QR code ●Wikidata item Print/export ●Download as PDF ●Printable version Appearance From Wikipedia, the free encyclopedia

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	136468-19-4^Y
PubChem CID	131575
ChemSpider	116274
UNII	JF10U4I82P
CompTox Dashboard (EPA)	DTXSID20927886
Chemical and physical data
Formula	C₁₁H₁₅NO
Molar mass	177.247 g·mol⁻¹
3D model (JSmol)	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. NicholsatPurdue University.^[1] It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogen effects in humans.^[1]^[2]^[3]^[4] 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,^[5] 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).^[6]

References[edit]

^ ^a ^b Marona-Lewicka D, Nichols DE (June 1994). "Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan". European Journal of Pharmacology. 258 (1–2): 1–13. CiteSeerX 10.1.1.688.1895. 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 (December 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)". The Journal of Pharmacology and Experimental Therapeutics. 279 (3): 1261–1267. PMID 8968349.

^ Rudnick G, Wall SC (February 1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Molecular Pharmacology. 43 (2): 271–276. PMID 8429828.

^ Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME (May 2018). "Pharmacological profile of mephedrone analogs and related new psychoactive substances" (PDF). Neuropharmacology. 134 (Pt A): 4–12. doi:10.1016/j.neuropharm.2017.07.026. PMID 28755886. S2CID 28786127.

^ Marona-Lewicka D, Nichols DE (December 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.

^ Scorza C, Silveira R, Nichols DE, Reyes-Parada M (July 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. S2CID 13714807.

v t e Empathogens/entactogens
Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 3-CMA 4-CAB 4-FA 4-MA 4-MMA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA mMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA DMMDA DMMDA-2 EIDA Lys-MDA MDEA MDMA (midomafetamine) MDMOH MDOH MMDA MMDA-2 MMDMA N-t-BOC-MDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MAPBT 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB IBF5MAP Indanes: 5-APDI 5-MAPDI Indoles: 5-IT 6-API Naphthalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI BFAI ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-MMC 4-EMC BK-5-MAPB Brephedrone Butylone Dimethylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine