MMAI
Chemical compound
- none
- In general: uncontrolled
- 5-Methoxy-6-methyl-2,3-dihydro-1H-inden-2-amine
- 136468-19-4
Y
- 131575
- 116274
- JF10U4I82P
- DTXSID20927886
- Interactive image
- 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][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
- ^ 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
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
alkylamines
