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MMAI

Chemical compound

Field	Value
image	MMAI-2D-skeletal.svg
image_class	skin-invert-image
width	225px
class	Selective serotonin releasing agent; Entactogen
ATC_prefix	None
legal_status	Uncontrolled
CAS_number_Ref
CAS_number	136468-19-4
PubChem	131575
ChemSpiderID	116274
UNII_Ref
UNII	JF10U4I82P
synonyms	MMAI; MMAi; 5-Methoxy-6-methyl-2-aminoindan
IUPAC_name	5-Methoxy-6-methyl-2,3-dihydro-1H-inden-2-amine
C	11	H = 15	N = 1	O = 1
SMILES	Cc1cc2CC(N)Cc2cc1OC
StdInChI	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
StdInChIKey	JLESVLCTIOAHPT-UHFFFAOYSA-N

| elimination_half-life =

5-Methoxy-6-methyl-2-aminoindane (MMAI) is a drug of the 2-aminoindane family developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a less neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogenic effects in humans. The drug has been sold as a designer drug and research chemical online since 2010.

Interactions

Pharmacology

Pharmacodynamics

The drug is one of the only known monoamine releasing agents (MRAs) with greater than 100-fold selectivity for the serotonin transporter (SERT) over the dopamine transporter (DAT). Receptor interaction data for MMAI have also been reported.

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

MMAI alone does not appear to produce serotonergic neurotoxicity with either acute or chronic administration in animals. However, subsequent research found that a single high dose of MMAI could produce significant serotonergic neurotoxicity. In addition, combination of MMAI with the dopamine releasing agent dextroamphetamine has been found to produce dose-dependent serotonergic neurotoxicity in animals. Hence, MMAI is not a fully non-neurotoxic MDMA analogue.

Compound	Monoamine release (, nM)		rowspan="2"	Ref	Serotonin	Norepinephrine	Dopamine
2-AI	10,000	86	439
MDAI	114	117	1,334
MMAI	31	3,101	10,000
MEAI	134	861	2,646
d-Amphetamine	698–1,765	6.6–7.2	5.8–24.8	vauthors = Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW	title = Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products	journal = Neuropsychopharmacology	volume = 38	issue = 4	pages = 552–562	date = March 2013	pmid = 23072836	pmc = 3572453	doi = 10.1038/npp.2012.204 }}
MDA	160–162	47–108	106–190
MDMA	50–85	54–110	51–278	vauthors = Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS	title = Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin	journal = Synapse	volume = 39	issue = 1	pages = 32–41	date = January 2001	pmid = 11071707	doi = 10.1002/1098-2396(20010101)39:13.0.CO;2-3	s2cid = 15573624 }}
3-MA	ND	58.0	103
Notes: The smaller the value, the more strongly the compound produces the effect. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs:

Chemistry

MMAI is the 2-aminoindane analogue of 3-methoxy-4-methylamphetamine (MMA).

References

(June 1994). "Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan". European Journal of Pharmacology.
(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.
(February 1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Molecular Pharmacology.
(May 2018). "Pharmacological profile of mephedrone analogs and related new psychoactive substances". Neuropharmacology.
(September 2021). "Molecular and clinical aspects of potential neurotoxicity induced by new psychoactive stimulants and psychedelics". Exp Neurol.
(May 2018). "Pharmacological profile of mephedrone analogs and related new psychoactive substances". Neuropharmacology.
(December 1997). "The Effect of Selective Serotonin Releasing Agents in the Chronic Mild Stress Model of Depression in Rats". Stress.
(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.
(July 1991). "Combined administration of a non-neurotoxic 3,4-methylenedioxymethamphetamine analogue with amphetamine produces serotonin neurotoxicity in rats". Neuropharmacology.
(July 1991). "[3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues". Eur J Pharmacol.
(March 2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology.
(July 2008). "Dopamine Transporters: Chemistry, Biology and Pharmacology". Wiley.
(2017). "Neuropharmacology of New Psychoactive Substances (NPS)".
(1999). "Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc".
(January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse.
(April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology.
(February 2016). "The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue". Neuropharmacology.
(June 2003). "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". Molecular Pharmacology.
(December 2020). "The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats". Psychopharmacology (Berl).
(March 2019). "2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors". Psychopharmacology (Berl).
(1993). "Novel serotonergic agents". Drug des Discov.

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2-aminoindanes david-e.-nichols designer-drugs entactogens methoxyphenethylamines monoaminergic-neurotoxins phenol-ethers serotonin-releasing-agents

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