MMAI

5-Methoxy-6-methyl-2-aminoindane (MMAI) is a drug of the 2-aminoindane group developed in the 1990s by a team led by David E. Nichols at Purdue University.^[1] It acts as a less neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogenic effects in humans.^[1][2][3][4] It has been sold as a designer drug and research chemical online since 2010.

MMAI

Clinical data
Other names	MMAI; MMAi; 5-Methoxy-6-methyl-2-aminoindan
Routes of administration	By mouth
Drug class	Selective serotonin releasing agent; Entactogen
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

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).^[5] Receptor interaction data for MMAI have also been reported.^[6][7]

MMAI has been shown to relieve stress-induced depression in rats more robustly than sertraline,^[8] 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).^[9]

MMAI alone does not appear to produce serotonergic neurotoxicity with either acute or chronic administration in animals.^[10][11] However, subsequent research found that a single high dose of MMAI could produce significant serotonergic neurotoxicity.^[10][11] In addition, combination of MMAI with the dopamine releasing agent dextroamphetamine has been found to produce dose-dependent serotonergic neurotoxicity in animals.^[10] Hence, MMAI is not a fully non-neurotoxic MDMA analogue.^[10][11]

MMAI is the 2-aminoindane analogue of 3-methoxy-4-methylamphetamine (MMA).^[12][3]

Activities of 2-aminoindanes and amphetamine relatives

Compound	Monoamine release (EC50Tooltip half-maximal effective concentration, nM)			Ref
	Serotonin	Norepinephrine	Dopamine
2-AI	>10,000	86	439	[6]
MDAI	114	117	1,334	[6]
MMAI	31	3,101	>10,000	[6]
MEAI	134	861	2,646	[6]
d-Amphetamine	698–1,765	6.6–7.2	5.8–24.8	[13][14][15][16][17]
MDA	160–162	47–108	106–190	[18][15][19]
MDMA	50–85	54–110	51–278	[13][20][21][18][19]
3-MA	ND	58.0	103	[15]
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: [6]