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NM-2-AI
Clinical data
Other names	N-Methyl-2-aminoindane; N-Methyl-2-AI; N-Methyl-AI; AM-80; Methaminoindan; Methoaminoindane
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name N-Methyl-2,3-dihydro-1H-inden-2-amine;
CAS Number	24445-44-1; HCl: 10408-85-2;
PubChem CID	15023225;
ChemSpider	13566342;
UNII	ZLW84Y27HG;
ChEMBL	ChEMBL1188235;
CompTox Dashboard (EPA)	DTXSID901010100 ;
Chemical and physical data
Formula	C10H13N
Molar mass	147.221 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNC2CC1=CC=CC=C1C2;
	InChI InChI=1S/C10H13N/c1-11-10-6-8-4-2-3-5-9(8)7-10/h2-5,10-11H,6-7H2,1H3; Key:SXWZQUCTTOBHJT-UHFFFAOYSA-N;

NM-2-AI, also known as N-methyl-2-aminoindane, is a drug of the 2-aminoindane group that has been sold online as a designer drug. It is a rigid analogue of methamphetamine.^[1]^[2] NM-2-AI acts as a selective norepinephrine releasing agent, but also has affinity for several monoamine receptors.^[3]^[4]

Pharmacology

Pharmacodynamics

NM-2-AI acts as a highly selective norepinephrine reuptake inhibitor and releasing agent in vitro and does not release serotonin or dopamine even at very high concentrations (100 μM).^[3]

NM-2AI has high affinity (2.4 μM IC₅₀) as a norepinephrine reuptake inhibitor but also has affinity as a TAAR1 receptor agonist (3.3 μM EC₅₀), an Alpha-2A adrenergic receptor agonist (0.49 μM K_i) and as a binding agent at the 5-HT1A (3.6 μM K_i) and 5-HT2A (5.4 μM K_i) receptors.^[4]

Pharmacokinetics

Metabolism

Scientists performed a study on NM2AI metabolism in silico and in vivo, in order to identify the main metabolites to be screened in the different biological samples. They performed the in silico metabolism prediction of NM2AI using MetaSiteTM software and subsequently verified the presence of metabolites in the blood, urine and hair of mice after NM-2-AI administration. LC-HRMS analysis identified seven main metabolites in the urine. They were identified, by their accurate masses and fragmentation patterns, as 2-aminoindane (2AI), two hydroxy-2-AI and four hydroxy-NM-2-AI; one of the hydroxy-NM-2-AI and one of the hydroxy-2-AI underwent also to conjugation. NM-2-AI and 2-AI were also detected by LC-HRMS in the hair and blood ^[5]

References

^ "N-methyl-2-AI". Cayman Chemical. Retrieved 27 June 2015.
^ Cannon JG, Perez JA, Pease JP, Long JP, Flynn JR, Rusterholz DB, Dryer SE (July 1980). "Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene". Journal of Medicinal Chemistry. 23 (7): 745–749. doi:10.1021/jm00181a009. PMID 7190613.
^ ^a ^b 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.
^ ^a ^b "N-METHYLINDAN-2-AMINE". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS), U.S. National Institutes of Health.
^ Mestria S, Odoardi S, Federici S, Bilel S, Tirri M, Marti M, Strano Rossi S (May 2021). "Metabolism Study of N-Methyl 2-Aminoindane (NM2AI) and Determination of Metabolites in Biological Samples by LC-HRMS". Journal of Analytical Toxicology. 45 (5): 475–483. doi:10.1093/jat/bkaa111. PMID 32860694.