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| Other names | NM2AI; N-Methyl-2-aminoindane; N-Methyl-2-AI; N-Methyl-AI; AM-80; Methaminoindan; Methoaminoindane |
| Drug class | Norepinephrine releasing agent; Stimulant |
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| Formula | C10H13N |
| Molar mass | 147.221 g·mol−1 |
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NM-2-AI, or NM2AI, also known as N-methyl-2-aminoindane, is a stimulant of the 2-aminoindane family that has been sold online as a designer drug.1 It is a rigid analogue of methamphetamine.23 NM-2-AI acts as a selective norepinephrine releasing agent, but also has affinity for several monoamine receptors.45
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).4
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 Ki) and as a binding agent at the 5-HT1A (3.6 μM Ki) and 5-HT2A (5.4 μM Ki) receptors.546
Pharmacokinetics
Metabolism
Scientists performed a study on NM-2-AI 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 NM-2-AI 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 7
References
References
- "N-Метил-2-инданамин (N-metyl-2AI)". АИПСИН (in Russian). Retrieved 1 January 2026.
- "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.
- 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.
- "N-METHYLINDAN-2-AMINE". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS), U.S. National Institutes of Health.
- Halberstadt AL, Brandt SD, Walther D, Baumann MH (March 2019). "2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors". Psychopharmacology (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940.
- 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.