NM-2-AI
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = N-Methyl-2,3-dihydro-1H-inden-2-amine
| image = N-methyl-2-aminoindane.svg
| width = 200px
| tradename =
| pregnancy_category =
| legal_status =
| legal_DE = NpSG
| legal_UK = PSA
| routes_of_administration =
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref =
| CAS_number = 24445-44-1
| CAS_number2 = 10408-85-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZLW84Y27HG
| index_label =
| index2_label = HCl
| ATC_prefix =
| ATC_suffix =
| PubChem = 15023225
| ChemSpiderID_Ref =
| ChemSpiderID = 13566342
| ChEMBL = 1188235
| synonyms = N-Methyl-2-aminoindane; N-Methyl-2-AI; N-Methyl-AI; AM-80; Methaminoindan; Methoaminoindane
| C=10 | H=13 | N=1
| smiles = CNC2CC1=CC=CC=C1C2
| StdInChI = 1S/C10H13N/c1-11-10-6-8-4-2-3-5-9(8)7-10/h2-5,10-11H,6-7H2,1H3
| StdInChIKey = 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.{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/14897 | title=N-methyl-2-AI | publisher=Cayman Chemical | access-date=27 June 2015}}{{cite journal | vauthors = Cannon JG, Perez JA, Pease JP, Long JP, Flynn JR, Rusterholz DB, Dryer SE | title = Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene | journal = Journal of Medicinal Chemistry | volume = 23 | issue = 7 | pages = 745–749 | date = July 1980 | pmid = 7190613 | doi = 10.1021/jm00181a009 }} NM-2-AI acts as a selective norepinephrine releasing agent, but also has affinity for several monoamine receptors.
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{{nbsp}}μM).{{cite journal | vauthors = Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME | title = Pharmacological profile of mephedrone analogs and related new psychoactive substances | journal = Neuropharmacology | volume = 134 | issue = Pt A | pages = 4–12 | date = May 2018 | pmid = 28755886 | doi = 10.1016/j.neuropharm.2017.07.026 | s2cid = 28786127 | url = https://edoc.unibas.ch/57357/1/20170920120908_59c23e44b5f0e.pdf }}
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.{{cite web | url= https://drugs.ncats.io/drug/ZLW84Y27HG | work = Inxight Drugs | title = N-METHYLINDAN-2-AMINE | publisher = National Center for Advancing Translational Sciences (NCATS), U.S. National Institutes of Health }}{{cite journal | vauthors = Halberstadt AL, Brandt SD, Walther D, Baumann MH | title = 2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors | journal = Psychopharmacology (Berl) | volume = 236 | issue = 3 | pages = 989–999 | date = March 2019 | pmid = 30904940 | pmc = 6848746 | doi = 10.1007/s00213-019-05207-1 | url = }}
=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 {{cite journal | vauthors = Mestria S, Odoardi S, Federici S, Bilel S, Tirri M, Marti M, Strano Rossi S | title = Metabolism Study of N-Methyl 2-Aminoindane (NM2AI) and Determination of Metabolites in Biological Samples by LC-HRMS | journal = Journal of Analytical Toxicology | volume = 45 | issue = 5 | pages = 475–483 | date = May 2021 | pmid = 32860694 | doi = 10.1093/jat/bkaa111 }}
References
{{Reflist}}
{{Stimulants}}
{{Monoamine releasing agents}}
{{TAAR modulators}}