Chemistry:NM-2-AI

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Short description: Chemical compound
NM-2-AI
N-methyl-2-aminoindane.svg
Clinical data
Other namesN-Methyl-2-aminoindane; AM-80
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC10H13N
Molar mass147.221 g·mol−1
3D model (JSmol)

NM-2-AI (N-methyl-2-aminoindane) is a psychoactive drug and research chemical that has been sold online as a designer drug. It is a rigid analogue of methamphetamine.[1][2] It is a derivative of 2-aminoindane.

Pharmacology

Pharmacodynamics

NM-2-AI acts as a highly selective norepinephrine reuptake inhibitor and releasing agent in vitro.[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 Ki) and as a binding agent at the 5-HT1A (3.6 µM Ki) and 5-HT2A (5.4 µM Ki) receptors[4]

Pharmacokinetics

Metabolism

Scientists performed a study on N-methyl-2-aminoindane (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

  1. ↑ "N-methyl-2-AI". Cayman Chemical. https://www.caymanchem.com/app/template/Product.vm/catalog/14897. 
  2. ↑ "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. July 1980. doi:10.1021/jm00181a009. PMID 7190613. 
  3. ↑ "Pharmacological profile of mephedrone analogs and related new psychoactive substances". Neuropharmacology 134 (Pt A): 4–12. May 2018. doi:10.1016/j.neuropharm.2017.07.026. PMID 28755886. https://edoc.unibas.ch/57357/1/20170920120908_59c23e44b5f0e.pdf. 
  4. ↑ "N-METHYLINDAN-2-AMINE". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS), U.S. National Institutes of Health. https://drugs.ncats.io/drug/ZLW84Y27HG. 
  5. ↑ "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. May 2021. doi:10.1093/jat/bkaa111. PMID 32860694. 



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