Chemistry:NM-2-AI

From HandWiki

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.[2][3] NM-2-AI acts as a selective norepinephrine releasing agent, but also has affinity for several monoamine receptors.[4][5]

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 Template: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.[5][4][6]

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]

See also

References

  1. "N-Метил-2-инданамин (N-metyl-2AI)" (in ru). https://aipsin.com/newsubstance/311/. 
  2. "N-methyl-2-AI". Cayman Chemical. https://www.caymanchem.com/app/template/Product.vm/catalog/14897. 
  3. "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. 
  4. 4.0 4.1 4.2 "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. 
  5. 5.0 5.1 "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. 
  6. "2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors". Psychopharmacology (Berl) 236 (3): 989–999. March 2019. doi:10.1007/s00213-019-05207-1. PMID 30904940. 
  7. "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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