NM-2-AI

Chemical compound
  • DE: NpSG (Industrial and scientific use only)
  • UK: Under Psychoactive Substances Act
Identifiers
  • 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 Edit this at Wikidata
Chemical and physical dataFormulaC10H13NMolar mass147.221 g·mol−13D model (JSmol)
  • Interactive image
  • 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 (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. Retrieved 27 June 2015.
  2. ^ 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.
  3. ^ 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.
  4. ^ "N-METHYLINDAN-2-AMINE". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS), U.S. National Institutes of Health.
  5. ^ 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.
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Phenylalkyl-
amines
(other than
cathinones)
Cyclized phenyl-
alkylamines
CathinonesTryptaminesChemical classes
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5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
  • See also: Receptor/signaling modulators
  • Adrenergics
  • Dopaminergics
  • Melatonergics
  • Monoamine reuptake inhibitors and releasing agents
  • Monoamine metabolism modulators
  • Monoamine neurotoxins
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