NM-2-AI

Summary

NM-2-AI, also known as N-methyl-2-aminoindane, is a psychoactive substance and a research chemical that has been distributed via online platforms as a designer drug. Structurally, it is a rigid counterpart to methamphetamine and is derived from 2-aminoindane.

Identifiers

IUPAC name
CAS Number	24445-44-1HCl: 10408-85-2
PubChem CID	15023225
ChemSpider	13566342
UNII	ZLW84Y27HG
ChEMBL	ChEMBL1188235
CompTox Dashboard (EPA)	DTXSID901010100
Chemical and physical data
Formula	C10H13N
Molar mass	147.221 g·mol−1

Pharmacology

Pharmacodynamics:

NM-2-AI exhibits pronounced pharmacological actions, serving as a highly selective norepinephrine reuptake inhibitor and releasing agent in vitro settings.

NM-2AI demonstrates considerable binding affinities across various receptor sites, with notable values such as a 2.4 µM IC50 as a norepinephrine reuptake inhibitor, a 3.3 µM EC50 as a TAAR1 receptor agonist, a 0.49 µM Ki as an Alpha-2A adrenergic receptor agonist, and significant binding activity at the 5-HT1A (3.6 µM Ki) and 5-HT2A (5.4 µM Ki) receptors.

Pharmacokinetics:

Metabolism:

In-depth investigations into the metabolism of N-methyl-2-aminoindane (NM2AI) involved both in-silico and in-vivo approaches to identify critical metabolites for screening in various biological samples. Employing MetaSiteTM software, researchers initially predicted the in-silico metabolism of NM2AI. Subsequent verification involved the analysis of blood, urine, and hair samples from mice administered NM-2-AI.

The analysis via LC-HRMS revealed the presence of seven primary metabolites in the urine, confidently identified based on accurate masses and fragmentation patterns. These metabolites encompass 2-aminoindane (2AI), two forms of hydroxy-2-AI, and four variations of hydroxy-NM-2-AI. Notably, one of the hydroxy-NM-2-AI and one of the hydroxy-2-AI metabolites also underwent conjugation. Furthermore, NM-2-AI and 2-AI were detected in both hair and blood samples through LC-HRMS analysis.

FAQ

• What is NM-2-AI?
• NM-2-AI, or N-methyl-2-aminoindane, is a psychoactive drug and research chemical that has been available online as a designer drug. It shares structural similarities with methamphetamine and is derived from 2-aminoindane.
• What are the pharmacological properties of NM-2-AI?
• NM-2-AI is primarily known for its pharmacological actions as a highly selective norepinephrine reuptake inhibitor and releasing agent. It also exhibits affinity for various receptors, including TAAR1, Alpha-2A adrenergic receptors, 5-HT1A, and 5-HT2A receptors.
• How does NM-2-AI affect norepinephrine reuptake?
• NM-2-AI acts as a norepinephrine reuptake inhibitor, meaning it inhibits the reabsorption of norepinephrine, a neurotransmitter associated with various physiological and psychological functions.
• Is NM-2-AI known to bind to other receptors?
• Yes, besides norepinephrine reuptake inhibition, NM-2-AI has an affinity for other receptors, including TAAR1, Alpha-2A adrenergic receptors, 5-HT1A, and 5-HT2A receptors. These interactions contribute to its complex pharmacological profile.
• What can you tell me about the metabolism of NM-2-AI?
• The metabolism of NM-2-AI has been investigated using both in-silico and in-vivo methods. Research revealed several primary metabolites present in biological samples, including urine, blood, and hair. These metabolites include 2-aminoindane (2AI), hydroxy-2-AI, and hydroxy-NM-2-AI, some of which undergo conjugation.
• Is NM-2-AI available for purchase?
• NM-2-AI has been available online as a designer drug. However, the legal status and availability of such substances can vary by region and change over time. It’s essential to stay informed about local regulations and restrictions.
• What are the potential risks and side effects associated with NM-2-AI?
• The consumption of psychoactive substances like NM-2-AI can entail various risks, including adverse side effects and potential health concerns. It’s crucial to exercise caution and seek professional advice when considering the use of such substances.
• Is NM-2-AI legal in my area?
• Legal regulations regarding NM-2-AI and similar compounds can differ significantly by country and region. It’s essential to be aware of and comply with local drug laws and regulations.
• Is NM-2-AI subject to regulatory changes?
• The legal status of designer drugs and research chemicals can change due to regulatory updates. It’s advisable to stay updated on any new regulations that may affect the availability and legality of NM-2-AI.
• Where can I find more information about NM-2-AI and related substances?

Stay informed by referring to scientific research, academic studies, and government resources that provide information on the pharmacology, effects, and regulatory status of NM-2-AI and other psychoactive substances.

References

1. “N-methyl-2-AI”. Cayman Chemical. Retrieved on June 27, 2015.
2. Cannon JG, Perez JA, Pease JP, Long JP, Flynn JR, Rusterholz DB, Dryer SE. “Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene.” Journal of Medicinal Chemistry. July 1980; 23(7): 745–749.
3. Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME. “Pharmacological profile of mephedrone analogs and related new psychoactive substances.” Neuropharmacology. May 2018; 134(Part A): 4–12.
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. “Metabolism Study of N-Methyl 2-Aminoindane (NM2AI) and Determination of Metabolites in Biological Samples by LC-HRMS.” Journal of Analytical Toxicology. May 2021; 45(5): 475–483.