NM-2-AI

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.^[1][2] NM-2-AI acts as a selective norepinephrine releasing agent, but also has affinity for several monoamine receptors.^[3][4]

NM-2-AI

Clinical data
Other names	N-Methyl-2-aminoindane; N-Methyl-2-AI; N-Methyl-AI; AM-80; Methaminoindan; Methoaminoindane
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 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
Chemical and physical data
Formula	C10H13N
Molar mass	147.221 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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

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).^[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 K_i) and as a binding agent at the 5-HT1A (3.6 μM K_i) and 5-HT2A (5.4 μM K_i) receptors.^[4][3][5]

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 ^[6]