NM-2-AI

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. 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	NM2AI; N-Methyl-2-aminoindane; N-Methyl-2-AI; N-Methyl-AI; AM-80; Methaminoindan; Methoaminoindane
Drug class	Norepinephrine releasing agent; Stimulant
ATC code	None
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 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 ^[6]

See also

• Substituted 2-aminoindane