BK-NM-AMT

BK-NM-AMT
Clinical data
Other namesβk-NM-αMT; β-Keto-N-methyl-αMT; β-Keto-N-methyl-AMT; α,N-dimethyl-β-ketotryptamine; 3-Indoylmethcathinone; β-Oxo-α-methyl-NMT
Drug classSerotonin–dopamine releasing agent; Entactogen
Identifiers
  • 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC12H14N2O
Molar mass202.257 g·mol−1
3D model (JSmol)
  • CC(C(=O)C1=CNC2=CC=CC=C21)NC
  • InChI=1S/C12H14N2O/c1-8(13-2)12(15)10-7-14-11-6-4-3-5-9(10)11/h3-8,13-14H,1-2H3
  • Key:NBPRBKHRAWWHFV-UHFFFAOYSA-N

BK-NM-AMT, or βk-NM-αMT, also known as β-keto-N-methyl-αMT or α,N-dimethyl-β-ketotryptamine, as well as 3-indoylmethcathinone, is a serotonin–dopamine releasing agent (SDRA) and putative entactogen of the tryptamine, α-alkyltryptamine, and β-ketotryptamine families. Along with certain other tryptamines, such as α-ethyltryptamine (αET), 5-chloro-αMT and 5-fluoro-αET, it is one of the few SDRAs known.

The drug is the N-methyl and β-keto analogue of α-methyltryptamine (αMT). It is a cathinone-like tryptamine and can be thought of as the tryptamine or indole analogue of the phenethylamine methcathinone. The EC50Tooltip half-maximal effective concentration values of BK-NM-AMT for monoamine release are 41.3 nM for serotonin and 92.8 nM for dopamine in rat brain synaptosomes, whereas it only induced 55% release of norepinephrine at a concentration of 10 μM.

Several 5-halogenated derivatives of BK-NM-AMT have also been described. These include BK-5F-NM-AMT, BK-5Cl-NM-AMT, and BK-5Br-NM-AMT. Like BK-NM-AMT, they induce serotonin and dopamine release. In contrast to many other tryptamines however, these novel β-keto-substituted tryptamine derivatives are inactive as agonists of serotonin receptors including the 5-HT1, 5-HT2, and 5-HT3 receptors. In addition, unlike other α-alkyltryptamines like αMT, these compounds are inactive as monoamine oxidase inhibitors (MAOIs).

BK-NM-AMT and its 5-halogenated analogues were patented by Matthew Baggott and Tactogen in late 2024.

Monoamine release of BK-NM-AMT and related compounds (EC50Tooltip half-maximal effective concentration, nM)
Compound5-HTTooltip SerotoninNETooltip NorepinephrineDATooltip DopamineTypeRef
Tryptamine32.6716164SDRA
α-Methyltryptamine (αMT)21.7–6879–11278.6–180SNDRA
5-Fluoro-αMT1912632SNDRA
5-Chloro-αMT16343454SDRA
BK-NM-AMT41.3ND (55% at 10 μM)92.8SDRA
BK-5F-NM-AMT190ND620ND
BK-5Cl-NM-AMT200ND865ND
BK-5Br-NM-AMT295ND2100ND
Notes: The smaller the value, the more strongly the substance releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds.