BK-NM-AMT
| Clinical data | |
|---|---|
| Other names | βk-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 class | Serotonin–dopamine releasing agent; Entactogen | 
| Identifiers | |
| 
 | |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| Chemical and physical data | |
| Formula | C12H14N2O | 
| Molar mass | 202.257 g·mol−1 | 
| 3D model (JSmol) | |
| 
 | |
| 
 | |
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 EC50 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.
| Compound | 5-HT | NE | DA | Type | Ref | |
|---|---|---|---|---|---|---|
| Tryptamine | 32.6 | 716 | 164 | SDRA | ||
| α-Methyltryptamine (αMT) | 21.7–68 | 79–112 | 78.6–180 | SNDRA | ||
| 5-Fluoro-αMT | 19 | 126 | 32 | SNDRA | ||
| 5-Chloro-αMT | 16 | 3434 | 54 | SDRA | ||
| BK-NM-AMT | 41.3 | ND (55% at 10 μM) | 92.8 | SDRA | ||
| BK-5F-NM-AMT | 190 | ND | 620 | ND | ||
| BK-5Cl-NM-AMT | 200 | ND | 865 | ND | ||
| BK-5Br-NM-AMT | 295 | ND | 2100 | ND | ||
| 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. | ||||||