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BK-NM-AMT, or βk-NM-αMT, also known as β-keto-N-methyl-αMT or as α,N-dimethyl-β-ketotryptamine, is a serotonin–dopamine releasing agent (SDRA) and putative entactogen of the tryptamine and α-alkyltryptamine families.[1][2][3][4] 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.[5][2]
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| Clinical data | |
|---|---|
| Other names | βk-NM-αMT; β-Keto-N-methyl-αMT; β-Keto-N-methyl-AMT; α,N-dimethyl-β-ketotryptamine |
| Drug class | Serotonin–dopamine releasing agent; Entactogen |
| Identifiers | |
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| PubChem CID | |
| ChemSpider | |
| Chemical and physical data | |
| Formula | C12H14N2O |
| Molar mass | 202.257 g·mol−1 |
| 3D model (JSmol) | |
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The drug is the N-methyl and β-keto analogue of α-methyltryptamine (αMT).[2][4] It is a cathinone-like tryptamine and can be thought of as the tryptamine analogue of the phenethylamine methcathinone.[2][4] The EC50 values of BK-NM-AMT for monoamine release are 41.3 nM for serotonin and 92.8 nM for dopamine, whereas it only induced 55% release of norepinephrine at a concentration of 10 μM.[2]
BK-NM-AMT was patented by Tactogen in October 2024.[3][4]
Several 5-halogenated derivatives of BK-NM-AMT have also been described and patented.[6] These include BK-5F-NM-AMT,[7][8] BK-5Cl-NM-AMT,[9][10] and BK-5Br-NM-AMT.[11][12] Like BK-NM-AMT, they induce serotonin and dopamine release.[6] 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.[6] In addition, unlike other α-alkyltryptamines like αMT, these compounds are inactive as monoamine oxidase inhibitors (MAOIs).[6]
| Compound | 5-HT | NE | DA | Type | Ref | |
|---|---|---|---|---|---|---|
| Tryptamine | 32.6 | 716 | 164 | SDRA | [13][5] | |
| α-Methyltryptamine (αMT) | 21.7–68 | 79–112 | 78.6–180 | SNDRA | [14][5] | |
| 5-Fluoro-αMT | 19 | 126 | 32 | SNDRA | [15] | |
| 5-Chloro-αMT | 16 | 3434 | 54 | SDRA | [5][15] | |
| BK-NM-AMT | 41.3 | ND (55% at 10 μM) | 92.8 | SDRA | [2][3] | |
| BK-5F-NM-AMT | 190 | ND | 620 | ND | [6] | |
| BK-5Cl-NM-AMT | 200 | ND | 865 | ND | [6] | |
| BK-5Br-NM-AMT | 295 | ND | 2100 | ND | [6] | |
| Notes: The smaller the value, the more strongly the substance releases the neurotransmitter. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. | ||||||
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