BK-NM-AMT explained

Class:Serotonin–dopamine releasing agent
Entactogen
Pubchem:82282492
Chemspiderid:26703861
Synonyms:βk-NM-αMT; β-Keto-N-methyl-αMT; β-Keto-N-methyl-AMT; α,N-dimethyl-β-ketotryptamine
Iupac Name:1-(1H-indol-3-yl)-2-(methylamino)propan-1-one
C:12
H:14
N:2
O:1
Smiles:CC(C(=O)C1=CNC2=CC=CC=C21)NC
Stdinchi: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
Stdinchikey:NBPRBKHRAWWHFV-UHFFFAOYSA-N

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]

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 analogue of the phenethylamine methcathinone. The values of BK-NM-AMT for monoamine release are 41.3nM for serotonin and 92.8nM for dopamine, whereas it only induced 55% release of norepinephrine at a concentration of 10μM.

BK-NM-AMT was patented by Tactogen in October 2024.

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. 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).

Monoamine release of BK-NM-AMT and related compounds (nM)
Compound data-sort-type="number" !data-sort-type="number" !data-sort-type="number" !Type Ref
32.6 716 164 SDRA [13]
α-Methyltryptamine (αMT) 21.7–68 79–112 78.6–180 SNDRA [14]
19 126 32 SNDRA [15]
16 3434 54 SDRA
41.3 (55% at 10μM) 92.8 SDRA
190 620
200 865
295 2100
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.

See also

Notes and References

  1. Web site: Yadav . Barkha J . Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate . VCU Scholars Compass . 16 July 2019 . 24 November 2024 . 40 .
  2. Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB . The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes . Psychopharmacology (Berl) . 236 . 3 . 915–924 . March 2019 . 30341459 . 6475490 . 10.1007/s00213-018-5063-9 .
  3. US . 20240335414 . Baggott MJ, Dalziel S . Tactogen Inc. . Specialized combinations for mental disorders or mental enhancement . 10 October 2024 .
  4. Web site: 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one . PubChem . U.S. National Library of Medicine . 13 November 2024.
  5. Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB . Alpha-ethyltryptamines as dual dopamine-serotonin releasers . Bioorg Med Chem Lett . 24 . 19 . 4754–4758 . October 2014 . 25193229 . 4211607 . 10.1016/j.bmcl.2014.07.062 .
  6. Web site: Advantageous tryptamine compositions for mental disorders or enhancement . Google Patents . 20 September 2021 . 11 November 2024.
  7. Web site: 1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one . PubChem . 11 November 2024.
  8. Web site: β-Oxo-5-fluoro-α-methyl-NMT . Isomer Design . 10 November 2024 . 11 November 2024.
  9. Web site: 1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one . PubChem . 11 November 2024.
  10. Web site: β-Oxo-5-chloro-α-methyl-NMT . Isomer Design . 10 November 2024 . 11 November 2024.
  11. Web site: 1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one . PubChem . 11 November 2024.
  12. Web site: β-Oxo-5-bromo-α-methyl-NMT . Isomer Design . 10 November 2024 . 11 November 2024.
  13. Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB . Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes . Psychopharmacology . 231 . 21 . 4135–4144 . October 2014 . 24800892 . 4194234 . 10.1007/s00213-014-3557-7 .
  14. Nagai F, Nonaka R, Satoh Hisashi Kamimura K . The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain . European Journal of Pharmacology . 559 . 2–3 . 132–137 . March 2007 . 17223101 . 10.1016/j.ejphar.2006.11.075 .
  15. Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS . Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys . Experimental and Clinical Psychopharmacology . 22 . 3 . 274–284 . June 2014 . 24796848 . 4067459 . 10.1037/a0036595 .

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