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BK-NM-AMT

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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]

BK-NM-AMT
Clinical data
Other namesβk-NM-αMT; β-Keto-N-methyl-αMT; β-Keto-N-methyl-AMT; α,N-dimethyl-β-ketotryptamine
Drug classSerotonin–dopamine releasing agent; Entactogen
Identifiers
  • 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one
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

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 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, 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]

Monoamine release of BK-NM-AMT and related compounds (EC50Tooltip half-maximal effective concentration, nM)
Compound 5-HTTooltip Serotonin NETooltip Norepinephrine DATooltip Dopamine 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.

See also

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References

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