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BK-NM-AMT

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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
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.[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]

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 or indole 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 in rat brain synaptosomes, whereas it only induced 55% release of norepinephrine at a concentration of 10 μM.[2]

Several 5-halogenated derivatives of BK-NM-AMT have also been described.[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]

BK-NM-AMT and its 5-halogenated analogues were patented by Matthew Baggott and Tactogen in late 2024.[3][4][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. 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.

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 (Thesis). p. 40. doi:10.25772/MJQW-8C64. 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 h "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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