BK-NM-AMT

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]

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
IUPAC name 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one
CAS Number	22942-93-4 Y
PubChem CID	82282492
ChemSpider	26703861
Chemical and physical data
Formula	C12H14N2O
Molar mass	202.257 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C(=O)C1=CNC2=CC=CC=C21)NC
InChI 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 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

• α,N-Dimethyltryptamine (NM-AMT)
• 1Z2MAP1O
• 1ZP2MA
• Serotonin–dopamine releasing agent § Examples of SDRAs