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 Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observe ...

of the

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the firs ...

α-alkyltryptamine Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all trypt ...

, and

β-ketotryptamine Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all trypt ...

families. Along with certain other tryptamines, such as

α-ethyltryptamine α-Ethyltryptamine (αET, AET), also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before bei ...

(αET), 5-chloro-αMT and 5-fluoro-αET, it is one of the few SDRAs known. The drug is the ''N''-

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

and β- keto analogue of α-methyltryptamine (αMT). It is a

cathinone Cathinone (; also known as β-ketoamphetamine) is a monoamine alkaloid found in the shrub ''Catha edulis'' (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to t ...

-like tryptamine and can be thought of as the tryptamine or

indole Indole is an organic compound with the formula . Indole is classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are derivatives of indole ...

analogue of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

methcathinone. The values of BK-NM-AMT for monoamine release are 41.3nM for

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

and 92.8nM for

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

in rat brain

synaptosome A synaptosome is an isolated synaptic terminal from a neuron. Synaptosomes are obtained by mild homogenization of nervous tissue under isotonic conditions and subsequent fractionation using differential and density gradient centrifugation. Liquid ...

s, whereas it only induced 55% release of

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

at a concentration of 10μM. Several 5-

halogenated In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs ...

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

s of BK-NM-AMT have also been described. These include

BK-5F-NM-AMT BK-5F-NM-AMT, or βk-5F-NM-αMT, also known as β-keto-5-fluoro-''N''-methyl-αMT or α,''N''-dimethyl-5-fluoro-β-ketotryptamine, is a monoamine releasing agent of the tryptamine, α-alkyltryptamine, and β-ketotryptamine families. It is known ...

, BK-5Cl-NM-AMT, and BK-5Br-NM-AMT. 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

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

s of

serotonin receptor 5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in multiple tissues including the central and peripheral nervous systems. They mediate both ex ...

s 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 inhibitor Monoamine oxidase inhibitors (MAOIs) are a drug class, class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressa ...

s (MAOIs). BK-NM-AMT and its 5-halogenated analogues were

patent A patent is a type of intellectual property that gives its owner the legal right to exclude others from making, using, or selling an invention for a limited period of time in exchange for publishing an sufficiency of disclosure, enabling discl ...

ed by Matthew Baggott and

Tactogen Tactogen is a public benefit corporation and start-up pharmaceutical company based in Palo Alto, California that is developing novel MDMA-like entactogens and psychedelics as medicines. Its stated goal is to develop new MDMA-like drugs with impr ...

in late 2024.

References

External links

β-Oxo-α-methyl-NMT - Isomer Design
{{Chemical classes of psychoactive drugs Alpha-Alkyltryptamines Beta-Ketotryptamines Entactogens Experimental entactogens N-Monoalkyltryptamines Serotonin-dopamine releasing agents

See also

References

External links