2-Methyltryptamine (2-MT, 2-Me-T, or 2-methyl-T) is a

serotonin receptor agonist A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin (5-hydroxytryptamine; 5-HT), a neurotransmitter and hormone and the endogenous ligand of t ...

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 ...

family. It shows dramatically reduced activity at

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 compared to

and mixed effects in terms of psychedelic-like effects in animals.

Pharmacology

2-MT shows

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

(K_i) for the serotonin 5-HT_1A and 5-HT_2A receptors, with K_i values of 1,095nM and 7,774nM, respectively. These affinities were respectively 34-fold and 3.2-fold lower than those of

in the same study. It also acts as an

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 ...

of the serotonin 5-HT_1A and 5-HT_2A receptors, with values of 12,534nM and 4,598nM, respectively. These activational potencies were respectively 14-fold and 19-fold lower than those of tryptamine in the same study. It does not produce

conditioned place preference Conditioned place preference (CPP) is a form of Pavlovian conditioning used to measure the motivational effects of objects or experiences. This motivation comes from the pleasurable aspect of the experience, so that the brain can be reminded of th ...

(CPP),

self-administration Self-administration is, in its Medicine, medical sense, the process of a subject administering a Pharmacology, pharmacological substance to themself. A clinical example of this is the subcutaneous "self-injection" of insulin by a Diabetes, diabetic ...

, or changes in

locomotor activity Locomotor activity is a measure of animal behavior which is employed in scientific research. Hyperlocomotion, also known as locomotor hyperactivity, hyperactivity, or increased locomotor activity, is an effect of certain drugs in animals in whi ...

in rodents. Findings on whether 2-MT produces the

head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...

(HTR), a behavioral proxy of

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

effects, are mixed. In one study, it produced the HTR at a dose of 3mg/kg

intraperitoneally Intraperitoneal injection or IP injection is the injection of a substance into the peritoneum (body cavity). It is more often applied to non-human animals than to humans. In general, it is preferred when large amounts of blood replacement fluids ...

, and this was completely blocked by the serotonin 5-HT_2A receptor

antagonist An antagonist is a character in a story who is presented as the main enemy or rival of the protagonist and is often depicted as a villain.ketanserin Ketanserin, sold under the brand name Sufrexal, is an antihypertensive agent which is used to treat arterial hypertension and vasospasm, vasospastic disorders. It is also used in scientific research as an antiserotonergic medication, agent in th ...

. In another study, both tryptamine and 2-MT did not produce the HTR at a dose of 3mg/kg intraperitoneally.

Chemistry

Derivatives

A number of

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 2-MT are known, including: * 2,α-Dimethyltryptamine (2,α-DMT or 2-Me-αMT) * 2,''N'',''N''-Trimethyltryptamine (2,''N'',''N''-TMT or 2-Me-DMT) * 2-Methyl-''N'',''N''-diethyltryptamine (2-Me-DET) * 5-Methoxy-2,''N'',''N''-trimethyltryptamine (5-MeO-2,''N'',''N''-TMT or 2-Me-5-MeO-DMT) These drugs were synthesized and tested by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

. He found that the drugs in this group became orally active but generally produced no or only mild

effects (with the exception of 2-Me-5-MeO-DMT). Instead, they caused effects like tactile enhancement and auditory distortion, among others. A couple of other derivatives, 2-methyl-5-MeO-DALT and 2-methyl-5-F-DALT, are also known. Further derivatives of 2-MT include the following: * 2-Methyl-5-HT (a moderately selective

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, ...

5-HT₃ receptor

full agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the agoni ...

) * 2-Methyl-5-chloro-DMT (ST-1936; a selective serotonin 5-HT₆ receptor agonist) * 2-Ethyl-5-methoxy-DMT (EMDT; a selective serotonin 5-HT₆ receptor agonist)

EMD-386088 EMD-386088 is an indole derivative which is used in scientific research. It acts as a potent 5-HT6 receptor partial agonist, with a Ki of 1 nM, a significantly higher affinity than older 5-HT6 agonists such as EMDT, although it possesses mode ...

(2-methyl-5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole) isn't technically a tryptamine but is very similar and is a serotonin 5-HT₆ receptor

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

as well as having moderate affinity for the serotonin 5-HT₃ receptor and acting as a

dopamine reuptake inhibitor A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular dop ...

. Yet another related compound is 2-HO-NMT, a tryptamine

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

References

External links

2-Methyl-T - Isomer Design
{{DEFAULTSORT:Methyltryptamine, 2- 5-HT1A agonists 5-HT2A agonists Psychedelic tryptamines

Pharmacology

Chemistry

Derivatives

See also

References

External links