6-Methoxytryptamine (6-MeO-T; developmental code name PAL-263) is a

monoamine releasing agent A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrati ...

and

serotonin receptor modulator 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 ...

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 is a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

5-methoxytryptamine 5-Methoxytryptamine (5-MT, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or ''O''-methylserotonin and as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. It has been shown to oc ...

Pharmacology

6-Methoxytryptamine is a potent

serotonin–norepinephrine–dopamine releasing agent A serotonin–norepinephrine–dopamine releasing agent (SNDRA), also known as a triple releasing agent (TRA), is a type of drug which induces the release of serotonin, norepinephrine/epinephrine, and dopamine in the brain and body. SNDRAs produc ...

(SNDRA), with values for monoamine release induction of 53.8nM 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, ...

, 113nM 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 ...

, and 465nM for

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 ...

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. It is also a

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 ...

of the

5-HT_2A receptor, but with very low potency; its and at this receptor were 2,443nM and 111%, respectively. In a series of tryptamine

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, 6-methoxytryptamine was the least potent serotonin 5-HT_2A receptor agonist, while

was the most potent serotonin 5-HT_2A receptor agonist, with 5-methoxytryptamine showing approximately 4,857-fold higher potency in terms of serotonin 5-HT_2A receptor agonism than 6-methoxytryptamine. Conversely, whereas 6-methoxytryptamine was a potent monoamine releasing agent, 5-methoxytryptamine showed very low potency in this regard.

History

6-Methoxytryptamine was first described in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

by the 1950s.

Derivatives

Certain β-carbolines and

harmala alkaloid Harmala alkaloids are several alkaloids that act as monoamine oxidase inhibitors (MAOIs). These alkaloids are found in the seeds of ''Peganum harmala'' (also known as harmal or Syrian rue), as well as ''Banisteriopsis caapi'' (ayahuasca), leave ...

s, such as harmine,

harmaline Harmaline, also known as 7-methoxyharmalan or as 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a fluorescent indole alkaloid from the group of harmala alkaloids and β-carbolines. It is the partly hydrogenated form of harmine. It is a rever ...

, and

tetrahydroharmine Tetrahydroharmine (THH) is a fluorescent indole alkaloid and β-carboline that occurs in the tropical liana species ''Banisteriopsis caapi''. Effects THH has been reported to produce psychoactive effects similar to those of harmaline in human ...

, are notable in being

naturally occurring A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical ...

cyclized tryptamine 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 ...

derivatives of 6-methoxytryptamine. The same is true of certain

iboga alkaloid Iboga-type alkaloids are a set of monoterpene indole alkaloids comprising naturally occurring compounds found in ''Tabernanthe'' and ''Tabernaemontana'', as well as synthetic structural analogs. Naturally occurring iboga-type alkaloids include ib ...

s, such as tabernanthine and

ibogaline Ibogaline is an alkaloid found in '' Tabernanthe iboga'' along with the related chemical compounds ibogaine, ibogamine, and other minor alkaloids. It is a relatively smaller component of ''Tabernanthe iboga'' root bark total alkaloids (TA) conte ...

Tabernanthalog Tabernanthalog (TBG, DLX-007) is a novel water-soluble, non-toxic ibogalog or simplified analogue of the psychoactive drug tabernanthine first synthesized by David E. Olson at UC Davis. Tabernanthalog is a non-hallucinogenic serotonin 5-HT2A ...

(DLX-007) is a

synthetic Synthetic may refer to: Science * Synthetic biology * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic elements, chemical elements that are not naturally found on Earth and therefore have to be created in ...

simplified

ibogalog Noribogaminalog, or ''N''-desmethylibogaminalog, also known as 1,2,3,4,5,6-hexahydroazepino ,5-bndole, is a chemical compound and parent structure of the ibogalog group of compounds. The ibogalogs that have been described include ibogaminalog, ...

analogue of tabernanthine that is under development for use as a potential

pharmaceutical drug Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...

in the treatment of

neuropsychiatric disorder A mental disorder, also referred to as a mental illness, a mental health condition, or a psychiatric disability, is a behavioral or mental pattern that causes significant distress or impairment of personal functioning. A mental disorder is ...

References

External links

6-MeO-T - Isomer Design
{{DEFAULTSORT:Methoxytryptamine, 6- 5-HT2A agonists Methoxy compounds Serotonin-norepinephrine-dopamine releasing agents Serotonin receptor modulators Tryptamines

Pharmacology

History

Derivatives

See also

References

External links