6-Hydroxytryptamine (6-HT or 6-HO-T) is a

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 related to

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, ...

. 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 ...

of serotonin (5-hydroxytryptamine; 5-HT) and of 4-hydroxytryptamine (4-HT).

Pharmacology

6-Hydroxytryptamine shows dramatically reduced

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 ...

for

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-HT_1A, 5-HT_1B, 5-HT_2A, and 5-HT_2C receptors (K_i = 1,590nM, 5,890nM, 11,500nM, and 5,500nM, respectively), compared to serotonin, 4-hydroxytryptamine,

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 ...

, and certain other tryptamines. It did not produce

hyperlocomotion 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 but did partially reverse

reserpine Reserpine is a drug that is used for the treatment of hypertension, high blood pressure, usually in combination with a thiazide diuretic or vasodilator. Large clinical trials have shown that combined treatment with reserpine plus a thiazide diur ...

-induced

hypoactivity 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 wh ...

. 6-Hydroxytryptamine appears to be less susceptible to

metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

monoamine oxidase Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The fi ...

(MAO) than serotonin.

History

6-Hydroxytryptamine 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 harmol,

harmalol Harmalol is a bioactive β-carboline and a member of the 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 ...

, and tetrahydroharmol, as well as their ''O''-

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 ...

(

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

) analogues including 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, 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-hydroxytryptamine. 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-HO-T - Isomer Design
{{DEFAULTSORT:Hydroxytryptamine, 6- Hydroxyarenes Serotonin receptor modulators Tryptamines

Pharmacology

History

Derivatives

See also

References

External links