4-Methoxytryptamine (4-MeO-T; developmental code name PAL-548) 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 ...
and
4-hydroxytryptamine
4-Hydroxytryptamine (4-HT, 4-HTA), also known as ''N'',''N''-didesmethylpsilocin, is a naturally occurring tryptamine alkaloid. It is closely related chemically to the neurotransmitter serotonin, the psychedelic psilocin, and is the active for ...
families.
It is the ''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 ...
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 ...
of
4-hydroxytryptamine
4-Hydroxytryptamine (4-HT, 4-HTA), also known as ''N'',''N''-didesmethylpsilocin, is a naturally occurring tryptamine alkaloid. It is closely related chemically to the neurotransmitter serotonin, the psychedelic psilocin, and is the active for ...
(4-HT) and 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
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
6-methoxytryptamine
6-Methoxytryptamine (6-MeO-T; developmental code name PAL-263) is a monoamine releasing agent and serotonin receptor modulator of the tryptamine family. It is a positional isomer of 5-methoxytryptamine.
Pharmacology
6-Methoxytryptamine is a pot ...
.
Pharmacology
The drug has been found to act as a
potent 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-HT2A 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 ...
, with an of 9.02nM and an of 108%.
It was inactive as 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 ...
, including of
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, ...
,
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 ...
, and
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 (all = >10,000nM), but was a very low-
potency
Potency may refer to:
* Potency (pharmacology), a measure of the activity of a drug in a biological system
* Virility
* Cell potency, a measure of the differentiation potential of stem cells
* In homeopathic dilutions, potency is a measure of ho ...
serotonin reuptake inhibitor
A serotonin reuptake inhibitor (SRI) is a type of drug which acts as a reuptake inhibitor of the neurotransmitter serotonin (5-hydroxytryptamine, or 5-HT) by blocking the drug action, action of the serotonin transporter (SERT). This in turn lea ...
( = 4,114nM).
History
4-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 at least 1962.
See also
*
Substituted 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 ...
*
4-Hydroxytryptamine
4-Hydroxytryptamine (4-HT, 4-HTA), also known as ''N'',''N''-didesmethylpsilocin, is a naturally occurring tryptamine alkaloid. It is closely related chemically to the neurotransmitter serotonin, the psychedelic psilocin, and is the active for ...
*
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 ...
*
6-Methoxytryptamine
6-Methoxytryptamine (6-MeO-T; developmental code name PAL-263) is a monoamine releasing agent and serotonin receptor modulator of the tryptamine family. It is a positional isomer of 5-methoxytryptamine.
Pharmacology
6-Methoxytryptamine is a pot ...
*
4-MeO-DMT
References
External links
4-MeO-T - Isomer Design
5-HT2A agonists
4-Hydroxytryptamines
Serotonin receptor modulators
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