5-methoxytryptamine
Sign in to saveAlso known as mexamine, 3-(2-aminoethyl)-5-methoxyindole, 2-(5-methoxyindol-3-yl)ethylamine, 5-methoxy-1H-indole-3-ethanamine, 2-(5-methoxy-1H-indol-3-yl)ethylamine, 2-(5-methoxy-1H-indol-3-yl)ethanamine, Lopac-M-6628, 2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
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 occur naturally in the pineal gland of the brain. It is formed via O-methylation of serotonin or N''-deacetylation of melatonin.
Research
1,582 papers- Melatonin and 5-methoxytryptamine in non-metazoans.Reproduction, nutrition, development · 1999
- Structural pharmacology and therapeutic potential of 5-methoxytryptamines.Nature · 2024
- The recreational tryptamine 5-MeO-DALT (N,N-diallyl-5-methoxytryptamine): a brief review.Progress in neuro-psychopharmacology & biological psychiatry · 2012
- On the significance of an alternate pathway of melatonin synthesis via 5-methoxytryptamine: comparisons across species.Journal of pineal research · 2016
- Is 5-methoxytryptamine a pineal hormone?Psychoneuroendocrinology · 1983
via PubMed
Wikidata facts
- Mass
- 190.110613
Show 2 more facts
- chemical formula
- C₁₁H₁₄N₂O
- canonical SMILES
- COC1=CC2=C(C=C1)NC=C2CCN
Sources (2)
via Wikidata · CC0
~8 min read
Article
20 sectionsContents
- Use and effects
- Pharmacology
- Pharmacodynamics
- Effects in animals and humans
- Pharmacokinetics
- Distribution
- Metabolism
- Chemistry
- Properties
- Analogues and derivatives
- Natural occurrence
- Biosynthesis
- History
- Society and culture
- Legal status
- Canada
- United States
- See also
- References
- External links
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 occur naturally in the pineal gland of the brain. It is formed via O-methylation of serotonin or N-deacetylation of melatonin.
5-MT is a highly potent and non-selective serotonin receptor agonist and shows serotonergic psychedelic-like effects in animals. However, it is inactive in humans, at least orally, likely due to rapid metabolism by monoamine oxidase (MAO). The levels and effects of 5-MT are dramatically potentiated by monoamine oxidase inhibitors (MAOIs) in animals.