Structure via PubChem · Public domain (PubChem)
۵-متوکسیتریپتامین
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.
Chemical data
- Formula
- C11H14N2O
- Molecular weight
- 190.24 g/mol
- IUPAC name
- 2-(5-methoxy-1H-indol-3-yl)ethanamine
- SMILES
- COC1=CC2=C(C=C1)NC=C2CCN
- InChIKey
- JTEJPPKMYBDEMY-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 51 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
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 4 more facts
- found in taxon
- Rhodospirillum rubrum
- chemical formula
- C₁₁H₁₄N₂O
- canonical SMILES
- COC1=CC2=C(C=C1)NC=C2CCN
- subject has role
- hallucinogen
Sources (2)
via Wikidata · CC0