Structure via PubChem · Public domain (PubChem)
3-O-methyldopamine
Sign in to saveAlso known as 3-methoxy-4-hydroxyphenethylamine, 3-MT, 4-(2-aminoethyl)-2-methoxy-phenol, 4-(2-azanylethyl)-2-methoxy-phenol, 4-(2-aminoethyl)-2-methoxyphenol, 4-(2-Amino-ethyl)-2-methoxy-phenol, 5-(2-Aminoethyl)guaiacol
3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a human trace amine and the major metabolite of the monoamine neurotransmitter dopamine. It is formed by the introduction of a methyl group to dopamine by the enzyme catechol-O-methyltransferase (COMT). 3-MT can be further metabolized by the enzyme monoamine oxidase (MAO) to form homovanillic acid (HVA), which is then typically excreted in the urine.
Chemical data
- Formula
- C9H13NO2
- Molecular weight
- 167.2 g/mol
- IUPAC name
- 4-(2-aminoethyl)-2-methoxyphenol
- SMILES
- COC1=C(C=CC(=C1)CCN)O
- InChIKey
- DIVQKHQLANKJQO-UHFFFAOYSA-N
- XLogP
- 0.2
- Polar surface area
- 55.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 167.094629
Show 4 more facts
- found in taxon
- Lyallia kerguelensis
- chemical formula
- C₉H₁₃NO₂
- canonical SMILES
- COC1=C(C=CC(=C1)CCN)O
- Commons category
- 3-Methoxytyramine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Occurrence
- Biological activity
- See also
- References
3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a human trace amine and the major metabolite of the monoamine neurotransmitter dopamine. It is formed by the introduction of a methyl group to dopamine by the enzyme catechol-O-methyltransferase (COMT). 3-MT can be further metabolized by the enzyme monoamine oxidase (MAO) to form homovanillic acid (HVA), which is then typically excreted in the urine.
== Occurrence == 3-Methoxytyramine occurs naturally in the prickly pear cactus (genus Opuntia), and is in general widespread throughout the Cactaceae. It has also been found in crown gall tumors on Nicotiana sp.
Excerpted from Wikipedia’s “3-O-methyldopamine” article, available under the CC BY-SA 4.0 licence.