3-Methoxytyramine

3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a human trace amine that occurs as a metabolite of the neurotransmitter dopamine.^[1] It is formed by the introduction of a methyl group to dopamine by the enzyme catechol-O-methyl transferase (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.

3-Methoxytyramine

Names
Preferred IUPAC name 4-(2-Aminoethyl)-2-methoxyphenol
Other names 3-O-Methyldopamine
Identifiers
CAS Number	554-52-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:1582
ChemSpider	1606 N
ECHA InfoCard	100.122.789
IUPHAR/BPS	6642
MeSH	3-methoxytyramine
PubChem CID	1669
UNII	JCH2767EDP Y
CompTox Dashboard (EPA)	DTXSID40862189
InChI InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3 N Key: DIVQKHQLANKJQO-UHFFFAOYSA-N N InChI=1/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3 Key: DIVQKHQLANKJQO-UHFFFAOYAB
SMILES COc1cc(ccc1O)CCN
Properties
Chemical formula	C9H13NO2
Molar mass	167.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Originally thought to be physiologically inactive, 3-MT has recently been shown to act as an agonist of human TAAR1.^[1][2]

Occurrence

3-Methoxytyramine occurs naturally in the prickly pear cactus (genus Opuntia),^[3] and is in general widespread throughout the Cactaceae.^[4] It has also been found in crown gall tumors on Nicotiana sp.^[5]

In humans, 3-methoxytyramine is a trace amine that occurs as a metabolite of dopamine.^[1]

Biosynthetic pathways for catecholamines and trace amines in the human brain[6][7][8] L-Phenylalanine L-Tyrosine L-DOPA Epinephrine Phenethylamine p-Tyramine Dopamine Norepinephrine N-Methylphenethylamine N-Methyltyramine p-Octopamine Synephrine 3-Methoxytyramine AADC AADC AADC primary pathway PNMT PNMT PNMT PNMT AAAH AAAH brain CYP2D6 minor pathway COMT DBH DBH In humans, catecholamines and phenethylaminergic trace amines are derived from the amino acid L-phenylalanine.

See also

• Tyramine
• 3,4-Dimethoxyphenethylamine

References

1. Khan MZ, Nawaz W (October 2016). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomed. Pharmacother. 83: 439–449. doi:10.1016/j.biopha.2016.07.002. PMID 27424325.
2. Sotnikova TD, Beaulieu JM, Espinoza S, et al. (2010). "The dopamine metabolite 3-methoxytyramine is a neuromodulator". PLOS ONE. 5 (10): e13452. Bibcode:2010PLoSO...513452S. doi:10.1371/journal.pone.0013452. PMC 2956650. PMID 20976142.
3. Neuwinger HD (1996). "Cactaceae". African ethnobotany: poisons and drugs: chemistry, pharmacology, toxicology. CRC Press. p. 271. ISBN 978-3-8261-0077-2. Retrieved on June 12, 2009 through Google Book Search.
4. Smith T. A. (1977). "Phenethylamine and related compounds in plants". Phytochemistry. 16 (1): 9–18. Bibcode:1977PChem..16....9S. doi:10.1016/0031-9422(77)83004-5.
5. Mitchell S. D., Firmin J. L., Gray D. O. (1984). "Enhanced 3-methoxytyramine levels in crown gall tumours and other undifferentiated plant tissues". Biochem. J. 221 (3): 891–5. doi:10.1042/bj2210891. PMC 1144120. PMID 6477503.
6. Broadley KJ (March 2010). "The vascular effects of trace amines and amphetamines". Pharmacology & Therapeutics. 125 (3): 363–375. doi:10.1016/j.pharmthera.2009.11.005. PMID 19948186.
7. Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends in Pharmacological Sciences. 26 (5): 274–281. doi:10.1016/j.tips.2005.03.007. PMID 15860375.
8. Wang X, Li J, Dong G, Yue J (February 2014). "The endogenous substrates of brain CYP2D". European Journal of Pharmacology. 724: 211–218. doi:10.1016/j.ejphar.2013.12.025. PMID 24374199.