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3-Methoxytyramine

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.

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

Biological activity

Originally thought to be physiologically inactive, 3-MT was subsequently found to act as an agonist of the rodent and human TAAR1. 3-MT can induce weak hyperlocomotion in mice and this effect is partially attenuated in TAAR1 knockout mice.

References

References

  1. (October 2016). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomed. Pharmacother..
  2. Neuwinger, Hans Dieter. (1996). "African ethnobotany: poisons and drugs: chemistry, pharmacology, toxicology". CRC Press.
  3. Smith T. A.. (1977). "Phenethylamine and related compounds in plants". Phytochemistry.
  4. Mitchell S. D.. (1984). "Enhanced 3-methoxytyramine levels in crown gall tumours and other undifferentiated plant tissues". Biochem. J..
  5. (2010). "The dopamine metabolite 3-methoxytyramine is a neuromodulator". PLOS ONE.
  6. (January 2011). "The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity". Journal of Neurochemistry.
  7. (October 2010). "The dopamine metabolite 3-methoxytyramine is a neuromodulator". PLOS ONE.
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methoxyphenethylamines phenethylamine-alkaloids phenols taar1-agonists trace-amines aminoethyl-compounds
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