N-Methyltyramine

Not to be confused with other methyltyramines.
Not to be confused with N-Methyltryptamine.
N-Methyltyramine
Names
Preferred IUPAC name
4-[2-(Methylamino)ethyl]phenol
Other names
Methyl-4-tyramine; 4-Hydroxy-N-methylphenethylamine; p-(2-Methylaminoethyl)phenol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.120 Edit this at Wikidata
UNII
  • InChI=1S/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3 checkY
    Key: AXVZFRBSCNEKPQ-UHFFFAOYSA-N checkY
  • InChI=1/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3
    Key: AXVZFRBSCNEKPQ-UHFFFAOYAV
  • Oc1ccc(cc1)CCNC
Properties
C9H13NO
Molar mass 151.209 g·mol−1
Appearance colorless crystalline solid
Density 1.03 g/mL
Melting point 130 to 131 °C (266 to 268 °F; 403 to 404 K)
Boiling point 271 °C (520 °F; 544 K) (183-185 °C at 9mm; 135 °C at 0.05 mm)
moderately soluble in water
Hazards
Flash point 120 °C (248 °F; 393 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Methyltyramine (NMT), also known as 4-hydroxy-N-methylphenethylamine, is a human trace amine[1][2] and natural phenethylamine alkaloid found in a variety of plants.[3] As the name implies, it is the N-methyl analog of tyramine, which is a well-known biogenic trace amine with which NMT shares many pharmacological properties. Biosynthetically, NMT is produced by the N-methylation of tyramine via the action of the enzyme phenylethanolamine N-methyltransferase in humans[1][2] and tyramine N-methyltransferase in plants.[4]

  1. ^ a b Cite error: The named reference Trace amine template 1 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference Trace amine template 2 was invoked but never defined (see the help page).
  3. ^ T. A. Smith (1977). "Phenethylamine and related compounds in plants." Phytochemistry 16 9 – 18.
  4. ^ Tyrosine metabolism - Reference pathway Archived 2019-07-26 at the Wayback Machine, Kyoto Encyclopedia of Genes and Genomes (KEGG)