5-Methoxytryptamine

5-Methoxytryptamine (5-MT), also known as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. 5-MT has been shown to occur naturally in the body in low levels. It is biosynthesized via the deacetylation of melatonin in the pineal gland.

5-Methoxytryptamine
Identifiers
  • 2-(5-Methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.009.231
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
  • O(c1cc2c(cc1)[nH]cc2CCN)C
  • InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3 Y
  • Key:JTEJPPKMYBDEMY-UHFFFAOYSA-N Y
  (verify)

5-MT acts as a full agonist at the 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors. It has no affinity for the 5-HT3 receptor and its affinity for the 5-HT1E receptor is very weak in comparison to the other 5-HT1 receptors. Its affinity for the 5-HT5A receptor is unknown.

Measured affinity for some receptors (incomplete list):

  • 5-HT1B receptors (Ki = 35 nM)
  • 5-HT1D receptors (Ki = 7.3 nM)
  • 5-HT1E receptors (Ki = 3151 nM)
  • 5-HT1F receptors (Ki = 1166 nM)
  • 5-HT2A receptors (Ki = 295 nM)
  • 5-HT2B receptors (Ki = 16.4 nM)
  • 5-HT2C receptors (Ki = 52.48 nM)
  • 5-HT4 receptors (Ki = 501.18 nM)
  • 5-HT6 receptors (Ki = 69.18 nM)
  • 5-HT7 receptors (Ki = 5.01 nM)
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