5-Methoxytryptamine

Identifiers
IUPAC name 2-(5-Methoxy-1H-indol-3-yl)ethanamine
CAS Number	608-07-1 Y
PubChem CID	1833
IUPHAR/BPS	107
ChemSpider	1767 Y
UNII	3VMW6141KC
KEGG	C05659 Y
ChEBI	CHEBI:2089 Y
ChEMBL	ChEMBL8165 Y
CompTox Dashboard (EPA)	DTXSID60209638
ECHA InfoCard	100.009.231
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.246 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1cc2c(cc1)[nH]cc2CCN)C
InChI 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
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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.^[1] It is biosynthesized via the deacetylation of melatonin in the pineal gland.^[1]

5-MT acts as a full agonist at the 5-HT₁, 5-HT₂, 5-HT₄, 5-HT₆, and 5-HT₇ receptors.^{[2][3][4][5][6][7][8]} It has no affinity for the 5-HT₃ receptor and its affinity for the 5-HT_1E receptor is very weak in comparison to the other 5-HT₁ receptors.^[5][9] Its affinity for the 5-HT_5A receptor is unknown.

Measured affinity for some receptors (incomplete list):

• 5-HT_1B receptors (K_i = 35 nM) ^[10]
• 5-HT_1D receptors (K_i = 7.3 nM)^[11]
• 5-HT_1E receptors (K_i = 3151 nM)^[12]
• 5-HT_1F receptors (K_i = 1166 nM)^[13]
• 5-HT_2A receptors (K_i = 295 nM)^[14]
• 5-HT_2B receptors (K_i = 16.4 nM)^[15]
• 5-HT_2C receptors (K_i = 52.48 nM) ^[16]
• 5-HT₄ receptors (K_i = 501.18 nM)^[17]
• 5-HT₆ receptors (K_i = 69.18 nM)^[18]
• 5-HT₇ receptors (K_i = 5.01 nM)^[19]