5-Methoxytryptamine

5-Methoxytryptamine

Systematic (IUPAC) name
2-(5-Methoxy-1H-indol-3-yl)ethanamine
Identifiers
CAS Number	608-07-1
PubChem	CID 1833
IUPHAR/BPS	107
ChemSpider	1767
KEGG	C05659
ChEBI	CHEBI:2089
ChEMBL	CHEMBL8165
Chemical data
Formula	C11H14N2O
Molar mass	190.242 g/mol
SMILES O(c1cc2c(cc1)ncc2CCN)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 Key:JTEJPPKMYBDEMY-UHFFFAOYSA-N
(verify)

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 it should also be noted that 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.

See also

Indorenate

• 2-Methyl-5-hydroxytryptamine
• 5-Benzyloxytryptamine
• 5-Carboxamidotryptamine
• α-Methyl-5-hydroxytryptamine
• Melatonin

References

1. Galzin AM, Eon MT, Esnaud H, Lee CR, Pévet P, Langer SZ. (1988). "Day-night rhythm of 5-methoxytryptamine biosynthesis in the pineal gland of the golden hamster (Mesocricetus auratus).". J Endocrinol. 118 (3): 389–397. doi:10.1677/joe.0.1180389. PMID 2460575.
2. Wu PH, Gurevich N, Carlen PL. (1988). "Serotonin-1A receptor activation in hippocampal CA1 neurons by 8-hydroxy-2-(di-n-propylamino)tetralin, 5-methoxytryptamine and 5-hydroxytryptamine.". Neurosci Lett. 86 (1): 72–76. doi:10.1016/0304-3940(88)90185-1. PMID 2966313.
3. Yamada J, Sugimoto Y, Yoshikawa T, Horisaka K. (1997). "Hyperglycemia induced by the 5-HT receptor agonist, 5-methoxytryptamine, in rats: involvement of the peripheral 5-HT2A receptor.". Eur J Pharmacol. 323 (2-3): 235–240. doi:10.1016/S0014-2999(97)00029-0. PMID 9128844.
4. Amemiya N, Hatta S, Takemura H, Ohshika H. (1996). "Characterization of the contractile response induced by 5-methoxytryptamine in rat stomach fundus strips.". Eur J Pharmacol. 318 (2-3): 403–409. doi:10.1016/S0014-2999(96)00777-7. PMID 9016931.
5. Craig DA, Eglen RM, Walsh LK, Perkins LA, Whiting RL, Clarke DE. (1990). "5-Methoxytryptamine and 2-methyl-5-hydroxytryptamine-induced desensitization as a discriminative tool for the 5-HT3 and putative 5-HT4 receptors in guinea pig ileum.". Naunyn Schmiedebergs Arch Pharmacol. 342 (1): 9–16. doi:10.1007/bf00178965. PMID 2402303.
6. Boess FG, Monsma FJ Jr, Carolo C, Meyer V, Rudler A, Zwingelstein C, Sleight AJ. (1997). "Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.". Neuropharmacology. 36 (4-5): 713–720. doi:10.1016/S0028-3908(97)00019-1. PMID 9225298.
7. Hemedah M, Coupar IM, Mitchelson FJ. (1999). "[3H]-Mesulergine labels 5-HT7 sites in rat brain and guinea-pig ileum but not rat jejunum.". Br J Pharmacol. 126 (1): 179–188. doi:10.1038/sj.bjp.0702293. PMC 1565797. PMID 10051134.
8. Glennon RA, Dukat M, Westkaemper RB (2000-01-01). "Serotonin Receptor Subtypes and Ligands". American College of Neurophyscopharmacology. Archived from the original on 21 April 2008. Retrieved 2008-04-11.
9. Roth, Brian (2006). The serotonin receptors. Humana Press. p. 133. ISBN 978-1-58829-568-2.