5-Methoxytryptamine

5-Methoxytryptamine
Identifiers
	IUPAC name 2-(5-Methoxy-1H-indol-3-yl)ethanamine;
CAS Number	608-07-1 ;
PubChem CID	1833;
IUPHAR/BPS	107;
ChemSpider	1767 ;
UNII	3VMW6141KC;
KEGG	C05659 ;
ChEBI	CHEBI:2089 ;
ChEMBL	ChEMBL8165 ;
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 ; 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 is 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 (not a complete 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]

References

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.
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.
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.
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.
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.
Boess FG, Monsma Jr FJ, 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.
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.
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.
Roth, Brian (2006). The serotonin receptors. Humana Press. p. 133. ISBN 978-1-58829-568-2.
S. Nigra / Domenech T, et al., 1997
Cortex / PEROUTKA ET AL., 1989
Cloned / ZGOMBICK JM, ET AL., 1992
Cloned / Adham N, et al., 1992
Cortex / HOYER ET AL., 1987
Cortex / WAINSCOTT DB, ET AL., 1996
Cloned / BONHAUS DW, ET AL., 1997
Caudate / ANSANAY H, ET AL.,1996
Cloned / Hirst WD, et.al.,2003
Cloned / BOESS FG, ET AL., 1994

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[pmid2460575-1] 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.

[pmid2966313-2] 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.

[pmid9128844-3] 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.

[pmid9016931-4] 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.

[pmid2402303-5] 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.

[pmid9225298-6] Boess FG, Monsma Jr FJ, 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.

[pmid10051134-7] 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.

[urlSerotonin_Receptor_Subtypes_and_Ligands-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.

[bookThe_Serotonin_Receptors-9] Roth, Brian (2006). The serotonin receptors. Humana Press. p. 133. ISBN 978-1-58829-568-2.

[Domenech-10] S. Nigra / Domenech T, et al., 1997

[PEROUTKA-11] Cortex / PEROUTKA ET AL., 1989

[ZGOMBICK-12] Cloned / ZGOMBICK JM, ET AL., 1992

[Adham-13] Cloned / Adham N, et al., 1992

[HOYER-14] Cortex / HOYER ET AL., 1987

[WAINSCOTT-15] Cortex / WAINSCOTT DB, ET AL., 1996

[BONHAUS-16] Cloned / BONHAUS DW, ET AL., 1997

[ANSANAY-17] Caudate / ANSANAY H, ET AL.,1996

[Hirst-18] Cloned / Hirst WD, et.al.,2003

[BOESS-19] Cloned / BOESS FG, ET AL., 1994

5-Methoxytryptamine

See also

References