5-metoxitriptamina

5-metoxitriptamina
Identificadores
Número CAS	608-07-1
PubChem	1833
ChemSpider	1767
UNII	3VMW6141KC
KEGG	C05659
ChEBI	2089
ChEMBL	8165
Datos químicos
Fórmula	C11H14N2O
	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
	[editar datos en Wikidata]

La 5-metoxitriptamina (abreviado 5-MT), también conocida como mexamina, es un derivado de la triptamina estrechamente relacionado con los neurotransmisores serotonina y melatonina. Se ha demostrado que la 5-MT se produce naturalmente en animales en bajos niveles. Se biosintetiza a través de la deacetilación de la melatonina en la glándula pineal.

La 5-MT actúa como un agonista total en los receptores 5-HT₁, 5-HT₂, 5-HT₄, 5-HT₆ y 5-HT₇. No tiene afinidad por el receptor 5-HT₃ y su afinidad por el receptor 5-HT_1E es muy débil en comparación con los otros receptores 5-HT₁. Se desconoce su afinidad por el receptor 5-HT₅.

Afinidad

Afinidad medida para el caso de algunos receptores:

Receptores 5-HT _1B (K_i = 35 nM)
Receptores 5-HT_1D (K_i = 7,3 nM)
Receptores 5-HT _1E (K_i = 3151 nM)
Receptores 5-HT _1F (K_i = 1166 nM)
Receptores 5-HT_2A (K _i = 295 nM)
Receptores 5-HT _2B (K_i = 16,4 nM)
Receptores 5-HT _2C (K_i = 52,48 nM)
Receptores 5-HT ₄ (K_i = 501,18 nM)
Receptores 5-HT ₆ (K_i = 69,18 nM)
Receptores 5-HT ₇ (K_i = 5,01 nM)

Véase también

2-metil-5-hidroxitriptamina
5-Benciloxitriptamina
5-Carboxamidotriptamina
α-metil-5-hidroxitriptamina

Referencias

1 2 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. PMID 2460575. doi:10.1677/joe.0.1180389.
↑ 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. PMID 2966313. doi:10.1016/0304-3940(88)90185-1.
↑ 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. PMID 9128844. doi:10.1016/S0014-2999(97)00029-0.
↑ 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. PMID 9016931. doi:10.1016/S0014-2999(96)00777-7.
1 2 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. PMID 2402303. doi:10.1007/bf00178965.
↑ 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. PMID 9225298. doi:10.1016/S0028-3908(97)00019-1.
↑ 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. PMC 1565797. PMID 10051134. doi:10.1038/sj.bjp.0702293.
↑ «Serotonin Receptor Subtypes and Ligands». American College of Neurophyscopharmacology. 1 de enero de 2000. Archivado desde el original el 21 de abril de 2008. Consultado el 11 de abril de 2008.
↑ 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

Datos: Q4352011
Multimedia: Category:5-Methoxytryptamine / Q4352011

[pmid2460575-1] 1 2 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. PMID 2460575. doi:10.1677/joe.0.1180389.

[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. PMID 2966313. doi:10.1016/0304-3940(88)90185-1.

[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. PMID 9128844. doi:10.1016/S0014-2999(97)00029-0.

[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. PMID 9016931. doi:10.1016/S0014-2999(96)00777-7.

[pmid2402303-5] 1 2 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. PMID 2402303. doi:10.1007/bf00178965.

[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. PMID 9225298. doi:10.1016/S0028-3908(97)00019-1.

[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. PMC 1565797. PMID 10051134. doi:10.1038/sj.bjp.0702293.

[urlSerotonin_Receptor_Subtypes_and_Ligands-8] «Serotonin Receptor Subtypes and Ligands». American College of Neurophyscopharmacology. 1 de enero de 2000. Archivado desde el original el 21 de abril de 2008. Consultado el 11 de abril de 2008.

[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