5-Methoxytryptamine

5-Methoxytryptamine
Clinical data
Other names	5-MeO-T; 5-OMe-T; 5-MeO-TPA; 5-MT; MT; 5-Hydroxytryptamine methyl ether; Serotonin methyl ether; O-Methylserotonin; O-Methyl-5-HT; Mexamine; Meksamin; Mekasamin; PAL-234
Drug class	Serotonin receptor agonist
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, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or O-methylserotonin and 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 formed via the deacetylation of melatonin in the pineal gland.^[1]

Pharmacology

Pharmacodynamics

5-MT acts as a full agonist of the serotonin 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.^{[citation needed]}

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]

It is an extremely potent serotonin 5-HT_2A receptor agonist in vitro, with an EC₅₀Tooltip half-maximal effective concentration of 0.503 nM.^[20] This was more potent than any other tryptamine evaluated in two large series of compounds.^[20]^[21] For comparison, 5-MeO-DMT had an EC₅₀ of 3.87 nM (7.7-fold lower) and DMT had an EC₅₀ of 38.3 nM (76-fold lower).^[21]

References

^ ^a ^b 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. S2CID 21620262.
^ 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.
^ ^a ^b 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-Schmiedeberg's Arch Pharmacol. 342 (1): 9–16. doi:10.1007/bf00178965. PMID 2402303. S2CID 24743785.
^ 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. S2CID 41813873.
^ 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
^ ^a ^b Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorg Med Chem Lett. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
^ ^a ^b Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.

External links

5-Methoxytryptamine - isomer design

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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. S2CID 21620262.

[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-Schmiedeberg's Arch Pharmacol. 342 (1): 9–16. doi:10.1007/bf00178965. PMID 2402303. S2CID 24743785.

[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. S2CID 41813873.

[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

[BloughLandavazoPartilla2014-20] Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorg Med Chem Lett. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.

[BloughLandavazoDecker2014-21] Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.

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5-Methoxytryptamine

Contents

Pharmacology

Pharmacodynamics

See also

References

External links