5-Methoxytryptamine Explained

Verifiedrevid:	477225243
Iupac Name:	2-(5-Methoxy-1H-indol-3-yl)ethanamine
Cas Number:	608-07-1
Unii:	3VMW6141KC
Pubchem:	1833
Iuphar Ligand:	107
Chemspiderid:	1767
Kegg:	C05659
Chebi:	2089
Chembl:	8165
C:	11
H:	14
N:	2
O:	1
Smiles:	O(c1cc2c(cc1)[nH]cc2CCN)C
Stdinchi:	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
Stdinchikey:	JTEJPPKMYBDEMY-UHFFFAOYSA-N

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.

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.^[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]

See also

• 2-Methyl-5-hydroxytryptamine
• 5-Benzyloxytryptamine
• 5-Carboxamidotryptamine
• 5-MeO-DMT
• α-Methyl-5-hydroxytryptamine

Notes and References

1. 10.1677/joe.0.1180389 . Galzin AM, Eon MT, Esnaud H, Lee CR, Pévet P, Langer SZ . Day-night rhythm of 5-methoxytryptamine biosynthesis in the pineal gland of the golden hamster (Mesocricetus auratus). . J. Endocrinol. . 118 . 3 . 389–397 . 1988 . 2460575 .
2. 10.1016/0304-3940(88)90185-1 . Wu PH, Gurevich N, Carlen PL . 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 . 1988 . 2966313 . 21620262 .
3. 10.1016/S0014-2999(97)00029-0 . Yamada J, Sugimoto Y, Yoshikawa T, Horisaka K . 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 . 1997 . 9128844 .
4. 10.1016/S0014-2999(96)00777-7 . Amemiya N, Hatta S, Takemura H, Ohshika H . Characterization of the contractile response induced by 5-methoxytryptamine in rat stomach fundus strips. . Eur J Pharmacol . 318 . 2–3 . 403–409 . 1996 . 9016931 .
5. Craig DA, Eglen RM, Walsh LK, Perkins LA, Whiting RL, Clarke DE . 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 . 1990 . 2402303 . 10.1007/bf00178965. 24743785 .
6. 10.1016/S0028-3908(97)00019-1 . Boess FG, Monsma Jr FJ, Carolo C, Meyer V, Rudler A, Zwingelstein C, Sleight AJ . Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells. . Neuropharmacology . 36 . 4–5 . 713–720 . 1997 . 9225298 . 41813873 .
7. Hemedah M, Coupar IM, Mitchelson FJ . [3H]-Mesulergine labels 5-HT7 sites in rat brain and guinea-pig ileum but not rat jejunum. . Br J Pharmacol. 126 . 1 . 179–188 . 1999 . 10051134 . 10.1038/sj.bjp.0702293 . 1565797 .
8. Web site: Serotonin Receptor Subtypes and Ligands . 2008-04-11 . Glennon RA, Dukat M, Westkaemper RB . 2000-01-01 . American College of Neurophyscopharmacology . https://web.archive.org/web/20080421160353/http://www.acnp.org/g4/GN401000039/Ch039.html. 21 April 2008 . live.
9. Book: Roth, Brian . The serotonin receptors . 2006 . Humana Press . 978-1-58829-568-2 . 133 .
10. S. Nigra / Domenech T, et al., 1997
11. Cortex / PEROUTKA ET AL., 1989
12. Cloned / ZGOMBICK JM, ET AL., 1992
13. Cloned / Adham N, et al., 1992
14. Cortex / HOYER ET AL., 1987
15. Cortex / WAINSCOTT DB, ET AL., 1996
16. Cloned / BONHAUS DW, ET AL., 1997
17. Caudate / ANSANAY H, ET AL.,1996
18. Cloned / Hirst WD, et.al.,2003
19. Cloned / BOESS FG, ET AL., 1994