5-Methoxytryptamine

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5-Methoxytryptamine
5-methoxytryptamine.png
Identifiers
  • 2-(5-Methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
IUPHAR/BPS
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UNII
KEGG
ChEBI
ChEMBL
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ECHA InfoCard 100.009.231 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H14N2O
Molar mass 190.246 g·mol−1
3D model (JSmol)
  • O(c1cc2c(cc1)[nH]cc2CCN)C
  • 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 Yes check.svgY
  • Key:JTEJPPKMYBDEMY-UHFFFAOYSA-N Yes check.svgY
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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 its affinity for the 5-HT1E receptor is very weak in comparison to the other 5-HT1 receptors. [5] [9] Its affinity for the 5-HT5A receptor is unknown.

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Indorenate

Measured affinity for some receptors (incomplete list):

See also

Related Research Articles

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5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission. The serotonin receptors are activated by the neurotransmitter serotonin, which acts as their natural ligand.

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The 5-HT3 receptor belongs to the Cys-loop superfamily of ligand-gated ion channels (LGICs) and therefore differs structurally and functionally from all other 5-HT receptors (5-hydroxytryptamine, or serotonin receptors) which are G protein-coupled receptors. This ion channel is cation-selective and mediates neuronal depolarization and excitation within the central and peripheral nervous systems.

<span class="mw-page-title-main">HTR3A</span> Protein-coding gene in the species Homo sapiens

5-hydroxytryptamine receptor 3A is a protein that in humans is encoded by the HTR3A gene.

5-HT<sub>4</sub> receptor Protein-coding gene in the species Homo sapiens

5-Hydroxytryptamine receptor 4 is a protein that in humans is encoded by the HTR4 gene.

The 5-HT1 receptors are a subfamily of the 5-HT serotonin receptors that bind to the endogenous neurotransmitter serotonin (also known as 5-hydroxytryptamine, or 5-HT). The 5-HT1 subfamily consists of five G protein-coupled receptors (GPCRs) that share 40% to 63% overall sequence homology, including 5-HT1A, 5-HT1B, 5-HT1D, 5-HT1E, and 5-HT1F. Receptors of the 5-HT1 type, specifically, the 5-HT1A and 5-HT1D receptor subtypes, are present on the cell bodies. Receptors of the 5-HT1 type, specifically, the 5-HT1B and 5-HT1D receptor subtypes, are also present on the nerve terminals. These receptors are broadly distributed throughout the brain and are recognized to play a significant part in regulating synaptic levels of 5-HT.

5-HT<sub>1E</sub> receptor Protein-coding gene in the species Homo sapiens

5-hydroxytryptamine (serotonin) 1E receptor (5-HT1E) is a highly expressed human G-protein coupled receptor that belongs to the 5-HT1 receptor family. The human gene is denoted as HTR1E.

5-HT<sub>1F</sub> receptor Protein-coding gene in the species Homo sapiens

5-hydroxytryptamine (serotonin) receptor 1F, also known as HTR1F is a 5-HT1 receptor protein and also denotes the human gene encoding it.

5-HT<sub>5A</sub> receptor Protein-coding gene in the species Homo sapiens

5-Hydroxytryptamine (serotonin) receptor 5A, also known as HTR5A, is a protein that in humans is encoded by the HTR5A gene. Agonists and antagonists for 5-HT receptors, as well as serotonin uptake inhibitors, present promnesic (memory-promoting) and/or anti-amnesic effects under different conditions, and 5-HT receptors are also associated with neural changes.

5-HT<sub>6</sub> receptor Protein-coding gene in the species Homo sapiens

The 5HT6 receptor is a subtype of 5HT receptor that binds the endogenous neurotransmitter serotonin (5-hydroxytryptamine, 5HT). It is a G protein-coupled receptor (GPCR) that is coupled to Gs and mediates excitatory neurotransmission. HTR6 denotes the human gene encoding for the receptor.

5-HT<sub>7</sub> receptor Protein-coding gene in the species Homo sapiens

The 5-HT7 receptor is a member of the GPCR superfamily of cell surface receptors and is activated by the neurotransmitter serotonin (5-hydroxytryptamine, 5-HT). The 5-HT7 receptor is coupled to Gs (stimulates the production of the intracellular signaling molecule cAMP) and is expressed in a variety of human tissues, particularly in the brain, the gastrointestinal tract, and in various blood vessels. This receptor has been a drug development target for the treatment of several clinical disorders. The 5-HT7 receptor is encoded by the HTR7 gene, which in humans is transcribed into 3 different splice variants.

<span class="mw-page-title-main">5-Carboxamidotryptamine</span> Chemical compound

5-Carboxamidotryptamine (5-CT) is a tryptamine derivative closely related to the neurotransmitter serotonin.

<span class="mw-page-title-main">2-Methyl-5-hydroxytryptamine</span> Chemical compound

2-Methyl-5-hydroxytryptamine (2-Methylserotonin, 2-Methyl-5-HT) is a tryptamine derivative closely related to the neurotransmitter serotonin which acts as a moderately selective full agonist at the 5-HT3 receptor.

<span class="mw-page-title-main">6-Fluoro-DMT</span> Chemical compound

6-Fluoro-N,N-dimethyltryptamine (6-Fluoro-DMT) is a synthetic drug of the tryptamine chemical class.

<span class="mw-page-title-main">Naphthylpiperazine</span> Chemical compound

1-(1-Naphthyl)piperazine (1-NP) is a drug which is a phenylpiperazine derivative. It acts as a non-selective, mixed serotonergic agent, exerting partial agonism at the 5-HT1A, 5-HT1B, 5-HT1D, 5-HT1E, and 5-HT1F receptors, while antagonizing the 5-HT2A, 5-HT2B, and 5-HT2C receptors. It has also been shown to possess high affinity for the 5-HT3, 5-HT5A, 5-HT6, and 5-HT7 receptors, and may bind to 5-HT4 and the SERT as well. In animals it produces effects including hyperphagia, hyperactivity, and anxiolysis, of which are all likely mediated predominantly or fully by blockade of the 5-HT2C receptor.

<span class="mw-page-title-main">5-Benzyloxytryptamine</span> Chemical compound

5-Benzyloxytryptamine (5-BT), is a tryptamine derivative which acts as an agonist at the 5-HT1D, 5-HT2 and 5-HT6 serotonin receptors, and an antagonist of TRPM8.

<span class="mw-page-title-main">5-Chloro-αMT</span> Chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%, and almost assuredly acts as a potent agonist of other serotonin receptors as well.

<span class="mw-page-title-main">Amesergide</span> Chemical compound

Amesergide is a serotonin receptor antagonist of the ergoline and lysergamide families related to methysergide which was under development by Eli Lilly and Company for the treatment of a variety of conditions including depression, anxiety, schizophrenia, male sexual dysfunction, migraine, and thrombosis but was never marketed. It reached phase II clinical trials for the treatment of depression, erectile dysfunction, and premature ejaculation prior to the discontinuation of its development.

References

  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. 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. S2CID   21620262.
  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. 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-Schmiedeberg's Arch Pharmacol. 342 (1): 9–16. doi:10.1007/bf00178965. PMID   2402303. S2CID   24743785.
  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.
  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.
  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