5-Methoxytryptamine

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5-Methoxytryptamine
File:5-methoxytryptamine.png
Systematic (IUPAC) name
2-(5-Methoxy-1H-indol-3-yl)ethanamine
Identifiers
CAS Number 608-07-1
PubChem CID 1833
IUPHAR/BPS 107
ChemSpider 1767
Chemical data
Formula C11H14N2O
Molar mass 190.242 g/mol[[Script error: No such module "String".]]
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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 synthesized from 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 it should also be noted that 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.

See also

References

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Amino acids
Endocannabinoids
Gasotransmitters
Monoamines
Purines

Adenosine · ADP · AMP · ATP

Trace amines
Others

2-Methyl-5-HT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-HO-αMT • 4-HO-DIPT • 4-HO-MET • 4-MeO-DMT • 4-Methyl-αET • 4-Methyl-αMT • 5-Benzyloxytryptamine • 5-Bromo-DMT • 5-Carboxamidotryptamine • 5-Fluoro-αMT • 5-HO-αMT • 5-HTP • 5-Fluoro-DMT • 5-Methyl-DMT • 5-Methoxytryptamine • 5-MeO-7,N,N-TMT • 5-MeO-αET  • 5-MeO-αMT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MIPT • 5,7-Dihydroxytryptamine • 7-Methyl-αET • 7-Methyl-DMT • αET • αMT • Aeruginascin • AL-37350A • BW-723C86 • Baeocystin • Bufotenidine • Bufotenin • DALT • Desformylflustrabromine • DET • DiPT • DMT • DPT • Ethocybin • EiPT • EMDT • Ethocin • FGIN-127 • FGIN-143 • Ibogaine • Iprocin • MET • MiPT • Miprocin • Melatonin • MS-245 • NAS • NMT • Norbaeocystin • Normelatonin • Oxypertine • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan • Yohimbine • Yuremamine • Zolmitriptan


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  1. ↑ 1.0 1.1 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. 
  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. 
  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. ↑ 5.0 5.1 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. 
  6. ↑ Boess FG, Monsma FJ Jr, 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. 
  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 Freely accessible. PMID 10051134. 
  8. ↑ Glennon RA, Dukat M, Westkaemper RB (2000-01-01). "Serotonin Receptor Subtypes and Ligands". American College of Neurophyscopharmacology. Retrieved 2008-04-11. 
  9. ↑ Roth, Brian (2006). The serotonin receptors. Humana Press. p. 133. ISBN 1588295680, 9781588295682 Check |isbn= value: invalid character (help).  More than one of |pages= and |page= specified (help)
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