Chemistry:5-Methoxytryptophan

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5-Methoxytryptophan (5-MTP), or 5-methoxy-L-tryptophan, also known as 5-methoxy-α-carboxytryptamine or as cytoguardin, is an endogenous metabolite of tryptophan with anti-inflammatory and anti-fibrotic effects.[1][2][3] It is biosynthesized in two steps by tryptophan hydroxylase (TPH) and then by hydroxyindole O-methyltransferase (HIOMT), with 5-hydroxytryptophan (5-HTP) as a metabolic intermediate.[1][2][3] 5-MTP is also a metabolic precursor of 5-methoxytryptamine.[4] The compound promotes sleep in rodents similarly to melatonin.[5] In contrast to melatonin, 5-MTP did not show affinity for melatonin receptors.[6] It was first described in the scientific literature by at least 1951.[7]

See also

References

  1. ↑ 1.0 1.1 "5-methoxytryptophan: an arsenal against vascular injury and inflammation". Journal of Biomedical Science 27 (1). July 2020. doi:10.1186/s12929-020-00671-w. PMID 32635910. 
  2. ↑ 2.0 2.1 "Control of Tissue Fibrosis by 5-Methoxytryptophan, an Innate Anti-Inflammatory Metabolite". Frontiers in Pharmacology 12. 2021. doi:10.3389/fphar.2021.759199. PMID 34858185. 
  3. ↑ 3.0 3.1 "5-methoxyindole metabolites of L-tryptophan: control of COX-2 expression, inflammation and tumorigenesis". Journal of Biomedical Science 21 (1): 17. March 2014. doi:10.1186/1423-0127-21-17. PMID 24589238. 
  4. ↑ "On the significance of an alternate pathway of melatonin synthesis via 5-methoxytryptamine: comparisons across species". Journal of Pineal Research 61 (1): 27–40. August 2016. doi:10.1111/jpi.12336. PMID 27112772. "5-MT was first detected in human urine in 1963 [126]. It is formed by melatonin deacetylation, 5-methoxytryptophan decarboxylation, and serotonin methylation [17, 127–129].". 
  5. ↑ "Melatonin: effects on brain and behavior". Neuroscience and Biobehavioral Reviews 4 (4): 451–458. 1980. doi:10.1016/0149-7634(80)90034-2. PMID 6110197. 
  6. ↑ "Central melatonin receptors: implications for a mode of action". Experientia 45 (10): 955–965. October 1989. doi:10.1007/BF01953053. PMID 2553471. 
  7. ↑ "395. The synthesis of 5-and 7-methoxytryptophan, and of some derivatives.". Journal of the Chemical Society (Resumed): 1808–1811. 1951. doi:10.1039/JR9510001808. 

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