5-Methoxytryptophan

5-Methoxytryptophan
Clinical data
Other names5-MTP; 5-Methoxy-L-tryptophan; L-5-Methoxytryptophan; 5-MeO-tryptophan; α-Carboxy-5-methoxytryptamine; 5-Methoxy-α-carboxytryptamine; Cytoguardin
ATC code
  • None
Identifiers
  • (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H14N2O3
Molar mass234.255 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1)NC=C2C[C@@H](C(=O)O)N
  • InChI=1S/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)/t10-/m0/s1
  • Key:KVNPSKDDJARYKK-JTQLQIEISA-N

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. ^ a b Wu KK, Kuo CC, Yet SF, Lee CM, Liou JY (July 2020). "5-methoxytryptophan: an arsenal against vascular injury and inflammation". Journal of Biomedical Science. 27 (1) 79. doi:10.1186/s12929-020-00671-w. PMC 7341587. PMID 32635910.
  2. ^ a b Wu KK (2021). "Control of Tissue Fibrosis by 5-Methoxytryptophan, an Innate Anti-Inflammatory Metabolite". Frontiers in Pharmacology. 12 759199. doi:10.3389/fphar.2021.759199. PMC 8632247. PMID 34858185.
  3. ^ a b Wu KK, Cheng HH, Chang TC (March 2014). "5-methoxyindole metabolites of L-tryptophan: control of COX-2 expression, inflammation and tumorigenesis". Journal of Biomedical Science. 21 (1): 17. doi:10.1186/1423-0127-21-17. PMC 3975872. PMID 24589238.
  4. ^ Tan DX, Hardeland R, Back K, Manchester LC, Alatorre-Jimenez MA, Reiter RJ (August 2016). "On the significance of an alternate pathway of melatonin synthesis via 5-methoxytryptamine: comparisons across species". Journal of Pineal Research. 61 (1): 27–40. 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. ^ Datta PC, King MG (1980). "Melatonin: effects on brain and behavior". Neuroscience and Biobehavioral Reviews. 4 (4): 451–458. doi:10.1016/0149-7634(80)90034-2. PMID 6110197.
  6. ^ Morgan PJ, Williams LM (October 1989). "Central melatonin receptors: implications for a mode of action". Experientia. 45 (10): 955–965. doi:10.1007/BF01953053. PMID 2553471.
  7. ^ Marchant RH, Harvey DG (1951). "395. The synthesis of 5-and 7-methoxytryptophan, and of some derivatives". Journal of the Chemical Society (Resumed): 1808–1811. doi:10.1039/JR9510001808.
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