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Kyotorphin

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Kyotorphin
Chemical structure of kyotorphin
Names
IUPAC name (2S)-2-amino]-5- (diaminomethylideneamino)pentanoic acid
Other names Kiotorphin
L-Tyrosyl-L-arginine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H23N5O4/c16-11(8-9-3-5-10(21)6-4-9)13(22)20-12(14(23)24)2-1-7-19-15(17)18/h3-6,11-12,21H,1-2,7-8,16H2,(H,20,22)(H,23,24)(H4,17,18,19)/t11-,12-/m0/s1Key: JXNRXNCCROJZFB-RYUDHWBXSA-N
  • InChI=1/C15H23N5O4/c16-11(8-9-3-5-10(21)6-4-9)13(22)20-12(14(23)24)2-1-7-19-15(17)18/h3-6,11-12,21H,1-2,7-8,16H2,(H,20,22)(H,23,24)(H4,17,18,19)/t11-,12-/m0/s1Key: JXNRXNCCROJZFB-RYUDHWBXBC
SMILES
  • O=C(O)(NC(=O)(N)Cc1ccc(O)cc1)CCC/N=C(\N)N
Properties
Chemical formula C15H23N5O4
Molar mass 337.380 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Kyotorphin (L-tyrosyl-L-arginine) is a neuroactive dipeptide which plays a role in pain regulation in the brain. It was first isolated from bovine brain, by Japanese scientists in 1979. Kyotorphin was named for the site of its discovery, Kyoto, Japan and because of its morphine- (or endorphin-) like analgesic activity. Kyotorphin has an analgesic effect, but it does not interact with the opioid receptors. Instead, it acts by releasing met-enkephalin and stabilizing it from degradation. It may also possess properties of neuromediator/neuromodulator. It has been shown that kyotorphin is present in the human cerebrospinal fluid and that its concentration is lower in patients with persistent pain.

References

  1. Takagi H, Shiomi H, Ueda H, Amano H (1979). "A novel analgesic dipeptide from bovine brain is a possible Met-enkephalin releaser". Nature. 282 (5737): 410–2. doi:10.1038/282410a0. PMID 228202. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. Nishimura K, Kaya K, Hazato T, Ueda H, Satoh M, Takagi H (1991). "". Masui (in Japanese). 40 (11): 1686–90. PMID 1766121. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
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