Kyotorphin

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.[1] 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.[2]

Kyotorphin

Names
IUPAC name (2S)-2-[[(2S)-2-Amino-3-(4-hydroxyphenyl)propanoyl]amino]-5- (diaminomethylideneamino)pentanoic acid
Other names Kiotorphin L-Tyrosyl-L-arginine
Identifiers
CAS Number	70904-56-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17537^Y
ChEMBL	ChEMBL273521^Y
ChemSpider	110353^Y
PubChem CID	123804
UNII	02N30CW3X0^Y
CompTox Dashboard (EPA)	DTXSID40221136
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/s1^Y Key: JXNRXNCCROJZFB-RYUDHWBXSA-N^Y 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/s1 Key: JXNRXNCCROJZFB-RYUDHWBXBC
SMILES O=C(O)[C@@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)CCC/N=C(\N)N
Properties
Chemical formula	C15H23N5O4
Molar mass	337.380 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References

1. Takagi H, Shiomi H, Ueda H, Amano H (November 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.
2. Nishimura K, Kaya K, Hazato T, Ueda H, Satoh M, Takagi H (November 1991). "[Kyotorphin like substance in human cerebrospinal fluid of patients with persistent pain]". Masui (in Japanese). 40 (11): 1686–90. PMID 1766121.