Kyotorphin

Kyotorphin

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^N
PubChem	123804
ChemSpider	110353^Y
ChEBI	CHEBI:17537^Y
ChEMBL	CHEMBL273521^Y
Jmol-3D images	Image 1
SMILES O=C(O)[C@@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)CCC/N=C(\N)N
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
Properties
Molecular formula	C₁₅H₂₃N₅O₄
Molar mass	337.37 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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]

References

^ 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.
^ 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]" (in Japanese). Masui 40 (11): 1686–90. PMID 1766121.