Morphiceptin - Misplaced Pages

Morphiceptin
Names

IUPAC name (2S)-1--N--1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide
Other names Tyr-Pro-Phe-Pro-NH2, PLO17
Identifiers
CAS Number	74135-04-9
3D model (JSmol)	Interactive image
ChemSpider	106565
PubChem CID	119303
UNII	97TZA8ANPC
CompTox Dashboard (EPA)	DTXSID10995574
InChI InChI=1S/C28H35N5O5/c29-21(16-19-10-12-20(34)13-11-19)27(37)33-15-5-9-24(33)26(36)31-22(17-18-6-2-1-3-7-18)28(38)32-14-4-8-23(32)25(30)35/h1-3,6-7,10-13,21-24,34H,4-5,8-9,14-17,29H2,(H2,30,35)(H,31,36)/t21-,22-,23-,24-/m0/s1Key: LSQXZIUREIDSHZ-ZJZGAYNASA-N InChI=1/C28H35N5O5/c29-21(16-19-10-12-20(34)13-11-19)27(37)33-15-5-9-24(33)26(36)31-22(17-18-6-2-1-3-7-18)28(38)32-14-4-8-23(32)25(30)35/h1-3,6-7,10-13,21-24,34H,4-5,8-9,14-17,29H2,(H2,30,35)(H,31,36)/t21-,22-,23-,24-/m0/s1Key: LSQXZIUREIDSHZ-ZJZGAYNABZ
SMILES c1ccc(cc1)C(C(=O)N2CCC2C(=O)N)NC(=O)3CCCN3C(=O)(Cc4ccc(cc4)O)N
Properties
Chemical formula	C₂₈H₃₅N₅O₅
Molar mass	521.6 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

Morphiceptin is a tetrapeptide (Tyr-Pro-Phe-Pro-NH₂) that is a selective μ-opioid receptor agonist. It is derived from β-casomorphin and has over 1,000 times selectivity for μ- over δ-opioid receptors. When injected intracerebroventricularly (into the ventricular system of the brain), morphiceptin had an analgesic ED₅₀ of 1.7 nmol per animal. The analgesic effects of morphiceptin were reversed by naloxone, meaning that the analgesic effect is mediated by the μ-opioid receptor.

Morphiceptin is the (1S,2S,3S,4S)-form whereas deproceptin is the (1S,2S,3S,4R)-form .

References

"Morphiceptin". ChemBase. Archived from the original on 15 March 2012. Retrieved 1 August 2011.
Chang, K (3 May 1982). "Analgesic activity of intracerebroventricular administration of morphiceptin and β-casomorphins: Correlation with the morphine (μ) receptor binding affinity". Life Sciences. 30 (18): 1547–1551. doi:10.1016/0024-3205(82)90242-9. PMID 6281604.