Morphiceptin

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Morphiceptin
Names
IUPAC name
(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide[1]
Other names
Tyr-Pro-Phe-Pro-NH2, PLO17
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • 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/s1 ☒N
    Key: LSQXZIUREIDSHZ-ZJZGAYNASA-N ☒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/s1
    Key: LSQXZIUREIDSHZ-ZJZGAYNABZ
  • c1ccc(cc1)C[C@@H](C(=O)N2CCC[C@H]2C(=O)N)NC(=O)[C@@H]3CCCN3C(=O)[C@H](Cc4ccc(cc4)O)N
Properties
C28H35N5O5
Molar mass 521.6 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Morphiceptin is a

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.[2]

Morphiceptin is the (1S,2S,3S,4S)-form whereas deproceptin is the (1S,2S,3S,4R)-form [84799-23-5].

See also

References

  1. ^ "Morphiceptin". ChemBase. Archived from the original on 15 March 2012. Retrieved 1 August 2011.
  2. PMID 6281604
    .


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