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Morphiceptin

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.[2]

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
  • 74135-04-9 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 106565 N
  • 119303
UNII
  • 97TZA8ANPC Y
  • DTXSID10995574
  • 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).
N verify (what is YN ?)

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

See also edit

References edit

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


morphiceptin, tetrapeptide, that, selective, opioid, receptor, agonist, derived, from, casomorphin, over, times, selectivity, over, opioid, receptors, when, injected, intracerebroventricularly, into, ventricular, system, brain, morphiceptin, analgesic, ed50, n. Morphiceptin is a tetrapeptide Tyr Pro Phe Pro NH2 that is a selective m opioid receptor agonist It is derived from b casomorphin and has over 1 000 times selectivity for m over d 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 m opioid receptor 2 Morphiceptin NamesIUPAC 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 PLO17IdentifiersCAS Number 74135 04 9 Y3D model JSmol Interactive imageChemSpider 106565 NPubChem CID 119303UNII 97TZA8ANPC YCompTox Dashboard EPA DTXSID10995574InChI 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 NKey LSQXZIUREIDSHZ ZJZGAYNASA N NInChI 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 ZJZGAYNABZSMILES c1ccc cc1 C C H C O N2CCC C H 2C O N NC O C H 3CCCN3C O C H Cc4ccc cc4 O NPropertiesChemical formula C28H35N5O5Molar mass 521 6 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Morphiceptin is the 1S 2S 3S 4S form whereas deproceptin is the 1S 2S 3S 4R form 84799 23 5 See also editCasokefamideReferences edit 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 b casomorphins Correlation with the morphine m receptor binding affinity Life Sciences 30 18 1547 1551 doi 10 1016 0024 3205 82 90242 9 PMID 6281604 Retrieved from https en wikipedia org w index php title Morphiceptin amp oldid 1105102058, wikipedia, wiki, book, books, library,

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