Morphiceptin: Difference between revisions
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| verifiedrevid = 442867817 |
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| ImageFile = Morphiceptin.svg |
| ImageFile = Morphiceptin.svg |
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| IUPACName = (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 |
| IUPACName = (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<ref name=ChemBase>{{cite web|title=Morphiceptin|url=http://www.chembase.com/cbid_119303.htm|publisher=ChemBase|access-date=1 August 2011|archive-url=https://web.archive.org/web/20120315180103/http://www.chembase.com/cbid_119303.htm|archive-date=15 March 2012|url-status=dead}}</ref> |
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| OtherNames = Tyr-Pro-Phe-Pro-NH2, PLO17 |
| OtherNames = Tyr-Pro-Phe-Pro-NH2, PLO17 |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 87777-29-5 |
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| CASNo = 74135-04-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 97TZA8ANPC |
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| PubChem = 119303 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 106565 |
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| SMILES = 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 |
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| 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 |
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| InChIKey = LSQXZIUREIDSHZ-ZJZGAYNABZ |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Solubility = }} |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = LSQXZIUREIDSHZ-ZJZGAYNASA-N }} |
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| Autoignition = }} |
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| AutoignitionPt = }} |
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'''Morphiceptin''' is a tetrapeptide (Tyr-Pro-Phe-Pro-NH<sub>2</sub>) that is a selective [[mu Opioid receptor|μ-opioid receptor]] [[agonist]]. It is derived from [[Casomorphin|β-casomorphin]] and has over |
'''Morphiceptin''' is a [[tetrapeptide]] (Tyr-Pro-Phe-Pro-NH<sub>2</sub>) that is a [[binding selectivity|selective]] [[mu Opioid receptor|μ-opioid receptor]] [[agonist]]. It is derived from [[Casomorphin|β-casomorphin]] and has over 1,000 times selectivity for μ- over [[delta Opioid receptor|δ-opioid receptors]]. When injected intracerebroventricularly (into the ventricular system of the brain), morphiceptin had an [[analgesic]] ED<sub>50</sub> 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.<ref name="Chang 1982">{{cite journal|last=Chang|first=K|title=Analgesic activity of intracerebroventricular administration of morphiceptin and β-casomorphins: Correlation with the morphine (μ) receptor binding affinity|journal=Life Sciences|date=3 May 1982|volume=30|issue=18|pages=1547–1551|doi=10.1016/0024-3205(82)90242-9|pmid=6281604}}</ref> |
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Morphiceptin is the (1S,2S,3S,4S)-form whereas [[deproceptin]] is the (1S,2S,3S,4R)-form [84799-23-5]. |
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== See also == |
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* [[Casokefamide]] |
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{{Reflist}} |
{{Reflist}} |
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{{ |
{{Opioidergics}} |
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[[Category: |
[[Category:Analgesics]] |
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[[Category: |
[[Category:Opioid peptides]] |
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[[Category:Tetrapeptides]] |