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M4264

Sigma-Aldrich

Morphiceptin hydrochloride

≥97% (HPLC)

Synonym(s):

β-Casomorphin 1-4 amide, Tyr-Pro-Phe-Pro-NH2

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About This Item

Empirical Formula (Hill Notation):
C28H35N5O5
CAS Number:
87777-29-5
Molecular Weight:
521.61
MDL number:
MFCD00133541
UNSPSC Code:
12352200
PubChem Substance ID:
24896813

assay

≥97% (HPLC)

storage temp.

−20°C

SMILES string

Cl.NC(Cc1ccc(O)cc1)C(=O)N2CCCC2C(=O)NC(Cc3ccccc3)C(=O)N4CCCC4C(N)=O

InChI

1S/C28H35N5O5.ClH/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);1H

InChI key

ARSDMYCQCLQDBN-UHFFFAOYSA-N

Biochem/physiol Actions

Agonist for μ opioid receptors

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
090H58305
090H58304

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R Goswami et al.
Journal of neurochemistry, 70(4), 1376-1382 (1998-04-02)
The mechanism by which opiates affect fetal development is unknown, but one potential target is the programmed cell death (apoptosis) pathway of neurons. Apoptosis was induced in both primary neuronal cultures from embryonic day 7 cerebral hemispheres of chick brain
Katarzyna Gach et al.
Peptides, 31(8), 1617-1624 (2010-05-04)
Morphiceptin (Tyr-Pro-Phe-Pro-NH(2)), a tetrapeptide present in the enzymatic digest of bovine beta-casein, is a selective ligand of the mu-opioid receptor. In the present study, we describe the synthesis of a series of novel morphiceptin analogs modified in positions 1-3. Two
Jakub Fichna et al.
Biochemical and biophysical research communications, 320(2), 531-536 (2004-06-29)
Analogs of morphiceptin (Tyr-Pro-Phe-Pro-NH2), a mu-selective opioid receptor ligand, with position 3-modifications, including altered size, lipophilicity, and electronic character, while maintaining aromaticity were synthesized. The activity of the new analogs in in vitro assays and in in vivo hot-plate test
Paolo Grieco et al.
Journal of medicinal chemistry, 48(9), 3153-3163 (2005-04-29)
We describe the design, the conformational behavior, and the biological activity at the mu-opioid receptor of new morphiceptin analogues. In these analogues a recently described dipeptide mimetic structure replaces both the N- and the C-terminal Xaa-Pro dipeptide of morphiceptin. Conformational
Jakub Fichna et al.
Peptides, 29(4), 633-638 (2008-02-01)
The morphiceptin-derived peptide [Dmt1, d-1-Nal3]morphiceptin, labeled mu-opioid receptor (MOP) with very high affinity and selectivity in the receptor binding assays. In the mouse hot plate test, [Dmt1, d-1-Nal3]morphiceptin given intracerebroventricularly (i.c.v.) produced profound supraspinal analgesia, being approximately 100-fold more potent
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