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Key Documents

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:
Molecular Weight:
521.61
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
Pricing and availability is not currently available.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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K J Chang et al.
Science (New York, N.Y.), 212(4490), 75-77 (1981-04-03)
The synthetic peptide NH2-Tyr-Pro-Phe-Pro-CONH2 (morphiceptin), which is the amide of a fragment of the milk protein beta-casein, has morphinelike activities and is highly specific for morphine (mu) receptors but not for enkephalin (delta) receptors. It is as active as morphine
Anna Janecka et al.
Biochemical pharmacology, 71(1-2), 188-195 (2005-11-18)
Cyclic analogs of the opioid peptides endomorphin-2 and morphiceptin of the type Tyr-X-Phe-Phe-Y-NH2 and Tyr-X-Phe-D-Pro-Y-NH2 (X = Lys or Asp and Y = Lys or Asp), respectively, were synthesized in order to test their structure-activity relationships. Antinociceptive activity of the
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
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
Toru Ota et al.
Journal of agricultural and food chemistry, 53(15), 6112-6116 (2005-07-21)
Morphiceptin (Tyr-Pro-Phe-Pro-NH(2)), tetrapeptide, was synthesized using dipeptidyl aminopeptidase IV (DP IV, EC 3.4.14.5) derived from Aspergillus oryzae RIB 915 as a catalyst. Tyr-Pro-OEt was incubated with Phe-Pro-NH(2) in the presence of DP IV under various conditions of temperature, concentrations of

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