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Merck
CN

E3148

Sigma-Aldrich

Endomorphin 2

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About This Item

Empirical Formula (Hill Notation):
C32H37N5O5
CAS Number:
141801-26-5
Molecular Weight:
571.67
MDL number:
MFCD01321064
UNSPSC Code:
12352200
PubChem Substance ID:
329799042

Key Documents

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storage temp.

−20°C

SMILES string

N[C@@H](Cc1ccc(O)cc1)C(=O)N2CCC[C@H]2C(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H](Cc4ccccc4)C(N)=O

InChI

1S/C32H37N5O5/c33-25(18-23-13-15-24(38)16-14-23)32(42)37-17-7-12-28(37)31(41)36-27(20-22-10-5-2-6-11-22)30(40)35-26(29(34)39)19-21-8-3-1-4-9-21/h1-6,8-11,13-16,25-28,38H,7,12,17-20,33H2,(H2,34,39)(H,35,40)(H,36,41)/t25-,26-,27-,28-/m0/s1

InChI key

XIJHWXXXIMEHKW-LJWNLINESA-N

Gene Information

human ... OPRM1(4988)
mouse ... OPRM1(18390)
rat ... OPRM1(25601)

Amino Acid Sequence

Tyr-Pro-Phe-Phe-NH2

General description

Endomorphin 2 is an endogenous ligand for μ-opioid receptor (MOR). It is a neuropeptide and has the sequence Tyr-Pro-Phe-Phe-NH2. It has a greater affinity for MOR1 receptor than MOR2. It resides in primary sensory afferent fibers, and might be the predominant ligand to regulate pain perception. In dynorphin-induced allodynia mice models, endomorphin has anti-allodynic effects. In tail flick test, it produces short-lived antinociception, which is naloxone-sensitive.

Biochem/physiol Actions

Potent, selective endogenous μ opioid receptor agonist.

Legal Information

Sold under license to US patent number 6,303,578

Storage Class Code

13 - Non 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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
044M4750V
071M4806V
049K4807
048K4851
067K4852

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Jakub Fichna et al.
Bioorganic & medicinal chemistry letters, 18(4), 1350-1353 (2008-01-22)
The mu-opioid agonists endomorphin-1 (Tyr-Pro-Trp-Phe-NH(2)) and endomorphin-2 (Tyr-Pro-Phe-Phe-NH(2)) exhibit an extremely high selectivity for the mu-opioid receptor and thus represent a potential framework for modification into mu-antagonists. Here we report on the synthesis and biological evaluation of novel [d-2-Nal(4)]endomorphin-2 analogs
Csaba Tömböly et al.
Journal of medicinal chemistry, 51(1), 173-177 (2007-12-08)
The constitutional similarity with different secondary structure preference between the Aba-Gly and the spiro-Aba-Gly scaffolds were exploited to design the novel endomorphin-2 analogs Tyr-spiro-( R/ S)-Aba-Gly-Phe-NH(2) ( 1 and 2) and Tyr-( R/ S)-Aba-Gly-Phe-NH(2) ( 3 and 4). The (
Steven Ballet et al.
Journal of medicinal chemistry, 49(13), 3990-3993 (2006-06-23)
The Aba-Gly scaffold, incorporated into Dmt-Tic ligands (H-Dmt-Tic-Gly-NH-CH2-Ph, H-Dmt-Tic-Gly-NH-Ph, H-Dmt-Tic-NH-CH2-Bid), exhibited mixed micro/delta or delta opioid receptor activities with micro agonism. Substitution of Tic by Aba-Gly coupled to -NH-CH2-Ph (1), -NH-Ph (2), or -Bid (Bid=1H-benzimidazole-2-yl) (3) shifted affinity (Ki(micro)=0.46, 1.48
L S Stone et al.
Neuroreport, 8(14), 3131-3135 (1997-10-23)
Two highly-selective mu-opioid receptor agonists, endomorphin-1 and -2, were recently purified from bovine brain and are postulated to be endogenous mu-opioid receptor ligands. We sought to determine the effects of these ligands at the spinal level in mice. Endomorphin-1 and
S Martin-Schild et al.
Peptides, 19(10), 1783-1789 (1999-01-08)
Evidence is presented that the recently discovered endogenous mu-selective agonist, endomorphin-2, is localized in primary sensory afferents. Endomorphin-2-like immunoreactivity was found to be colocalized in a subset of substance P- and mu opiate receptor-containing fibers in the superficial laminae of
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