Skip to Content
Merck
All Photos(1)

Key Documents

E3148

Sigma-Aldrich

Endomorphin 2

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C32H37N5O5
CAS Number:
Molecular Weight:
571.67
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

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.[1] It resides in primary sensory afferent fibers, and might be the predominant ligand to regulate pain perception.[2] In dynorphin-induced allodynia mice models, endomorphin has anti-allodynic effects. In tail flick test, it produces short-lived antinociception, which is naloxone-sensitive.[3]

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

I E Goldberg et al.
The Journal of pharmacology and experimental therapeutics, 286(2), 1007-1013 (1998-08-08)
The recently isolated peptides endomorphin-1 and endomorphin-2 have been suggested to be the endogenous ligands for the mu receptor. In traditional opioid receptor binding assays in mouse brain homogenates, both endomorphin-1 and endomorphin-2 competed both mu1 and mu2 receptor sites
Gianfranco Balboni et al.
Journal of medicinal chemistry, 49(18), 5610-5617 (2006-09-01)
Substitution of Gly with side-chain-protected or unprotected Lys in lead compounds containing the opioid pharmacophore Dmt-Tic [H-Dmt-Tic-Gly-NH-CH(2)-Ph, mu agonist/delta antagonist; H-Dmt-Tic-Gly-NH-Ph, mu agonist/delta agonist; and H-Dmt-Tic-NH-CH(2)-Bid, delta agonist (Bid = 1H-benzimidazole-2-yl)] yielded a new series of compounds endowed with distinct
Jakub Fichna et al.
Journal of medicinal chemistry, 50(3), 512-520 (2007-02-03)
To synthesize potent antagonists of the mu-opioid receptor, we prepared a series of endomorphin-1 and endomorphin-2 analogues with 3-(1-naphthyl)-d-alanine (d-1-Nal) or 3-(2-naphthyl)-d-alanine (d-2-Nal) in position 4. Some of these analogues displayed weak antagonist properties. We tried to strengthen these properties
Masami Tanaka et al.
PloS one, 4(5), e5532-e5532 (2009-05-15)
MicroRNAs are a family of 19- to 25-nucleotides noncoding small RNAs that primarily function as gene regulators. Aberrant microRNA expression has been described for several human malignancies, and this new class of small regulatory RNAs has both oncogenic and tumor
Renata Perlikowska et al.
Bioorganic & medicinal chemistry, 17(11), 3789-3794 (2009-05-14)
Endogenous mu-opioid receptor (MOR) selective peptides, endomorphin-1 (EM-1) and endomorphin-2 (EM-2), unlike so called 'typical opioids', are characterized by the presence of Pro(2) residue, which is a spacer connecting aromatic pharmacophoric residues. In order to investigate structural requirements for position

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service