E3148
Endomorphin 2
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About This Item
Empirical Formula (Hill Notation):
C32H37N5O5
CAS Number:
Molecular Weight:
571.67
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
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)
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
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Storage Class
11 - Combustible Solids
Regulatory Information
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Tingyou Li et al.
Journal of medicinal chemistry, 50(12), 2753-2766 (2007-05-15)
Endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2) and [Dmt1]EM-2 (Dmt = 2',6'-dimethyl-l-tyrosine) analogues, containing alkylated Phe3 derivatives, 2'-monomethyl (2, 2'), 3',5'- and 2',6'-dimethyl (3, 3', and 4', respectively), 2',4',6'-trimethyl (6, 6'), 2'-ethyl-6'-methyl (7, 7'), and 2'-isopropyl-6'-methyl (8, 8') groups or Dmt (5, 5'), had the
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
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