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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

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

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’.

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Attila Keresztes et al.
Journal of medicinal chemistry, 51(14), 4270-4279 (2008-06-25)
Endomorphins were subjected to a number of structural modifications in a search for their bioactive conformations. The alicyclic beta-amino acids cis-(1 S,2 R)ACPC/ACHC, cis-(1 R,2 S)ACPC/ACHC, trans-(1 S,2 S)ACPC/ACHC, and trans-(1 R,2 R)ACPC/ACHC were introduced into endomorphins to examine the
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 (
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
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
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