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E3273

Sigma-Aldrich

Endomorphin 1

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About This Item

Empirical Formula (Hill Notation):
C34H38N6O5
CAS Number:
189388-22-5
Molecular Weight:
610.70
MDL number:
MFCD01321063
UNSPSC Code:
12352200
PubChem Substance ID:
329799045

storage temp.

−20°C

SMILES string

N[C@@H](Cc1ccc(O)cc1)C(=O)N2CCC[C@H]2C(=O)N[C@@H](Cc3c[nH]c4ccccc34)C(=O)N[C@@H](Cc5ccccc5)C(N)=O

InChI

1S/C34H38N6O5/c35-26(17-22-12-14-24(41)15-13-22)34(45)40-16-6-11-30(40)33(44)39-29(19-23-20-37-27-10-5-4-9-25(23)27)32(43)38-28(31(36)42)18-21-7-2-1-3-8-21/h1-5,7-10,12-15,20,26,28-30,37,41H,6,11,16-19,35H2,(H2,36,42)(H,38,43)(H,39,44)/t26-,28-,29-,30-/m0/s1

InChI key

ZEXLJFNSKAHNFH-SYKYGTKKSA-N

Gene Information

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

Amino Acid Sequence

Tyr-Pro-Trp-Phe-NH2

Biochem/physiol Actions

Potent, selective endogenous μ opioid receptor agonist.

Legal Information

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

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
034M4845V
072M4798V
060M4813
068K4851
068K4852

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Gina F Marrone et al.
ACS chemical neuroscience, 7(12), 1717-1727 (2016-09-21)
The mu opioid receptor gene undergoes extensive alternative splicing. Mu opioids can be divided into three classes based on the role of different groups of splice variants. Morphine and methadone require only full length seven transmembrane (7TM) variants for analgesia
Sarah A Nickolls et al.
PloS one, 8(12), e83691-e83691 (2014-01-01)
Agonists at the µ-opioid receptor are known to produce potent analgesic responses in the clinical setting, therefore, an increased understanding of the molecular interactions of ligands at this receptor could lead to improved analgesics. As historically morphine has been shown
M G Paterlini et al.
Biophysical journal, 78(2), 590-599 (2000-02-02)
A series of diastereoisomers of endomorphin-1 (EM1, Tyr(1)-Pro(2)-Trp(3)-Phe(4)-NH(2)) have been synthesized and their potency measured using the guinea pig ileum assay. [D-Phe(4)]EM1 possessed 1/10 the potency of EM1, while potencies of [D-Tyr(1)]EM1 and [D-Trp(3)]EM1 were 50- and 100-fold lower, respectively.
Laura Pont et al.
Electrophoresis, 37(5-6), 795-808 (2015-12-20)
In this work, an untargeted metabolomic approach based on sensitive analysis by on-line solid-phase extraction capillary electrophoresis mass spectrometry (SPE-CE-MS) in combination with multivariate data analysis is proposed as an efficient method for the identification of biomarkers of Huntington's disease
S Ide et al.
Japanese journal of pharmacology, 83(4), 306-311 (2000-09-23)
Endomorphin-1 is a novel endogenous peptide that is highly selective for the mu-opioid receptor over the delta- and kappa-opioid receptors. The structural basis of high selectivity of endomorphin-1 to the mu-opioid receptor was examined using chimeric receptors between mu- and
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