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Safety Information

E6136

Sigma-Aldrich

α-Endorphin human

≥97% (HPLC)

Synonym(s):

β-Lipotropin (61-76), human, synthetic, β-Lipotropin 61-76, LPH (61-76), Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr

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About This Item

Empirical Formula (Hill Notation):
C77H120N18O26S
CAS Number:
59004-96-5
Molecular Weight:
1745.95
MDL number:
MFCD00076381
UNSPSC Code:
12352200
PubChem Substance ID:
24894621

Assay

≥97% (HPLC)

UniProt accession no.

P01189

storage temp.

−20°C

SMILES string

CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc2ccc(O)cc2)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(O)=O

InChI

1S/C77H120N18O26S/c1-38(2)31-51(70(113)91-60(39(3)4)74(117)94-63(42(7)100)77(120)121)88-73(116)55-18-14-29-95(55)76(119)62(41(6)99)93-67(110)48(23-25-56(80)102)85-71(114)53(36-96)89-65(108)47(17-12-13-28-78)84-66(109)49(24-26-59(105)106)86-72(115)54(37-97)90-75(118)61(40(5)98)92-68(111)50(27-30-122-8)87-69(112)52(33-43-15-10-9-11-16-43)83-58(104)35-81-57(103)34-82-64(107)46(79)32-44-19-21-45(101)22-20-44/h9-11,15-16,19-22,38-42,46-55,60-63,96-101H,12-14,17-18,23-37,78-79H2,1-8H3,(H2,80,102)(H,81,103)(H,82,107)(H,83,104)(H,84,109)(H,85,114)(H,86,115)(H,87,112)(H,88,116)(H,89,108)(H,90,118)(H,91,113)(H,92,111)(H,93,110)(H,94,117)(H,105,106)(H,120,121)/t40-,41-,42-,46+,47+,48+,49+,50+,51+,52+,53+,54+,55+,60+,61+,62+,63+/m1/s1

InChI key

NXSIJWJXMWBCBX-NWKQFZAZSA-N

Gene Information

human ... POMC(5443)

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Amino Acid Sequence

Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr

General description

α-Endorphin is one of the three endorphins found in the brain, which has morphine-mimetic activities. It is a hexadecapeptide with a primary structure of H-Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-SerGln-Thr-Pro-Leu-Val-Thr-OH. It is a fragment of β-Endorphin (β-LPH61-91), which is an endogenous opioid ligand, and is denoted as (β-LPH61-76). It is found in the hypothalamus and pituitary.

Biochem/physiol Actions

α-Endorphin is a substrate for transglutaminase, and has stimulatory effects on immune system function. It influences the self-stimulating tendencies in rat, related to electrical stimulation of the ventral tegmentum area neurons. It counteracts the effect of γ-endorphin and promotes this behavior in rats. The functionality of α-endorphin is comparable to that of psychostimulant drugs, and as it acts in an opposing manner to γ-endorphin, these peptides might have a central role in the homeostasis of brain function.

Other Notes

Lyophilized from 0.1% TFA in H2O

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
043M4781V
091M4804V
059K4848
117K4790
026K4779

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B Bucher et al.
European journal of pharmacology, 147(2), 305-308 (1988-03-01)
Isolated rat tail arteries were perfused and vasoconstriction was evoked by electrical field stimulation (2 pulses at 1 Hz every 2 min). The vasoconstriction was depressed by DAGO (IC50 = 611 nM) and beta-endorphin (IC50 = 37 nM). Structuraly analogues
P Sacerdote et al.
Peptides, 10(3), 565-569 (1989-05-01)
We evaluated the chemotactic activity of beta-endorphin and beta-endorphin-related peptides on human monocytes. We tested beta-endorphin(1-31) and fragments (1-16), (1-17), (1-27) in which the N-terminal of the opioid is preserved, N-acetyl-beta-endorphin(1-31) and fragments (6-31) and (28-31) in which the C-terminal
Effects of [Des-Tyr 1]-gamma-endorphin and alpha-endorphin on substantia nigra self-stimulation.
D M Dorsa et al.
Pharmacology, biochemistry, and behavior, 10(6), 899-905 (1979-06-01)
N Ling et al.
Proceedings of the National Academy of Sciences of the United States of America, 73(11), 3942-3946 (1976-11-01)
The isolation and primary structure of two peptides with morphinomimetic activity, obtained from an extract of porcine hypothalamus-neurohypophysis, are described. The amino acid sequence of the two peptides, named alpha-endorphin and gamma-endophin, was determined by mass spectrometry and danxyl-Edman methods
A A Waterfield et al.
European journal of pharmacology, 58(1), 11-18 (1979-09-01)
For characterisation in vitro, four parallel assays were used: the guinea-pig ileum and mouse vas deferens as pharmacological models at 36 degrees C and the inhibition of binding of [3H]-naltrexone, [3H]-leucine-enkephalin and [3H]-methione-enkephalin at 0 degrees C. The Leu65-analogue of
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