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Merck

E6261

β-Endorphin human

≥95% (HPLC)

Synonym(s):

β-Lipotropin 61-91, β-Lipotropin C-fragment, LPH (61-91)

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About This Item

Empirical Formula (Hill Notation):
C158H251N39O46S
CAS Number:
Molecular Weight:
3464.98
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352202
MDL number:
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Quality Level

assay

≥95% (HPLC)

UniProt accession no.

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](Cc3ccccc3)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc4ccc(O)cc4)[C@@H](C)O)[C@@H](C)O)C(C)C)[C@@H](C)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc5ccc(O)cc5)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI

1S/C158H251N39O46S/c1-17-84(9)126(153(237)182-102(44-29-34-65-163)137(221)186-112(74-118(166)206)142(226)171-86(11)131(215)183-110(73-94-48-52-96(204)53-49-94)146(230)177-99(41-26-31-62-160)135(219)175-98(40-25-30-61-159)134(218)170-78-122(210)173-106(158(242)243)56-59-124(213)214)193-154(238)127(85(10)18-2)192-132(216)87(12)172-143(227)113(75-119(167)207)185-136(220)100(42-27-32-63-161)178-147(231)111(72-92-38-23-20-24-39-92)184-144(228)107(68-81(3)4)188-155(239)129(89(14)201)195-152(236)125(83(7)8)191-148(232)108(69-82(5)6)187-151(235)116-45-35-66-197(116)157(241)130(90(15)202)196-140(224)103(54-57-117(165)205)179-149(233)114(79-198)189-138(222)101(43-28-33-64-162)176-139(223)104(55-58-123(211)212)180-150(234)115(80-199)190-156(240)128(88(13)200)194-141(225)105(60-67-244-16)181-145(229)109(71-91-36-21-19-22-37-91)174-121(209)77-168-120(208)76-169-133(217)97(164)70-93-46-50-95(203)51-47-93/h19-24,36-39,46-53,81-90,97-116,125-130,198-204H,17-18,25-35,40-45,54-80,159-164H2,1-16H3,(H2,165,205)(H2,166,206)(H2,167,207)(H,168,208)(H,169,217)(H,170,218)(H,171,226)(H,172,227)(H,173,210)(H,174,209)(H,175,219)(H,176,223)(H,177,230)(H,178,231)(H,179,233)(H,180,234)(H,181,229)(H,182,237)(H,183,215)(H,184,228)(H,185,220)(H,186,221)(H,187,235)(H,188,239)(H,189,222)(H,190,240)(H,191,232)(H,192,216)(H,193,238)(H,194,225)(H,195,236)(H,196,224)(H,211,212)(H,213,214)(H,242,243)/t84-,85-,86-,87-,88+,89+,90+,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,125-,126-,127-,128-,129-,130-/m0/s1

InChI key

JMHFFDIMOUKDCZ-NTXHZHDSSA-N

Gene Information

human ... POMC(5443)

General description

β-Endorphin is a potent endogenous opioid protein that is derived from propiomelanocortin, a protein found in the brain, anterior pituitary, skin, immune system, and other peripheral sites. β-endorphin, however, is localized to the brain and spinal cord. It is one of the major opioid peptides, and is the derivative of the C-terminal of β-lipotropin. It is made of 31 amino acids.

Application

Human β-Endorphin is suitable for-
  • radioimmunoassay to determine the portal blood β-endorphin levels in lactating ewes, and its relation to bouts of suckling
  • to assess the melanogenesis, proliferation and dendricity of melanocytes
  • to assess the expression of μ-opioid receptor, in human skin organ culture, on exposure to β-endorphin
  • to examine the effects on cardiovascular functions of β-endorphin injection nucleus in amygdaloideus centralis (AC), into either nucleus paraventricularis (NPV) or rostral ventrolateral medulla (RVL)

Biochem/physiol Actions

β-Endorphin acts as a ligand for both μ and δ opioid receptors in different parts of the brain. It is released in response to painful stimuli and has potent antinociceptive activity. When given supraspinally, this activity is mediated through its action on ε-opioid receptors in brain that results in the release of Met-enkephalin. This activity is also mediated by its interaction with δ2-opioid receptors in the spinal cord. When introduced intrathecally, this function is an outcome of its interaction with μ and κ-opioid receptors in the rat. In autoimmune disorders, the elevated production of cytokines results in the production of β-endorphin, in pituitary and lymphocytes. This acts as a negative regulator of antibody production, and is thus, implicated in autoimmune diseases.
Potent endogenous opioid protein that is derived from propiomelanocortin, a protein found in the brain, anterior pituitary, skin, immune system, and other peripheral sites. It is released in response to painful stimuli and has potent antinociceptive activity that is mediated through its action on μ receptors in brain and by μ and κ receptors in the spinal cord.
Potent endogenous opioid protein; released in response to painful stimuli and has potent antinociceptive activity.

Other Notes

Lyophilized from 0.1% TFA in H2O


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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H Mørch et al.
Autoimmunity, 21(3), 161-171 (1995-01-01)
The immune system and the neuroendocrine system are closely interconnected having such means of bidirectional communication and regulation. In this review, a hypothesis is put forward regarding the possible role of beta-endorphins in the pathogenesis of autoimmune diseases: It is
M Bigliardi-Qi et al.
The Journal of investigative dermatology, 114(3), 527-532 (2000-02-26)
It has been reported that opioid peptides modulate the differentiation of normal human keratinocytes and that mu-opiate receptors are expressed in human epidermis. The regulation of keratinocyte differentiation is particularly important in psoriasis, and one of the markers for hyperproliferative
M Narita et al.
Japanese journal of pharmacology, 76(3), 233-253 (1998-05-21)
Recently, mu-, delta- and kappa-opioid receptors have been cloned and relatively well-characterized. In addition to three major opioid receptor types, more extensive studies have suggested the possible existence of other opioid receptor types that can be classified as non-mu, non-delta



Global Trade Item Number

SKUGTIN
E6261-1MG04061826152683
E6261-.5MG04061833604458
E6261-250UG04061832676722