An endogenous opioid peptide
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β-Endorphin (1-27) (human) (trifluoroacetate salt)

Item No. 24957

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Molecular Formula
C139H217N33O40S • XCF3COOH
Formula Weight
3022.5
Purity
≥95%
Formulation (Request formulation change)
A lyophilized powder
Solubility(Learn about Variance in Solubility)
DMSO: 1 mg/ml
SMILES
[H]N[C@H](C(NCC(NCC(N[C@H](C(N[C@H](C(N[C@]([C@@H](C)O)([H])C(N[C@@H](CO)C(N[C@@H](CCC(O)=O)C(N[C@@H](CCCCN)C(N[C@@H](CO)C(N[C@@H](CCC(N)=O)C(N[C@]([C@@H](C)O)([H])C(N1CCC[C@H]1C(N[C@@H](CC(C)C)C(N[C@@H](C(C)C)C(N[C@]([C@@H](C)O)([H])C(N[C@@H](CC(C)C)C(N[C@H](C(N[C@@H](CCCCN)C(N[C@@H](CC(N)=O)C(N[C@H](C(N[C@]([C@H](CC)C)([H])C(N[C@]([C@H](CC)C)([H])C(N[C@@H](CCCCN)C(N[C@@H](CC(N)=O)C(N[C@H](C(N[C@H](C(O)=O)CC2=CC=C(O)C=C2)=O)C)=O)=O)=O)=O)=O)C)=O)=O)=O)CC3=CC=CC=C3)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)CCSC)=O)CC4=CC=CC=C4)=O)=O)=O)CC5=CC=C(O)C=C5.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C139H217N33O40S.C2HF3O2/c1-17-73(9)110(134(206)157-89(38-27-30-55-142)119(191)160-97(64-104(145)181)124(196)149-75(11)115(187)163-99(139(211)212)63-83-42-46-85(179)47-43-83)168-135(207)111(74(10)18-2)167-116(188)76(12)150-125(197)98(65-105(146)182)159-118(190)87(36-25-28-53-140)153-128(200)96(62-81-34-23-20-24-35-81)158-126(198)93(58-70(3)4)162-136(208)113(78(14)176)170-133(205)109(72(7)8)166-129(201)94(59-71(5)6)161-132(204)102-39-31-56-172(102)138(210)114(79(15)177)171-122(194)90(48-50-103(144)180)154-130(202)100(68-173)164-120(192)88(37-26-29-54-141)152-121(193)91(49-51-108(185)186)155-131(203)101(69-174)165-137(209)112(77(13)175)169-123(195)92(52-57-213-16)156-127(199)95(61-80-32-21-19-22-33-80)151-107(184)67-147-106(183)66-148-117(189)86(143)60-82-40-44-84(178)45-41-82;3-2(4,5)1(6)7/h19-24,32-35,40-47,70-79,86-102,109-114,173-179H,17-18,25-31,36-39,48-69,140-143H2,1-16H3,(H2,144,180)(H2,145,181)(H2,146,182)(H,147,183)(H,148,189)(H,149,196)(H,150,197)(H,151,184)(H,152,193)(H,153,200)(H,154,202)(H,155,203)(H,156,199)(H,157,206)(H,158,198)(H,159,190)(H,160,191)(H,161,204)(H,162,208)(H,163,187)(H,164,192)(H,165,209)(H,166,201)(H,167,188)(H,168,207)(H,169,195)(H,170,205)(H,171,194)(H,185,186)(H,211,212);(H,6,7)/t73-,74-,75-,76-,77+,78+,79+,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,109-,110-,111-,112-,113-,114-;/m0./s1
InChi Key
VDZGCWQLKFHRNB-RKIQCASHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    β-Endorphin (1-27) is an endogenous peptide that binds to μ-, δ-, and κ-opioid receptors (Kis = 5.31, 6.17, and 39.82 nM, respectively, in COS-1 cells expressing rat receptors).1 It binds to rat and mouse brain membrane preparations (IC50s = 1.1 and 5.7 nM, respectively) and induces chemotaxis of human monocytes in vitro when used at a concentration of 1 nM.2,3,4 Intracerebroventricular administration of β-endorphin (1-27) increases the latency to tail withdrawal in response to thermal stimulation in mice with a median antinociceptive dose (AD50) of 1,500 pmol per animal.2 It inhibits antinociception induced by β-endorphin (Item Nos. 24153 | 24955) in mice in response to thermal stimuli when administered at a dose of 65 pmol per animal. In rats, β-endorphin (1-27) does not affect drug-associated place preference when administered at doses up to 20 μg, i.c.v., but inhibits β-endorphin-induced place preference when administered at a dose of 10 μg per animal.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mansour, A., Hoversten, M.T., Taylor, L.P., et al. The cloned μ, δ and κ receptors and their endogenous ligands: Evidence for two opioid peptide recognition cores. Brain Res. 700(1-2), 89-98 (1995).

    2. Hammonds, R.G., Jr., Nicolas, P., and Li, C.H. β-Endorphin-(1-27) is an antagonist of β-endorphin analgesia. Proc. Natl. Acad. Sci. USA 81(5), 1389-1390 (1984).

    3. Garzón, J., and Sánchez-Blázquez, P. αN-acetyl derivatives of β-endorphin-(1-31) and -(1-27) regulate the supraspinal antinociceptive activity of different opioids in mice. Life Sci. 48(14), 1417-1427 (1991).

    4. Sacerdote, P., and Panerai, A.E. Analysis of the beta-endorphin structure-related activity on human monocyte chemotaxis: Importance of the N- and C-terminal. Peptides 10(3), 565-569 (1989).

    5. Bals-Kubik, R., Herz, A., and Shippenberg, T.S. β-endorphin-(1-27) is a naturally occurring antagonist of the reinforcing effects of opioids. Naunyn Schmiedebergs Arch. Pharmacol. 338(4), 392-396 (1988).