An antagonist of the μ-opioid receptor
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CTOP (trifluoroacetate salt)

Item No. 27377

Technical Information
Formal Name
D-phenylalanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-ornithyl-L-threonyl-3-mercapto-L-valyl-L-threoninamide-cyclic (2→7)-disulfide, trifluoroacetate salt
Synonyms
  • Phe-Cys-Tyr-Trp-Orn-Thr-Pen-Thr
Molecular Formula
C50H67N11O11S2• XCF3COOH
Formula Weight
Purity
≥98%
Formulation
A solid
Ethanol: slightly solubleWater: slightly soluble
λmax
220, 269, 386 nm
SMILES
O=C1[C@@]([C@@H](C)O)([H])NC([C@@](CCCN)([H])NC([C@@H](CC2=CNC3=C2C=CC=C3)NC([C@H](CC4=CC=C(O)C=C4)NC([C@](NC([C@H](N)CC5=CC=CC=C5)=O)([H])CSSC(C)(C)[C@@H](C(N[C@@H]([C@@H](C)O)C(N)=O)=O)N1)=O)=O)=O)=O.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C50H67N11O11S2.C2HF3O2/c1-26(62)39(42(53)65)59-49(72)41-50(3,4)74-73-25-38(58-43(66)33(52)21-28-11-6-5-7-12-28)47(70)56-36(22-29-16-18-31(64)19-17-29)45(68)57-37(23-30-24-54-34-14-9-8-13-32(30)34)46(69)55-35(15-10-20-51)44(67)60-40(27(2)63)48(71)61-41;3-2(4,5)1(6)7/h5-9,11-14,16-19,24,26-27,33,35-41,54,62-64H,10,15,20-23,25,51-52H2,1-4H3,(H2,53,65)(H,55,69)(H,56,70)(H,57,68)(H,58,66)(H,59,72)(H,60,67)(H,61,71);(H,6,7)/t26-,27-,33-,35+,36+,37-,38+,39+,40+,41-;/m1./s1
InChi Key
BPLOKJUPZTYYLV-XQGGKHMTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    CTOP is a peptide antagonist of the μ-opioid receptor (IC50 = 2.8 nM).1 It is selective for μ-opioid receptors over δ-opioid receptors (IC50 = 13,500 nM) and somatostatin receptors (IC50 = 24,000 nM). CTOP inhibits the antinociceptive effect of morphine in the tail flick test in mice (ED50 = 0.018 nmol) and reverses morphine-induced increases in locomotor activity (ED50 = 0.02 nmol).2 It also induces withdrawal symptoms in a mouse model of chronic, but not acute, morphine dependence.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pelton, J.T., Kazmierski, W., Gluya, K., et alDesign and synthesis of conformationally constrained somatostatin analogues with high potency and specificity for μ opioid receptors. J. Med. Chem. 29(11), 2370-2375 (2013).

    2. Gulya, K., Kriván, M., Nyolczas, N., et alCentral effects of the potent and highly selective μ opioid antagonist D-Phe-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2 (CTOP) in mice. Eur. J. Pharmacol. 150(3), 355-360 (1988).