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P5296

Sigma-Aldrich

CTOP

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C50H67N11O11S2
CAS Number:
103429-31-8
Molecular Weight:
1062.26
MDL number:
MFCD00076708
UNSPSC Code:
12352200
PubChem Substance ID:
329820226
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

UniProt accession no.

Q64387

storage temp.

−20°C

SMILES string

C[C@@H](O)[C@H](NC(=O)[C@H]1NC(=O)[C@@H](NC(=O)[C@H](CCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc4ccc(O)cc4)NC(=O)[C@H](CSSC1(C)C)NC(=O)[C@H](N)Cc5ccccc5)[C@@H](C)O)C(N)=O

InChI

1S/C50H67N11O11S2/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/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)/t26-,27-,33-,35+,36+,37-,38+,39+,40+,41-/m1/s1

InChI key

PZWWYAHWHHNCHO-FGHAYEPSSA-N

Gene Information

mouse ... Pnoc(18155)

Amino Acid Sequence

Phe-Cys-Tyr-Trp-Orn-Thr-Pen-Thr-NH2 [Disulfide Bridge: 2-7]

General description

D-Pen-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2 (CTOP) is a selective cyclic μ-opioid receptor antagonist.

Application

CTOP has been used:
  • to study the anxiogenic effects induced by CTOP in mice and rat.
  • to study the effect of μ-opioid antagonist, CTOP on the bovine milk-derived LF (BLF)-induced analgesia.
  • to determine whether μ-opioid receptors act cooperatively with 5-hydroxytryptamine (5-HT1A) receptors to regulate the behaviors generated in the elevated T-maze (ETM).

Biochem/physiol Actions

D-Pen-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2 (CTOP) inhibits acute morphine-induced hypermotility and analgesic effect of morphine in a dose-dependent manner in vivo.
Selective ligand for μ-opioid receptors.

Linkage

Somatostatin analog

Storage Class Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Elena I Varlinskaya et al.
Alcoholism, clinical and experimental research, 33(6), 991-1000 (2009-03-24)
Ethanol consumption is considerably elevated during adolescence. Attractiveness of alcohol for humans during the adolescent developmental period is based, in part, on its ability to induce social facilitation--a facilitation of social interactions not only evident in human adolescents but also
Chronic pain induces anxiety with concomitant changes in opioidergic function in the amygdala.
Narita M
Neuropsychopharmacology, 31(4), 739-750 (2006)
Ruth Drdla-Schutting et al.
Science (New York, N.Y.), 335(6065), 235-238 (2012-01-17)
Painful stimuli activate nociceptive C fibers and induce synaptic long-term potentiation (LTP) at their spinal terminals. LTP at C-fiber synapses represents a cellular model for pain amplification (hyperalgesia) and for a memory trace of pain. μ-Opioid receptor agonists exert a
G T C Wong et al.
Acta anaesthesiologica Scandinavica, 54(4), 510-518 (2009-11-03)
Ischemic pre- or post-conditioning of the heart has been shown to involve opioid receptors. Remifentanil, an ultra-short-acting selective mu opioid receptor agonist in clinical use, pre-conditions the rat heart against ischemia-reperfusion injury. This study investigates whether remifentanil post-conditioning is also
Céline Heinl et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(46), 16748-16756 (2011-11-18)
In addition to analgesia, opioids may also produce paradoxical pain amplification [opioid-induced hyperalgesia (OIH)] either on abrupt withdrawal or during continuous long-term application. Here, we assessed antinociceptive and pronociceptive effects of three clinically used opioids at C-fiber synapses in the
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