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Merck
CN

O6887

[β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Me-Tyr2, Orn8]-Oxytocin

≥93% (HPLC), solid

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About This Item

Empirical Formula (Hill Notation):
C48H74N12O12S2
CAS Number:
77327-45-8
Molecular Weight:
1075.30
NACRES:
NA.32
PubChem Substance ID:
329818919
UNSPSC Code:
51111800
MDL number:
MFCD00135712

Key Documents

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Product Name

[β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Me-Tyr2, Orn8]-Oxytocin, ≥93% (HPLC), solid

InChI key

ZWVZXPFUQHTUKV-SZQHDTAUSA-N

SMILES string

CC[C@H](C)C1NC(=O)[C@H](Cc2ccc(OC)cc2)NC(=O)CC3(CCCCC3)SSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CCCN)C(=O)NCC(N)=O

InChI

1S/C48H74N12O12S2/c1-4-27(2)40-46(70)56-31(16-17-36(50)61)42(66)57-33(23-37(51)62)43(67)58-34(47(71)60-21-9-11-35(60)45(69)55-30(10-8-20-49)41(65)53-25-38(52)63)26-73-74-48(18-6-5-7-19-48)24-39(64)54-32(44(68)59-40)22-28-12-14-29(72-3)15-13-28/h12-15,27,30-35,40H,4-11,16-26,49H2,1-3H3,(H2,50,61)(H2,51,62)(H2,52,63)(H,53,65)(H,54,64)(H,55,69)(H,56,70)(H,57,66)(H,58,67)(H,59,68)/t27-,30-,31-,32-,33-,34-,35-,40-/m0/s1

assay

≥93% (HPLC)

form

solid

storage temp.

−20°C

Quality Level

200

Gene Information

human ... OXT(5020), OXTR(5021)
rat ... OXT(18429), OXTR(18430)

Application

[β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Me-Tyr2, Orn8]-Oxytocin has been used as an oxytocin receptor antagonist:
  • to study the influence of blockading the oxytocin receptors in the anterior cingulate cortex on helping behavior
  • to determine the receptors that mediate vasopressin-stimulated anion secretion across cultured porcine vas deferens epithelial cell monolayers
  • to study the influence of oxytocin receptors inhibition on intravenous and in situ oxytocin effects on the urinary bladder and cardiovascular activities in sham rats

Biochem/physiol Actions

Potent oxytocin antagonist.
[β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Me-Tyr2, Orn8]-also acts as an arginine vasopressin receptor 1A (AVPR1A) antagonist.

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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Certificates of Analysis (COA)

Lot/Batch Number
SLCM4561
SLCM9103
SLCN4472
SLCK2105
SLCJ5031

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R J Windle et al.
The Journal of endocrinology, 152(2), 257-264 (1997-02-01)
The effect of three oxytocin receptor antagonists on the renal actions of oxytocin and vasopressin was investigated in conscious male rats infused with hypotonic saline. Infusion of oxytocin at 100 pg/min produced plasma concentrations of 12.7 +/- 3.3 pmol/l and
M Mayntz et al.
Physiology & behavior, 65(1), 151-156 (1998-11-12)
This experiment was to test the hypothesis that suckling behavior in Bos taurus is related to milk ejection. Intra-gland milk transport was manipulated by applying four different treatments to four cow-calf pairs: T1, injection of oxytocin during the post-stimulation period;
M R Melis et al.
European journal of pharmacology, 328(2-3), 115-123 (1997-06-11)
A dose of N-methyl-D-aspartic acid (NMDA, 50 ng) that induces penile erection and yawning when injected into the paraventricular nucleus of the hypothalamus, increased the concentration of NO2- from 1.10 +/- 0.28 microM to 7.32 +/- 1.12 microM and of
T M D'Cunha et al.
Hormones and behavior, 59(1), 14-21 (2010-10-12)
Female rats with maternal experience display a shorter onset of maternal responsiveness compared to those with no prior experience. This phenomenon called 'maternal memory' is critically dependent on the nucleus accumbens (NA) shell. We hypothesized that activation of OT receptors
M R Melis et al.
European journal of pharmacology, 294(1), 1-9 (1995-12-27)
In order to provide further support for a role of central nitric oxide as a mediator of penile erection and yawning, the nitric oxide donors sodium nitroprusside, hydroxylamine, isoamyl nitrite and S-nitroso-N-acetyl-penicillamine were injected into the lateral ventricles (i.c.v.) or
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