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O6887

Sigma-Aldrich

[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
MDL number:
MFCD00135712
UNSPSC Code:
51111800
PubChem Substance ID:
329818919
NACRES:
NA.32

Quality Level

200

Assay

≥93% (HPLC)

form

solid

storage temp.

−20°C

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

InChI key

ZWVZXPFUQHTUKV-SZQHDTAUSA-N

Gene Information

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

Amino Acid Sequence

β-Mercapto-β,β-Cyclopentamethylenepropionyl-MeTyr-Ile-Gln-Asn-Cys-Pro-Orn-Gly-NH2 [Disulfide Bridge: 1-6]

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 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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R C Lambert et al.
Neuroscience, 57(4), 1027-1038 (1993-12-01)
During suckling, the periodic and synchronous bursting activity of oxytocin neurons has been shown to be facilitated by oxytocin itself, acting via several target sites, including the magnocellular nuclei. To investigate the role of the endogenous oxytocin released within the
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 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;
J Hirata et al.
The journal of obstetrics and gynaecology research, 22(5), 497-506 (1996-10-01)
In order to elucidate the roles of inositol trisphosphate (IP3) and oxytocin (OT) receptors in rabbit parturition, the concentration of IP3 induced by OT and the OT receptor levels were determined in rabbit myometria before and after parturition. The effects
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