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O6887

Sigma-Aldrich

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

≥93% (HPLC), solid

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1 MG
$273.00

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

$273.00

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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)

Related Categories

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[1]
  • to determine the receptors that mediate vasopressin-stimulated anion secretion across cultured porcine vas deferens epithelial cell monolayers[2]
  • 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[3]

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.[2]

Storage Class

11 - Combustible Solids

wgk_germany

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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Salvatora Succu et al.
Neuropharmacology, 49(7), 1017-1025 (2005-08-10)
The effect of four peptides derived from the C-terminal portion of rat pro-VGF(556-617) (VGF(556-576), VGF(588-617), VGF(599-617), and VGF(588-597)), on penile erection and nitric oxide production in the paraventricular nucleus of the hypothalamus was studied in male rats after injecting into
M R Melis et al.
Brain research bulletin, 36(6), 527-531 (1995-01-01)
The effect of the central administration of nitroglycerin, a potent organic nitrate vasodilator, on penile erection and yawning was studied in male rats. When given intracerebroventricularly (ICV), nitroglycerin (33-99 micrograms) induced the above responses dose-dependently. The minimal effective dose was
A Benelli et al.
Neuropeptides, 27(4), 245-250 (1994-10-01)
In intact, non-ovariectomized female rats in spontaneous behavioral estrus, the i.c.v. injection of oxytocin significantly increased lordosis quotient and lordosis duration, starting from a dose of 1 ng/rat. On the other hand, the oxytocin antagonist, d(CH2)5Tyr(Me)-[Orn]8-vasotocin, injected at the same
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;
Atsuko Saito et al.
Journal of comparative physiology. A, Neuroethology, sensory, neural, and behavioral physiology, 197(4), 329-337 (2011-01-13)
Oxytocin facilitates social recognition in rats and mice, onset of maternal behavior in virgin mice and formation of pair bonds without copulation in prairie voles. However, the relationship between this peptide and paternal behavior in primates remains largely unknown. We
View All Related Papers

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