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O6887

Sigma-Aldrich

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

≥93% (HPLC), solid

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Empirical Formula (Hill Notation):
C48H74N12O12S2
CAS Number:
Molecular Weight:
1075.30
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

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

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This Item
V4253O3251V2255
Oxytocin

Sigma-Aldrich

O3251

Oxytocin

form

solid

form

powder

form

lyophilized powder

form

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

Gene Information

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

Gene Information

human ... AVPR1A(552), AVPR2(554), OXT(5020), OXTR(5021)
mouse ... AVPR1A(54140), AVPR2(12000)
rat ... AVPR1A(25107), AVPR2(25108), OXT(18429), OXTR(18430)

Gene Information

human ... OXT(5020), OXTR(5021)
rat ... Oxtr(25342)

Gene Information

human ... AVPR1A(552)
mouse ... AVPR1A(54140)
rat ... AVPR1A(25107)

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

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Customers Also Viewed

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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
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 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
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
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

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