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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

Formule empirique (notation de Hill):
C48H74N12O12S2
Numéro CAS:
77327-45-8
Poids moléculaire :
1075.30
Numéro MDL:
MFCD00135712
Code UNSPSC :
51111800
ID de substance PubChem :
329818919
Nomenclature NACRES :
NA.32

Niveau de qualité

200

Pureté

≥93% (HPLC)

Forme

solid

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

ZWVZXPFUQHTUKV-SZQHDTAUSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "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, 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
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
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