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V1880

Sigma-Aldrich

[deamino-Pen1, O-Me-Tyr2, Arg8]-Vasopressin

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C49H70N14O12S2
CAS Number:
67269-08-3
Molecular Weight:
1111.30
MDL number:
MFCD00076745
UNSPSC Code:
51111800
PubChem Substance ID:
24900721
NACRES:
NA.32

sterility

non-sterile

Assay

≥97% (HPLC)

form

powder

solubility

water: 0.5 mg/mL, clear, colorless

shipped in

ambient

storage temp.

−20°C

SMILES string

COc1ccc(CC2NC(=O)CC(C)(C)SSCC(NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(Cc3ccccc3)NC2=O)C(=O)N4CCCC4C(=O)NC(CCCNC(N)=N)C(=O)NCC(N)=O)cc1

InChI

1S/C49H70N14O12S2/c1-49(2)24-40(67)57-32(22-28-13-15-29(75-3)16-14-28)43(70)60-33(21-27-9-5-4-6-10-27)44(71)58-31(17-18-37(50)64)42(69)61-34(23-38(51)65)45(72)62-35(26-76-77-49)47(74)63-20-8-12-36(63)46(73)59-30(11-7-19-55-48(53)54)41(68)56-25-39(52)66/h4-6,9-10,13-16,30-36H,7-8,11-12,17-26H2,1-3H3,(H2,50,64)(H2,51,65)(H2,52,66)(H,56,68)(H,57,67)(H,58,71)(H,59,73)(H,60,70)(H,61,69)(H,62,72)(H4,53,54,55)

InChI key

HNOGCDKPALYUIG-UHFFFAOYSA-N

Gene Information

human ... AVPI1(60370)
mouse ... AVPI1(69534)
rat ... AVPI1(171386) , LOC689723(689723)

Amino Acid Sequence

3-Mercapto-3-methylbutyryl-Tyr-OMet-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide Bridge: 1-6]

Application

[Deamino-Pen1, O-Me-Tyr2, Arg8]-Vasopressin was used to inhibit the V1 receptor, and study the role of arginine vasopressin receptors V1 and V2 on brain damage, brain edema formation and functional outcome after transient focal cerebral ischemia.

Biochem/physiol Actions

[Deamino-Pen1, O-Me-Tyr2, Arg8]-Vasopressin is a V1 antagonist that stabilizes the cardiocirculatory function in normal human as well as in patients suffering from catecholamine-resistant vasodilatory shock. It also stimulates three acid-base transporters and hence increases the capability of the cell to regulate pHi.

Preparation Note

[deamino-Pen1, O-Me-Tyr2, Arg8]-Vasopressin dissolves in water at 0.5 mg/ml to yield a clear, colorless solution.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H332

Precautionary Statements

P261 - P271 - P304 + P340 + P312

Hazard Classifications

Acute Tox. 4 Inhalation

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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A Heinemann et al.
British journal of pharmacology, 125(6), 1120-1127 (1998-12-24)
The vasopressin receptor subtype involved in the enhancement by vasopressin of adrenoceptor-mediated vasoconstriction was investigated in rat isolated perfused mesenteric arteries. [Arg8]vasopressin (1-10 nM) dose-dependently increased the perfusion pressure and enhanced the pressor response to the adrenoceptor agonist methoxamine (40
M D Chen et al.
Psychoneuroendocrinology, 23(5), 497-503 (1998-11-05)
Insulin-induced hypoglycemia causes somnolence in rhesus monkeys, a phenomenon usually considered an aspecific consequence of neuroglycopenia. Previous observations from our laboratory have raised the possibility that arginine vasopressin (AVP) may also play a role in this decrease in wakefulness. In
L E Heisler et al.
Neuroendocrinology, 60(3), 297-304 (1994-09-01)
The objective of the present study was to examine the role of vasopressin in the regulation of LH secretion in the rhesus monkey. The effect of vasopressin administration on basal LH secretion and vasopressin antagonism on stress-induced inhibition of LH
R H Derijk et al.
The American journal of physiology, 266(1 Pt 2), R9-14 (1994-01-01)
Previously, we have reported that intravenous administration of bacterial endotoxin (lipopolysaccharide, LPS) in rats kept at a subthermoneutral ambient temperature of 24 degrees C results in a fall in colonic temperature that involved the release of antipyretic products by peripheral
H J Lenz et al.
Gastroenterology, 98(6), 1490-1492 (1990-06-01)
In awake rats, physical restraint inhibited pentagastrin-stimulated gastric acid secretion by more than 50%. This inhibitory effect was abolished by either ganglionic or noradrenergic blockade. Adrenalectomy, as well as pretreatment with a vasopressin V1-receptor antagonist, significantly attenuated the gastric inhibitory
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