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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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T Funabashi et al.
Neuroscience letters, 260(1), 37-40 (1999-02-23)
In the present study, we examined the effect of arginine-vasopressin (AVP) V1 receptor antagonist ([Deamino-Pen1, Tyr(Me)2, Arg8]-vasopressin) injection (1 microg/2 microl saline) into the third ventricle in the proestrous rat on serum concentrations of luteinizing hormone (LH) and prolactin (PRL)
F G Snijdewint et al.
Neurotoxicology and teratology, 10(4), 321-325 (1988-07-01)
Two vasopressin antagonists, d(CH2)5[Tyr(Me)2]AVP and dP[Tyr(Me)2]AVP, were given to Wistar rats from postnatal day 1 to 21 in order to investigate the influence on development and later diuresis. The latter antagonist significantly reduced body growth from day 3 postnatally onwards.
G J Boer et al.
Neuroscience letters, 156(1-2), 17-20 (1993-06-25)
In order to establish whether vasopressin (VP) influences brain cell survival, [3H]thymidine was injected in 10-day-old vasopressin-deficient Brattleboro rat pups, as well as in Wistar pups treated, neonatally, with the VP antagonist dP[Tyr(Me)2]VP followed by subsequent measurement of [3H]DNA in
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
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
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