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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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M Kagawa et al.
No shinkei geka. Neurological surgery, 21(12), 1103-1107 (1993-12-01)
Centrally released arginine vasopressin (AVP) has been reported to increase the water permeability of brain capillaries under both normal and pathological conditions. It is not known, however, whether AVP regulates the permeability of brain capillaries via a V1 receptor or
N G Milton et al.
The Journal of physiology, 469, 525-534 (1993-09-01)
1. The actions of peripheral arginine vasopressin (AVP) on the febrile responses of conscious rabbits induced by peripherally administered polyinosinic:polycytidylic acid (poly(I).poly(C)) have been studied using an AVP V1 receptor antagonist ([deamino-Pen1, O-Me-Tyr2, Arg8]-vasopressin). 2. Temperature responses were monitored continuously
M T Su et al.
British journal of pharmacology, 123(4), 625-630 (1998-03-28)
1. In this study, we investigated the effects of different drugs (a kappa-opioid receptor agonist U-50,488, a vasopressin receptor antagonist dPTyr(Me)AVP or an N-methyl-D-aspartate (NMDA) receptor antagonist MK-801) on the development of morphine tolerance in rat hippocampal slices. 2. Hippocampal
H J Lenz et al.
The Journal of clinical investigation, 85(1), 25-32 (1990-01-01)
Proximal duodenal bicarbonate secretion is an important factor in humans and animals protecting the mucosa against acid-peptic damage. This study examined the mechanisms responsible for the central nervous system regulation of duodenal bicarbonate secretion by calcitonin gene-related peptide (CGRP) in
C F Ferris et al.
European journal of pharmacology, 154(2), 153-159 (1988-09-13)
Flank marking, a form of olfactory communication displayed by hamsters, is dependent upon vasopressin-sensitive neurons in the anterior hypothalamus. In the present study two vasopressin type-1 (V1) receptor antagonists, d(CH2)5Tyr(Me)AVP and dPTyr(Me)AVP were tested for their ability to block flank
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