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V2013

Sigma-Aldrich

[deamino-Cys1, Val4, D-Arg8]-Vasopressin

≥95%

Synonym(s):

Val4−dDAVP

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About This Item

Empirical Formula (Hill Notation):
C46H65N13O11S2
Molecular Weight:
1040.22
MDL number:
MFCD00080166
UNSPSC Code:
51111800
PubChem Substance ID:
329829030
NACRES:
NA.32

biological source

synthetic (organic)

sterility

non-sterile

assay

≥95%

form

powder

solubility

50% acetic acid: soluble 1 mg/mL, clear, colorless

shipped in

ambient

storage temp.

−20°C

SMILES string

CC(C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)CCSSC[C@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N4CCC[C@H]4C(=O)N[C@H](CCCNC(N)=N)C(=O)NCC(N)=O

InChI

1S/C46H65N13O11S2/c1-25(2)38-44(69)56-32(22-35(47)61)41(66)57-33(45(70)59-18-7-11-34(59)43(68)54-29(10-6-17-51-46(49)50)39(64)52-23-36(48)62)24-72-71-19-16-37(63)53-30(21-27-12-14-28(60)15-13-27)40(65)55-31(42(67)58-38)20-26-8-4-3-5-9-26/h3-5,8-9,12-15,25,29-34,38,60H,6-7,10-11,16-24H2,1-2H3,(H2,47,61)(H2,48,62)(H,52,64)(H,53,63)(H,54,68)(H,55,65)(H,56,69)(H,57,66)(H,58,67)(H4,49,50,51)/t29-,30+,31+,32+,33+,34+,38+/m1/s1

InChI key

KEBRFHAVFOSSOX-WSFLLCRESA-N

Gene Information

human ... AVPR2(554)
mouse ... AVPR2(12000)
rat ... AVPR2(25108)

Amino Acid Sequence

Mpa-Tyr-Phe-Val-Asn-Cys-Pro-Arg-Gly-NH2

Application

[Deamino-Cys1, Val4, D-Arg8]-Vasopressin was used to prepare sample for qualitative detection of desmopressin in plasma by using liquid chromatography-electrospray tandem mass spectrometry.

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 can also stimulate three acid-base transporters and hence increases the capability of the cell to regulate pHi.

Preparation Note

[deamino-Cys1, Val4, D-Arg8]-Vasopressin dissolves in water at 1 mg/ml to yield a clear, colorless solution.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Ana Pena et al.
Journal of medicinal chemistry, 50(4), 835-847 (2007-02-16)
The neurohypophyseal peptides arginine vasopressin (AVP) and oxytocin (OT) mediate a wide variety of peripheral and central physiological and behavioral effects by acting on four different G-protein coupled receptors, termed V1a (vascular), V1b (pituitary), V2 (renal), and OT (uterine). We
G Croiset et al.
Brain research, 759(1), 18-23 (1997-06-06)
Subcutaneously (s.c.) administered [Arg8]vasopressin (AVP) potentiated seizures induced by intracerebroventricular (i.c.v.) injection of 1.95 mg pilocarpine (a muscarinic cholinergic agonist). A bell-shaped relation between dose and effect was found. I.c.v. pretreatment with a V1, V2 or oxytocin receptor antagonist was
Simone Esposito et al.
Analytical and bioanalytical chemistry, 402(9), 2789-2796 (2012-02-10)
This work describes a liquid chromatography-electrospray tandem mass spectrometry method for detection of desmopressin in human plasma in the low femtomolar range. Desmopressin is a synthetic analogue of the antidiuretic hormone arginine vasopressin and it might be used by athletes
S Lundin et al.
Peptides, 15(5), 809-814 (1994-01-01)
The gastrointestinal absorption of a series of vasopressin (VP) analogues with enhanced enzymatic stability was determined in chronically catheterized, conscious rats. The following peptides were used: [Mpa1,D-Arg8]vasopressin (dDAVP), [Mpa1,Asn4,D-Arg8]VP, [Mpa1,Val4,D-Arg8]VP, [Mpa1,(CH3)3Ala4,D-Arg8]VP, [Mpa1,Tyr(ethyl)2,D-Arg8]VP, and [Mpa1,D-Tyr(ethyl)2,Ile3,Val4,D-Arg8]VP. The peptides were administered by gavage
Martin W Dünser et al.
Circulation, 107(18), 2313-2319 (2003-05-07)
Vasodilatory shock is a potentially lethal complication of severe disease in critically ill patients. Currently, catecholamines are the most widely used vasopressor agents to support blood pressure, but loss of catecholamine pressor effects is a well-known clinical dilemma. Arginine vasopressin
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