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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)

Quality Level

200

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
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
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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