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V2381

Sigma-Aldrich

[Adamantaneacetyl1, O-Et-D-Tyr2, Val4, Aminobutyryl6, Arg8,9]-Vasopressin

≥95% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C62H94N16O11
CAS Number:
112465-00-6
Molecular Weight:
1239.51
MDL number:
MFCD00133935
UNSPSC Code:
51111800
PubChem Substance ID:
24900733

biological source

synthetic (organic)

Assay

≥95% (HPLC)

form

powder

solubility

H2O: soluble 1 mg/mL, clear, colorless

shipped in

ambient

storage temp.

−20°C

SMILES string

CCOc1ccc(CC(NC(=O)CC23CC4CC(CC(C4)C2)C3)C(=O)NC(Cc5ccccc5)C(=O)NC(C(C)C)C(=O)NC(CC(N)=O)C(=O)NC(CC)C(=O)N6CCCC6C(=O)NC(CCCNC(N)=N)C(=O)NC(CCCNC(N)=N)C(N)=O)cc1

InChI

1S/C62H94N16O11/c1-5-42(59(88)78-24-12-17-48(78)57(86)74-44(16-11-23-70-61(67)68)53(82)73-43(52(64)81)15-10-22-69-60(65)66)72-55(84)47(30-49(63)79)76-58(87)51(35(3)4)77-56(85)46(28-36-13-8-7-9-14-36)75-54(83)45(29-37-18-20-41(21-19-37)89-6-2)71-50(80)34-62-31-38-25-39(32-62)27-40(26-38)33-62/h7-9,13-14,18-21,35,38-40,42-48,51H,5-6,10-12,15-17,22-34H2,1-4H3,(H2,63,79)(H2,64,81)(H,71,80)(H,72,84)(H,73,82)(H,74,86)(H,75,83)(H,76,87)(H,77,85)(H4,65,66,69)(H4,67,68,70)

InChI key

LEXYSBQMSSPQTG-UHFFFAOYSA-N

Gene Information

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

Amino Acid Sequence

Ada-TyrOEt-Phe-Val-Asn-Abu-Pro-Arg-Arg-NH2

Application

[Adamantaneacetyl1, O-Et-D-Tyr2, Val4, Aminobutyryl6, Arg8,9]-Vasopressin was used to inhibit the V2 receptor for studying the role of arginine vasopressin receptors V1 and V2 in brain damage, brain edema formation and functional outcome after transient focal cerebral ischemia.

Biochem/physiol Actions

[Adamantaneacetyl1, O-Et-D-Tyr2, Val4, Aminobutyryl6, Arg8,9]-Vasopressin is a V2 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. Additionally, vasopressin can induce anion secretion by Human and Porcine Vas Deferens Epithelia.

Preparation Note

[Adamantaneacetyl1, O-Et-D-Tyr2, Val4, Aminobutyryl6, Arg8,9]-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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J R Haselton et al.
The American journal of physiology, 275(4 Pt 2), R1334-R1342 (1998-10-02)
Several lines of evidence support the existence of an oligosynaptic projection from the paraventricular nucleus of the hypothalamus (PVN) to the kidney in the rat. We sought to provide evidence that this neural pathway is capable of influencing renal function
M Manning et al.
Nature, 329(6142), 839-840 (1987-10-04)
Early reports that acyclic analogues of oxytocin and vasopressin (AVP) have drastically reduced agonistic activities established as dogma that an intact hexapeptide ring structure is essential for the pharmacological activities of analogues of neurohypophysial hormones. Thus, virtually all the many
S Tanabe et al.
Pharmacology, biochemistry, and behavior, 63(4), 549-553 (1999-08-26)
Arginine-vasopressin fragment 4-9 (AVP4-9) has been demonstrated in animal studies to facilitate learning and memory. To clarify the mechanisms of this facilitation, we focused on the effects of AVP4-9 on rodent cholinergic systems. AVP4-9 (0.1 microM) enhanced the basal and
Travis M Hagedorn et al.
Biology of reproduction, 77(3), 416-424 (2007-04-20)
Experiments were conducted to characterize the effects of oxytocin (OT) and vasopressin (VP) on epithelial cells isolated from human (1 degree HVD) and porcine (1 degree PVD) vas deferens and an immortalized epithelial cell line derived from porcine vas deferens
Abedin Vakili et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 25(8), 1012-1019 (2005-03-04)
Brain edema formation is one of the most important mechanisms responsible for brain damage after ischemic stroke. Despite considerable efforts, no specific therapy is available yet. Arginine vasopressin (AVP) regulates cerebral water homeostasis and has been involved in brain edema
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