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V0130

Sigma-Aldrich

[Arg8]-Vasotocin acetate salt

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C43H67N15O12S2
CAS Number:
74927-14-3
Molecular Weight:
1050.22
MDL number:
MFCD00133923
UNSPSC Code:
51111800
PubChem Substance ID:
24900689
NACRES:
NA.32

Quality Level

200

assay

≥97% (HPLC)

solubility

H2O: soluble 20 mg/mL, clear, colorless

UniProt accession no.

P01185

storage temp.

−20°C

SMILES string

CC[C@@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](N)CSSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(N)=O

InChI

1S/C43H67N15O12S2/c1-3-21(2)34-41(69)53-26(12-13-31(45)60)37(65)55-28(17-32(46)61)38(66)56-29(20-72-71-19-24(44)35(63)54-27(39(67)57-34)16-22-8-10-23(59)11-9-22)42(70)58-15-5-7-30(58)40(68)52-25(6-4-14-50-43(48)49)36(64)51-18-33(47)62/h8-11,21,24-30,34,59H,3-7,12-20,44H2,1-2H3,(H2,45,60)(H2,46,61)(H2,47,62)(H,51,64)(H,52,68)(H,53,69)(H,54,63)(H,55,65)(H,56,66)(H,57,67)(H4,48,49,50)/t21-,24+,25+,26+,27+,28+,29+,30+,34+/m1/s1

InChI key

OXDZADMCOWPSOC-QLWWDPKZSA-N

Gene Information

human ... AVP(551)

Amino Acid Sequence

Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide Bridge: 1-6]

Application

[Arg8]-Vasotocin acetate salt was used as a test compound for studying whether it can regulate the interspecific cooperative behaviour in fish. The product was used for inducing parturition in viviparous females to study reproduction in oviparous and viviparous lizard females of species Zootoca vivipara.

Biochem/physiol Actions

[Arg8]-Vasotocin (AVT) is a neurohypophyseal peptide of the vasopressin/oxytocin hormone family that mediates social behaviors, coregulates the adrenocortical stress response as well as maintains water balance. AVT stimulates neurones in the mammalian central nervous system.

Preparation Note

[Arg8]-Vasotocin acetate salt dissolves in water at 20 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)

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C D Ingram et al.
Journal of neuroendocrinology, 6(4), 415-422 (1994-08-01)
Using extracellular recordings from brainstem slices in vitro, it was demonstrated that a high proportion (38/56) of neurones in the dorsal vagal complex of dioestrus, virgin female rats exhibit an excitatory response to [Arg8]-vasotocin (AVT). Pharmacological characterization suggests that these
D J Conklin et al.
General and comparative endocrinology, 114(1), 36-46 (1999-03-30)
Arginine vasotocin (AVT) is present in the neurohypophysis of all nonmammalian vertebrates and it appears to be the antecedent of the neurohypophysial nonapeptide hormones. Relatively little is known about AVT receptors in lower vertebrates, especially fish, and the present study
David Kabelik et al.
Brain, behavior and evolution, 72(4), 283-294 (2008-11-20)
The neuropeptide arginine vasotocin (AVT) and its mammalian homologue arginine vasopressin (AVP) are neuromodulators known to be steroid sensitive and associated with social behaviors in a number of vertebrate taxa. However, the role of AVT/P in the regulation of aggression
R Mihai et al.
Neuroscience, 62(3), 783-792 (1994-10-01)
The excitatory effect of [Arg8]-vasopressin and its potential contribution to the circadian cycle of electrical activity in the suprachiasmatic nucleus of the rat was investigated using extracellular recordings from hypothalamic slices from virgin female rats. The majority of neurons tested
Rute Mendonça et al.
Brain, behavior and evolution, 82(3), 166-176 (2013-10-11)
The nonapeptide arginine vasotocin (AVT) and its mammalian homologue arginine vasopressin are well known for their role in the modulation of several intraspecific social behaviours, such as social approach/withdrawal and aggression. Recently, we suggested that AVT might also be important
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