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Key Documents

T3149

Sigma-Aldrich

Tocinoic acid

≥97% (HPLC)

Synonym(s):

[Ile3]-Pressinoic acid

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About This Item

Empirical Formula (Hill Notation):
C30H44N8O10S2
CAS Number:
Molecular Weight:
740.85
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:

Assay

≥97% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

storage temp.

−20°C

SMILES string

CCC(C)C1NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(N)CSSCC(NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC1=O)C(O)=O

InChI

1S/C30H44N8O10S2/c1-3-14(2)24-29(46)34-18(8-9-22(32)40)26(43)36-20(11-23(33)41)27(44)37-21(30(47)48)13-50-49-12-17(31)25(42)35-19(28(45)38-24)10-15-4-6-16(39)7-5-15/h4-7,14,17-21,24,39H,3,8-13,31H2,1-2H3,(H2,32,40)(H2,33,41)(H,34,46)(H,35,42)(H,36,43)(H,37,44)(H,38,45)(H,47,48)

InChI key

ITRWUGOBSKHPTA-UHFFFAOYSA-N

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Amino Acid Sequence

Cys-Tyr-Ile-Gln-Asn-Cys [Disulfide bridge: 1-6]

Application

Tocinoic acid is an oxytocin receptor antagonist and is used to study effects of oxytocin and 5-HT1A receptors on the prosocial effects of 3,4 methylenedioxymethamphetamine (MDMA; ecstasy). It can also be used as a test compound for studying whether the release of protein disulfide isomerase activity is stimulated by activated platelets or not.

Biochem/physiol Actions

Tocinoic acid contains the ring structure of oxytocin that inhibits the release of melanocyte-stimulating hormones (MSH) the rat pituitary in vitro.

Other Notes

N-terminal hexapeptide fragment of oxytocin.

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

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M A Lang et al.
The American journal of physiology, 251(1 Pt 2), R77-R81 (1986-07-01)
To characterize the V2 receptor (for antidiuretic hormone), we have studied the effect of a number of neurohypophysial hormone analogues on cyclic AMP (cAMP) accumulation and short-circuit current in cultured epithelia formed by A6 cells. A6 is the designation of
K Chen et al.
Blood, 79(9), 2226-2228 (1992-05-01)
The release of protein disulfide isomerase by activated platelets was hypothesized on the basis of reported intermolecular and intramolecular thiol-disulfide exchange and disulfide reduction involving released thrombospondin in the supernatant solution of activated platelets (Danishefsky, Alexander, Detwiler: Biochemistry, 23:4984, 1984;
P L Yeo et al.
Analytical chemistry, 65(21), 3061-3066 (1993-11-01)
Methodology is described for characterization of the kinetics and equilibria of thiol/disulfide interchange reactions of the disulfide bonds in the neurohypophyseal peptide hormones arginine vasopressin and oxytocin and the related peptides pressinoic acid and tocinoic acid. Thiol/disulfide interchange reaction mixtures
D Despeyroux et al.
Rapid communications in mass spectrometry : RCM, 5(4), 156-159 (1991-04-01)
A method has been developed for the determination of the amino-acid sequence of a cyclic peptide containing cystine. It is based on the reduction of the peptide in a reductive matrix prior to ionization by fast-atom bombardment. The amino-acid sequence
M Salzet et al.
Brain research, 601(1-2), 173-184 (1993-01-22)
A large number of oxytocin (OT)-like neurons were detected in the sex segmental ganglia (SG5, SG6) of three species of leeches belonging to different orders: Theromyzon tessulatum, Hirudo medicinalis and Erpobdella octoculata. In this latter species, an epitope close to

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