Tocinoic acid

Tocinoic acid is a peptide oxytocin receptor antagonist which is used in scientific research.^[1] Intracerebroventricular injection of the drug has been found to block the prosocial behavior induced by the serotonin releasing agent MDMA without affecting baseline social behavior in animals.^[2][3][4][1] Similar findings have been made for the non-peptide selective oxytocin receptor antagonist L-368899.^[2][5] However, in other studies, other oxytocin receptor antagonists have been ineffective in blocking MDMA-induced prosocial behavior.^[1][6][7] The reasons for these discrepancies are unclear.^[2][1]

Tocinoic acid

Clinical data
Other names	TOC; 7-de-Pro-3-de-Leu-3-de-GlyNH2-deoxytocin
Drug class	Oxytocin receptor antagonist
Identifiers
IUPAC name (4R,7S,10S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxylic acid
CAS Number	34330-23-9
PubChem CID	3082393
ChemSpider	2339833
Chemical and physical data
Formula	C30H44N8O10S2
Molar mass	740.85 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC[C@H](C)C1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)O)CC(=O)N)CCC(=O)N
InChI 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)/t14-,17-,18-,19-,20-,21-,24?/m0/s1 Key:ITRWUGOBSKHPTA-LYZHYIKWSA-N

See also

• Atosiban
• Entactogen § Mechanism of action