Tocinoic acid explained

Class:	Oxytocin receptor antagonist
Cas Number:	34330-23-9
Pubchem:	3082393
Chemspiderid:	2339833
Synonyms:	TOC; 7-de-Pro-3-de-Leu-3-de-GlyNH2-deoxytocin
Iupac Name:	(4R,7S,10S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2''S'')-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
C:	30
H:	44
N:	8
O:	10
S:	2
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
Stdinchi:	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
Stdinchikey:	ITRWUGOBSKHPTA-LYZHYIKWSA-N

Tocinoic acid is a peptide oxytocin receptor antagonist which is used in scientific research. 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.^{[1] [2] [3] [4]} Similar findings have been made for the non-peptide selective oxytocin receptor antagonist L-368899.^[5] However, in other studies, other oxytocin receptor antagonists have been ineffective in blocking MDMA-induced prosocial behavior.^{[6] [7]} The reasons for these discrepancies are unclear.

See also

• Atosiban
• Empathogen § Mechanism of action

Notes and References

1. Wronikowska-Denysiuk O, Mrozek W, Budzyńska B . The Role of Oxytocin and Vasopressin in Drug-Induced Reward-Implications for Social and Non-Social Factors . Biomolecules . 13 . 3 . 405 . February 2023 . 36979340 . 10046619 . 10.3390/biom13030405 . free .
2. Carson DS, Guastella AJ, Taylor ER, McGregor IS . A brief history of oxytocin and its role in modulating psychostimulant effects . Journal of Psychopharmacology . 27 . 3 . 231–247 . March 2013 . 23348754 . 10.1177/0269881112473788 .
3. McGregor IS, Callaghan PD, Hunt GE . From ultrasocial to antisocial: a role for oxytocin in the acute reinforcing effects and long-term adverse consequences of drug use? . British Journal of Pharmacology . 154 . 2 . 358–368 . May 2008 . 18475254 . 2442436 . 10.1038/bjp.2008.132 .
4. Dunlap LE, Andrews AM, Olson DE . Dark Classics in Chemical Neuroscience: 3,4-Methylenedioxymethamphetamine . ACS Chemical Neuroscience . 9 . 10 . 2408–2427 . October 2018 . 30001118 . 6197894 . 10.1021/acschemneuro.8b00155 .
5. Kuteykin-Teplyakov K, Maldonado R . Looking for prosocial genes: ITRAQ analysis of proteins involved in MDMA-induced sociability in mice . European Neuropsychopharmacology . 24 . 11 . 1773–1783 . November 2014 . 25241352 . 10.1016/j.euroneuro.2014.08.007 . 10230/23309 . free .
6. Kamilar-Britt P, Bedi G . The prosocial effects of 3,4-methylenedioxymethamphetamine (MDMA): Controlled studies in humans and laboratory animals . Neuroscience and Biobehavioral Reviews . 57 . 433–446 . October 2015 . 26408071 . 4678620 . 10.1016/j.neubiorev.2015.08.016 .
7. Heifets BD, Salgado JS, Taylor MD, Hoerbelt P, Cardozo Pinto DF, Steinberg EE, Walsh JJ, Sze JY, Malenka RC . Distinct neural mechanisms for the prosocial and rewarding properties of MDMA . Science Translational Medicine . 11 . 522 . December 2019 . 31826983 . 7123941 . 10.1126/scitranslmed.aaw6435 .