TC OT 39

TC OT 39
Clinical data
Other names	"Compound 39"; SynOTA
Drug class	Oxytocin receptor agonist; Vasopressin receptor modulator
ATC code	None;
Identifiers
	IUPAC name (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide;
CAS Number	479232-57-0;
PubChem CID	135413563;
ChemSpider	23249746;
UNII	RMV6SD8REW;
CompTox Dashboard (EPA)	DTXSID301031871 ;
Chemical and physical data
Formula	C32H40N8O2S
Molar mass	600.79 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cc1cc(ccc1CNC(=O)N2CCC[C@H]2C(=S)N3CCCN(CC3)C)C(=O)N4Cc5cnn(c5Nc6c4cccc6)C;
	InChI InChI=1S/C32H40N8O2S/c1-22-18-23(30(41)40-21-25-20-34-37(3)29(25)35-26-8-4-5-9-27(26)40)11-12-24(22)19-33-32(42)39-15-6-10-28(39)31(43)38-14-7-13-36(2)16-17-38/h4-5,8-9,11-12,18,20,28,35H,6-7,10,13-17,19,21H2,1-3H3,(H,33,42)/t28-/m0/s1; Key:KSNHHKZYKYNBEI-NDEPHWFRSA-N;

TC OT 39, also known as "compound 39", is a non-peptide partial agonist of the oxytocin and vasopressin V₂ receptors (K_i = 147 nM and >1,000 nM, respectively) and antagonist of the vasopressin V_1A receptor (K_i = 330 nM).^[3]^[1] The EC₅₀Tooltip half-maximal effective concentration values of the drug were 33 nM at the oxytocin receptor and 850 nM at the vasopressin V₂ receptor.^[1] TC OT 39 was first described in the scientific literature by Gary R. W. Pitt and colleagues in 2004.^[3]^[1] The drug was the first small-molecule oxytocin receptor agonist to be described, though it was the lead optimized compound of a described series of compounds.^[3]^[1] Subsequently, improved analogues like WAY-267,464 (2010), LIT-001 (2018), and LIT-002 (2026) were described.^[3]^[4]^[5]^[6]

References

1 2 3 4 5 Pitt GR, Batt AR, Haigh RM, Penson AM, Robson PA, Rooker DP, Tartar AL, Trim JE, Yea CM, Roe MB (September 2004). "Non-peptide oxytocin agonists". Bioorganic & Medicinal Chemistry Letters. 14 (17): 4585–4589. doi:10.1016/j.bmcl.2004.04.107. PMID 15357997.
↑ Pederson, Cort (30 November 2015). "Preclinical Testing of Novel Oxytocin Receptor Activators in Models of Autism Phenotypes". apps.dtic.mil. Retrieved 19 July 2026.
1 2 3 4 Nashar PE, Whitfield AA, Mikusek J, Reekie TA (2022). "The Current Status of Drug Discovery for the Oxytocin Receptor". Methods Mol Biol. 2384: 153–174. doi:10.1007/978-1-0716-1759-5_10. PMID 34550574.
↑ Ring RH, Schechter LE, Leonard SK, Dwyer JM, Platt BJ, Graf R, Grauer S, Pulicicchio C, Resnick L, Rahman Z, Sukoff Rizzo SJ, Luo B, Beyer CE, Logue SF, Marquis KL, Hughes ZA, Rosenzweig-Lipson S (January 2010). "Receptor and behavioral pharmacology of WAY-267464, a non-peptide oxytocin receptor agonist". Neuropharmacology. 58 (1): 69–77. doi:10.1016/j.neuropharm.2009.07.016. PMID 19615387.
↑ Frantz MC, Pellissier LP, Pflimlin E, Loison S, Gandía J, Marsol C, Durroux T, Mouillac B, Becker JA, Le Merrer J, Valencia C, Villa P, Bonnet D, Hibert M (October 2018). "LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism". J Med Chem. 61 (19): 8670–8692. doi:10.1021/acs.jmedchem.8b00697. PMID 30199637.
↑ Hibert M, Zhao Q, Noel-Duchesneau L, Peron F, Brugoux A, Bolot F, Marsol C, Bonnet D, Verner E, Kos I, Iminov R, Kondratov I, Orcel H, Couvineau P, Cong X, Ben Boubaker R, Mouillac B, Valencia C, Gizzi P, Daubeuf F, Garnier D, Villa P, Poirier R, Mery S, Laboute T, Le Merrer J, Becker J (April 2026). "LIT-002, a highly potent and selective nonpeptide oxytocin receptor agonist that improves social interaction in mouse models of autism". SSRN Electronic Journal. doi:10.2139/ssrn.6624262.

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[PittBattHaigh2004-1] 1 2 3 4 5 Pitt GR, Batt AR, Haigh RM, Penson AM, Robson PA, Rooker DP, Tartar AL, Trim JE, Yea CM, Roe MB (September 2004). "Non-peptide oxytocin agonists". Bioorganic & Medicinal Chemistry Letters. 14 (17): 4585–4589. doi:10.1016/j.bmcl.2004.04.107. PMID 15357997.

[Pederson2015-2] Pederson, Cort (30 November 2015). "Preclinical Testing of Novel Oxytocin Receptor Activators in Models of Autism Phenotypes". apps.dtic.mil. Retrieved 19 July 2026.

[NasharWhitfieldMikusek2022-3] 1 2 3 4 Nashar PE, Whitfield AA, Mikusek J, Reekie TA (2022). "The Current Status of Drug Discovery for the Oxytocin Receptor". Methods Mol Biol. 2384: 153–174. doi:10.1007/978-1-0716-1759-5_10. PMID 34550574.

[RingSchechterLeonard2010-4] Ring RH, Schechter LE, Leonard SK, Dwyer JM, Platt BJ, Graf R, Grauer S, Pulicicchio C, Resnick L, Rahman Z, Sukoff Rizzo SJ, Luo B, Beyer CE, Logue SF, Marquis KL, Hughes ZA, Rosenzweig-Lipson S (January 2010). "Receptor and behavioral pharmacology of WAY-267464, a non-peptide oxytocin receptor agonist". Neuropharmacology. 58 (1): 69–77. doi:10.1016/j.neuropharm.2009.07.016. PMID 19615387.

[FrantzPellissierPflimlin2018-5] Frantz MC, Pellissier LP, Pflimlin E, Loison S, Gandía J, Marsol C, Durroux T, Mouillac B, Becker JA, Le Merrer J, Valencia C, Villa P, Bonnet D, Hibert M (October 2018). "LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism". J Med Chem. 61 (19): 8670–8692. doi:10.1021/acs.jmedchem.8b00697. PMID 30199637.

[HibertZhaoNoel-Duchesneau2026-6] Hibert M, Zhao Q, Noel-Duchesneau L, Peron F, Brugoux A, Bolot F, Marsol C, Bonnet D, Verner E, Kos I, Iminov R, Kondratov I, Orcel H, Couvineau P, Cong X, Ben Boubaker R, Mouillac B, Valencia C, Gizzi P, Daubeuf F, Garnier D, Villa P, Poirier R, Mery S, Laboute T, Le Merrer J, Becker J (April 2026). "LIT-002, a highly potent and selective nonpeptide oxytocin receptor agonist that improves social interaction in mouse models of autism". SSRN Electronic Journal. doi:10.2139/ssrn.6624262.

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TC OT 39

See also

References