CTW0404

CTW0404
Identifiers
	IUPAC name (2S,4R)-N-(2-morpholin-4-ylethyl)-4-(2-phenylethyl)piperidine-2-carboxamide;
PubChem CID	156012687;
ChemSpider	129472747;
ChEMBL	ChEMBL4637675;
Chemical and physical data
Formula	C20H31N3O2
Molar mass	345.487 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN[C@@H](C[C@@H]1CCC2=CC=CC=C2)C(=O)NCCN3CCOCC3;
	InChI InChI=1S/C20H31N3O2/c24-20(22-10-11-23-12-14-25-15-13-23)19-16-18(8-9-21-19)7-6-17-4-2-1-3-5-17/h1-5,18-19,21H,6-16H2,(H,22,24)/t18-,19+/m1/s1; Key:YQSGRDPBXKGAPX-MOPGFXCFSA-N;

CTW0404 is an experimental drug which is described as a positive allosteric modulator of the 5-HT_2A receptor, with neutral or negative modulation of the related 5-HT_2B and 5-HT_2C subtypes. It does not produce the head-twitch response in animal studies, and reduces the head-twitch response produced by DOI, suggesting that it may be a biased allosteric modulator selective for certain signalling pathways.^[1]^[2]^[3]^[4]

References

^ Wold EA, Garcia EJ, Wild CT, Miszkiel JM, Soto CA, Chen J, et al. (July 2020). "Discovery of 4-Phenylpiperidine-2-Carboxamide Analogues as Serotonin 5-HT_2C Receptor-Positive Allosteric Modulators with Enhanced Drug-like Properties". Journal of Medicinal Chemistry. 63 (14): 7529–7544. doi:10.1021/acs.jmedchem.9b01953. PMC 8434884. PMID 32567857.
^ Salinsky LM, Merritt CR, Zamora JC, Giacomini JL, Anastasio NC, Cunningham KA (2023). "μ-opioid receptor agonists and psychedelics: pharmacological opportunities and challenges". Frontiers in Pharmacology. 14: 1239159. doi:10.3389/fphar.2023.1239159. PMC 10598667. PMID 37886127.
^ Zamora JC, Merritt CR, Bolinger AA, Fox RG, Wild CT, Wold EA, et al. (2024). "Serendipitous Discovery of Novel 5-HT2AR Positive Allosteric Modulators (PAMs) Derived From 5-HT2CR PAM Scaffolds". The Journal of Pharmacology and Experimental Therapeutics. 389: 87. doi:10.1124/jpet.087.985400.
^ WO 2023/023287, Zhou J, Cunningham KA, Bolinger AA, Anastasio NC, "Novel heterocyclic compounds as serotonin (5-ht) 5-ht2a and 5-ht2c receptor positive allosteric modulators.", published 22 February 2024, assigned to The Board of Regents of the University of Texas System

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[1] Wold EA, Garcia EJ, Wild CT, Miszkiel JM, Soto CA, Chen J, et al. (July 2020). "Discovery of 4-Phenylpiperidine-2-Carboxamide Analogues as Serotonin 5-HT_2C Receptor-Positive Allosteric Modulators with Enhanced Drug-like Properties". Journal of Medicinal Chemistry. 63 (14): 7529–7544. doi:10.1021/acs.jmedchem.9b01953. PMC 8434884. PMID 32567857.

[2] Salinsky LM, Merritt CR, Zamora JC, Giacomini JL, Anastasio NC, Cunningham KA (2023). "μ-opioid receptor agonists and psychedelics: pharmacological opportunities and challenges". Frontiers in Pharmacology. 14: 1239159. doi:10.3389/fphar.2023.1239159. PMC 10598667. PMID 37886127.

[Zamora_2024-3] Zamora JC, Merritt CR, Bolinger AA, Fox RG, Wild CT, Wold EA, et al. (2024). "Serendipitous Discovery of Novel 5-HT2AR Positive Allosteric Modulators (PAMs) Derived From 5-HT2CR PAM Scaffolds". The Journal of Pharmacology and Experimental Therapeutics. 389: 87. doi:10.1124/jpet.087.985400.

[4] WO 2023/023287, Zhou J, Cunningham KA, Bolinger AA, Anastasio NC, "Novel heterocyclic compounds as serotonin (5-ht) 5-ht2a and 5-ht2c receptor positive allosteric modulators.", published 22 February 2024, assigned to The Board of Regents of the University of Texas System

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[2]

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[4]

See also

References