AC-90179

AC-90179 is a piperidine derivative which acts as an inverse agonist at the 5-HT2A serotonin receptor and an antagonist at 5-HT2C. It was developed as a potential antipsychotic but was not pursued for medical applications due to poor oral bioavailability, however it continues to be used as a tool compound in pharmacological research.[1][2]

AC-90179
Identifiers
IUPAC name
  • 2-(4-methoxyphenyl)-N-[(4-methylphenyl)methyl]-N-(1-methylpiperidin-4-yl)acetamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC23H30N2O2
Molar mass366.505 g·mol−1
3D model (JSmol)
SMILES
  • CC1=CC=C(C=C1)CN(C2CCN(CC2)C)C(=O)CC3=CC=C(C=C3)OC
InChI
  • InChI=1S/C23H30N2O2/c1-18-4-6-20(7-5-18)17-25(21-12-14-24(2)15-13-21)23(26)16-19-8-10-22(27-3)11-9-19/h4-11,21H,12-17H2,1-3H3
  • Key:AHGNJBSTWQOSAB-UHFFFAOYSA-N

See also

References
  1. Weiner DM, Burstein ES, Nash N, Croston GE, Currier EA, Vanover KE, Harvey SC, Donohue E, Hansen HC, Andersson CM, Spalding TA, Gibson DF, Krebs-Thomson K, Powell SB, Geyer MA, Hacksell U, Brann MR (October 2001). "5-hydroxytryptamine2A receptor inverse agonists as antipsychotics". The Journal of Pharmacology and Experimental Therapeutics. 299 (1): 268–76. PMID 11561089.
  2. Vanover KE, Harvey SC, Son T, Bradley SR, Kold H, Makhay M, Veinbergs I, Spalding TA, Weiner DM, Andersson CM, Tolf BR, Brann MR, Hacksell U, Davis RE (September 2004). "Pharmacological characterization of AC-90179 [2-(4-methoxyphenyl)-N-(4-methyl-benzyl)-N-(1-methyl-piperidin-4-yl)-acetamide hydrochloride]: a selective serotonin 2A receptor inverse agonist". The Journal of Pharmacology and Experimental Therapeutics. 310 (3): 943–51. doi:10.1124/jpet.104.066688. PMID 15102927. S2CID 12205122.


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.