WY-46824

WY-46824
Identifiers
  • 1-[1-(3-chlorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H29ClN2O
Molar mass336.90 g·mol−1
3D model (JSmol)
  • CN1CCN(CC1)CC(C2=CC(=CC=C2)Cl)C3(CCCCC3)O
  • InChI=1S/C19H29ClN2O/c1-21-10-12-22(13-11-21)15-18(16-6-5-7-17(20)14-16)19(23)8-3-2-4-9-19/h5-7,14,18,23H,2-4,8-13,15H2,1H3
  • Key:GRUIIAQNNWQJPW-UHFFFAOYSA-N

WY-46824 is a norepinephrine-dopamine reuptake inhibitor related to venlafaxine. It was disclosed by Paige Mahaney and colleagues from Wyeth in 2008.[1] The compound was mentioned in an earlier article from 2007 but was not the main focus of that study.[2]

WY-46824 has binding affinities of 46 nM for the norepinephrine transporter (NET), 58 nM for the dopamine transporter (DAT), and 18795 nM for the serotonin transporter (SERT). The racemic mixture of WY-46824 was resolved into its constituent enantiomers, with the (S)-enantiomer being the more active one. The N-desmethyl derivative of WY-46824 also shows similar activity.

References

  1. ^ Mahaney PE, Gavrin LK, Trybulski EJ, Stack GP, Vu TA, Cohn ST, et al. (July 2008). "Structure-activity relationships of the cycloalkanol ethylamine scaffold: discovery of selective norepinephrine reuptake inhibitors". Journal of Medicinal Chemistry. 51 (13): 4038–49. doi:10.1021/jm8002262. PMID 18557608.
  2. ^ Mason JN, Deecher DC, Richmond RL, Stack G, Mahaney PE, Trybulski E, et al. (November 2007). "Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter". The Journal of Pharmacology and Experimental Therapeutics. 323 (2): 720–9. doi:10.1124/jpet.107.125716. PMID 17673606. S2CID 17713759.