WY-46824

WY-46824
Identifiers
IUPAC name
  • 1-[1-(3-chlorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H29ClN2O
Molar mass336.90 g·mol−1
3D model (JSmol)
SMILES
  • CN1CCN(CC1)CC(C2=CC(=CC=C2)Cl)C3(CCCCC3)O
InChI
  • 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 that was disclosed by Paige Mahaney, et al. of Wyeth in 2008.[1] The compound actually appears in an article a year earlier in 2007 but is not the main focus of the work.[2] It has NET binding of 46 nM, DAT = 58 nM and SERT = 18795 nM. The racemic compound was resolved into its constituent enantiomers, and the (S) enantiomer is the more active one. The N-desmethyl derivative 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.
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