WY-46824

Chemical compound
WY-46824
Identifiers
  • 1-[1-(3-chlorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol
CAS Number
  • 122718-49-4 checkY
PubChem CID
  • 10314993
ChemSpider
  • 8490458
UNII
  • 99T4HMN9HV
ChEMBL
  • ChEMBL511347
CompTox Dashboard (EPA)
  • DTXSID50438031 Edit this at Wikidata
Chemical and physical data
FormulaC19H29ClN2O
Molar mass336.90 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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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Piperazines
Simple piperazines
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PhenylpiperazinesBenzylpiperazinesDiphenylalkylpiperazines
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Adamantanes
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