S33005

S33005
Clinical data
Other names(–)-1-(1-dimethylaminomethyl) 5-methoxybenzocyclobutan-1-yl) cyclohexanol
Identifiers
  • 1-[7-[(dimethylamino)methyl]-4-methoxy-7-bicyclo[4.2.0]octa-1(6),2, 4-trienyl]cyclohexan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H27NO2
Molar mass289.419 g·mol−1
3D model (JSmol)
  • CN(C)CC1(CC2=C1C=C(C=C2)OC)C3(CCCCC3)O
  • InChI=1S/C18H27NO2/c1-19(2)13-17(18(20)9-5-4-6-10-18)12-14-7-8-15(21-3)11-16(14)17/h7-8,11,20H,4-6,9-10,12-13H2,1-3H3
  • Key:UBIQMAFTTDZGEX-UHFFFAOYSA-N

S33005 is a serotonin–norepinephrine reuptake inhibitor (SNRI) that was under development by Servier for the treatment of depression and related disorders. It is structurally related to venlafaxine but has a more complex molecular structure. Venlafaxine appears to be a sigma modulator,[1] but it is not known if S33005 shares this activity.

Synthesis

"The 1-cyano-benzocyclobutenes used as starting material are obtained, for example, by subjecting a β-[orthohalogeno-phenyl]-propionitrile to intramolecular condensation in the presence of potassium amide, or by brominating a benzocyclobutene in position 1 with N-bromosuccinimide, followed by exchange of the bromine atom for a cyano group by means of sodium cyanide."[2]

See also

References

  1. ^ Dhir A, Kulkarni SK (June 2007). "Involvement of sigma-1 receptor modulation in the antidepressant action of venlafaxine". Neuroscience Letters. 420 (3): 204–8. doi:10.1016/j.neulet.2007.04.055. PMID 17532136. S2CID 25971336.
  2. ^ U.S. patent 3,622,614
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