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S33005

Clinical data
Other names	(–)-1-(1-dimethylaminomethyl) 5-methoxybenzocyclobutan-1-yl) cyclohexanol
Identifiers
IUPAC name 1--4-methoxy-7-bicycloocta-1(6),2, 4-trienyl]cyclohexan-1-ol
CAS Number	242473-60-5
PubChem CID	9925999
ChemSpider	8101634
UNII	C53PYU3EBT
CompTox Dashboard (EPA)	DTXSID001030367
Chemical and physical data
Formula	C18H27NO2
Molar mass	289.419 g·mol
3D model (JSmol)	Interactive image
SMILES CN(C)CC1(CC2=C1C=C(C=C2)OC)C3(CCCCC3)O
InChI 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, 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--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."

See also

• Milnacipran

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

External links

• PubMed search
• Binding Database
• The patent and synthesis discussion can be found in U.S. patent 6,107,345

• Tertiary alcohols
• Experimental antidepressants
• Benzocyclobutenes
• Phenol ethers
• Serotonin–norepinephrine reuptake inhibitors
• Sigma agonists