S33005

S33005

Clinical data
Other names	(–)-1-(1-dimethylaminomethyl) 5-methoxybenzocyclobutan-1-yl) cyclohexanol
Identifiers
IUPAC name 1-[7-[(dimethylamino)methyl]-4-methoxy-7-bicyclo[4.2.0]octa-1(6),2, 4-trienyl]cyclohexan-1-ol
CAS Number	242473-60-5 Y
PubChem CID	9925999
ChemSpider	8101634
UNII	C53PYU3EBT
Chemical and physical data
Formula	C18H27NO2
Molar mass	289.419 g·mol−1
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-[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."

See also

• Milnacipran

External links

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