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S33005

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
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 aserotonin–norepinephrine reuptake inhibitor (SNRI) that was underdevelopment byServier for the treatment of depression and related disorders. It is structurally related tovenlafaxine 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

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"The 1-cyano-benzocyclobutenes used as starting material are obtained, for example, by subjecting a β-[orthohalogeno-phenyl]-propionitrile tointramolecularcondensation in the presence ofpotassium amide, or by brominating abenzocyclobutene in position 1 withN-bromosuccinimide, followed by exchange of the bromine atom for a cyano group by means ofsodium cyanide."[2]

See also

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References

[edit]
  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

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SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
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TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
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MAOATooltip Monoamine oxidase A-selective
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
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