Desmethylcitalopram

Last updated
Desmethylcitalopram
Desmethylcitalopram.svg
Desmethylcitalopram molecule spacefill.png
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Pharmacokinetic data
Elimination half-life 50 h
Identifiers
  • (RS/S)-1-[3-(Methylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.057.776 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H19FN2O
Molar mass 310.372 g·mol−1
3D model (JSmol)
  • CNCCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
  • InChI=1S/C19H19FN2O/c1-22-10-2-9-19(16-4-6-17(20)7-5-16)18-8-3-14(12-21)11-15(18)13-23-19/h3-8,11,22H,2,9-10,13H2,1H3 X mark.svgN
  • Key:PTJADDMMFYXMMG-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Desmethylcitalopram is an active metabolite of the antidepressant drugs citalopram (racemic) and escitalopram (the S-enantiomer, which would be called desmethylescitalopram). [1] [2] Like citalopram and escitalopram, desmethylcitalopram functions as a selective serotonin reuptake inhibitor (SSRI), and is responsible for some of its parents' therapeutic benefits.

See also

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In 1971, the company hired Klaus Bøgesø as a medicinal chemist. Over the years Bøgesø turned out to have a Midas touch at the game of drug hunting, creating more molecules that made it to the market than almost any other medicinal chemist in the field. The challenge facing him in 1971 following his recruitment was to produce a selective norepinephrine reuptake inhibitor. Like other companies at the time, Lundbeck had little interest in an SSRI. Bøgesø began from an accident in the laboratory. Trying to create a derivative of their norepinephrine reuptake inhibiting antidepressant melitracen, Lundbeck chemists accidentally produced a new chemical — a phenylphthalene. Against all the odds, just like melitracen, this was also a selective norepinephrine reuptake inhibitor. Two potential antidepressants came out of this — talopram and tasulopram, which were pressed into clinical trials. Both however turned out to be energizing, and in a number of cases there were suicide attempts. The fact that there were suicide attempts appeared to confirm another proposal of Paul Kielholz, that activating antidepressants might lead to suicide. Lundbeck's experience suggested that norepinephrine reuptake inhibitors were likely to lead to just this problem. Lundbeck retreated, scared. If norepinephrine reuptake inhibitors were likely to trigger suicide, the greatest hazard of an antidepressant, then Kielholz's view suggested that an SSRI would be less likely to lead to suicide. Bøgesø's job was to see whether the new series of drugs could be converted into a series of SSRIs. Following a lead from Carlsson on how to do this, he converted talopram into citalopram, the most selective serotonin reuptake inhibitor to come to the market.

<span class="mw-page-title-main">Didesmethylcitalopram</span> Chemical compound

Didesmethylcitalopram is an active metabolite of the antidepressant drug citalopram (racemic). Didesmethylescitalopram is an active metabolite of the antidepressant escitalopram, the S-enantiomer of citalopram. Like citalopram and escitalopram, didesmethyl(es)citalopram functions as a selective serotonin reuptake inhibitor (SSRI), and is responsible for some of its parents' therapeutic benefits.

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References

  1. "Desmethylcitalopram". Human Metabolome Database.
  2. Brøsen K, Naranjo CA (August 2001). "Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram". European Neuropsychopharmacology. 11 (4): 275–83. doi:10.1016/s0924-977x(01)00101-8. PMID   11532381. S2CID   11837037.