Cotriptyline

Last updated
Cotriptyline
Cotriptyline.png
Cotriptyline-3D-balls.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1-(10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-3-(dimethylamino)propan-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H21NO
Molar mass 291.394 g·mol−1
3D model (JSmol)
  • O=C(/C=C2/c1c(cccc1)CCc3c2cccc3)CN(C)C

Cotriptyline (SD-2203-01) is a tricyclic antidepressant (TCA) which was never marketed. [1]

Synthesis

Patent: Cotriptyline synthesis.svg
Patent:

The Grignard addition between dibenzosuberone [1210-35-1] (1) and ethynylmagnesium bromide [4301-14-8] (2) gives CID:11680257 (3). A Mannich reaction with formaldehyde and dimethylamine would give [5391-33-3] (4). The α-hydroxy-alkyne rearranges upon addition of sulphuric acid to an enone (5), which is cotriptyline proper. A reduction of the keto group to the alcohol can be made to occur without touching alkene to give CID:213985 (6).

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References

  1. Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN   0-412-46630-9.
  2. Boissier Dr Jacques Robert, Roger Ratouis, DE 1913701A1 (1969 to Soc Ind Fab Antibiotiques Sifa).