Northiaden

Last updated
Northiaden
Northiaden.svg
Clinical data
Other namesN-Desmethyldosulepin; N-Desmethyldothiepin; Nordosulepin; Nordothiepin
Identifiers
  • (3E)-3-(6H-Benzo[c][1]benzothiepin-11-ylidene)-N-methylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C18H19NS
Molar mass 281.42 g·mol−1
3D model (JSmol)
  • CNCC/C=C/1\C2=CC=CC=C2CSC3=CC=CC=C31
  • InChI=1S/C18H19NS/c1-19-12-6-10-16-15-8-3-2-7-14(15)13-20-18-11-5-4-9-17(16)18/h2-5,7-11,19H,6,12-13H2,1H3/b16-10+
  • Key:FTELXJYVTOFJAI-MHWRWJLKSA-N

Northiaden, also known as N-desmethyldosulepin, is the major active metabolite of the tricyclic antidepressant (TCA) dosulepin (dothiepin; Prothiaden). [1]

Synthesis

Synthesis: Northiaden synthesis.svg
Synthesis:

Obtained from dothiepin by carbamate hydrolysis method using chloroethylformate.

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References

  1. Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 607–. ISBN   978-1-60913-345-0.
  2. Rajšner, M., Svátek, E., Metyšová, J., & Protiva, M. (1969). Neurotropic and psychotropic compounds. XXXIII. Contribution to the chemistry of 11-(3-dimethylaminopropylidene)-6,11-dihydrodibenzo[b,e]thiepin (Prothiadene) and of related compounds. Collection of Czechoslovak Chemical Communications, 34(7), 1963–1975. https://doi.org/10.1135/cccc19691963