Chemistry:Cimemoxin

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Short description: Chemical compound
Cimemoxin
Cimemoxin.svg
Clinical data
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC7H16N2
Molar mass128.219 g·mol−1
3D model (JSmol)

Cimemoxin (INN), or cyclohexylmethylhydrazine, is a hydrazine monoamine oxidase inhibitor (MAOI) antidepressant which was never marketed.[1]

Synthesis

It possesses 50 times the relative activity of iproniazid and 25x nialamide (see patent).

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Synthesis:[2][3][4]

3-Cyclohexene-1-carbaldehyde [100-50-5] (aka 1,2,3,6-Tetrahydrobenzaldehyde) is reacted with N-acetylhydrazine to give the hydrazone, which is reduced by catalytic hydrogenation. The acetyl group is removed by acid hydrolysis.

See also

References

  1. World Health Organization (2011). "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances". https://www.who.int/medicines/services/inn/StemBook_2011_Final.pdf. Retrieved 2012-05-20. 
  2. "Synthesis of new monoamine oxidase inhibitors". Chimica Therapeutica (5–6): 320–326. 1966. 
  3. Boissier JR, Ratouis R, "ouvelle hydrazine et ses sels et procédé de préparation", FR patent 1405420, issued 1965, assigned to Soc Ind Fab Antibiotiques Sifa.
  4. "N-hexahydrobenzyl hydrazine and its salts and process for preparation thereof" GB patent 1102228, issued 1968, assigned to Soc Ind Fab Antibiotiques Sifa.