Cimemoxin

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Cimemoxin
File:Cimemoxin.svg
Clinical data
ATC code
  • None
Identifiers
  • cyclohexylmethylhydrazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC7H16N2
Molar mass128.219 g·mol−1
3D model (JSmol)
  • NNCC1CCCCC1
  • InChI=1S/C7H16N2/c8-9-6-7-4-2-1-3-5-7/h7,9H,1-6,8H2
  • Key:BDHMBGHSWFWYSP-UHFFFAOYSA-N

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).

File:Cimemoxin synthesis.svg
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" (PDF). Retrieved 2012-05-20.
  2. ↑ Boissier JR, Ratouis R, Dumont C, Lesbros J (1966). "Synthesis of new monoamine oxidase inhibitors". Chimica Therapeutica (5–6): 320–326.
  3. ↑ FR 1405420, Boissier JR, Ratouis R, "ouvelle hydrazine et ses sels et procédé de préparation", issued 1965, assigned to Soc Ind Fab Antibiotiques Sifa. 
  4. ↑ GB 1102228, "N-hexahydrobenzyl hydrazine and its salts and process for preparation thereof", issued 1968, assigned to Soc Ind Fab Antibiotiques Sifa. 
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