Chemistry:Cimemoxin

From HandWiki
Short description: Chemical compound
Cimemoxin
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).

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.




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