Cimemoxin

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

Cimemoxin
Clinical data
ATC code
  • None
Identifiers
  • cyclohexylmethylhydrazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
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

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" (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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