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Cimemoxin

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Chemical compound
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
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.

Synthesis

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

Synthesis:

3-Cyclohexene-1-carbaldehyde (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 procĂ©dĂ© de prĂ©paration", 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. 
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
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MT1Tooltip Melatonin receptor 1
MT2Tooltip Melatonin receptor 2
Unsorted
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7


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