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Cimemoxin

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Cimemoxin
Clinical data
ATC code
  • None
Identifiers
  • cyclohexylmethylhydrazine
CAS Number
PubChemCID
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

Cimemoxin (INN), orcyclohexylmethylhydrazine, is ahydrazinemonoamine oxidase inhibitor (MAOI)antidepressant which was never marketed.[1]

Synthesis

[edit]

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

[edit]

References

[edit]
  1. ^World Health Organization (2011)."The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances"(PDF). Retrieved2012-05-20.
  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. 
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
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α2
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β
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D1-like
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MT1Tooltip Melatonin receptor 1
MT2Tooltip Melatonin receptor 2
Unsorted
5-HT1
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5-HT1D
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5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7


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