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
IUPAC name cyclohexylmethylhydrazine
CAS Number	3788-16-7 Y
PubChem CID	71824
ChemSpider	64848
UNII	584QS921R2
ChEMBL	ChEMBL2106052
CompTox Dashboard (EPA)	DTXSID30191314
Chemical and physical data
Formula	C7H16N2
Molar mass	128.219 g·mol−1
3D model (JSmol)	Interactive image
SMILES NNCC1CCCCC1
InChI 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

• Monoamine oxidase inhibitor
• Hydrazine (antidepressant)