Cimemoxin

Cimemoxin
Clinical data
ATC code	None;
Identifiers
	IUPAC name cyclohexylmethylhydrazine;
CAS Number	3788-16-7 ;
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;

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.

References

^ World Health Organization (2011). "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). Retrieved 2012-05-20.
^ Boissier JR, Ratouis R, Dumont C, Lesbros J (1966). "Synthesis of new monoamine oxidase inhibitors". Chimica Therapeutica (5–6): 320–326.
^ FR 1405420, Boissier JR, Ratouis R, "ouvelle hydrazine et ses sels et procédé de préparation", issued 1965, assigned to Soc Ind Fab Antibiotiques Sifa.
^ 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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[WHO2011-1] 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.

[1]

[2]

[3]

[4]

Synthesis

See also

References