Feclemine

Feclemine
Clinical data
Other names	phenecyclamine; phenetamine, Fenetamin, Giacosil, Licabile, Licaran, Spasmexan, UCB-1545, Licabile.
Identifiers
	IUPAC name 2-[Cyclohexyl(phenyl)methyl]-N,N,N',N'-tetraethylpropane-1,3-diamine;
PubChem CID	3030835;
ChemSpider	2295996;
UNII	5P7U986QGO;
ChEBI	CHEBI:135518;
ChEMBL	ChEMBL2106137;
CompTox Dashboard (EPA)	DTXSID80863211 ;
Chemical and physical data
Formula	C24H42N2
Molar mass	358.614 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)CC(CN(CC)CC)C(C1CCCCC1)C2=CC=CC=C2;
	InChI InChI=1S/C24H42N2/c1-5-25(6-2)19-23(20-26(7-3)8-4)24(21-15-11-9-12-16-21)22-17-13-10-14-18-22/h9,11-12,15-16,22-24H,5-8,10,13-14,17-20H2,1-4H3; Key:QDMORDTWFMWOFA-UHFFFAOYSA-N;

Feclemine is a spasmolytic drug.^[1]

Synthesis

The chemical synthesis is discussed:^[2]^[3]^[4]

Sodamide is used to alkylate cyclohexylphenylacetonitrile [3893-23-0] (1) (also used for drofenine) with 2-chloro-N,N,N',N'-tetraethylpropane-1,3-diamine [3492-54-4] (HCl: [94465-65-3]) to give (2). Some rearrangement is possible to give a mixture of regioisomers. Sodamide catalyzed cleavage of the nitrile group in a separate step then completes the synthesis of feclemine (3).

Precursor:^[5] Alcohol:^[6]

References

^ Crema, A., Benzi, G., Frigo, G. M., Berté, F. (1 July 1965). "Method for evaluating spasmolytic activity of drugs on the bile duct". Journal of Pharmacy and Pharmacology. 17 (7): 405–408. doi:10.1111/j.2042-7158.1965.tb07695.x.
^ Morren et al., Ind. Chim. Belge 20, 733 (1955).
^ Morren Henri, US2781398 (1957 to Union Chimique Belge Sa).
^ Henri Morren, GB776705 (1957); CA, 52, 20065e
^ Schütz S, Kurz J, Plümpe H, Bock M, Otten H. [Basically alkylated imides of naphthalene-1,4,5,8-tetracarboxylic acid and their chemotherapeutic effects]. Arzneimittelforschung. 1971;21(6):739-63. PMID: 4998088.
^ Schütz S, Kurz J, Plümpe H, Bock M, Otten H. [Basically alkylated imides of naphthalene-1,4,5,8-tetracarboxylic acid and their chemotherapeutic effects]. Arzneimittelforschung. 1971;21(6):739-63. PMID: 4998088.

[1] Crema, A., Benzi, G., Frigo, G. M., Berté, F. (1 July 1965). "Method for evaluating spasmolytic activity of drugs on the bile duct". Journal of Pharmacy and Pharmacology. 17 (7): 405–408. doi:10.1111/j.2042-7158.1965.tb07695.x.

[2] Morren et al., Ind. Chim. Belge 20, 733 (1955).

[3] Morren Henri, US2781398 (1957 to Union Chimique Belge Sa).

[4] Henri Morren, GB776705 (1957); CA, 52, 20065e

[5] Schütz S, Kurz J, Plümpe H, Bock M, Otten H. [Basically alkylated imides of naphthalene-1,4,5,8-tetracarboxylic acid and their chemotherapeutic effects]. Arzneimittelforschung. 1971;21(6):739-63. PMID: 4998088.

[6] Schütz S, Kurz J, Plümpe H, Bock M, Otten H. [Basically alkylated imides of naphthalene-1,4,5,8-tetracarboxylic acid and their chemotherapeutic effects]. Arzneimittelforschung. 1971;21(6):739-63. PMID: 4998088.

[1]

[2]

[3]

[4]

[5]

[6]