Feclemine

Feclemine
Clinical data
Other names	Fenetamin; Giacosil; Licabile; Licaran; Phenecyclamine; Phenetamine; Spasmexan; UCB-1545;
Identifiers
	IUPAC name 2-[Cyclohexyl(phenyl)methyl]-N,N,N',N'-tetraethylpropane-1,3-diamine;
CAS Number	3590-16-7;
PubChem CID	3030835;
ChemSpider	2295996;
UNII	5P7U986QGO;
ChEBI	CHEBI:135518;
ChEMBL	ChEMBL2106137;
PDB ligand	PD072576 (PDBe, RCSB PDB);
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 (phenetamine) is a spasmolytic drug.^[1]

Synthesis

The chemical synthesis is discussed:^[2]

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:^[3] Alcohol:^[3]

References

^ Crema A, Benzi G, Frigo GM, Berté F (July 1965). "Method for evaluating spasmolytic activity of drugs on the bile duct". The Journal of Pharmacy and Pharmacology. 17 (7): 405–408. doi:10.1111/j.2042-7158.1965.tb07695.x. PMID 4379262.
^ Morren HG, Denayer R, Trolin S, Strubbe H, Linz R, Dony G, et al. (1955). "Antispasmodics with musculotropic action derived from 1,3-bis(dialkylamino)propane". Industrie Chimique Belge. 20: 733–745.
^ ^a ^b Schütz S, Kurz J, Plümpe H, Bock M, Otten H (June 1971). "[Basically alkylated imides of naphthalene-1,4,5,8-tetracarboxylic acid and their chemotherapeutic effects]". Arzneimittel-Forschung (in German). 21 (6): 739–763. PMID 4998088.

[1] Crema A, Benzi G, Frigo GM, Berté F (July 1965). "Method for evaluating spasmolytic activity of drugs on the bile duct". The Journal of Pharmacy and Pharmacology. 17 (7): 405–408. doi:10.1111/j.2042-7158.1965.tb07695.x. PMID 4379262.

[2] Morren HG, Denayer R, Trolin S, Strubbe H, Linz R, Dony G, et al. (1955). "Antispasmodics with musculotropic action derived from 1,3-bis(dialkylamino)propane". Industrie Chimique Belge. 20: 733–745.

[Schutz_1971-3] Schütz S, Kurz J, Plümpe H, Bock M, Otten H (June 1971). "[Basically alkylated imides of naphthalene-1,4,5,8-tetracarboxylic acid and their chemotherapeutic effects]". Arzneimittel-Forschung (in German). 21 (6): 739–763. PMID 4998088.

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