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

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.
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.