feclemine
{{Short description|Spasmolytic drug}}
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{{Infobox drug
| drug_name = Feclemine
| image = Feclemine.svg
| width = 150
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| CAS_number = 3590-16-7
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| PubChem = 3030835
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID = 2295996
| DTXSID = DTXSID80863211
| UNII = 5P7U986QGO
| KEGG =
| ChEBI = 135518
| ChEMBL = 2106137
| NIAID_ChemDB =
| PDB_ligand = PD072576
| synonyms = {{ubl|Fenetamin|Giacosil|Licabile|Licaran|Phenecyclamine|Phenetamine|Spasmexan|UCB-1545}}
| IUPAC_name = 2-[Cyclohexyl(phenyl)methyl]-N,N,N',N'-tetraethylpropane-1,3-diamine
| C=24 | H=42 | N=2
| SMILES = CCN(CC)CC(CN(CC)CC)C(C1CCCCC1)C2=CC=CC=C2
| StdInChI = 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
| StdInChIKey = QDMORDTWFMWOFA-UHFFFAOYSA-N
}}
Feclemine (phenetamine) is a spasmolytic drug.{{cite journal | vauthors = Crema A, Benzi G, Frigo GM, Berté F | title = Method for evaluating spasmolytic activity of drugs on the bile duct | journal = The Journal of Pharmacy and Pharmacology | volume = 17 | issue = 7 | pages = 405–408 | date = July 1965 | pmid = 4379262 | doi = 10.1111/j.2042-7158.1965.tb07695.x }}
Synthesis
The chemical synthesis is discussed:{{cite journal | vauthors = Morren HG, Denayer R, Trolin S, Strubbe H, Linz R, Dony G, Collard R | title = Antispasmodics with musculotropic action derived from 1,3-bis(dialkylamino)propane | journal = Industrie Chimique Belge | volume = 20 | pages = 733–745 | date = 1955 }}
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).
File:Feclemine sidechain synthesis.svg
Precursor: Alcohol:{{cite journal | vauthors = Schütz S, Kurz J, Plümpe H, Bock M, Otten H | title = [Basically alkylated imides of naphthalene-1,4,5,8-tetracarboxylic acid and their chemotherapeutic effects] | journal = Arzneimittel-Forschung | volume = 21 | issue = 6 | pages = 739–763 | date = June 1971 | pmid = 4998088 | language = German }}