Cilobamine

Cilobamine

Clinical data
ATC code	none
Identifiers
IUPAC name (2R,3R)-2-(3,4-Dichlorophenyl)-3-[(1-methylethyl)amino]bicyclo[2.2.2]octan-2-ol
CAS Number	69429-84-1
PubChem CID	299379
ChemSpider	8557262
UNII	067U1T4S30
ChEMBL	ChEMBL2106470
Chemical and physical data
Formula	C17H23Cl2NO
Molar mass	328.28 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1Cl)[C@@]3(O)[C@H](NC(C)C)C2CCC3CC2

Cilobamine is a drug which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI) and has stimulant and antidepressant effects. ^{[1] [2]}

It can clearly be seen that the structure is based on dichloroisoprenaline that has been fused onto the bicycloalkane scaffold.

Synthesis

Patent:

An intramolecular Dieckmann cyclization on methyl 4-(2-methoxy-2-oxoethyl)cyclohexanecarboxylate (3) with sodium hydride base provides methyl 3-oxobicyclo[2.2.2]octane-2-carboxylate (4). Treatment with sodium nitrite introduces an isonitroso group adjacent to the ketone, giving 3-Hydroxyiminobicyclo[2.2.2]octan-2-one (5). Addition of the aryl Grignard reagent, and reduction of the oxime gives (6). A reductive amination of the primary amino group with acetone then completes the synthesis of cilobamine (7).

See also

• Fencamfamine
• Manifaxine

References

1. Leeson GA, Shaath ZA, Biedenbach SA, Yarrington JT, Okerholm RA (April 1984). "Dose related induction of the drug metabolizing enzymes of rat liver by cilobamine". Fundamental and Applied Toxicology. 4 (2 Pt 1): 261–9. doi:10.1016/0272-0590(84)90127-1. PMID   6724198.
2. Wager S, Quitkin F, Stewart J, McGrath P, Harrison W, Markowitz J, Tricamo E (1988). "Cilobamine in the treatment of atypical depression". Human Psychopharmacology: Clinical and Experimental. 3 (3): 201–205. doi:10.1002/hup.470030308. S2CID   145253439.
3. DE2003744 idem Jules Freedman, U.S. patent 3,651,142 (1970 to Colgate Palmolive Co).