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| Other names | Eseroline |
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| Formula | C13H18N2O |
| Molar mass | 218.300 g·mol−1 |
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Eseroline is a drug which acts as anopioidagonist.[1] It is a metabolite of theacetylcholinesterase inhibitorphysostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible,[2][3] and it produces fairly potentanalgesic effects mediated through theμ-opioidreceptor.[4] This mixture of activities gives eseroline an unusual pharmacological profile,[5][6] although its uses are limited by side effects such asrespiratory depression[7] andneurotoxicity.[8]
The alkylation ofphenacetin (1) withdimethyl sulfate givesN-methylphenetidine (2). Treatment with 2-bromopropanoyl bromide gives 2-bromo-N-(4-ethoxyphenyl)-N-methylpropanamide (3). Treatment withaluminium trichloride results in 1,3-dimethyl-5-hydroxyoxindole (4). Alkylation withdiethyl sulfate gives 5-ethoxy-1,3-dimethylindolin-2-one (5). Base-catalyzed treatment withchloroacetonitrile gives 2-(5-ethoxy-1,3-dimethyl-2-oxoindol-3-yl)acetonitrile (6).Catalytic hydrogenation of the nitrile group gives (7). Mono-methylation of the primary amine gives (8). Intramolecularreductive amination giveseserethole (9). Cleavage of the ethyl ether protecting group gave (-)-eseroline (10). Optional treatment withmethyl isocyanide (MIC) leads tophysostigmine.
