Quinisocaine
Chemical compound
From Wikipedia, the free encyclopedia
Quinisocaine (INN), also known as dimethisoquin (BAN and USAN), is a topical anesthetic used as an antipruritic.[1]
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| ECHA InfoCard | 100.001.546 |
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| Formula | C17H24N2O |
| Molar mass | 272.392 g·mol−1 |
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Synthesis
Quinisocaine can be synthesized starting from phthalaldehydic acid.[2][3][4] Patent:[5][6] The Henry reaction between phthalaldehydic acid (1) and 1-nitropentane occurs by a mechanism that involves a hydroxy acid (2). Expulsion of water then gives the lactone 3. Reduction of the nitro group via catalytic hydrogenation leads to the amine 4. Treatment of that amine with sodium hydroxide leads to ring opening of the lactone ring to the intermediary amino acid (5). This cyclizes spontaneously to the lactam to give the isoquinoline derivative 7. Dehydration by means of strong acid gives 3-butylisocarbostyril (8). Phosphorus oxychloride converts the oxygen function to the corresponding chloride via the enol forms 3-butyl-1-chloroisoquinoline (9). Displacement of halogen with the sodium salt from 2-dimethylaminoethanol (10) affords dimethisoquin (11).
