Abstract
The crystal structures of the tertiary amine local anesthetics dibucaine hydrochloride monohydrate (C20H29N3O2·HCl·H2O) and dimethisoquin hydrochloride monohydrate (C17H24N2O·HCl·H2O) have been determined. Dibucaine forms crystals inP21/c witha=10.669(3),b = 35.981(5),c= 11.417(2) Å,β= 89.654(3) ° andZ= 8. Dimethisoquin crystallizes in the space groupP¯1 witha = 5.338(6),b=7.579(8),c= 22.336(24) Å,a = 85.513(1), β = 87.447(1), γ=84.863(1) °, andZ=2. Intensity data were collected with an automatic diffractometer, using CuKα for dibucaine and MoKα for dimethisoquin. The structures were solved using direct methods and refined by full-matrix least-squares procedures to final values ofR= 12.8% for dibucaine andR = 8.8% for dimethisoquin. The structures of both local anesthetics feature planar fused ring systems and extended side chains, one of which contains the tertiary amine that forms hydrogen bonds with other local anesthetic molecules and the chlorine and solvent atoms. The possible sites of action of the anesthetics in the cell membrane are discussed on the basis of these structures.
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Hayward, B.S., Donohue, J. Crystal structures of two local anesthetics: Dibucaine·HCl·H2O and Dimethisoquin·HCl·H2O. Journal of Crystal and Molecular Structure 7, 275–294 (1977). https://doi.org/10.1007/BF01351374
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DOI: https://doi.org/10.1007/BF01351374