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Science 4 May 1990:
Vol. 248. no. 4955, pp. 583 - 585
DOI: 10.1126/science.2159183
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Articles

Science, Vol 248, Issue 4955, 583-585
Copyright © 1990 by American Association for the Advancement of Science

articles

Anesthesia cutoff phenomenon: interfacial hydrogen bonding

JS Chiou, SM Ma, H Kamaya, and I Ueda

Department of Anesthesia, University of Utah School of Medicine, Salt Lake City.

Anesthesia "cutoff" refers to the phenomenon of loss of anesthetic potency in a homologous series of alkanes and their derivatives when their sizes become too large. In this study, hydrogen bonding of 1-alkanol series (ethanol to eicosanol) to dipalmitoyl-L-alpha-phosphatidylcholine (DPPC) was studied by Fourier transform infrared spectroscopy (FTIR) in DPPC-D2O-in-CCl4 reversed micelles. The alkanols formed hydrogen bonds with the phosphate moiety of DPPC and released the DPPC-bound deuterated water, evidenced by increases in the bound O-H stretching signal of the alkanol-DPPC complex and also in the free O-D stretching band of unbound D2O. These effects increased according to the elongation of the carbon chain of 1-alkanols from ethanol (C2) to 1-decanol (C10), but suddenly almost disappeared at 1-tetradecanol (C14). Anesthetic potencies of these alkanols, estimated by the activity of brine shrimps, were linearly related to hydrogen bond-breaking activities below C10 and agreed with the FTIR data in the cutoff at C10.


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