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PHOTOPHYSICAL STUDIES OF LOCAL ANESTHETICS, TETRACAINE and PROCAINE: DRUG AGGREGATIONS
Author(s) -
Mertz C. J.,
Marques A. D. S.,
Williamson L. Neil,
Lin C. T.
Publication year - 1990
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1990.tb01734.x
Subject(s) - tetracaine , procaine , chemistry , dibucaine , excimer , photochemistry , tertiary amine , fluorescence , organic chemistry , anesthesia , medicine , physics , quantum mechanics , lidocaine
— The effects of solvent and concentration on the photophysical properties of tertiary amine local anesthetics, tetracaine and procaine were studied experimentally using low temperature (77 K) emission spectroscopy and confirmed theoretically using a HAM/3 method. For tetracaine free base in methylcyclohexane, a broad fluorescence band observed at ˜375 nm for concentrations greater than 1 × 10 −3 M is assigned to the molecular self‐associated species. The disappearance of this band in ethanol (i.e. a model hydrophobic environment) indicates a greater tendency of neutral tetracaine towards molecular hetero‐association. In an aqueous solution of procainc‐HCl, a broad emission band centered at ˜400 nm is detected even at a concentration as low as 1 × 10 −4 M and is attributed to the charged aggregates of procaine‐HCI. Two general observations for procaine, tetracaine and dibucaine are noted: (1) the monocation and free base local anesthetics in ethanol solutions give identical photophysical properties, suggesting that the monocation drug species in ethanol is H+ dissociative. and (2) the lowest singlet excited state of neutral local anesthetics is calculated to have a charge‐transfer character originating from a non‐bonding electron in the N of tertiary amine group to the π* orbital of aromatic ring. The possible pharmacological implications of the deprotonation, the drug aggregations and the charge‐transfer excitations of local anesthetics on the molecular basis of anesthesia are discussed.