Premium
Ciliotoxicity of intranasal formulations: Menthol enantiomers
Author(s) -
Su XiangYao,
Po Alain Li Wan,
Millership Jeffrey S.
Publication year - 1993
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530050203
Subject(s) - menthol , chemistry , enantiomer , vapours , differential scanning calorimetry , nasal administration , stereochemistry , chromatography , organic chemistry , pharmacology , medicine , physics , neuroscience , biology , thermodynamics
It is shown, using in vitro measurements of beat frequency of rat tracheal cilia, that (+)‐(1S, 2R, 5S)‐menthol and (−)−(1R, 2S, 5R)−menthol have equipotent ciliotoxicities despite the fact that inhalation of menthol vapours from the crystals of the pure enantiomers show clearly that the (−)−(1R, 2S, 5R)‐menthol produces a more potent cooling sensation. Differential scanning calorimetry demonstrates the formation of a racemic compound when equimolar amounts of the two enantiomers are admixed. © 1993 Wiley‐Liss, Inc.