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INVESTIGATION OF PROTRIPTYLINE PHOTOPRODUCTS WHICH CAUSE CELL MEMBRANE DISRUPTION
Author(s) -
Gasparro Francis P.,
Kochevar Irene E.
Publication year - 1982
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.1751-1097.1982.tb02573.x
Subject(s) - chemistry , quantum yield , solvent , photochemistry , ethanol , fluorescence , yield (engineering) , photodissociation , aqueous solution , methanol , hydrochloride , lysis , absorption (acoustics) , nuclear chemistry , chromatography , organic chemistry , biochemistry , physics , materials science , quantum mechanics , metallurgy , acoustics
— Protriptyline (PTL; N‐methyl‐5H‐dibenzo[a,d]cycloheptene‐5‐propylamine) hydrochloride is a skin photosensitizing agent in humans. The fluorescence and photochemical behavior of PTL varies with the solvent. In water, 40% ethanol and ethanol in the hydrochloride salt of PTL has a fluorescence quantum yield of 0.81. The fluorescence quantum yield of PTL free base in selected organic solvents is between 0.41 and 0.17; in ethanol it remains at 0.81. Photolysis of PTL in acidic aqueous solution yields at least five photoproducts which were separated by high‐performance liquid chromatography. Three of these photoproducts lysed red blood cells. One of the photoproducts has been identified as a cyclobutyl photodimer of PTL based on its mass spectrum and UV absorption and its ability to undergo photore‐versal with 254 nm irradiation. The others were not cyclobutyl dimers. The yield of lytic products decreased as the ethanol content was increased and were not formed from PTL free base in any solvent.