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8-Chlorotheophylline

Chemical compound

Chemical compound

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8-Chlorotheophylline, also known as 1,3-dimethyl-8-chloroxanthine, is a stimulant drug of the xanthine chemical class, with physiological effects similar to caffeine. Its main use is in combination (salt) with diphenhydramine in the antiemetic dimenhydrinate (Dramamine). Diphenhydramine reduces nausea but causes drowsiness, and the stimulant properties of 8-Chlorotheophylline help reduce that side effect.

Despite being classified as a xanthine stimulant, 8-chlorotheophylline generally not produce any hyperlocomotion above control in mice and does not appear to cross the blood-brain barrier well.

The 8-chloro modification is not selected for pharmacological properties; instead, it was to raise the acidity of the xanthine amine group enough to form a co-salt with diphenhydramine.

The drug is also sold in combination with promethazine, again as a salt.

References

References

  1. (May 1981). "Adenosine receptors and behavioral actions of methylxanthines". Proceedings of the National Academy of Sciences of the United States of America.
  2. (3 June 1949). "Note on the Chemistry of Dramamine". Science.
  3. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=8461 "The anti-emetic action of both the hydrochloride and the teoclate (8-chlorotheophylline) salts is used for the prevention of nausea in cases of motion sickness and post-operative vomiting."
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xanthines chloroarenes adenosine-receptor-antagonists
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