8-Chlorotheophylline

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8-Chlorotheophylline

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: Over-the-counter (OTC)
Identifiers
IUPAC name 8-chloro-1,3-dimethyl-7H-purine-2,6-dione
JSmol)	Interactive image
SMILES Cn2c(=O)c1[nH]c(Cl)nc1n(C)c2=O
InChI InChI=1S/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10) Y Key:RYIGNEOBDRVTHA-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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.^[1] 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.^[2]

Despite being classified as a xanthine stimulant, 8-chlorotheophylline can generally not produce any locomotor activity above control in mice and does not appear to cross the blood-brain barrier well.^{[citation needed]}

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.^[2]

The drug is also sold in combination with promethazine, again as a salt.^[3]

References