8-Chlorotheophylline

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. Diphenhydramine reduces nausea but causes drowsiness, and the stimulant properties of 8-Chlorotheophylline help ward off that side-effect.

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
CAS Number	85-18-7^N
PubChem CID	10661
ChemSpider	10211^Y
UNII	GE2UA340FM
ChEBI	CHEBI:59771^Y
ChEMBL	ChEMBL88611^Y
CompTox Dashboard (EPA)	DTXSID5043764
ECHA InfoCard	100.001.446
Chemical and physical data
Formula	C7H7ClN4O2
Molar mass	214.61 g·mol^−1
3D model (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)

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.

References

1. Snyder SH, Katims JJ, Annau Z, Bruns RF, Daly JW (May 1981). "Adenosine receptors and behavioral actions of methylxanthines". Proceedings of the National Academy of Sciences of the United States of America. 78 (5): 3260–4. Bibcode:1981PNAS...78.3260S. doi:10.1073/pnas.78.5.3260. PMC 319541. PMID 6265942.