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 (Dramamine). Diphenhydramine reduces nausea but causes drowsiness, and the stimulant properties of 8-Chlorotheophylline help reduce that side effect.^[2]

8-Chlorotheophylline

Clinical data
Other names	1,3-Dimethyl-8-chloroxanthine Teoclate
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 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]