8-Chlorotheophylline

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 ;
PubChem CID	10661;
ChemSpider	10211 ;
UNII	GE2UA340FM;
ChEBI	CHEBI:59771 ;
ChEMBL	ChEMBL88611 ;
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) ; Key:RYIGNEOBDRVTHA-UHFFFAOYSA-N ;
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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.^[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

^ 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.
^ ^a ^b Cusic JW (3 June 1949). "Note on the Chemistry of Dramamine". Science. 109 (2840): 574. doi:10.1126/science.109.2840.574.a. PMID 17743285. S2CID 239515706.
^ 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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[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.

[chem-dram-2] Cusic JW (3 June 1949). "Note on the Chemistry of Dramamine". Science. 109 (2840): 574. doi:10.1126/science.109.2840.574.a. PMID 17743285. S2CID 239515706.

[3] ttps://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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