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8-Chlorotheophylline

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Chemical compound

Pharmaceutical compound
8-Chlorotheophylline
Skeletal formula of 8-chlorotheophylline
Space-filling model of the 8-chlorotheophylline molecule
Clinical data
Other names
  • 1,3-Dimethyl-8-chloroxanthine
  • Teoclate
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 8-chloro-1,3-dimethyl-7H-purine-2,6-dione
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.001.446Edit this at Wikidata
Chemical and physical data
FormulaC7H7ClN4O2
Molar mass214.61 g·mol−1
3D model (JSmol)
  • Cn2c(=O)c1[nH]c(Cl)nc1n(C)c2=O
  • InChI=1S/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10) checkY
  • Key:RYIGNEOBDRVTHA-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

8-Chlorotheophylline, also known as1,3-dimethyl-8-chloroxanthine, is astimulantdrug of thexanthine chemical class, with physiological effects similar tocaffeine.[1] Its main use is in combination (salt) withdiphenhydramine in theantiemeticdimenhydrinate (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 generally does not produce anyhyperlocomotion above control in mice and does not appear to cross theblood-brain barrier well.[citation needed]

The 8-chloro modification is not selected for pharmacological properties; instead, it was to raise the acidity of the xanthineamine group enough to form a co-salt with diphenhydramine.[2]

The drug is also sold in combination withpromethazine as a salt.[3]

References

[edit]
  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.
  2. ^abCusic 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. ^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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