Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 8-Chlorotheophylline: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 470106641 of page 8-Chlorotheophylline for the Chem/Drugbox validation project (updated: 'CAS_number'). |
redundant - everything is cited except one sentence that already has a "citation needed" note |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:8-Chlorotheophylline|oldid=470106641}} 470106641] of page [[8-Chlorotheophylline]] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 477227071 |
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| IUPAC_name = 8-chloro-1,3-dimethyl-7''H''-purine-2,6-dione |
| IUPAC_name = 8-chloro-1,3-dimethyl-7''H''-purine-2,6-dione |
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| image = 8-Chlorotheophylline.svg |
| image = 8-Chlorotheophylline.svg |
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| alt = Skeletal formula of 8-chlorotheophylline |
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| width = 180 |
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| image2 = 8-Chlorotheophylline 3D spacefill.png |
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| alt2 = Space-filling model of the 8-chlorotheophylline molecule |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_status = |
| legal_status = OTC |
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| routes_of_administration = Oral |
| routes_of_administration = Oral |
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<!--Identifiers--> |
<!--Identifiers--> |
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| synonyms = {{unbulletedlist|1,3-Dimethyl-8-chloroxanthine|Teoclate}} |
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| CAS_number_Ref = {{cascite| |
| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = |
| CAS_number = 85-18-7 |
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| ATC_prefix = none |
| ATC_prefix = none |
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| ATC_suffix = |
| ATC_suffix = |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=7 | H=7 | Cl=1 | N=4 | O=2 |
| C=7 | H=7 | Cl=1 | N=4 | O=2 |
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| smiles = Cn2c(=O)c1[nH]c(Cl)nc1n(C)c2=O |
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| molecular_weight = 214.61 g/mol |
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| smiles = O=C2N(c1nc(Cl)nc1C(=O)N2C)C |
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| InChI = 1/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10) |
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| InChIKey = RYIGNEOBDRVTHA-UHFFFAOYAD |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10) |
| StdInChI = 1S/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10) |
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| StdInChIKey = RYIGNEOBDRVTHA-UHFFFAOYSA-N |
| StdInChIKey = RYIGNEOBDRVTHA-UHFFFAOYSA-N |
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}} |
}} |
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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]].<ref>{{cite journal | vauthors = Snyder SH, Katims JJ, Annau Z, Bruns RF, Daly JW | title = Adenosine receptors and behavioral actions of methylxanthines | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 78 | issue = 5 | pages = 3260–4 | date = May 1981 | pmid = 6265942 | pmc = 319541 | doi = 10.1073/pnas.78.5.3260 | bibcode = 1981PNAS...78.3260S | doi-access = free }}</ref> 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.<ref name=chem-dram/> |
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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|blood-brain barrier]] well.{{CN|date=May 2022}} |
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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.<ref name="chem-dram">{{cite journal |last1=Cusic |first1=John W. |title=Note on the Chemistry of Dramamine |journal=Science |date=3 June 1949 |volume=109 |issue=2840 |pages=574 |doi=10.1126/science.109.2840.574.a|pmid=17743285 |s2cid=239515706 }}</ref> |
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The drug is also sold in combination with [[promethazine]], again as a salt.<ref>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."</ref> |
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== References == |
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{{Reflist|2}} |
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{{Stimulants}} |
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{{Adenosinergics}} |
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{{DEFAULTSORT:Chlorotheophylline, 8-}} |
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[[Category:Xanthines]] |
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[[Category:Chloroarenes]] |
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[[Category:Adenosine receptor antagonists]] |
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{{nervous-system-drug-stub}} |
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