8-Chlorotheophylline

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8-Chlorotheophylline
8-Chlorotheophylline.svg
8-Chlorotheophylline 3D spacefill.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 8-chloro-1,3-dimethyl-7H-purine-2,6-dione
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.446 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C7H7ClN4O2
Molar mass 214.61 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) Yes check.svgY
  • Key:RYIGNEOBDRVTHA-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Related Research Articles

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Xanthine is a purine base found in most human body tissues and fluids, as well as in other organisms. Several stimulants are derived from xanthine, including caffeine, theophylline, and theobromine.

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<span class="mw-page-title-main">Allopurinol</span> Medication

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<span class="mw-page-title-main">Diphenhydramine</span> Antihistamine medication

Diphenhydramine (DPH) is an antihistamine and sedative mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremor in parkinsonism, and nausea. It is taken by mouth, injected into a vein, injected into a muscle, or applied to the skin. Maximal effect is typically around two hours after a dose, and effects can last for up to seven hours.

<span class="mw-page-title-main">Dimenhydrinate</span> Anti-emetic and antihistamine medication

Dimenhydrinate, sold under the brand name Dramamine, among others, is an over-the-counter drug used to treat motion sickness and nausea. Dimenhydrinate is a theoclate salt composed of diphenhydramine, an ethanolamine derivative, and 8-chlorotheophylline, a chlorinated theophylline derivative, in a 1:1 ratio.

<span class="mw-page-title-main">Guaifenesin</span> Expectorant medication

Guaifenesin, also known as glyceryl guaiacolate, is an expectorant medication that aids in the elimination of sputum from the respiratory tract. Chemically it is an ether of guaiacol and glycerine. It is often used in combination with other medications. It is taken by mouth.

<span class="mw-page-title-main">Amantadine</span> Medication used to treat dyskinesia

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<span class="mw-page-title-main">Picrotoxin</span> Chemical compound

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<span class="mw-page-title-main">Fasciculation</span> Spontaneous, involuntary muscle twitch

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<span class="mw-page-title-main">Phenmetrazine</span> Chemical compound

Phenmetrazine is a stimulant drug first synthesized in 1952 and originally used as an appetite suppressant, but withdrawn from the market in the 1980s due to widespread abuse. It was initially replaced by its analogue phendimetrazine which functions as a prodrug to phenmetrazine, but now it is rarely prescribed, due to concerns of abuse and addiction. Chemically, phenmetrazine is a substituted amphetamine containing a morpholine ring.

<span class="mw-page-title-main">Polysubstance use</span> Use of multiple psychoactive substances

Polysubstance use or poly drug use refers to the use of combined psychoactive substances. Polysubstance use may be used for entheogenic, recreational, or off-label indications, with both legal and illegal substances. In many cases one drug is used as a base or primary drug, with additional drugs to leaven or compensate for the side effects, or tolerance, of the primary drug and make the experience more enjoyable with drug synergy effects, or to supplement for primary drug when supply is low.

A combination drug or a fixed-dose combination (FDC) is a medicine that includes two or more active ingredients combined in a single dosage form. Terms like "combination drug" or "combination drug product" can be common shorthand for an FDC product, although the latter is more precise if in fact referring to a mass-produced product having a predetermined combination of drugs and respective dosages. And it should also be distinguished from the term "combination product" in medical contexts, which without further specification can refer to products that combine different types of medical products—such as device/drug combinations as opposed to drug/drug combinations. Note that when a combination drug product is a "pill", then it may also be a kind of "polypill" or combopill.

<span class="mw-page-title-main">Febuxostat</span> Chemical compound

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<span class="mw-page-title-main">Etanautine</span> Chemical compound

Etanautine, also known as diphenhydramine monoacefyllinate, is an anticholinergic used as an antiparkinsonian agent. It is a 1:1 salt of diphenhydramine with acefylline, similar to the diphenhydramine/8-chlorotheophylline combination product dimenhydrinate.

<span class="mw-page-title-main">Nefopam</span> Analgesic medication

Nefopam, sold under the brand name Acupan among others, is a centrally acting, non-opioid painkilling medication, that is primarily used to treat moderate to severe pain.

<span class="mw-page-title-main">Doxofylline</span> Chemical compound

Doxofylline is a phosphodiesterase inhibiting bronchodilator used in the treatment of chronic respiratory diseases such as asthma and COPD. Like theophylline, it is a xanthine derivative.

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.
  2. 1 2 Cusic, John W. (3 June 1949). "Note on the Chemistry of Dramamine". Science. 109 (2840): 574–574. doi:10.1126/science.109.2840.574.a.
  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."