Xanthines

Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class and is the most commonly consumed psychoactive substance globally. It is mainly used for its eugeroic (wakefulness promoting), ergogenic (physical performance-enhancing), or nootropic (cognitive-enhancing) properties; it is also used recreationally or in social settings. Caffeine acts by blocking the binding of adenosine at a number of adenosine receptor types, inhibiting the centrally depressant effects of adenosine and enhancing the release of acetylcholine. Caffeine has a three-dimensional structure similar to

Theobromine, also known as xantheose, is the principal alkaloid of Theobroma cacao (cacao plant). Theobromine is slightly water-soluble (330 mg/L) with a bitter taste. In industry, theobromine is used as an additive and precursor to some cosmetics. It is found in chocolate and several other foods, including tea (Camellia sinensis), some American hollies (yaupon and guayusa) and the kola nut. It is a white or colourless solid, but commercial samples can appear yellowish.

Xanthine ( or , from Ancient Greek for its yellowish-white appearance; archaically xanthic acid; systematic name 3,7-dihydropurine-2,6-dione) 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.

thumb|right|upright|Theophylline extended-release tablets in Japan Theophylline, also known as 1,3-dimethylxanthine, is a drug that inhibits phosphodiesterase and blocks adenosine receptors. It is used to treat chronic obstructive pulmonary disease (COPD) and asthma. Its pharmacology is similar to other methylxanthine drugs (e.g., theobromine and caffeine). Trace amounts of theophylline are naturally present in tea, coffee, chocolate, yerba mate, guarana, and kola nut.

Fenethylline (BAN, USAN) or fenetylline (INN) is a codrug of amphetamine and theophylline and so a mutual prodrug of both. It is also spelled phenethylline; other names for it are amphetaminoethyltheophylline and amfetyline. The drug was marketed for use as a psychostimulant under the brand names Captagon, Biocapton, and Fitton. The brand name "Captagon" (or in lowercase as "captagon") is often used generically to describe illicitly produced fenethylline.

Aminophylline is a compound of the bronchodilator theophylline with ethylenediamine in 2:1 ratio. The ethylenediamine improves solubility, and the aminophylline is usually found as a dihydrate.

Pentoxifylline, also known as oxpentifylline, is a xanthine derivative used as a drug to treat muscle pain in people with peripheral artery disease. It was approved for medical use in 1984 and is available as generic and sold under many brand names worldwide like Trental.

Linagliptin, sold under the brand name Tradjenta among others, is a medication used to treat type 2 diabetes (but not type 1) in conjunction with exercise and diet. Linagliptin is a dipeptidyl peptidase-4 inhibitor that works by increasing the production of insulin and decreasing the production of glucagon by the pancreas. It is generally less preferred than metformin and sulfonylureas as an initial treatment. It is taken by mouth.

Paraxanthine, also known as 1,7-dimethylxanthine, is an isomer of theophylline and theobromine, two well-known stimulants found in coffee, tea, and chocolate. It is a member of the xanthine family of alkaloids, which also includes theophylline and theobromine in addition to caffeine.

crystalline material

chemical compound

Xanthosine is a nucleoside derived from xanthine and ribose. It is the biosynthetic precursor to 7-methylxanthosine by the action of 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (active alkaloid in chocolate), which in turn is the precursor to caffeine, the alkaloid in coffee and tea.

group of stereoisomers

Istradefylline, sold under the brand name Nourianz, is a medication used as an add-on treatment to levodopa/carbidopa in adults with Parkinson's disease (PD) experiencing "off" episodes. Istradefylline reduces "off" periods resulting from long-term treatment with the antiparkinson drug levodopa. An "off" episode is a time when a patient's medications are not working well, causing an increase in PD symptoms, such as tremor and difficulty walking.

IBMX (3-isobutyl-1-methylxanthine), like other methylxanthine derivatives, is both a: competitive non-selective phosphodiesterase inhibitor which raises intracellular cAMP, activates PKA, inhibits TNFα and leukotriene synthesis, and reduces inflammation and innate immunity, and nonselective adenosine receptor antagonist.

Diprophylline (INN) or dyphylline (USAN) (trade names Dilor, Lufyllin) is a xanthine derivative with bronchodilator and vasodilator effects. It is used in the treatment of respiratory disorders like asthma, cardiac dyspnea, and bronchitis. It acts as an adenosine receptor antagonist and phosphodiesterase inhibitor.

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. 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.

Doxofylline (also known as doxophylline) 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.

8-Phenyltheophylline (8-phenyl-1,3-dimethylxanthine, 8-PT) is a drug derived from the xanthine family which acts as a potent and selective antagonist for the adenosine receptors A1 and A2A, but unlike other xanthine derivatives has virtually no activity as a phosphodiesterase inhibitor. It has stimulant effects in animals with similar potency to caffeine. Coincidentally 8-phenyltheophylline has also been found to be a potent and selective inhibitor of the liver enzyme CYP1A2 which makes it likely to cause interactions with other drugs which are normally metabolised by CYP1A2.

Proxyphylline is a xanthine derivative that acts as a cardiac stimulant, vasodilator and bronchodilator.

Bamifylline is a drug of the xanthine chemical class which acts as a selective adenosine A1 receptor antagonist.

Acefylline (INN), also known as 7-theophyllineacetic acid, is a stimulant drug of the xanthine chemical class. It acts as an adenosine receptor antagonist. It is combined with diphenhydramine in the pharmaceutical preparation etanautine to help offset diphenhydramine induced drowsiness.

Reproterol is a short-acting β2 adrenoreceptor agonist used in the treatment of asthma.

Rolofylline (KW-3902) is an experimental diuretic which acts as a selective adenosine A1 receptor antagonist. It was discovered at NovaCardia, Inc. which was purchased by Merck & Co., Inc. in 2007.

Dimethazan (Elidin) is a stimulant drug of the xanthine class related to caffeine and theophylline. It also has tranquilizing and respiratory-stimulating effects and has been sold as an antidepressant.

Etamiphylline or etamiphyllin (INN) is a xanthine intended for use as an anti-asthma agent. It has shown poor to absent effects in human clinical trials.

Enprofylline (3-propylxanthine) is a xanthine derivative used in the treatment of asthma, which acts as a bronchodilator. It acts primarily as a competitive nonselective phosphodiesterase inhibitor with relatively little activity as a nonselective adenosine receptor antagonist.

8-Cyclopentyl-1,3-dimethylxanthine (8-Cyclopentyltheophylline, 8-CPT, CPX) is a drug which acts as a potent and selective antagonist for the adenosine receptors, with some selectivity for the A1 receptor subtype, as well as a non-selective phosphodiesterase inhibitor. It has stimulant effects in animals with slightly higher potency than caffeine.

Cafaminol (brand names Rhinetten, Rhinoptil), also known as methylcoffanolamine, is a vasoconstrictor and anticatarrhal of the methylxanthine family related to caffeine which is used as a nasal decongestant in Germany. It was introduced in 1974 and was still in use as of 2000.

Xanthinol is a drug prepared from theophylline used as a vasodilator. It is most often used as the salt with niacin (nicotinic acid), known as xanthinol nicotinate. It is a derivative of vitamin B3 (niacin), and can be found in a wide array dietary supplements. It has been marketed to increase the brain metabolism of glucose and ability to obtain ATP. Xanthinol is also used as an agent to reduced cholesterol as it is a vasodilator. It was approved as a medication in Canada in 1998, but it has since had its classification as a medication withdrawn. Xanthinol is indicated to improve cerebrovascu

Ambuphylline (or bufylline) is a combination of theophylline and aminoisobutanol used as a bronchodilator. It also acts and may be used as a diuretic.

Cafedrine (, ), sold under the brand name Akrinor among others, is a chemical linkage of norephedrine and theophylline and is a cardiac stimulant and antihypotensive agent used to increase blood pressure in people with hypotension. It has been marketed in Europe, South Africa, and Indonesia.

Furafylline is a methylxanthine derivative that was introduced in hope of being a long-acting replacement for theophylline in the treatment of asthma. It is an inhibitor of CYP1A2.

8-Cyclopentyl-1,3-dipropylxanthine (DPCPX, PD-116,948) is a drug which acts as a potent and selective antagonist for the adenosine A1 receptor. It has high selectivity for A1 over other adenosine receptor subtypes, but as with other xanthine derivatives DPCPX also acts as a phosphodiesterase inhibitor, and is almost as potent as rolipram at inhibiting PDE4. It has been used to study the function of the adenosine A1 receptor in animals, which has been found to be involved in several important functions such as regulation of breathing and activity in various regions of the brain, and DPCPX has a

Pentifylline (marketed as Cosaldon) is a vasodilator.

Propentofylline (HWA 285) is a xanthine derivative drug with purported neuroprotective effects.

Fencamine (Altimina, Sicoclor), also known as methamphetaminoethylcaffeine, is a psychostimulant drug of the amphetamine class. It is closely related to fenethylline. It is a prodrug of amphetamine and/or methamphetamine. The drug also contains a caffeine moiety in its chemical structure.

Methylliberine is an isolate of coffee beans, tea, cola nuts, guarana, cocoa, and yerba mate. It is structurally related to Liberine.

Theodrenaline (), also known as noradrenalinoethyltheophylline or as noradrenaline theophylline, is a chemical linkage of norepinephrine (noradrenaline) and theophylline used as a cardiac stimulant. It is sometimes combined with cafedrine.

MRS-1706 is a selective inverse agonist for the adenosine A2B receptor. It inhibits release of interleukins and has an antiinflammatory effect.