Catechol ethers

Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, Papaver somniferum. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) as codeine/paracetamol or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children. In Europe, it is not recommended as a cough medicine for those under 12 y

Oxycodone, sold under the brand names Endone and OxyContin (which is the extended-release form) among others, is a semi-synthetic opioid used medically for the treatment of moderate to severe pain. It is a highly addictive and commonly abused drug. It is usually taken orally, and is available in immediate-release and controlled-release formulations. Onset of pain relief typically begins within fifteen minutes and lasts for up to six hours with the immediate-release formulation. In the United Kingdom, it is available by injection. Combination products are also available with paracetamol (acetam

Papaverine (Latin papaver, "poppy") is an opium alkaloid antispasmodic drug, used primarily in the treatment of visceral spasms and vasospasms (especially those involving the intestines, heart, or brain), occasionally in the treatment of erectile dysfunction and acute mesenteric ischemia. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the analgesic morphine and its derivatives (such as codeine).

Donepezil, sold under the brand name Aricept among others, is a medication used to treat dementia of the Alzheimer's type. It appears to result in a small benefit in mental function and ability to function. Use, however, has not been shown to change the progression of the disease. Treatment should be stopped if no benefit is seen. It is taken by mouth or via a transdermal patch.

Verapamil, sold under various trade names, is a calcium channel blocker medication used for the treatment of high blood pressure, angina (chest pain from not enough blood flow to the heart), and supraventricular tachycardia. It may also be used for the prevention of migraines and cluster headaches. It is given by mouth or by injection into a vein.

Carvedilol, sold under the brand name Coreg among others, is a beta blocker medication, that may be prescribed for the treatment of high blood pressure (hypertension) and chronic heart failure with reduced ejection fraction (also known as HFrEF or systolic heart failure). Beta-blockers as a collective medication class are not recommended as routine first-line treatment of high blood pressure for all patients, due to evidence demonstrating less effective cardiovascular protection and a less favourable safety profile when compared to other classes of blood pressure-lowering medications.

Guaifenesin, also known as glyceryl guaiacolate, sold under the brand name Mucinex, among others, is an expectorant medication taken by mouth and marketed as an aid to eliminate sputum from the respiratory tract. Chemically, it is an ether of guaiacol and glycerine. It may be used in combination with other medications. A 2014 study found that guaifenesin does not affect sputum volume in upper respiratory infections (the upper respiratory system includes most breathing parts above the lungs). It has been alleged to work in 2023 by making airway secretions more liquid.

Brucine is an alkaloid closely related to strychnine, most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more toxic than brucine. In chemical synthesis, it can be used as a tool for stereospecific chemical syntheses.

Prazosin, sold under the brand name Minipress among others, is a medication used to treat high blood pressure, symptoms of an enlarged prostate, and nightmares related to post-traumatic stress disorder (PTSD). It is an α1 blocker. It is a less preferred treatment of high blood pressure. Other uses may include heart failure and Raynaud syndrome. It is taken by mouth.

Carbofuran is a carbamate insecticide, banned in the US, the EU and Canada but still widely used in South America, Australia and Asia. It is a systemic insecticide, which means that the plant absorbs it through the roots, and from there the plant distributes it throughout its organs where insecticidal concentrations are attained. Carbofuran also has contact activity against pests. It is one of the most toxic pesticides still in use.

Dihydrocodeine is a semi-synthetic opioid analgesic prescribed for pain or severe dyspnea, or as an antitussive, either alone or compounded with paracetamol (acetaminophen) (as in co-dydramol) or aspirin. It was developed in Germany in 1908 and first marketed in 1911.

Mebeverine is a drug used to alleviate some of the symptoms of irritable bowel syndrome. It works by relaxing the muscles in and around the gut.

Aliskiren (brand names Tekturna and Rasilez) is the first in a class of drugs called direct renin inhibitors. It is used for essential (primary) hypertension. While used for high blood pressure, other better studied medications are typically recommended due to concerns of higher side effects and less evidence of benefit.

Methocarbamol, sold under the brand name Robaxin among others, is a medication used for short-term musculoskeletal pain. It may be used together with rest, physical therapy, and pain medication. It has limited use for rheumatoid arthritis and cerebral palsy. Effects generally begin within half an hour. It is taken by mouth or injection into a vein.

Oxprenolol, sold under the brand name Trasicor among others, is a non-selective beta blocker with some intrinsic sympathomimetic activity. It is used for the treatment of angina pectoris, abnormal heart rhythms, and high blood pressure.

Apremilast, sold under the brand name Otezla among others, is a medication for the treatment of certain types of psoriasis and psoriatic arthritis. The drug acts as a selective inhibitor of the enzyme phosphodiesterase 4 (PDE4). It is taken by mouth.

Bosentan, sold under the brand name Tracleer among others, is a dual endothelin receptor antagonist medication used in the treatment of pulmonary artery hypertension (PAH).

Propoxur is a carbamate, non-systemic, synthetic insecticide, produced from catechol, and was introduced in 1959 by Bayer.

Bevantolol (INN) was a drug candidate for angina and hypertension that acted as both a beta blocker and a calcium channel blocker. It was discovered and developed by Warner-Lambert but in January 1989 the company announced that it had withdrawn the New Drug Application; the company's chairman said: "Who needs the 30th beta blocker?" it wasn't marketed in the US, UK, or Europe and the authors of a Cochrane review could find no product monograph for it.

Bosutinib, sold under the brand name Bosulif, is a small molecule BCR-ABL and src tyrosine kinase inhibitor used for the treatment of chronic myelogenous leukemia.

Dipivefrine, or dipivefrin, also known as epinephrine pivalate and sold under the brand name Propine among others, is a sympathomimetic medication which is used in the treatment of open-angle glaucoma. It is available as a 0.1% ophthalmic solution (eye drop).

Acetyldihydrocodeine is an opiate derivative discovered in Germany in 1914 and was used as a cough suppressant and analgesic. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative derivative of thebacon, where only the 6-7 bond is unsaturated. Acetyldihydrocodeine can be described as the 6-acetyl derivative of dihydrocodeine and is metabolised in the liver by demethylation and deacetylation to produce dihydromorphine.

Codeinone is an isoquinolone alkaloid found in the opium poppy. As an analgesic, it is one-third the potency of codeine. It is an important intermediate in the production of hydrocodone–a painkiller about three-quarters the potency of morphine–as well as of oxycodone, though the latter can also be synthesized from thebaine.

Methoxsalen (or Xanthotoxin, 8-methoxypsoralen) sold under the brand name Oxsoralen and Melanocyl among others, is a medication used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to ultraviolet (UVA) light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. Levels of individual patient PUVA exposure were originally determined using the Fitzpatrick scale. The scale was developed after patients demonstrated symptoms of phototoxicity after oral ingestion of methoxsa

Itopride (INN; brand name Ganaton) is a prokinetic benzamide derivative. These drugs inhibit dopamine and acetylcholine esterase enzyme and have a gastrokinetic effect. Itopride is indicated for the treatment of functional dyspepsia and other gastrointestinal conditions. It is a combined D2 receptor antagonist and acetylcholinesterase inhibitor. Itopride is the dimethoxy analog of trimethobenzamide.

Carbosulfan is an organic compound adherent to the carbamate class. At normal conditions, it is brown viscous liquid. It is not very stable; it decomposes slowly at room temperature. Its solubility in water is low but it is miscible with xylene, hexane, chloroform, dichloromethane, methanol and acetone. Carbosulfan is used as an insecticide. The European Union banned use of carbosulfan in 2007.

3,4-Dimethoxyphenethylamine (DMPEA or 3,4-DMPEA), also known as homoveratrylamine, 3-desmethoxymescaline, or '''O,O-dimethyldopamine''', is a chemical compound of the phenethylamine family. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline (3,4,5-trimethoxyphenethylamine; 3,4,5-TMPEA) and to 3,4-dimethoxyamphetamine (3,4-DMA).

Cutamesine (SA 4503) is a synthetic sigma receptor agonist which is selective for the σ1 receptor, a chaperone protein mainly found in the endoplasmic reticulum of cells in the central nervous system. These σ1 receptors play a key role in the modulation of Ca2+ release and apoptosis. Cutamesine's activation of the σ1 receptor is tied to a variety of physiological phenomena in the CNS, including activation of dopamine-releasing neurons and repression of the MAPK/ERK pathway.

Oxypertine, sold under the brand name Oxypertine among others, is an antipsychotic medication of the pertine group which was previously used in the treatment of schizophrenia but is no longer marketed. It was also evaluated for the treatment of anxiety.

Guacetisal is a drug that has been used to treat inflammatory respiratory diseases. Chemically, it is an ester resulting from the combination of aspirin and guaiacol.

Amosulalol (INN) is an antihypertensive drug. It has much higher affinity for α1-adrenergic receptors than for β-adrenergic receptors. It is not approved for use in the United States. ==Synthesis== upright=2|class=skin-invert-image

Ciladopa (developmental code name AY-27,110) is a dopamine agonist with a similar chemical structure to dopamine. It was under investigation as an antiparkinsonian agent but was discontinued due to concerns of tumorogenesis in rodents.

Acotiamide, sold under the brand names Acofide, and Dyspevict is a medication manufactured and approved in Japan and Russia for the treatment of postprandial fullness, upper abdominal bloating, and early satiation due to functional dyspepsia. It acts as an acetylcholinesterase inhibitor.

Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid (BIA) that is derived directly from (S)-reticuline through the action of berberine bridge enzyme. It is a precursor of other BIAs, notably berberine, noscapine, (S)-tetrahydropalmatine, and (S)-stylopine, as well as the alkaloids protopine, and sanguinarine. It is found in many plants, including opium poppy, Croton flavens, and certain plants in the genus Erythrina.

2C-O-4, also known as 4-isopropoxy-2,5-dimethoxyphenethylamine, is a phenethylamine of the 2C family. It is also a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin. It produces hallucinogenic or psychedelic effects. Because of the low potency of 2C-O-4, and the inactivity of 2C-O, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further analogues.

Nisoxetine (developmental code name LY-94939), originally synthesized in the Lilly research laboratories during the early 1970s, is a potent and selective inhibitor for the reuptake of norepinephrine (noradrenaline) into synapses. It currently has no clinical applications in humans, although it was originally researched as an antidepressant. Nisoxetine is now widely used in scientific research as a standard selective norepinephrine reuptake inhibitor. It has been used to research obesity and energy balance, and exerts some local analgesia effects.

Denopamine (INN) is a drug which acts as a β1 adrenergic receptor agonist. It is used in the treatment of angina and may also have potential uses in the treatment of congestive heart failure and for clearing pulmonary edema. It is marketed in Japan under the brand name Kalgut and available as tablets of 5 and 10 mg, and 5% fine granules.

Befunolol (INN) is a beta blocker with intrinsic sympathomimetic activity used in the management of open-angle glaucoma. It also acts as a β adrenoreceptor partial agonist. Befunolol was introduced in Japan in 1983 by Kakenyaku Kako Co. under the trade name Bentos.

Bunazosin (INN) is an α1-adrenergic receptor antagonist. Bunazosin was initially developed to treat benign prostatic hyperplasia (BPH). It has been approved in Japan in a topical form to treat glaucoma. The mechanism of action is a reduction of aqueous outflow through the uveoscleral pathway resulting in lowering the intraocular pressure. It also may act to improve blood flow to the ocular nerve. Systemic Alpha-1 adrenergic receptor antagonists have been implicated in Intraoperative Floppy Iris Syndrome (IFIS). Bunazosin potentially could have the same effect but there has been no research to

Tiapamil (INN; also known as dimeditiapramine) is a calcium antagonist or calcium channel blocker. It is an experimental drug that has never been marketed.

Codoxime (Codossima) is an opiate analogue that is a derivative of hydrocodone, where the 6-ketone group has been replaced by carboxymethyloxime. It has primarily antitussive effects and was found to have moderate potential to cause dependence in animal studies.

Pacrinolol is a beta adrenergic receptor antagonist.

Ensaculin (KA-672) is a drug from the coumarin family, which has been researched as a potential treatment for dementia. It acts on a number of receptor systems, being both a weak NMDA antagonist and a 5HT1A agonist. Animal studies have shown promising nootropic effects, although efficacy in humans has yet to be proven. It was well tolerated in human trials, with the main side effect being orthostatic hypotension (low blood pressure upon standing).

Aspidophytine is an indole alkaloid that has attracted significant attention from synthetic chemists. An extract of the cockroach plant, aspidophytine is an insecticidal substance particularly effective against cockroaches. It is one of the two components of the dimer haplophytine.

Benzquinamide is a discontinued antiemetic drug used in post-operative care. It was first synthesised by Pfizer in the 1960s.

Vesnarinone (INN) is a cardiotonic agent. A mixed phosphodiesterase 3 inhibitor and ion-channel modifier that has modest, dose-dependent, positive inotropic activity, but minimal negative chronotropic activity. Vesnarinone improves ventricular performance most in patients with the worst degree of heart failure.

Cryogenine, also known as vertine or (10α)-4,5-dimethoxy-2-hydroxylythran-12-one, is a biphenylquinolizidine lactone alkaloid from the plants Sinicuichi (Heimia salicifolia) and H. myrtifolia. The compound has no psychoactive properties in humans up to 310 mg, but has shown anti-inflammatory activity similar to aspirin.

Devapamil is a calcium channel blocker. It is also known as desmethoxyverapamil, which is a phenylalkylamine (PAA) derivative. Devapamil not only inhibits by blocking the calcium gated channels, but also by depolarizing the membrane during the sodium-potassium exchanges.

Bufetolol is a beta-adrenoceptor antagonist.