Quaternary ammonium compounds

Thiamine, also known as thiamin and vitamin B1, is a vitamin – an essential micronutrient for humans and animals. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosphorylated forms of thiamine are required for some metabolic reactions, including the breakdown of glucose and amino acids.

Acetylcholine (ACh) is an organic compound that functions in the brain and body of many types of animals (including humans) as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Parts in the body that use or are affected by acetylcholine are referred to as cholinergic.

Choline is a cation with the chemical formula . Choline forms various salts, such as choline chloride and choline bitartrate. An essential nutrient for animals, it is a structural component of phospholipids and cell membranes.

Carnitine is a quaternary ammonium compound involved in metabolism in most mammals, plants, and some bacteria. In support of energy metabolism, carnitine transports long-chain fatty acids from the cytosol into mitochondria to be oxidized for free energy production, and also participates in removing products of metabolism from cells. Given its key metabolic roles, carnitine is concentrated in tissues like skeletal and cardiac muscle that metabolize fatty acids as an energy source. Generally individuals, including strict vegetarians, synthesize enough L-carnitine in vivo.

thumb|Amanita muscaria

chemical compound

Neostigmine, sold under the brand name Bloxiverz, among others, is a medication used to treat myasthenia gravis, Ogilvie syndrome, and urinary retention without the presence of a blockage. It is also used in anaesthesia to end the effects of non-depolarising neuromuscular blocking medication. It is given by injection either into a vein, muscle, or under the skin. After injection effects are generally greatest within 30 minutes and last up to 4 hours.

chemical compound

Safranin (Safranin O or basic red 2) is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring cell nuclei red. This is the classic counterstain in both Gram stains and endospore staining. It can also be used for the detection of cartilage, mucin and mast cell granules.

Berberine is an organic compound classified as benzylisoquinoline alkaloid. Chemically, it is a quaternary ammonia compound.

chemical compound

Trimethylglycine is an amino acid derivative with the formula . A colorless, water-soluble solid, it occurs in plants. Trimethylglycine is a zwitterion: the molecule contains both a quaternary ammonium group and a carboxylate group. Trimethylglycine was the first betaine discovered; originally it was simply called betaine because it was discovered in sugar beets (Beta vulgaris subsp. vulgaris). Several other betaines are now known.

aminosteroid muscle relaxant

Denatonium is an organic ion and one of the bitterest chemical compounds known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharinate. Commercially, it is usually available in salts such as denatonium benzoate (under trade names such as Denatrol, BITTERANT-b, BITTER+PLUS, Bitrex, Bitrix, Toxishield and Aversion) or as denatonium saccharinate (BITTERANT-s).

mixture of chemical compounds

chemical compound

pharmaceutical drug

thumb|right|Letter from Perkin's son, with a sample of dyed silk Mauveine, also known as aniline purple and '''Perkin's mauve''', was one of the first synthetic dyes. It was discovered serendipitously by William Henry Perkin in 1856 while he was attempting to synthesise the phytochemical quinine for the treatment of malaria. It is also among the first chemical dyes to have been mass-produced.

muscle relaxant used intravenously for medical use in general anesthesia

Carbachol, also known as carbamylcholine and sold under the brand name Miostat among others, is a cholinomimetic drug that binds and activates acetylcholine receptors. Thus it is classified as a cholinergic agonist. It is primarily used for various ophthalmic purposes, such as for treating glaucoma, or for use during ophthalmic surgery. It is generally administered as an ophthalmic solution (i.e., eye drops).

chemical compound

chemical compound

Pralidoxime (2-pyridine aldoxime methyl chloride) or 2-PAM, usually as the chloride or iodide salts, belongs to a family of compounds called oximes that bind to organophosphate-inactivated acetylcholinesterase. It is used to treat organophosphate poisoning in conjunction with atropine and either diazepam or midazolam. It is a white solid.

chemical compound acting as osmotic regulator in marine organisms and fishes

thumb|400x400px|Cocamidopropyl betaine is an example of a betaine

chemical compound

quaternary ammonium surfactant and antiseptic agent

chemical compound

chemical compound

Miltefosine, sold under the trade name Impavido among others, is a medication mainly used to treat leishmaniasis and infectious diseases caused by Naegleria fowleri and Balamuthia mandrillaris. This includes the three forms of leishmaniasis: cutaneous, visceral and mucosal/mucocutaneous. It may be used with liposomal amphotericin B or paromomycin. It is taken by mouth.

Bethanechol is a parasympathomimetic choline carbamate that selectively stimulates muscarinic receptors without any effect on nicotinic receptors. Unlike acetylcholine, bethanechol is not hydrolyzed by cholinesterase and will therefore have a long duration of action. Bethanechol is sold under the brand names Duvoid (Roberts), Myotonachol (Glenwood), Urecholine (Merck Frosst), and Urocarb (Hamilton). The name bethanechol refers to its structure as the urethane of beta-methylcholine.

Citicoline (INN), also known as cytidine diphosphate-choline (CDP-choline) or '''cytidine 5'-diphosphocholine''' is an intermediate in the generation of phosphatidylcholine from choline, a common biochemical process in cell membranes. Citicoline is naturally occurring in the cells of human and animal tissue, in particular the organs.

Desmosine is an amino acid found uniquely in elastin, a protein found in connective tissue such as skin, lungs, and elastic arteries.

class of cation containing nitrogen with 4 electrically neutral substituents

Trigonelline is an alkaloid with chemical formula . It is a zwitterion formed by the methylation of the nitrogen atom of niacin (vitamin B3). Trigonelline is a product of niacin metabolism that is excreted in the urine of mammals.

chemical compound

chemical compound

chemical compound

Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.

chemical compound

Edrophonium, formerly sold under the brand name Tensilon among others, is a readily reversible acetylcholinesterase inhibitor. It prevents breakdown of the neurotransmitter acetylcholine and acts by competitively inhibiting the enzyme acetylcholinesterase, mainly at the neuromuscular junction.

chemical compound

chemical compound

chemical compound

Acriflavine (INN: acriflavinium chloride) is a topical antiseptic. It has the form of an orange or brown powder. It may be harmful in the eyes or if inhaled. It is a dye and it stains the skin and may irritate. The hydrochloride form is more irritating than the neutral form. It is derived from acridine. Commercial preparations are often mixtures with proflavine. It is known by a variety of commercial names.

Sanguinarine is a polycyclic quaternary alkaloid. It is extracted from some plants, including the bloodroot plant (Sanguinaria canadensis, from whose scientific name its name is derived), the Mexican prickly poppy (Argemone mexicana), Chelidonium majus, and Macleaya cordata.

Neurine is an alkaloid found in egg yolk, brain, bile and in cadavers. It is formed during putrefaction of biological tissues by the dehydration of choline. It is a poisonous, syrupy liquid with a fishy odor.

Obidoxime is a member of the oxime family used to treat organophosphate poisoning. Oximes are drugs known for their ability to reverse the binding of organophosphorus compounds to the enzyme acetylcholinesterase (AChE).

chemical compound

chemical compound

Methacholine (INN, USAN) (trade name Provocholine), also known as acetyl-β-methylcholine, is a synthetic choline ester that acts as a non-selective muscarinic receptor agonist in the parasympathetic nervous system.

Sinapine is an alkaloidal amine found in some seeds, particularly oil seeds of plants in the family Brassicaceae. It is the choline ester of sinapic acid.

mixture of chemical compounds

Acetyl-L-carnitine (ALCAR or ALC), also known as levacecarnine, is an acetylated form of L-carnitine. It is naturally produced by the human body, and it is available as a dietary supplement. Acetylcarnitine is broken down in the blood by plasma esterases to carnitine which is used by the body to transport fatty acids into the mitochondria for breakdown and energy production.

Isavuconazonium, sold under the brand name Cresemba, is a systemic antifungal medication of the triazole class which is used to treat invasive aspergillosis and mucormycosis. It is used as the sulfate. It is taken by mouth or given via injection into a vein.

Bretylium (also bretylium tosylate) is an antiarrhythmic agent. It blocks the release of noradrenaline from nerve terminals. In effect, it decreases output from the peripheral sympathetic nervous system. It also acts by blocking K+ channels and is considered a class III antiarrhythmic. The dose is 5–10 mg/kg and side effects are high blood pressure followed by low blood pressure and ventricular ectopy.

chemical compound

Methylnaltrexone (MNTX, brand name Relistor), used in form of methylnaltrexone bromide (INN, USAN, BAN), is a medication that acts as a peripherally acting μ-opioid receptor antagonist that acts to reverse some of the side effects of opioid drugs such as constipation without significantly affecting pain relief or precipitating withdrawals. Because MNTX is a quaternary ammonium cation, it cannot cross the blood–brain barrier, and so has antagonist effects throughout the body, counteracting effects such as itching and constipation, but without affecting opioid effects in the brain such as pain r

Pyrvinium (Viprynium) is an anthelmintic effective for pinworms. Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate. Pyrvinium was identified as a potent Wnt inhibitor, acting through activation of Casein kinase CK1α.