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51-34-3CN1[C@@H]2CC(OC(=O)[C@H](CO)c3ccccc3)C[C@H]1[C@@H]1O[C@@H]12STECJAGHUSJQJN-FWXGHANASA-N51-34-3CHEMBL1906925、CHEMBL3084722、CHEMBL4065982CHEBI:16794DescriptionScopolamine is a type of alkaloid that exists in a variety of Solanaceae plants such as Scopolia japonica, Datura metel L., and so on. It is the main active ingredient in these plants.Apart from scopolamine, several other chemical ingredients also exist in Scopolia japonica, including hyoscyamine, anisodamine, anisodine, and so on. Hyoscyamine is an inhibitor of parasympathetic nerve, with the analgesic and antispasmodic functions, especially for sciatica, sometimes for the treatment of epilepsy, seasickness, etc., and its pharmacological effects are similar to atropine. However, its clinical application is less because of its toxicity. The clinical applications of anisodamine are treating infectious toxic shock, vascular disorders, various neuralgia, smooth muscle spasms, vertigo, fundus disorders and sudden deafness, and other diseases. It has definite curative effect and is widely used in clinical in China. Its synthetic product is called “654-2,” which now still is an effective drug to treat infectious shock and other vascular diseases. While anisodine is used to treat vascular headache, retinal vasospasm, ischemic optic neuritis, cerebrovascular disease, acute paralysis, central dysfunction caused by carbon monoxide poisoning, tremor, paralysis, bronchial asthma, motion sickness, organophosphorus pesticide poisoning, and so on .
HistoryScopolamine is the main active ingredient of Scopolia japonica, Datura metel L., and other Solanaceae plants. As early as 1892, the chemist E.Schmidt first isolated it from the Scopolia japonica, so named it as scopolamine. Due to its obvious deficiencies in solubility and usage, the researchers modified its structure as scopolamine butylbromide, which was synthesized and used scopolamine and bromo-n-butane with heating refluxing method. Preparation method of scopolamine butylbromide is simple, and it’s easy to be synthesized. There are about 170 domestic enterprises producing its raw materials currently.European Pharmacopoeia (9th ed.), United States Pharmacopeia (36), and the Japanese Pharmacopoeia (16th ed.) contained bromine scopolamine; British Pharmacopoeia (2015) contained the raw materials and preparations of scopolamine butylbromide, including tablets and injections. Pharmacopoeia of the People’s Republic of China (2015) contained its raw materials, injection, and capsules.
UsesScopolamine is used for practically the same indications as atropine, but it should be noted that it has a sedative effect on motor activity, and it is recommended for the treatment of Parkinsonian symptoms.
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Usescholinergic (ophthalmic).
General DescriptionScopolamine (hyoscine) is found in variousmembers of the Solanaceae (e.g., H. niger, Duboisia myoporoides,Scopolia spp., and Datura metel). Scopolamineusually is isolated from the mother liquor remaining from theisolation of hyoscyamine.Hyoscine is the older name for this alkaloid, althoughscopolamine is the accepted name in the United States.Scopolamine is the levo component of the racemic mixturethat is known as atroscine. The alkaloid is racemized readilyin the presence of dilute alkali.The alkaloid occurs in the form of a levorotatory, viscousliquid that is only slightly soluble in water but very solublein alcohol, chloroform, or ether. It forms crystalline saltswith most acids, with the hydrobromide being the most stableand the most popularly accepted. An aqueous solution ofthe hydrobromide containing 10% mannitol is said to be lessprone to decomposition than unprotected solutions.
DefinitionChEBI: A tropane alkaloid that is the (S)-tropic acid ester of 6beta,7beta-epoxy-1alphaH,5alphaH-tropan-3alpha-ol.