Names | |||
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IUPAC name 6β,7β-Epoxytropan-3α-ol | |||
Systematic IUPAC name (1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol | |||
Other names 6,7-Epoxytropine; Scopanol; Scopin; 6β,7β-Epoxy-1αH,5αH-tropan-3α-ol | |||
Identifiers | |||
3D model (JSmol) | |||
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Properties | |||
C8H13NO2 | |||
Molar mass | 155.197 g·mol−1 | ||
Melting point | 75 to 76 °C (167 to 169 °F; 348 to 349 K) [1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Scopine is a tropane alkaloid found in a variety of plants including Mandragora root, [2] Senecio mikanioides (Delairea odorata), [3] Scopolia carniolica , [4] and Scopolia lurida . [5]
Scopine can be prepared by the hydrolysis of scopolamine. [1] [6] [7] It can also be prepared in three steps from N-methoxycarbonylpyrrole and 1,1,3,3-tetrabromoacetone; the reagents are combined in a [4+3] cycloaddition, followed by a diastereoselective reduction with diisobutylaluminum hydride, and finally a Prilezhaev epoxidation with trifluoroperacetic acid affords scopine. [8]
A besom is a broom, a household implement used for sweeping. The term is now mostly reserved for a traditional broom constructed from a bundle of twigs tied to a stout pole. The twigs used could be broom, heather or similar. The song "Buy Broom Buzzems" from Northern England refers to both types of twig. From the phrase broom besom the more common broom comes. In Scotland, besoms are still occasionally to be found at the edge of forests where they are stacked for use in early response to an outbreak of fire.
Deliriants are a subclass of hallucinogen. The term was coined in the early 1980s to distinguish these drugs from psychedelics and dissociatives such as LSD and ketamine, respectively, due to their primary effect of causing delirium, as opposed to the more lucid and less disturbed states produced by other types of hallucinogens. The term generally refers to anticholinergic drugs, which are substances that inhibit the function of the neurotransmitter acetylcholine. Common examples of deliriants include plants of the genera Datura and Brugmansia as well as higher than recommended dosages of diphenhydramine (Benadryl). A number of plant deliriants such as that of the Solanaceae family, particularly in the Americas have been used by some indigenous cultures to reach delirious and altered states for traditions or rituals, such as rites of passage, divination or communicating with the ancestors. Despite their long history of use, deliriants are the least-studied class of hallucinogens in terms of their behavioral and neurological effects.
Chromium hexacarbonyl (IUPAC name: hexacarbonylchromium) is a chromium(0) organometallic compound with the formula Cr(CO)6. It is homoleptic complex, which means that all the ligands are identical. It is a white, air-stable solid with a high vapor pressure.
Imidazolidine is a heterocyclic compound (CH2)2(NH)2CH2. The parent imidazolidine is lightly studied, but related compounds substituted on one or both nitrogen centers are more common. Generally, they are colorless, polar, basic compounds. Imidazolidines are cyclic 5-membered examples of the general class of aminals.
Mandragora officinarum is the type species of the plant genus Mandragora in the nightshade family Solanaceae. It is often known as mandrake, although this name is also used for other plants. As of 2015, sources differed significantly in the species they use for Mandragora plants native to the Mediterranean region. The main species found around the Mediterranean is called Mandragora autumnalis, the autumn mandrake. In a broader circumscription, all the plants native to the regions around the Mediterranean Sea are placed in M. officinarum, which thus includes M. autumnalis. The names autumn mandrake and Mediterranean mandrake are then used. Whatever the circumscription, Mandragora officinarum is a perennial herbaceous plant with ovate leaves arranged in a rosette, a thick upright root, often branched, and bell-shaped flowers followed by yellow or orange berries.
In organic chemistry, the Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen. It is named after Karl Friedrich Schmidt (1887–1971), who first reported it in 1924 by successfully converting benzophenone and hydrazoic acid to benzanilide. The intramolecular reaction was not reported until 1991 but has become important in the synthesis of natural products. The reaction is effective with carboxylic acids to give amines (above), and with ketones to give amides (below).
Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol. It is a poisonous white hygroscopic crystalline powder. It is a heterocyclic alcohol and an amine.
Selenoxide elimination is a method for the chemical synthesis of alkenes from selenoxides. It is most commonly used to synthesize α,β-unsaturated carbonyl compounds from the corresponding saturated analogues. It is mechanistically related to the Cope reaction.
Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.
Organochromium chemistry is a branch of organometallic chemistry that deals with organic compounds containing a chromium to carbon bond and their reactions. The field is of some relevance to organic synthesis. The relevant oxidation states for organochromium complexes encompass the entire range of possible oxidation states from –4 (d10) in Na4[Cr–IV(CO)4] to +6 (d0) in oxo-alkyl complexes like Cp*CrVI(=O)2Me.
The biosynthesis of cocaine has long attracted the attention of biochemists and organic chemists. This interest is partly motivated by the strong physiological effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases, one phase leading to the N-methylpyrrolinium ring, which is preserved in the final product. The second phase incorporates a C4 unit with formation of the bicyclic tropane core.
Strychnine total synthesis in chemistry describes the total synthesis of the complex biomolecule strychnine. The first reported method by the group of Robert Burns Woodward in 1954 is considered a classic in this research field.
Anisodine, also known as daturamine and α-hydroxyscopolamine, is an antispasmodic and anticholinergic drug used in the treatment of acute circulatory shock in China. It is a tropane alkaloid and is found naturally in plants of the family Solanaceae like Scopolia tanguticus Anisodine acts as a muscarinic acetylcholine receptor antagonist and α1-adrenergic receptor antagonist.
Scopolia japonica, also Japanese belladonna or Korean scopolia, is a flowering plant species in the genus Scopolia - one of the eight genera in tribe Hyoscyameae of the nightshade family Solanaceae.
Scopolia carniolica, the European scopolia or henbane bell, is a poisonous plant belonging to the family Solanaceae. It has dark violet flowers on long hanging stems. It grows to 60 centimetres (24 in) in height. Its toxicity derives from its high levels of tropane alkaloids, particularly atropine. The concentration of atropine is highest in the roots.
Metal carbonyl hydrides are complexes of transition metals with carbon monoxide and hydride as ligands. These complexes are useful in organic synthesis as catalysts in homogeneous catalysis, such as hydroformylation.
Littorine is a tropane alkaloid found in a variety of plants including Datura and Atropa belladonna. It is closely related in chemical structure to atropine, hyoscyamine, and scopolamine, which all share a common biosynthetic pathway.
2-Carbomethoxytropinone (2-CMT) is a commonly used organic intermediate in the synthesis of cocaine and its analogues. As of at least 1999 no reaction pathway has been discovered that synthesizes cocaine-like compounds without utilizing the reduction of 2-CMT. The structure of cocaine was discovered by Richard Willstätter in 1898 after he synthesized it from 2-carbomethoxytropinone. Although it was originally believed that 2-CMT in nature was ultimately derived from ornithine and acetic acid, subsequent research has indicated other pathways exist for the biosynthesis of 2-CMT. A β-keto ester, 2-CMT exists in equilibrium with its keto–enol tautomer.
Trifluoroperacetic acid is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF
3COOOH. It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones. It is the most reactive of the organic peroxy acids, allowing it to successfully oxidise relatively unreactive alkenes to epoxides where other peroxy acids are ineffective. It can also oxidise the chalcogens in some functional groups, such as by transforming selenoethers to selones. It is a potentially explosive material and is not commercially available, but it can be quickly prepared as needed. Its use as a laboratory reagent was pioneered and developed by William D. Emmons.
Carbonyl olefin metathesis is a type of metathesis reaction that entails, formally, the redistribution of fragments of an alkene and a carbonyl by the scission and regeneration of carbon-carbon and carbon-oxygen double bonds respectively. It is a powerful method in organic synthesis using simple carbonyls and olefins and converting them into less accessible products with higher structural complexity.