Names | |||
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Preferred IUPAC name (1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol | |||
Other names α-Tropine; Tropanol | |||
Identifiers | |||
3D model (JSmol) | |||
ChemSpider | |||
ECHA InfoCard | 100.003.986 | ||
MeSH | Tropine | ||
PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
C8H15NO | |||
Molar mass | 141.214 g·mol−1 | ||
Appearance | White hygroscopic crystalline powder [1] [2] [3] or plates | ||
Odor | Amine-like [2] | ||
Density | 1.045 g/cm3 at 25 °C [2] 1.016 g/cm3 at 100 °C | ||
Melting point | 64 °C (147 °F; 337 K) | ||
Boiling point | 233 °C (451 °F; 506 K) | ||
Solubility | Very soluble in water, diethyl ether, ethanol [4] | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | Toxic | ||
GHS labelling: | |||
Danger | |||
H301, H302, H312, H332 | |||
P261, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P405, P501 | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol. [4] It is a poisonous white hygroscopic crystalline powder. [3] It is a heterocyclic alcohol and an amine. [3]
Tropine is a central building block of many chemicals active in the nervous system, including tropane alkaloids. Some of these compounds, such as long-acting muscarinic antagonists are used as medicines because of these effects. [5]
Tropine is a natural product found in the plants of deadly nightshade (Atropa belladonna) and devil's trumpet (Datura stramonium). [1]
It can be prepared by hydrolysis of atropine [6] or other solanaceous alkaloids. [3]
Datura stramonium, known by the common names thornapple, jimsonweed, or devil's trumpet, is a poisonous flowering plant in the Daturae tribe of the nightshade family Solanaceae. Its likely origin was in Central America, and it has been introduced in many world regions. It is an aggressive invasive weed in temperate climates and tropical climates across the world. D. stramonium has frequently been employed in traditional medicine to treat a variety of ailments. It has also been used as a hallucinogen, taken entheogenically to cause intense, sacred or occult visions. It is unlikely ever to become a major drug of abuse owing to effects upon both mind and body frequently perceived as being highly unpleasant, giving rise to a state of profound and long-lasting disorientation or delirium with a potentially fatal outcome. It contains tropane alkaloids which are responsible for the psychoactive effects, and may be severely toxic.
Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings.
Atropa belladonna, commonly known as belladonna or deadly nightshade, is a toxic perennial herbaceous plant in the nightshade family Solanaceae, which also includes tomatoes, potatoes and aubergine (eggplant). It is native to Europe and Western Asia, including Turkey. Its distribution extends from Ireland in the west to western Ukraine and the Iranian province of Gilan in the east. It is also naturalised or introduced in some parts of Canada, North Africa and the United States.
Hyoscyamine is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone.
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae and Solanaceae.
Ecgonine is a tropane alkaloid found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself.
In enzymology, a tropinone reductase II (EC 1.1.1.236) is an enzyme that catalyzes the chemical 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.
Anisodamine, also known as 7β-hydroxyhyoscyamine, is an anticholinergic and α1 adrenergic receptor antagonist used in the treatment of acute circulatory shock in China. It is given orally or by injection, as a racemic mixture (racanisodamine) or as a hydrobromide salt. Eye drops at 0.5% concentration for slowing the progression of myopia is also available in China.
Methylatropine is a belladonna derivative.
Secondary metabolism produces a large number of specialized compounds that do not aid in the growth and development of plants but are required for the plant to survive in its environment. Secondary metabolism is connected to primary metabolism by using building blocks and biosynthetic enzymes derived from primary metabolism. Primary metabolism governs all basic physiological processes that allow a plant to grow and set seeds, by translating the genetic code into proteins, carbohydrates, and amino acids. Specialized compounds from secondary metabolism are essential for communicating with other organisms in mutualistic or antagonistic interactions. They further assist in coping with abiotic stress such as increased UV-radiation. The broad functional spectrum of specialized metabolism is still not fully understood. In any case, a good balance between products of primary and secondary metabolism is best for a plant’s optimal growth and development as well as for its effective coping with often changing environmental conditions. Well known specialized compounds include alkaloids, polyphenols including flavonoids, and terpenoids. Humans use many of these compounds for culinary, medicinal and nutraceutical purposes.
Bruguiera exaristata, commonly known as the rib-fruited mangrove or rib-fruited orange mangrove, is a mangrove of the family Rhizophoraceae.
Tropacocaine is a cocaine-related alkaloid and a contaminant of street cocaine.
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.
Tropine acyltransferase is an enzyme with systematic name acyl-CoA:tropine O-acyltransferase. This enzyme catalyses the following chemical reaction
Pseudotropine acyltransferase is an enzyme with systematic name acyl-CoA:pseudotropine O-acyltransferase. This enzyme catalyses the following chemical reaction
Apoatropine (atropatropine) is a member of class of tropane alkaloids. Chemically, it is an ester formed from tropine and atropic acid. Apoatropine can be found in plants of family Solanaceae. It is a bitter crystalline alkaloid. Examples of related tropane alkaloids include atropine, hyoscyamine, and hyoscine. Though apoatropine is found in various plants, it can also be prepared by the dehydration of atropine using nitric acid. Apoatropine is used as a pigment.
Pseudotropine is a derivative of tropane and an isomer of tropine. Pseudotropine can be found in the Coca plant along with several other alkaloids
An O-acylpseudotropine is any derivative of pseudotropine in which the alcohol group is substituted with an acyl group.