Tropane alkaloid

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Chemical structure of tropane which forms the core of tropane alkaloids Tropane.svg
Chemical structure of tropane which forms the core of tropane alkaloids
Chemical structure and phylogeny of tropane alkaloids. Displayed are 3 chemical compounds that occur as natural products in 5 plant species Tropane alkaloids biochemistry.png
Chemical structure and phylogeny of tropane alkaloids. Displayed are 3 chemical compounds that occur as natural products in 5 plant species

Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. [1] 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. [2] [3] [4] [5] [6] [7] Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.

Contents

Classification

Anticholinergics

Anticholinergic drugs [8] and deliriants: [9]

All three acetylcholine-inhibiting chemicals can also be found in the leaves, stems, and flowers in varying, unknown amounts in Brugmansia (angel trumpets), a relative of Datura . The same is also true of many other plants belonging to subfamily Solanoideae of the Solanaceae, the alkaloids being concentrated particularly in the leaves and seeds. However, the concentration of alkaloids can vary greatly, even from leaf to leaf and seed to seed. [10] [11]

Stimulants

Stimulants and cocaine-related alkaloids:

Others

Synthetic analogs of tropane alkaloids also exist, such as the phenyltropanes. They are not considered to be alkaloids per definition.

Biosynthesis

The biosynthesis of the tropane alkaloids have attracted intense interest because of their high physiological activity as well as the presence of the bicyclic tropane core. [12]

Final stages in the pathway for the biosynthesis of the tropane alkaloid cocaine. CocaineBiosyn2.png
Final stages in the pathway for the biosynthesis of the tropane alkaloid cocaine.

Related Research Articles

<i>Datura</i> Genus of poisonous, potentially psychoactive plants

Datura is a genus of nine species of highly poisonous, vespertine-flowering plants belonging to the nightshade family (Solanaceae). They are commonly known as thornapples or jimsonweeds, but are also known as devil's trumpets. Other English common names include moonflower, devil's weed, and hell's bells. All species of Datura are extremely poisonous and potentially psychoactive, especially their seeds and flowers, which can cause respiratory depression, arrhythmias, fever, delirium, hallucinations, anticholinergic syndrome, psychosis, and even death if taken internally.

<span class="mw-page-title-main">Scopolamine</span> Tropane alkaloid & anticholinergic drug

Scopolamine, also known as hyoscine, or Devil's Breath, is a natural or synthetically produced tropane alkaloid and anticholinergic drug that is formally used as a medication for treating motion sickness and postoperative nausea and vomiting. It is also sometimes used before surgery to decrease saliva. When used by injection, effects begin after about 20 minutes and last for up to 8 hours. It may also be used orally and as a transdermal patch since it has been long known to have transdermal bioavailability.

<i>Datura stramonium</i> Species of flowering plant in the nightshade family Solanaceae

Datura stramonium, known by the common names thorn apple, jimsonweed, devil's snare, or devil's trumpet, is a poisonous flowering plant of the nightshade family Solanaceae. It is a species belonging to the Datura genus and Daturae tribe. 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 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.

<span class="mw-page-title-main">Atropine</span> Tropane alkaloid anticholinergic medication & used as antidote for nerve agent poisoning

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.

<i>Atropa</i> Genus of plants

Atropa is a genus of flowering plants in the nightshade family, Solanaceae: tall, calcicole, herbaceous perennials, bearing large leaves and glossy berries particularly dangerous to children, due to their combination of an attractive, cherry-like appearance with a high toxicity. Atropa species favour temperate climates and alkaline soils, often growing in light shade in woodland environments associated with limestone hills and mountains. Their seeds can remain viable in the soil for long periods, germinating when the soil of sites in which plants once grew is disturbed by human activity or by natural causes, e.g. the windthrow of trees. The best-known member of the genus Atropa is deadly nightshade - the poisonous plant par excellence in the minds of many. The pharmacologically active ingredients of Atropa species include atropine, scopolamine, and hyoscyamine, all tropane alkaloids having anticholinergic, deliriant, antispasmodic and mydriatic properties. The genus is named for Άτροπος (Atropos) - lit. 'she who may not be turned (aside)' - one of the Three Fates and cutter of the thread of life / bringer of death - in reference to the extreme toxicity of A.belladonna and its fellow species - of which three others are currently accepted.

<i>Atropa belladonna</i> Species of toxic flowering plant in the nightshade family.

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 eggplant (aubergine). It is native to Europe, North Africa, and Western Asia. 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 and the United States.

<span class="mw-page-title-main">Hyoscyamine</span> Tropane alkaloid

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 deadly nightshade. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.

<span class="mw-page-title-main">Besom</span> Type of broom

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.

<i>Brugmansia</i> Genus of flowering plants in the nightshade family Solanaceae

Brugmansia is a genus of seven species of flowering plants in the nightshade family Solanaceae. They are woody trees or shrubs, with pendulous flowers, and have no spines on their fruit. Their large, fragrant flowers give them their common name of angel's trumpets, a name sometimes used for the closely related genus Datura.

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.

<i>Hyoscyamus niger</i> Species of plant

Hyoscyamus niger, commonly known as henbane, black henbane, or stinking nightshade, is a poisonous plant in the nightshade family Solanaceae. It is native to temperate Europe and Siberia, and naturalised in Great Britain and Ireland.

<span class="mw-page-title-main">Deliriant</span> Class of psychoactive drugs

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.

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.

<span class="mw-page-title-main">Anisodamine</span> Chemical compound

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.

<span class="mw-page-title-main">Anisodine</span> Chemical compound

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.

<span class="mw-page-title-main">Meteloidine</span> Chemical compound

Meteloidine is an alkaloid found in some Brugmansia and Datura species. Its also found in Erythroxylum australe and is said to be cocaine-like alkaloid.

<span class="mw-page-title-main">Psychoactive plant</span>

Psychoactive plants are plants, or preparations thereof, that upon ingestion induce psychotropic effects. As stated in a reference work:

Psychoactive plants are plants that people ingest in the form of simple or complex preparations in order to affect the mind or alter the state of consciousness.

<span class="mw-page-title-main">Solanaceae</span> Family of flowering plants that includes tomatoes, potatoes and tobacco

The Solanaceae, or nightshades, are a family of flowering plants that ranges from annual and perennial herbs to vines, lianas, epiphytes, shrubs, and trees, and includes a number of agricultural crops, medicinal plants, spices, weeds, and ornamentals. Many members of the family contain potent alkaloids, and some are highly toxic, but many—including tomatoes, potatoes, eggplant, bell and chili peppers—are used as food. The family belongs to the order Solanales, in the asterid group and class Magnoliopsida (dicotyledons). The Solanaceae consists of about 98 genera and some 2,700 species, with a great diversity of habitats, morphology and ecology.

<span class="mw-page-title-main">Methylecgonine</span> Chemical compound

Methylecgonine is a prominent tropane alkaloid found in coca leaves. It is metabolite of cocaine, and maybe is used as precursor for it. It also occurs as minor alkaloid in roots of many Datura species such as Datura stramonium and Datura innoxia.

References

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