Apoatropine

Last updated
Apoatropine
Apoatropine.svg
Names
IUPAC name
(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) 2-phenylprop-2-enoate
Other names
Apoatropine Hydrochloride, Atropamin Hydrochloride, Atropyltropeine Hydrochloride, Apoascyamine, and Atropane.
Identifiers
3D model (JSmol)
ECHA InfoCard 100.007.188 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-906-7
PubChem CID
UNII
  • InChI=1S/C17H21NO2/c1-12(13-6-4-3-5-7-13)17(19)20-16-10-14-8-9-15(11-16)18(14)2/h3-7,14-16H,1,8-11H2,2H3 [1]
    Key: WPUIZWXOSDVQJU-UHFFFAOYSA-N
  • CN1C2CCC1CC(C2)OC(=O)C(=C)C3=CC=CC=C3
Properties
C17H21NO2
Molar mass 271.360 g·mol−1
AppearanceWhite or off whiteish and crystalline
Melting point >236 °C (HCl salt, decomposes) [2]
Soluble in water, alcohol, and ether
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Considered poisonous
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[ citation needed ]

Toxicity

It is said to be 20 times more toxic than atropine. [3]

Related Research Articles

<span class="mw-page-title-main">Alkaloid</span> Class of naturally occurring chemical compounds

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.

<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 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 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.

<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.

<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.

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

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.

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.

<span class="mw-page-title-main">Tropane alkaloid</span> Class of chemical compounds

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.

<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.

<i>Duboisia myoporoides</i> Species of plant

Duboisia myoporoides, or corkwood, is a shrub or tree native to high-rainfall areas on the margins of rainforest in eastern Australia. It has a thick and corky bark. The leaves are obovate to elliptic in shape, 4–15 cm long and 1–4 cm wide. The small white flowers are produced in clusters. This is followed by globose purple-black berries.

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

Methylatropine is a belladonna derivative.

<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 - notably Anisodus tanguticus (syn. Scopolia tangutica. Anisodine acts as a muscarinic acetylcholine receptor antagonist and α1-adrenergic receptor antagonist.

<span class="mw-page-title-main">Plant secondary metabolism</span>

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.

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

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.

<i>Mandragora</i> (genus) Genus of plants

Mandragora is a plant genus belonging to the nightshade family (Solanaceae). Members of the genus are known as mandrakes. Between three and five species are placed in the genus. The one or two species found around the Mediterranean constitute the mandrake of ancient writers such as Dioscorides. Two or three further species are found eastwards into China. All are perennial herbaceous plants, with large tap roots and leaves in the form of a rosette. Individual flowers are bell-shaped, whitish through to violet, and followed by yellow or orange berries.

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

The Solanaceae, or the 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">Pseudotropine</span> Chemical compound

Pseudotropine is a derivative of tropane and an isomer of tropine. Pseudotropine can be found in the Coca plant along with several other alkaloids

References

  1. Pubchem. "Apoatropine". nih.gov.
  2. "Apoatropine Hydrochloride". Santa Cruz Biotechnology.
  3. Krantz, J. C.; Forrest, J. W.; Heisse, C. K. (1954). "Contribution to the Pharmacology of Apoatropine and Its Methyl Bromide". Experimental Biology and Medicine. 86 (3): 511–512. doi:10.3181/00379727-86-21150. ISSN   1535-3702. PMID   13194706. S2CID   40304336.