Anisodamine

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Anisodamine
Anisodamine.svg
Clinical data
Other names7β-hydroxyhyoscyamine
ATC code
  • None
Identifiers
  • [(1S,3S,5S,7S)-7-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenyl-propanoate
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard 100.164.962 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H23NO4
Molar mass 305.374 g·mol−1
3D model (JSmol)
  • O=C(O[C@@H]1C[C@@H]2N(C)[C@H](C1)C[C@@H]2O)[C@@H](c3ccccc3)CO
  • InChI=1S/C17H23NO4/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3/t12-,13+,14-,15+,16+/m1/s1 Yes check.svgY
  • Key:WTQYWNWRJNXDEG-LEOABGAYSA-N Yes check.svgY
   (verify)

Anisodamine, also known as 7β-hydroxyhyoscyamine, is an anticholinergic and α1 adrenergic receptor antagonist used in the treatment of acute circulatory shock in China. [1] It is given orally or by injection, as a racemic mixture (racanisodamine) or as a hydrobromide salt. [2] Eye drops at 0.5% concentration for slowing the progression of myopia is also available in China. [3]

Anisodamine is a naturally occurring tropane alkaloid found in some plants of the family Solanaceae including Datura. [4] [5] Its Mandarin Chinese name 山莨菪 is given after Anisodus tanguticus (Chinese : ; pinyin :shān làng dàng). [6]

See also

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 or mad apple. Other English common names include moonflower, devil's weed, and hell's bells. All species of Datura are extremely poisonous and psychoactive, especially their seeds and flowers, which can cause respiratory depression, arrhythmias, fever, delirium, hallucinations, anticholinergic syndrome, psychosis, and 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 used as a medication to treat 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 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.

<span class="mw-page-title-main">Atropine</span> 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 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.

<span class="mw-page-title-main">Secondary metabolite</span> Type of organic compound

Secondary metabolites, also called specialised metabolites, secondary products, or natural products, are organic compounds produced by any lifeform, e.g. bacteria, archaea, fungi, animals, or plants, which are not directly involved in the normal growth, development, or reproduction of the organism. Instead, they generally mediate ecological interactions, which may produce a selective advantage for the organism by increasing its survivability or fecundity. Specific secondary metabolites are often restricted to a narrow set of species within a phylogenetic group. Secondary metabolites often play an important role in plant defense against herbivory and other interspecies defenses. Humans use secondary metabolites as medicines, flavourings, pigments, and recreational drugs.

<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 Atropa belladonna. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.

<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">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 such as LSD and dissociatives such as ketamine, 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.

<span class="mw-page-title-main">Muscarinic antagonist</span> Drug that binds to but does not activate muscarinic cholinergic receptors

A muscarinic receptor antagonist (MRA), also called an antimuscarinic, is a type of anticholinergic agent that blocks the activity of the muscarinic acetylcholine receptor. The muscarinic receptor is a protein involved in the transmission of signals through certain parts of the nervous system, and muscarinic receptor antagonists work to prevent this transmission from occurring. Notably, muscarinic antagonists reduce the activation of the parasympathetic nervous system. The normal function of the parasympathetic system is often summarised as "rest-and-digest", and includes slowing of the heart, an increased rate of digestion, narrowing of the airways, promotion of urination, and sexual arousal. Muscarinic antagonists counter this parasympathetic "rest-and-digest" response, and also work elsewhere in both the central and peripheral nervous systems.

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.

<i>Anisodus tanguticus</i> Species of plant

Anisodus tanguticus is a species of flowering plant belonging to tribe Hyoscyameae of subfamily Solanoideae of the nightshade family Solanaceae. It is thus closely related to Henbane and Deadly Nightshade. Solanaceae is a plant family which includes many important agricultural plants such as the potato and the tomato. It is mostly found growing in the Qinghai-Tibetan Plateau. A. tanguticus is collected and used mostly for its medicinal effects caused by the plant's biologically active nicotine and tropane alkaloids. It has a significant impact in China as one of the 50 fundamental herbs used in traditional Chinese medicine.

<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.

<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">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">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.

Scopine is a tropane alkaloid found in a variety of plants including Mandragora root, Senecio mikanioides, Scopolia carniolica, and Scopolia lurida.

<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, is 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">Apoatropine</span> Chemical compound

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.

References

  1. Varma DR, Yue TL (March 1986). "Adrenoceptor blocking properties of atropine-like agents anisodamine and anisodine on brain and cardiovascular tissues of rats". British Journal of Pharmacology . 87 (3): 587–94. doi:10.1111/j.1476-5381.1986.tb10201.x. PMC   1916562 . PMID   2879586.
  2. "Pharmacopoeia Search: "山莨菪碱"". 中国药典. Archived from the original on 2017-12-03.
  3. "消旋山莨菪碱滴眼液防治少年儿童假性近视的疗效分析". 国际医药卫生导报 (in Chinese (China)). 14 (15): 67–68. 2008. doi:10.3760/cma.j.issn.1007-1245.2008.15.027. Archived from the original on 2023-03-27. Retrieved 2017-12-03.
  4. Ye N, Li J, Gao C, Xie Y (August 2013). "Simultaneous determination of atropine, scopolamine, and anisodamine in Flos daturae by capillary electrophoresis using a capillary coated by graphene oxide". Journal of Separation Science . 36 (16): 2698–702. doi:10.1002/jssc.201300304. PMID   23868645.
  5. Zhang WW, Song MK, Cui YY, et al. (October 2008). "Differential neuropsychopharmacological influences of naturally occurring tropane alkaloids anisodamine versus scopolamine". Neuroscience Letters. 443 (3): 241–5. doi:10.1016/j.neulet.2008.07.048. PMID   18672024. S2CID   2730169.
  6. "消旋山莨菪碱" (in Chinese (China)). 中国药典. Archived from the original on 2017-12-03. Retrieved 3 December 2017.