Tigloidine

Last updated
Tigloidine
Tigloidine.svg
Clinical data
Trade names Tropigline
Identifiers
  • (8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) (E)-2-methylbut-2-enoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.007.101 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C13H21NO2
Molar mass 223.316 g·mol−1
3D model (JSmol)
  • CC=C(C)C(=O)OC1CC2CCC(C1)N2C
  • InChI=1S/C13H21NO2/c1-4-9(2)13(15)16-12-7-10-5-6-11(8-12)14(10)3/h4,10-12H,5-8H2,1-3H3/b9-4+
  • Key:UVHGSMZRSVGWDJ-RUDMXATFSA-N

Tigloidine is a tropane alkaloid that naturally occurs as a minor constituent of a number of solanaceous plants, including Duboisia myoporoides , [1] Physalis peruviana , [2] and Mandragora turcomanica .

It was formerly marketed as an antiparkinsonian drug [3] under the trade name Tropigline. [4]

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, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.

<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.

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

Thebaine (paramorphine), also known as codeine methyl enol ether, is an opiate alkaloid, its name coming from the Greek Θῆβαι, Thēbai (Thebes), an ancient city in Upper Egypt. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects. At high doses, it causes convulsions similar to strychnine poisoning. The synthetic enantiomer (+)-thebaine does show analgesic effects apparently mediated through opioid receptors, unlike the inactive natural enantiomer (−)-thebaine. While thebaine is not used therapeutically, it is the main alkaloid extracted from Papaver bracteatum and can be converted industrially into a variety of compounds, including hydrocodone, hydromorphone, oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine, butorphanol and etorphine.

<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">Apocynaceae</span> Dogbane and oleander family of flowering plants

Apocynaceae is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison Members of the family are native to the European, Asian, African, Australian, and American tropics or subtropics, with some temperate members. The former family Asclepiadaceae is considered a subfamily of Apocynaceae and contains 348 genera. A list of Apocynaceae genera may be found here.

<span class="mw-page-title-main">Tomatillo</span> Species of plant

The tomatillo, also known as the Mexican husk tomato, is a plant of the nightshade family bearing small, spherical, and green or green-purple fruit of the same name. Tomatillos originated in Mexico and were cultivated in the pre-Columbian era. A staple of Mexican cuisine, they are eaten raw and cooked in a variety of dishes, particularly salsa verde. The tomatillo is a perennial plant but is generally grown for agriculture each year as if it were an annual.

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

Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being ergine, were initially characterized in ergot. Some of these are implicated in the condition ergotism, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives.

<span class="mw-page-title-main">Ergotamine</span> Chemical compound in the ergot family of alkaloids

Ergotamine, sold under the brand names Cafergot and Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural similarity to several neurotransmitters, and has biological activity as a vasoconstrictor.

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

Yohimbine, also known as quebrachine, is an indole alkaloid derived from the bark of the African tree Pausinystalia johimbe; also from the bark of the unrelated South American tree Aspidosperma quebracho-blanco. Yohimbine is an α2-adrenergic receptor antagonist, and has been used in a variety of research projects. It is a veterinary drug used to reverse sedation in dogs and deer.

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

Ergoloid mesylates (USAN), co-dergocrine mesilate (BAN) or dihydroergotoxine mesylate, trade name Hydergine, is a mixture of the methanesulfonate salts of three dihydrogenated ergot alkaloids.

<i>Physalis</i> Genus of flowering plants

Physalis is a genus of approximately 75 to 90 flowering plants in the nightshade family (Solanaceae), which are native to the Americas and Australasia. At least 46 species are endemic to Mexico. Cultivated and weedy species have been introduced worldwide. A defining feature of Physalis is a large, papery husk derived from the calyx, which partly or fully encloses the fruit. Many species bear edible fruit, and some species are cultivated.

<i>Physalis peruviana</i> Species of cultivated South American fruit

Physalis peruviana is a species of plant in the nightshade family (Solanaceae) native to Colombia, Ecuador and Peru. It is commonly known as Cape gooseberry, goldenberry or ground cherry, as poha in Hawaii, and as Harankash in Egypt, while in its countries of origin it is called aguaymanto, uvilla or uchuva, in addition to numerous indigenous and regional names.

<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.

<i>Echinopsis peruviana</i> Species of plant

Echinopsis peruviana, the Peruvian torch cactus, is a fast-growing columnar cactus native to the western slope of the Andes in Peru, between about 2,000–3,000 m (6,600–9,800 ft) above sea level.

<i>Duboisia</i> Genus of plants

Duboisia is a genus of small perennial shrubs and trees that grow up to 14 metres tall, with extremely light wood and a thick corky bark. There are four species; all occur in Australia, and one also occurs in New Caledonia.

Pituri, also known as mingkulpa, is a mixture of leaves and wood ash traditionally chewed as a stimulant by Aboriginal Australians widely across the continent. Leaves are gathered from any of several species of native tobacco (Nicotiana) or from at least one distinct population of the species Duboisia hopwoodii. Various species of Acacia, Grevillea and Eucalyptus are burned to produce the ash. The term "pituri" may also refer to the plants from which the leaves are gathered or from which the ash is made. Some authors use the term to refer only to the plant Duboisia hopwoodii and its leaves and any chewing mixture containing its leaves.

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

Tiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It has also been also isolated from the defensive secretion of certain beetles.

In enzymology, a scopoletin glucosyltransferase is an enzyme that catalyzes the chemical reaction

<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">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.

References

  1. Barger G, Martin WF, Mitchell W (1937). "383. The minor alkaloids of Duboisia myoporoides". Journal of the Chemical Society (Resumed): 1820. doi:10.1039/JR9370001820. hdl: 1842/35366 .
  2. Beresford PJ, Woolley JG (1974). "Biosynthesis of ticloidine in Physalis peruviana". Phytochemistry. 13 (10): 2143–2144. doi:10.1016/0031-9422(74)85016-8.
  3. "Approved Names". British Medical Journal. 1 (5080): 1175. 1958. doi:10.1136/bmj.1.5080.1175. PMC   2028565 .
  4. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 1663–. ISBN   978-3-88763-075-1.