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Atropa
Atropa
belladonna, commonly known as belladonna or deadly nightshade, is a perennial herbaceous plant in the nightshade family Solanaceae, which includes tomatoes, potatoes, and aubergine. It is native to Europe, North Africa, and Western Asia. Its distribution extends from Great Britain
Great Britain
in the west to western Ukraine
Ukraine
and the Iranian province of Gilan
Gilan
in the east. It is also naturalised and/or introduced in some parts of Canada and the United States. The foliage and berries are extremely toxic when ingested, containing tropane alkaloids.[1][2] These toxins include atropine, scopolamine and hyoscyamine, which cause delirium and hallucinations,[1][2][3] and are also used as pharmaceutical anticholinergics. Atropa
Atropa
belladonna has unpredictable effects.[1] The antidote for belladonna poisoning is physostigmine or pilocarpine, the same as for atropine.[4] It has a long history of use as a medicine, cosmetic, and poison.[1][2] Before the Middle Ages, it was used as an anesthetic for surgery; the ancient Romans used it as a poison (the wife of Emperor Augustus
Augustus
and the wife of Claudius
Claudius
both were rumored to have used it for murder); and, predating this, it was used to make poison-tipped arrows. The genus name Atropa
Atropa
comes from Atropos
Atropos
("unable to be turned aside"), one of the three Fates in Greek mythology, who cut the thread of life after her sisters had spun and measured it; and the name "bella donna" is derived from Italian and means "beautiful woman" because the herb was used in eye-drops by women to dilate the pupils of the eyes to make them appear seductive.[2][5][6]

Contents

1 Description 2 Distribution 3 Cultivation 4 Naming and taxonomy 5 Toxicity 6 Legal status 7 Uses

7.1 Cosmetics 7.2 Medicinal uses

7.2.1 Alternative medicine

7.3 Recreational drug 7.4 Poison

8 Folklore

8.1 Flying ointment 8.2 Female attractiveness

9 Etymology 10 See also 11 References 12 External links

Description[edit]

Atropa
Atropa
belladonna

Atropa
Atropa
belladonna is a branching herbaceous perennial rhizomatous hemicryptophyte, often growing as a subshrub from a fleshy rootstock. Plants grow to 2 m (6.6 ft) tall with ovate leaves 18 cm (7.1 in) long. The bell-shaped flowers are dull purple with green tinges and faintly scented. The fruits are berries, which are green, ripening to a shiny-black, and approximately 1.5 cm (0.59 in) in diameter. The berries are sweet and are consumed by animals that disperse the seeds in their droppings, even though they contain toxic alkaloids. (See Toxicity)[7] There is a pale-yellow flowering form called Atropa
Atropa
belladonna var. lutea with pale yellow fruit. Distribution[edit] Atropa
Atropa
belladonna is native to temperate southern and central Europe but has been cultivated and introduced outside its native range. In southern Sweden it was recorded in Flora of Skåne in 1870 as grown in apothecary gardens near Malmö.[8] In Britain it is native only on calcareous soils, on disturbed ground, field margins, hedgerows and open woodland. More widespread as an alien, it is often a relic of cultivation as a medicinal herb. Seed
Seed
is spread mainly by birds.[9] It is naturalized in parts of North America, where it is often found in shady, moist locations with limestone-rich soils. It is considered a weed species in parts of the world,[10] where it colonizes areas with disturbed soils.[11] Cultivation[edit] Atropa
Atropa
belladonna is rarely used in gardens, but, when grown, it is usually for its large upright habit and showy berries.[12] Germination of the small seeds is often difficult, due to hard seed coats that cause seed dormancy. Germination
Germination
takes several weeks under alternating temperature conditions, but can be sped up with the use of gibberellic acid.[13] The seedlings need sterile soil to prevent damping off and resent root disturbance during transplanting.[citation needed] Naming and taxonomy[edit] The name Atropa
Atropa
belladonna was published by Linnaeus in Species Plantarum in 1753.[14] It is in the nightshade family (Solanaceae), which it shares with potatoes, tomatoes, eggplants, jimsonweed, tobacco, wolfberry, and chili peppers. The common names for this species include belladonna, deadly nightshade, divale, dwale,[15] banewort, devil's berries, naughty man's cherries, death cherries, beautiful death, devil's herb, great morel, and dwayberry.[16] The name Atropa
Atropa
is thought to be derived from that of the Greek goddess Atropos, one of the three Greek fates or destinies who would determine the course of a man's life by the weaving of threads that symbolized his birth, the events in his life, and finally his death, with Atropos
Atropos
cutting these threads to mark the last of these.[17][18] The name "belladonna" comes from the Italian language, meaning "beautiful lady";[15] originating either from its usage as cosmetic for the face or, more probably, from its usage to increase the pupil size in women.[17][18] Toxicity[edit]

Flowers of belladonna

Belladonna is one of the most toxic plants found in the Eastern Hemisphere,[19] and its use by mouth increases risk in numerous clinical conditions, such as complications of pregnancy, cardiovascular diseases, gastrointestinal disorders, and psychiatric disorders, among others.[1][2] All parts of the plant contain tropane alkaloids.[1][20] Roots have up to 1.3%, leaves 1.2%, stalks 0.65%, flowers 0.6%, ripe berries 0.7%, and seeds 0.4% tropane alkaloids; leaves reach maximal alkaloid content when the plant is budding and flowering, roots are most poisonous in the end of the plant’s vegetation period.[21] Belladonna nectar is transformed by bees into honey that also contains tropane alkaloids.[22] The berries pose the greatest danger to children because they look attractive and have a somewhat sweet taste.[16][23][24] The root of the plant is generally the most toxic part, though this can vary from one specimen to another.[16][20] The active agents in belladonna, atropine, hyoscine (scopolamine), and hyoscyamine, have anticholinergic properties.[2][25] The symptoms of belladonna poisoning include dilated pupils, sensitivity to light, blurred vision, tachycardia, loss of balance, staggering, headache, rash, flushing, severely dry mouth and throat, slurred speech, urinary retention, constipation, confusion, hallucinations, delirium, and convulsions.[2][26][27] In 2009, A. belladonna berries were mistaken for blueberries by an adult woman; the six berries she ate were documented to result in severe anticholinergic syndrome.[28] The plant's deadly symptoms are caused by atropine's disruption of the parasympathetic nervous system's ability to regulate involuntary activities, such as sweating, breathing, and heart rate. The antidote for belladonna poisoning is physostigmine or pilocarpine, the same as for atropine.[29] Atropa
Atropa
belladonna is also toxic to many domestic animals, causing narcosis and paralysis.[30] However, cattle and rabbits eat the plant seemingly without suffering harmful effects.[27] In humans, its anticholinergic properties will cause the disruption of cognitive capacities, such as memory and learning.[25] Legal status[edit] Belladonna cultivation is legal in Southern and Eastern Europe, Pakistan, North America, and Brazil.[21] All parts of the belladonna plant can be cultivated, bought, kept, and distributed (sold, traded or given) without a legal license or medical prescription in the US. Sales of belladonna in the US conform to US supplement laws or are regulated by the FDA.[31] Belladonna leaves and roots can be bought with a medical prescription in pharmacies throughout Germany.[32] Uses[edit] Cosmetics[edit] The common name "belladonna" originates from its historic use by women, as "Bella Donna" is Italian for "beautiful lady". Drops prepared from the belladonna plant were used to dilate women's pupils, an effect considered to be attractive and seductive.[5][6] Belladonna drops act as a muscarinic antagonist, blocking receptors in the muscles of the eye that constrict pupil size.[33] Belladonna is currently rarely used cosmetically, as it carries the adverse effects of causing minor visual distortions, inability to focus on near objects, and increased heart rate. Prolonged usage was reputed to cause blindness.[34] Medicinal uses[edit] Scientific evidence to recommend the use of A. belladonna in its natural form for any condition is insufficient,[1][2] although some of its components, in particular l-atropine, which was purified from belladonna in the 1830s, have accepted medical uses.[27] Donnatal is a prescription pharmaceutical, approved in the United States by the FDA, that combines natural belladonna alkaloids in a specific, fixed ratio with phenobarbital to provide peripheral anticholinergic/antispasmodic action and mild sedation. According to its labeling, it is possibly effective for use as adjunctive therapy in the treatment of irritable bowel syndrome (irritable colon, spastic colon, mucous colitis) and acute enterocolitis.[35] Belladonna has been used in herbal medicine for centuries as a pain reliever, muscle relaxer, and anti-inflammatory, and to treat menstrual problems, peptic ulcer disease, histaminic reaction, and motion sickness.[1][2][36] At least one 19th-century eclectic medicine journal explained how to prepare a belladonna tincture for direct administration to patients.[37] Belladonna tinctures, decoctions, and powders, as well as alkaloid salt mixtures, are still produced for pharmaceutical use, and these are often standardised at 1037 parts hyoscyamine to 194 parts atropine and 65 parts scopolamine.[citation needed] The alkaloids are compounded with phenobarbital and/or kaolin and pectin for use in various functional gastrointestinal disorders. The tincture, used for identical purposes, remains in most pharmacopoeias, with a similar tincture of Datura stramonium
Datura stramonium
having been in the US Pharmacopoeia at least until the late 1930s. Cigarettes with belladonna leaves soaked in opium tincture were a prescription medicine as recently as 1930.[21] The combination of belladonna and opium, in powder, tincture, or alkaloid form, is particularly useful by mouth or as a suppository for diarrhoea and some forms of visceral pain; it can be made by a compounding pharmacist, and may be available as a manufactured fixed combination product in some countries (e.g., B&O Supprettes). Scopolamine
Scopolamine
is used as the hydrobromide salt for GI complaints and motion sickness, and to potentiate the analgesic and anxiolytic effects of opioid analgesics. It was formerly used in a painkiller called "twilight sleep" in childbirth.[38] Atropine
Atropine
sulphate is used as a mydriatic and cycloplegic for eye examinations. It is also used as an antidote to organophosphate and carbamate poisoning, and is loaded in an autoinjector for use in case of a nerve gas attack. Atropinisation (administration of a sufficient dose to block nerve gas effects) results in 100 percent blockade of the muscarinic acetylcholine receptors, and atropine sulphate is the benchmark for measuring the power of anticholinergic drugs. Hyoscyamine
Hyoscyamine
is used as the sulphate or hydrobromide for GI problems and Parkinson's disease. Its side-effect profile is intermediate to those of atropine and scopolamine, and can also be used to combat the toxic effects of organophosphates. Hyoscyamine
Hyoscyamine
was the primary alkaloid in Asthmador, a nonpresciption treatment for the relief of bronchial asthma, until Asthmador was discontinued. Alternative medicine[edit]

A homeopathic preparation of belladonna

Belladonna preparations are used in homeopathy as alternative medicine treatments for various conditions.[1][39][40] In homeopathic practices, belladonna was prescribed by German physician, Samuel Hahnemann, as a topical medication for inflammation and pain.[1] In the form of Doktor Koster's Antigaspills, belladonna was a homeopathic medication for upset stomach and excessive flatulence.[41] There is insufficient scientific evidence justifying the use of belladonna for these or any other clinical disorders.[1] In one study, the most common preparation was diluted to the 30C level in homeopathic notation. This level of dilution does not contain any of the original plant,[40] although preparations with lesser dilutions that contain trace amounts of belladonna may exist. In 2010 and again in 2016, the US Food and Drug Administration
Food and Drug Administration
warned against the use of homeopathic teething tablets found to contain belladonna.[42][43] Recreational drug[edit] Atropa
Atropa
belladonna and related plants, such as Datura stramonium (commonly known as jimson weed or jimsonweed), have occasionally been used as recreational drugs because of the vivid hallucinations and delirium they produce. However, these hallucinations are most commonly described as very unpleasant, and recreational use is considered extremely dangerous because of the high risk of unintentional fatal overdose.[44][45][46] In addition, the central nervous system effects of atropine include memory disruption, which may lead to severe confusion.[47] The major effects of belladonna consumption last for three to four hours, visual hallucinations can last for three to four days, and some negative aftereffects are preserved for several days.[21][48] The use of belladonna as a recreational drug is reported to bring about predominantly bad trips that the users want never to repeat for as long as they live.[48] Trips induced by belladonna are threatening, dark, demonic, hellish, frightening, and terrifying.[21] Occasionally, belladonna can induce out-of-body experiences,[49] a heightened sense of awareness,[50] and enhance sexual, mystical and lucid dreaming experiences often in combination with other psychoactive plants.[51][52] Positive experiences induced by belladonna consumption are rare.[21] Historically, the plant was an important, active ingredient in witches' flying ointments : complex, transdermally-absorbed hallucinogens with a fatty or oily base, which caused a deathlike trance in which vivid hallucinations of flight and bacchanalian carousal were experienced[53][see below]. Poison[edit] The tropane alkaloids of A. belladonna were used as poisons, and early humans made poisonous arrows from the plant.[54] In Ancient Rome, it was used as a poison by Agrippina the Younger, wife of Emperor Claudius
Claudius
on advice of Locusta, a lady specialized in poisons, and Livia, who is rumored to have used it to kill her husband Emperor Augustus.[54][55] Macbeth of Scotland, when he was still one of the lieutenants of King Duncan I of Scotland, used it during a truce to poison the troops of the invading Harold Harefoot, King of England, to the point that the English troops were unable to stand their ground and had to retreat to their ships.[18] Medical historians also suspect that Solomon Northup, a free black man who was kidnapped and sold into slavery in 1841, was poisoned using a combination of Atropa
Atropa
belladonna and laudanum.[56] Folklore[edit] Main articles: European witchcraft
European witchcraft
and shamanism

Leaves of belladonna

Flying ointment[edit] In the past, witches were believed to use a mixture of belladonna, opium poppy and other plants, typically poisonous (such as monkshood and poison hemlock), in flying ointment, which they applied to help them fly to gatherings with other witches. Carlo Ginzburg
Carlo Ginzburg
and others have argued that flying ointments were preparations meant to encourage hallucinatory dreaming; a possible explanation for the inclusion of belladonna and opium poppy in flying ointments concerns the known antagonism between tropane alkaloids of belladonna (scopolamine) and opiate alkaloids in the opium poppy, Papaver somniferum
Papaver somniferum
(to be specific, morphine), which produces a dream-like waking state. This antagonism was known in folk medicine, discussed in traditional medicine formularies.[57][58] The belladonna herb was also notable for its unpredictable effects from toxicity.[59][60] Female attractiveness[edit] Among the ancient folk traditions of the Romanian (Moldavian) / Ukrainian region of Bukovina
Bukovina
in the Carpathians
Carpathians
is the ritual for a Bukovinian girl to enhance her attractiveness by making an offering to deadly nightshade. She entered the fields on a Sunday in Shrovetide, clad in her Sunday best, accompanied by her mother and bringing a bag of bread, salt, and brandy. She would dig up a deadly nightshade root and leave the three offerings in its place. As she returned home, she carried the root on the top of her head. On the way both to and from home, she avoided all quarrels and arguments. If asked by anyone on the way back what she was taking home, she would not divulge the truth or the spell would break.[61] Etymology[edit] Atropa
Atropa
means "inflexible", and is derived from the Greek Atropos, the name of one of the three Moirai. Belladonna is derived from Italian, meaning "beautiful lady". The juice of A. belladonna was applied as a decoction to beautify by inducing pallid skin and dilated eyes.[62] See also[edit]

List of poisonous plants List of plants poisonous to equines

References[edit]

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Atropa
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Atropa
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Atropa
Bella-donna L. seeds" (PDF). Bulgarian Journal of Plant Physiology. 23 (1–2): 61–66. Retrieved 2008-07-08.  ^ " Solanaceae
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Atropa
Atropa
belladonna L". Plant
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Name Details. IPNI. 2003-07-02. Retrieved 2008-03-01. Solanaceae
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Atropa
belladonna L. Species Plantarum
Species Plantarum
2 1753 "Habitat in Austriae, Angliae montibus sylvosis."  ^ a b Spiegl, Fritz (1996). Fritz Spiegl's Sick Notes: An Alphabetical Browsing-Book of Derivatives, Abbreviations, Mnemonics and Slang for Amusement and Edification of Medics, Nurses, Patients and Hypochondriacs. Washington, DC: Taylor & Francis. pp. 21–22. ISBN 1-85070-627-1.  ^ a b c Grieve, Margaret; Leyel, C. F. (1971). Modern Herbal. Courier Dover Publications. p. 584. ISBN 0-486-22799-5. Retrieved 2008-07-08.  ^ a b Edward Harris Ruddock (1867). The Homoeopathic Vade Mecum of Modern Medicine and Surgery: For the Use of Junior Practitioners, Students, Clergymen, Missionaries, Heads of Families, Etc (2 ed.). Jarrold and Sons. pp. 503–508.  ^ a b c R. Groombridge, ed. (1839). The Naturalist: Illustrative of the Animal, Vegetable, and Mineral Kingdoms. R. Groombridge. p. 193.  Notes: v.4-5 (1838-1839) ^ "Herbarium: Selection of species from European flora".  ^ a b "Committee for Veterinary Medicinal Products, Atropa
Atropa
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Atropa
belladonna L. or its variety acuminata Royle ex Lindl)". Wellness.com.  ^ a b Giancarlo Pepeu; Maria Grazia Giovannini (2004). "Acetylcholine: I. Muscarinic Receptors". In Gernot Riedel; Bettina Platt. From messengers to molecules: memories are made of these (illustrated ed.). Springer. ISBN 978-0-306-47862-8.  ^ Mallinson T (2010). "Deadly Nightshade: Atropa
Atropa
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IV: Atropa
Atropa
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Atropa
belladonna mistaken for blueberries". Eur J Ophthalmol. 19 (1): 170–2. PMID 19123171.  ^ Potter, Samuel O.L. (1893). A Handbook of Materia Medica Pharmacy and Therapeutics. London: P. Blakiston's. p. 53.  ^ North Carolina State University Department of Plant
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Biology (2000). "Poisonous Vascular Plants". NC State University. Archived from the original on 6 July 2008. Retrieved 2008-07-07.  ^ "Belladonna. Legal Status". erowid.  ^ Lindequist, U. (1992). "Atropa". Haegers Handbuch der pharmazeutischen Praxis (in German) (5th ed.). Berlin: Springer. p. 429.  ^ " Atropine
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Eye Drops". Archived from the original on 8 July 2008. Retrieved 2008-07-08.  ^ Wood, George Bacon (1867). A Treatise on Therapeutics, and Pharmacology or Materia Medica. Vol. 1. Philadelphia: J.B. Lippincott & Co. pp. 792–795.  ^ " Donnatal Extentabs Prescribing Information". PBM Pharmaceuticals. 2009. Archived from the original on 2008-12-27. Retrieved 2009-03-04.  ^ Ebadi, Manuchair (2007). Pharmacodynamic Basis of Herbal Medicine. CRC Press. p. 203. ISBN 9780849370502.  ^ Joseph R. Buchanan; R.S. Newton (1854). Wm. Phillips and co., ed. "Officinal preparations". The Eclectic Medical Journal. Wm. Phillips and co.  ^ "Twilight Sleep: The Dammerschlaf of the Germans". Canadian Medical Association Journal. 5 (9): 805–808. 1915. PMC 1584452 . PMID 20310688.  ^ Vaughan, John Griffith; Patricia Ann Judd; David Bellamy (2003). The Oxford Book of Health Foods. Oxford University Press. p. 59. ISBN 0-19-850459-4.  ^ a b Brien S, Lewith G, Bryant T (November 2003). "Ultramolecular homeopathy has no observable clinical effects. A randomized, double-blind, placebo-controlled proving trial of Belladonna 30C". Br J Clin Pharmacol. 56 (5): 562–8. doi:10.1046/j.1365-2125.2003.01900.x. PMC 1884394 . PMID 14651731.  ^ Lambert, Angela (September 3, 2014). The Lost Life of Eva Braun. St. Martin's Press. p. 262. ISBN 1466879963.  ^ "Consumer Updates - Hyland's Teething Tablets: Questions and Answers".  ^ CNN, Jen Christensen and Jamie Gumbrecht. "Teething tablets may be linked to 10 children's deaths".  ^ Dewitt MS, Swain R, Gibson LB (1997). "The dangers of jimson weed and its abuse by teenagers in the Kanawha Valley of West Virginia". West Virginia Medical Journal. 93 (4): 182–5. PMID 9274142.  ^ Micke MM (October 1996). "The case of hallucinogenic plants and the Internet". J Sch Health. 66 (8): 277–80. doi:10.1111/j.1746-1561.1996.tb03397.x. PMID 8899584.  ^ Cummins BM, Obetz SW, Wilson MR (June 1968). "Belladonna poisoning as a facet of pschyodelia". JAMA. 204 (11): 1011. doi:10.1001/jama.204.11.1011. PMID 5694682.  ^ Hardy TK, Wakely D (1962). "The amnesic properties of hyoscine and atropine in pre-anæsthetic medication". Anaesthesia. 17 (3): 331–336. doi:10.1111/j.1365-2044.1962.tb13473.x. PMID 13904669.  ^ a b "Belladonna Reports". erowid.  ^ "Total Out Of Body Experience. Atropa
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External links[edit]

Data related to Atropa
Atropa
belladonna at Wikispecies Media related to Atropa
Atropa
belladonna at Wikimedia Commons "Compounds in deadly nightshade". USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. Beltsville, Maryland: National Germplasm Resources Laboratory. Archived from the original on 2004-11-10. Retrieved 2005-07-28. 

v t e

Ancient anaesthesia

Plants / animals

Aconitum
Aconitum
(aconite) Atropa
Atropa
belladonna (belladonna) Cannabis

medical use

Castoreum Coca Conium
Conium
(hemlock) Datura innoxia
Datura innoxia
(thorn-apple) Datura metel
Datura metel
(devil's trumpet) Hyoscyamus niger
Hyoscyamus niger
(henbane) Lactucarium Mandragora officinarum
Mandragora officinarum
(mandrake) Opium Saussurea
Saussurea
(saw-wort) Willow

People

Abulcasis Avenzoar Avicenna Celsus Dioscorides Galen Hippocrates Rhazes Sabuncuoğlu Sushrutha Theophrastus Zhang

Compounds

Aconitine Atropine Cocaine Coniine Hyoscine Δ9-THC Hyoscyamine Morphine Salicylate

v t e

Hallucinogens

Psychedelics (5-HT2A agonists)

Benzofurans

2C-B-FLY 2CBFly-NBOMe 5-MeO-BFE 5-MeO-DiBF Bromo-DragonFLY F-2 F-22 TFMFly

Lyserg‐ amides

1P-ETH-LAD 1P-LSD 2-Butyllysergamide 3-Pentyllysergamide AL-LAD ALD-52 BU-LAD Diallyllysergamide Dimethyllysergamide Ergometrine ETH-LAD IP-LAD LAE-32 LPD-824 LSA LSD LSD-Pip LSH LSM-775 LSZ Methylergometrine Methylisopropyllysergamide Methysergide MLD-41 PARGY-LAD PRO-LAD

Phenethyl‐ amines

2C-x

2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V

25x-NBx

25x-NB3OMe

25B-NB3OMe 25C-NB3OMe 25D-NB3OMe 25E-NB3OMe 25H-NB3OMe 25I-NB3OMe 25N-NB3OMe 25P-NB3OMe 25T2-NB3OMe 25T4-NB3OMe 25T7-NB3OMe 25TFM-NB3OMe

25x-NB4OMe

25B-NB4OMe 25C-NB4OMe 25D-NB4OMe 25E-NB4OMe 25H-NB4OMe 25I-NB4OMe 25N-NB4OMe 25P-NB4OMe 25T2-NB4OMe 25T4-NB4OMe 25T7-NB4OMe 25TFM-NB4OMe

25x-NBF

25B-NBF 25C-NBF 25D-NBF 25E-NBF 25H-NBF 25I-NBF 25P-NBF 25T2-NBF 25T7-NBF 25TFM-NBF

25x-NBMD

25B-NBMD 25C-NBMD 25D-NBMD 25E-NBMD 25F-NBMD 25H-NBMD 25I-NBMD 25P-NBMD 25T2-NBMD 25T7-NBMD 25TFM-NBMD

25x-NBOH

25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25F-NBOH 25H-NBOH 25I-NBOH 25P-NBOH 25T2-NBOH 25T7-NBOH 25TFM-NBOH

25x-NBOMe

25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25P-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe

Atypical structures

25I-NB34MD 2CBCB-NBOMe 2CBFly-NBOMe NBOMe-mescaline

3C-x

3C-AL 3C-BZ 3C-DFE 3C-E 3C-P

4C-x

4C-B 4C-D 4C-T-2

DOx

DOT DOB DOC DOEF DOET DOF DOI DOiPR DOM DON DOPR DOTFM MEM

HOT-x

HOT-2 HOT-7 HOT-17

MDxx

DMMDA DMMDA-2 Lophophine MDA MMDA MMDA-2 MMDA-3a MMDMA

Mescaline
Mescaline
(subst.)

2-Bromomescaline 3-TE 4-TE 3-TM 4-TM Allylescaline Asymbescaline Buscaline Cyclopropylmescaline Difluoromescaline Difluoroescaline Escaline Fluoroproscaline Isobuscaline Isoproscaline Jimscaline Mescaline Metaescaline Methallylescaline Proscaline Thioproscaline Trifluoroescaline Trifluoromescaline

TMAs

TMA TMA-2 TMA-3 TMA-4 TMA-5 TMA-6

Others

2C-B-BUTTERFLY 2C-B-DragonFLY 2CB-5-hemifly 2-TOM 5-TOET 5-TOM 2CB-Ind 2CD-5EtO BOB BOD βk-2C-B βk-2C-I DESOXY DMCPA DMBMPP DOB-FLY Fenfluramine Ganesha Macromerine MMA TCB-2 TOMSO

Piperazines

BZP pFPP

Tryptamines

alpha-alkyltryptamines

4,5-DHP-α-MT 5-MeO-α-ET 5-MeO-α-MT α-ET α-MT

x-DALT

(Daltocin) 4-HO-DALT (Daltacetin) 4-AcO-DALT 5-MeO-DALT DALT

x-DET

(Ethacetin) 4-AcO-DET (Ethocin) 4-HO-DET 5-MeO-DET (T-9) DET (Ethocybin) 4-PO-DET

x-DiPT

1-Me-5-MeO-DiPT (Ipracetin) 4-AcO-DiPT (Iprocin) 4-HO-DiPT (Foxy Methoxy) 5-MeO-DiPT DiPT

x-DMT

4,5-DHP-DMT 2,N,N-TMT 4-AcO-DMT 4-HO-5-MeO-DMT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-DMT 5-N,N-TMT 7,N,N-TMT α,N,N-TMT (Bufotenin) 5-HO-DMT DMT Norbaeocystin (Psilocin) 4-HO-DMT (Psilocybin) 4-PO-DMT

x-DPT

(Depracetin) 4-AcO-DPT (Deprocin) 4-HO-DPT 5-MeO-DPT (The Light) DPT

Ibogaine-related

18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine

x-MET

(Metocin) 4-HO-MET (Metocetin) 4-AcO-MET 5-MeO-MET MET

x-MiPT

(Mipracetin) 4-AcO-MiPT (Miprocin) 4-HO-MiPT 5-Me-MiPT (Moxy) 5-MeO-MiPT MiPT

Others

4-HO-DBT 4-HO-EPT 4-HO-McPT (Lucigenol) 4-HO-MPMI (Meprocin) 4-HO-MPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MPMI Aeruginascin Baeocystin DBT DCPT EiPT EPT MPT PiPT

Others

5-MeO-DiBF AL-38022A ALPHA Dimemebfe Efavirenz Lorcaserin M-ALPHA RH-34 Also empathogens in general (e. g.: 5-APB, 5-MAPB, 6-APB
6-APB
and other substituted benzofurans, MDAI, MDMA).

Dissociatives (NMDAR antagonists)

Arylcyclo‐ hexylamines

Ketamine-related

2-Fluorodeschloroketamine Arketamine
Arketamine
((R)-ketamine) Deschloroketamine Ethketamine
Ethketamine
(N-Ethylnorketamine) Esketamine
Esketamine
((S)-ketamine) Ketamine Methoxetamine Methoxmetamine Methoxyketamine Norketamine Tiletamine

PCP-related

3'-HO-PCP 3'-MeO-PCE 3'-MeO-PCMo 3'-MeO-PCP BDPC Dieticyclidine
Dieticyclidine
(PCDE) Eticyclidine
Eticyclidine
(PCE) Methoxydine
Methoxydine
(4'-MeO-PCP) PCPr Phencyclidine
Phencyclidine
(PCP) Rolicyclidine
Rolicyclidine
(PCPy) Tenocyclidine
Tenocyclidine
(TCP)

Others

BTCP Gacyclidine PRE-084

Diarylethylamines

Diphenidine Ephenidine Fluorolintane Methoxphenidine

Morphinans

Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan

Others

2-EMSB 2-MDP 8A-PDHQ Aptiganel Budipine Delucemine Dexoxadrol Dizocilpine Etoxadrol Herkinorin Ibogaine Midafotel NEFA Neramexane Nitrous oxide Noribogaine Perzinfotel RB-64 Remacemide Salvinorin A Selfotel Xenon

Deliriants (mAChR antagonists)

Atropine Benactyzine Benzatropine Benzydamine Biperiden BRN-1484501 Brompheniramine BZ CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Chloropyramine Chlorphenamine Clemastine CS-27349 Cyclizine Cyproheptadine Dicycloverine Dimenhydrinate Diphenhydramine Ditran Doxylamine EA-3167 EA-3443 EA-3580 EA-3834 Elemicin Flavoxate Hyoscyamine JB-318 JB-336 Meclozine Mepyramine Myristicin Orphenadrine Oxybutynin Pheniramine Phenyltoloxamine Procyclidine Promethazine Scopolamine Tolterodine Trihexyphenidyl Tripelennamine Triprolidine WIN-2299

Others

Cannabinoids (CB1 agonists)

Natural

THC (Dronabinol) THCV

Synthetic

AM-x

AM-087 AM-251 AM-279 AM-281 AM-356 AM-374 AM-381 AM-404 AM-411 AM-630 AM-661 AM-678 AM-679 AM-694 AM-735 AM-855 AM-881 AM-883 AM-905 AM-906 AM-919 AM-926 AM-938 AM-1116 AM-1172 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-1710 AM-1714 AM-1902 AM-2201 AM-2212 AM-2213 AM-2232 AM-2233 AM-2389 AM-3102 AM-4030 AM-4054 AM-4056 AM-4113 AM-6545

CP x

CP 47,497 CP 55,244 CP 55,940 (±)-CP 55,940 (+)-CP 55,940 (-)-CP 55,940

HU-x

HU-210 HU-211 HU-239 HU-243 HU-308 HU-320 HU-331 HU-336 HU-345

JWH-x

JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-047 JWH-048 JWH-051 JWH-057 JWH-073 JWH-081 JWH-098 JWH-116 JWH-120 JWH-122 JWH-133 JWH-139 JWH-147 JWH-148 JWH-149 JWH-149 JWH-161 JWH-164 JWH-166 JWH-167 JWH-171 JWH-175 JWH-176 JWH-181 JWH-182 JWH-184 JWH-185 JWH-192 JWH-193 JWH-193 JWH-194 JWH-195 JWH-196 JWH-197 JWH-198 JWH-199 JWH-200 JWH-203 JWH-205 JWH-210 JWH-210 JWH-213 JWH-220 JWH-229 JWH-234 JWH-249 JWH-250 JWH-251 JWH-253 JWH-258 JWH-300 JWH-302 JWH-307 JWH-336 JWH-350 JWH-359 JWH-387 JWH-398 JWH-424

Misc. designer cannabinoids

4-HTMPIPO 5F-AB-FUPPYCA 5F-AB-PINACA 5F-ADB 5F-ADB-PINACA 5F-ADBICA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-NNE1 5F-PB-22 5F-SDB-006 A-796,260 A-836,339 AB-001 AB-005 AB-CHFUPYCA AB-CHMINACA AB-FUBINACA AB-PINACA ADAMANTYL-THPINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADBICA ADSB-FUB-187 AMB-FUBINACA APICA APINACA APP-FUBINACA CB-13 CUMYL-PICA CUMYL-PINACA CUMYL-THPINACA DMHP EAM-2201 FAB-144 FDU-PB-22 FUB-144 FUB-APINACA FUB-JWH-018 FUB-PB-22 FUBIMINA JTE 7-31 JTE-907 Levonantradol MDMB-CHMICA MDMB-CHMINACA MDMB-FUBINACA MEPIRAPIM MAM-2201 MDA-19 MN-18 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan NM-2201 NNE1 Org 28611 Parahexyl PTI-1 PTI-2 PX-1 PX-2 PX-3 QUCHIC QUPIC RCS-4 RCS-8 SDB-005 SDB-006 STS-135 THC-O-acetate THC-O-phosphate THJ-018 THJ-2201 UR-144 WIN 55,212-2 XLR-11

D2 agonists

Apomorphine Aporphine Bromocriptine Cabergoline Lisuride Memantine Nuciferine Pergolide Phenethylamine Piribedil Pramipexole Ropinirole Rotigotine Salvinorin A Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABAA enhancers

CI-966 Eszopiclone Ibotenic acid Muscimol
Muscimol
(Amanita muscaria) Zaleplon Zolpidem Zopiclone

Inhalants (Mixed MOA)

Aliphatic hydrocarbons

Butane Gasoline Kerosene Propane

Aromatic hydrocarbons

Toluene

Ethers

Diethyl ether Enflurane

Haloalkanes

Chlorofluorocarbons Chloroform

κOR agonists

2-EMSB Alazocine Bremazocine Butorphan Butorphanol Cyclazocine Cyclorphan Cyprenorphine Diprenorphine Enadoline Herkinorin Heroin HZ-2 Ibogaine Ketazocine Levallorphan Levomethorphan Levorphanol LPK-26 Metazocine Morphine Nalbuphine Nalmefene Nalorphine Noribogaine Oxilorphan Pentazocine Phenazocine Proxorphan Racemethorphan Racemorphan Salvinorin A Spiradoline Tifluadom U-50488 U-69,593 Xorphanol

Others

Glaucine Isoaminile Noscapine Pukateine

Acetylcholine receptor
Acetylcholine receptor
modulators

v t e

Muscarinic acetylcholine receptor
Muscarinic acetylcholine receptor
modulators

mAChRs

Agonists

77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B Alvameline AQRA-741 Arecoline Bethanechol Bevonium Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline Choline cis-Dioxolane Clozapine Desmethylclozapine
Desmethylclozapine
(norclozapine) Ethoxysebacylcholine Itameline LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberyldicholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796

Antagonists

3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide
Aclidinium bromide
(+formoterol) Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g., brompheniramine, buclizine, captodiame, chlorphenamine (chlorpheniramine), cinnarizine, clemastine, cyproheptadine, dimenhydrinate, dimetindene, diphenhydramine, doxylamine, meclizine, mepyramine (pyrilamine), mequitazine, perlapine, phenindamine, pheniramine, phenyltoloxamine, promethazine, propiomazine, triprolidine) AQ-RA 741 Atropine Atropine
Atropine
methonitrate Atypical antipsychotics (e.g., clozapine, fluperlapine, olanzapine (+fluoxetine), rilapine, quetiapine, tenilapine, zotepine) Benactyzine Benzatropine
Benzatropine
(benztropine) Benzilone Benzilylcholine mustard Benzydamine BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine
Dicycloverine
(dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine
Etybenzatropine
(ethybenztropine) Fenpiverinium Fentonium Fesoterodine Flavoxate Glycopyrronium bromide
Glycopyrronium bromide
(+beclometasone/formoterol, +indacaterol) Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide
Ipratropium bromide
(+salbutamol) Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide
Octatropine methylbromide
(anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine
Profenamine
(ethopropazine) Propantheline bromide Propiverine Quinidine Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine
Scopolamine
(hyoscine) Scopolamine
Scopolamine
butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIs (e.g., femoxetine, paroxetine) Telenzepine Terodiline Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g., amitriptyline (+perphenazine), amitriptylinoxide, butriptyline, cidoxepin, clomipramine, desipramine, desmethyldesipramine, dibenzepin, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nitroxazepine, northiaden (desmethyldosulepin), nortriptyline, protriptyline, quinupramine, trimipramine) Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Trospium chloride Typical antipsychotics (e.g., chlorpromazine, chlorprothixene, cyamemazine (cyamepromazine), loxapine, mesoridazine, thioridazine) Umeclidinium bromide
Umeclidinium bromide
(+vilanterol) WIN-2299 Xanomeline Zamifenacin

Precursors (and prodrugs)

Acetyl-coA Adafenoxate Choline
Choline
(lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate
Meclofenoxate
(centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol

See also: Receptor/signaling modulators • Nicotinic acetylcholine receptor modulators • Acetylcholine
Acetylcholine
metabolism/transport modulators

v t e

Nicotinic acetylcholine receptor
Nicotinic acetylcholine receptor
modulators

nAChRs

Agonists (and PAMs)

5-HIAA A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatoxin-a AR-R17779 Bephenium hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol (alcohol) Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin JNJ-39393406 Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine
Nicotine
(tobacco) NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Pyrantel Rivanicline RJR-2429 Sazetidine A SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium
Suxamethonium
(succinylcholine) Suxethonium (succinyldicholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tribendimidine Tropisetron UB-165 Varenicline WAY-317,538 XY-4083

Antagonists (and NAMs)

18-MAC 18-MC α-Neurotoxins (e.g., α-bungarotoxin, α-cobratoxin, α-conotoxin, many others) ABT-126 Alcuronium Allopregnanolone Amantadine Anatruxonium AQW051 Atracurium Barbiturates
Barbiturates
(e.g., pentobarbital, sodium thiopental) BNC-210 Bungarotoxins (e.g., α-bungarotoxin, κ-bungarotoxin) Bupropion BW-A444 Candocuronium iodide
Candocuronium iodide
(chandonium iodide) Chlorisondamine Cisatracurium Coclaurine Coronaridine Curare Cyclopropane Dacuronium bromide Decamethonium Dehydronorketamine Desflurane Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dihydrochandonium Dimethyltubocurarine
Dimethyltubocurarine
(metocurine) Dioscorine Dipyrandium Dizocilpine
Dizocilpine
(MK-801) Doxacurium Encenicline Enflurane Erythravine Esketamine Fazadinium Gallamine Gantacurium chloride Halothane Hexafluronium Hexamethonium
Hexamethonium
(benzohexonium) Hydroxybupropion Hydroxynorketamine Ibogaine Isoflurane Ketamine Kynurenic acid Laudanosine Laudexium
Laudexium
(laudolissin) Levacetylmethadol Levomethadone Malouetine ME-18-MC Mecamylamine Memantine Methadone Methorphan
Methorphan
(racemethorphan) Methyllycaconitine Metocurine Mivacurium Morphanol
Morphanol
(racemorphan) Neramexane Nitrous oxide Norketamine Pancuronium bromide Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium bromide Progesterone Promegestone Radafaxine Rapacuronium bromide Reboxetine Rocuronium bromide Sevoflurane Stercuronium iodide Surugatoxin Thiocolchicoside Toxiferine Tramadol Trimetaphan camsilate
Trimetaphan camsilate
(trimethaphan camsylate) Tropeinium Tubocurarine Vanoxerine Vecuronium bromide Xenon

Precursors (and prodrugs)

Acetyl-coA Adafenoxate Choline
Choline
(lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate
Meclofenoxate
(centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol

See also: Receptor/signaling modulators • Muscarinic acetylcholine receptor modulators • Acetylcholine
Acetylcholine
metabolism/transport modulators

Taxon identifiers

Wd: Q156091 BioLib: 40738 EoL: 5701795 EPPO: ATRBE GBIF: 3802655 GRIN: 6051 iNaturalist: 55619 IPNI: 814358-1 ITIS: 30488 NCBI: 33113 PalDat: Atropa_bella-donna Plantarium: 6026 Plant
Plant
List: kew-2665943 Tropicos: 296

.