Datura

This article is about the plant genus. For the Italian dance group, see Datura (band). For the former town in California, see Datura, California. For The Tori Amos song, see Datura (song). Datura Datura stramonium Scientific classification Kingdom: Plantae (unranked): Angiosperms (unranked): Eudicots (unranked): Asterids Order: Solanales Family: Solanaceae Subfamily: Solanoideae Tribe: Datureae Genus: Datura L. Type species Datura stramonium L. Species See text below Datura is a genus of nine species of vespertine flowering plants belonging to the family Solanaceae. Its precise and natural distribution is uncertain, owing to its extensive cultivation and naturalization throughout the temperate and tropical regions of the globe. Its distribution within the Americas, however, is most likely restricted to the United States and Mexico, where the highest species diversity occurs. Some South American plants formerly thought of as Daturas are now treated as belonging to the distinct genus Brugmansia1 (Brugmansia differs from Datura in that it is woody, making shrubs or small trees, and in that it has pendulous flowers, rather than erect ones). Other related genera include Hyoscyamus and Atropa. Contents 1 Description 2 Species and cultivars 3 Cultivation 4 Toxicity 4.1 Effects of ingestion 4.2 Treatment 5 See also 6 References 7 External links // Description Datura are herbaceous, leafy annuals and short-lived perennials which can reach up to 2 meters in height. The leaves are alternate, 10–20 cm long and 5–18 cm broad, with a lobed or toothed margin. The flowers are erect or spreading (not pendulous like those of the closely allied Brugmansia), trumpet-shaped, 5–20 cm long and 4–12 cm broad at the mouth; colors vary from white to yellow, pink, and pale purple. The fruit is a spiny capsule 4–10 cm long and 2–6 cm broad, splitting open when ripe to release the numerous seeds. The seeds disperse freely over pastures, fields and even wasteland locations. Datura belongs to the classic "witches' weeds," along with deadly nightshade, henbane, and mandrake. Most parts of the plants contain toxic hallucinogens, and datura has a long history of use for causing delirious states and death. It was well known as an essential ingredient of love potions and witches' brews.2 The word datura comes from the Hindi dhatūrā ("thorn apple"); record of this name dates back to 1662 (OED). Nathaniel Hawthorne refers to one type in The Scarlet Letter as apple-Peru. In Mexico, its common name toloache. The larvae of some Lepidoptera (butterfly and moth) species, including Hypercompe indecisa, eat some datura species. Species and cultivars It is difficult to classify a datura as to its species, and it often happens that descriptions of new species are accepted prematurely. Later it is found that these "new species" are simply varieties that have evolved due to conditions at a specific location. They usually disappear in a few years. Contributing to the confusion are the facts that various species such as D. wrightii and D. inoxia are very similar in appearance, and that the variation within a species can be extreme. For example, Datura have the interesting property of being able to change size of plant, size of leaf, and size of flowers, all depending on location. The same species, when growing in a half-shady damp location can develop into a magnificent flowering bush half as tall as a person, but when growing in a very dry location will only grow into a thin little plant just higher than his ankles, with tiny flowers and a few miniature leaves.2 Today, experts classify only nine species of Datura:2 Datura ceratocaula Jacq. Datura discolor Bernh. – Desert Thorn-apple Datura ferox L. – Long Spined Thorn-apple Datura inoxia Mill. – Thorn-apple, Downy Thorn-apple, Indian-apple, Moonflower, Sacred Datura, Toloatzin, Toloache Datura leichhardtii F.Muell. ex Benth. (syn. D. pruinosa) – Leichhardt's Datura Datura metel L. Datura quercifolia Kunth – Oak-leaf Thorn-apple Datura stramonium L. (syn. D. inermis) – Jimsonweed, Thorn-apple Datura wrightii Regel – Sacred Datura, Sacred Thorn-apple American Brugmansia & Datura Society, Inc. (ABADS), is designated in the 2004 edition of the International Code of Nomenclature for Cultivated Plants as the official International Cultivar Registration Authority for Datura. This role was delegated to ABADS by the International Society for Horticultural Science in 2002. Cultivation Fruit D. inoxia with ripe, split-open fruit Datura are usually planted annually from the seed produced in the spiny pods, but with care, plants can be overwintered. Most species are suited to being planted outside or in containers. As a rule, they need warm, sunny places and soil that will keep their roots dry. When grown outdoors in good locations, the plants tend to reseed themselves and may become invasive. In containers, they should have porous, aerated potting soil with adequate drainage. The plants are susceptible to fungi in the root area, so organic enrichers such as compost and manure should be avoided.2 Toxicity All Datura plants contain tropane alkaloids such as scopolamine, hyoscyamine, and atropine, primarily in their seeds and flowers. Because of the presence of these substances, Datura has been used for centuries in some cultures as a poison and hallucinogen.23 There can be a 5:1 toxin variation across plants, and a given plant's toxicity depends on its age, where it is growing, and the local weather conditions. This variation makes Datura exceptionally hazardous as a drug. In traditional cultures, a great deal of experience with, and detailed knowledge of, Datura was critical in order to minimize harm.2 Many tragic incidents result from modern recreational users ingesting Datura. For example, in the 1990s and 2000s, the United States media contained stories of adolescents and young adults dying or becoming seriously ill from intentionally ingesting Datura.45 There are also several reports in the medical literature of deaths from Datura stramonium and Datura ferox intoxication.678 Children are especially vulnerable to atropine poisoning, and their prognosis is likely to be fatal.910 In some parts of Europe and India, Datura has been a popular poison for suicide and murder. From 1950–1965, the State Chemical Laboratories in Agra, India investigated 2,778 deaths that were caused by ingesting Datura.2 The U.S. Centers for Disease Control and Prevention reported accidental poisoning resulting in hospitalization for a family of six who inadvertently ingested Datura used as an ingredient in stew.11 In some places it is prohibited to buy, sell or cultivate Datura plants.2 Effects of ingestion Due to the potent combination of anticholinergic substances it contains, Datura intoxication typically produces effects similar to that of an anticholinergic delirium (as contrasted to hallucination): a complete inability to differentiate reality from fantasy; hyperthermia; tachycardia; bizarre, and possibly violent behavior; and severe mydriasis with resultant painful photophobia that can last several days. Pronounced amnesia is another commonly reported effect.12 No other psychoactive substance has received as many "train wreck" (i.e., severely negative experience) reports as has Datura. The overwhelming majority of those who describe their use of Datura find their experiences extremely mentally and physically unpleasant and often physically dangerous.12 Treatment Due to their agitated behavior and confused mental state, victims of Datura poisoning are typically hospitalized. Gastric lavage (stomach pumping) and the administration of activated charcoal can be used to reduce the stomach's absorption of the ingested material. The drug physostigmine is used to reverse the effect of the poisons. Benzodiazepines can be given to curb the patient's agitation, and supportive care with oxygen, hydration, and symptomatic treatment is often provided. Observation of the patient is indicated until the symptoms resolve, usually from 24–36 hours after ingestion of the Datura.13 See also Datura bernhardii Datura kymatocarpa Datura lanosa Datura reburra Datura suaveolens Datura stramonium, aka Jimson Weed Donnatal, a pharmaceutical containing the active alkaloids in datura; scopolamine, hyoscyamine, and atropine, as a drug References Wikimedia Commons has media related to: Datura Wikispecies has information related to: Datura ^ Hawkes, J.G. (ed.); R.N. Lester, M. Nee, N. Estrada (1991). Solanaceae III – Taxonomy, Chemistry, Evolution (Proceedings of Third International Conference on Solanaceae). Royal Botanic Gardens, Kew. pp. 197–210. ISBN 0947643311.  ^ a b c d e f g h Preissel, Ulrike; Hans-Georg Preissel (2002). Brugmansia and Datura: Angel's Trumpets and Thorn Apples. Buffalo, New York: Firefly Books. pp. 106–129. ISBN 1-55209-598-3. http://www.amazon.com/Brugmansia-Datura-Angels-Trumpets-Apples/dp/1552095584.  ^ Adams, Jr., James D.; Cecilia Garcia (2005-10-10). "Spirit, Mind and Body in Chumash Healing". Evidence-based Complementary and Alternative Medicine 2 (4): 459–463. doi:10.1093/ecam/neh130. PMID 16322802. PMC 1297503. http://ecam.oxfordjournals.org/cgi/content/full/2/4/459. Retrieved 2008-01-21.  ^ "Suspected Moonflower Intoxication (Ohio, 2002)". CDC. http://www.cdc.gov/mmwr/preview/mmwrhtml/mm5233a2.htm. Retrieved September 30, 2006.  ^ Leinwand, Donna (2006-11-01). "Jimson weed users chase high all the way to hospital". USA TODAY. http://www.usatoday.com/news/nation/2006-11-01-jimson_x.htm. Retrieved February 15, 2009.  ^ Michalodimitrakis M, Koutselinis A. (1984). Discussion of "Datura stramonium;" a fatal poisoning." J Forensic Sci. 29:961–962. ^ Boumba VA, Mitselou A, Vougiouklakis T. Fatal poisoning from ingestion of Datura stramonium seeds. Vet Hum Toxicol.46:81–82. ^ Steenkamp PA, Harding NM, van Heerden FR, van Wyck BE. (2004). Fatal poisoning: identification of atropine and scopalamine by high performance liquid chromatography/photoiodide array/mass spectrometry. Forensic Sci Int. 145:31–39. ^ Taha SA. (1984). Datura intoxication in Riyadh. Trans R Soc Trop Med Hyg. 78(1):134–135. ^ Djibo A, Bouzou SB. (2000). [Acute intoxication with "sobi-lobi" (Datura). Four cases in Niger]. Bull Soc Pathol Exot. 93:294–297. ^ Bontoyan, W; et al (2010-02-05). "Jimsonweed Poisoning Associated with a Homemade Stew – Maryland, 2008". Centers for Disease Control and Prevention – Morbidity and Mortality Weekly Report 59 (4): 102–103. http://www.cdc.gov/mmwr/pdf/wk/mm5904.pdf. Retrieved 2010-02-11.  ^ a b Freye, Enno (2009-09-21). Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs. Springer Netherlands. pp. 217–218. ISBN 978-90-481-2447-3. http://www.springerlink.com/content/u42k03r4v3234615/.  ^ Bliss, Molly (2001-03). "Datura Plant Poisoning". Clinical Toxology Review 23 (6). http://www.maripoisoncenter.com/images/pdfs/ctrs/CTR%20Datura%20Plant%20Poisoning.pdf. Retrieved 2009-10-12. dead link External links USDA Natural Resources Conservation Service PLANTS Profile: Datura USDA Germplasm Resources Information Network (GRIN) Species Records of Datura Datura wrightii Specimen Pictures and Information JimsonWeed: History, Perceptions, Traditional Uses, and Potential Therapeutic Benefits of the Genus Datura HerbalGram. 2006;69:40–50 © American Botanical Council by Kofi Busia & Fiona Heckels Account of accidental minor poisoning by Datura from the British Medical Journal Erowid Datura Vault Clinical Toxicology Review of Datura Poisoning v · d · eHallucinogens Psychedelics 5-HT2AR agonists Lysergamides: AL-LAD • ALD-52 • BU-LAD • CYP-LAD • DAM-57 • Diallyllysergamide • Ergometrine (Ergonovine, Ergobasine) • ETH-LAD • LAE-32 • LSA (Ergine, Lysergamide) • LSD • LSH • LPD-824 • LSM-775 • Lysergic Acid 2-Butyl Amide • Lysergic Acid 2,4-Dimethylazetidide • Methylergometrine • Methylisopropyllysergamide • Methysergide • MLD-41 • PARGY-LAD • PRO-LAD; Phenethylamines: Aleph • 2C-B • 2C-B-FLY • 2CBFly-NBOMe • 2C-C • 2C-D • 2CD-5EtO • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • 2CBCB-NBOMe • 25B-NBOMe • 25I-NBMD • 25I-NBOH • 25I-NBOMe • 3C-E • 3C-P • Br-DFLY • DESOXY • DMMDA • DMMDA-2 • DOB • DOC • DOEF • DOET • DOF • DOI • DOM • DON • DOPR • DOTFM • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • IAP • Isoproscaline • Jimscaline • Lophophine • MDA • MDEA • MDMA • MMA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Methallylescaline • Proscaline • TCB-2 • TFMFly • TMA; Piperazines: pFPP • TMFPP; Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine • 2,N,N-TMT • 4,N,N-TMT • 4-HO-5-MeO-DMT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-Acetoxy-DPT • 4-Acetoxy-MiPT • 4-HO-DPT • 4-HO-MET • 4-Propionyloxy-DMT • 4-HO-MPMI • 5-Me-MIPT • 5-N,N-TMT • 5-AcO-DMT • 5-MeO-2,N,N-TMT • 5-MeO-4,N,N-TMT • 5-MeO-α,N,N-TMT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-EiPT • 5-MeO-MET • 5-MeO-MIPT • 5-MeO-MPMI • 7,N,N-TMT • α,N,N-TMT • α-ET • α-MT • AL-37350A • Baeocystin • Bufotenin • DALT • DBT • DCPT • DET • DIPT • DMT • DPT • EiPT • Ethocin • Ethocybin • Iprocin • MET • Miprocin • MIPT • Norbaeocystin • PiPT • Psilocin • Psilocybin; Others: AL-38022A • Ibogaine • Noribogaine • Voacangine Dissociatives NMDAR antagonists Adamantanes: Amantadine • Memantine • Rimantadine; Arylcyclohexylamines: 3-MeO-PCP • 4-MeO-PCP • Dieticyclidine • Esketamine • Eticyclidine • Gacyclidine • Ketamine • Methoxetamine • Neramexane • Phencyclidine • PCPr • Rolicyclidine • Tenocyclidine • Tiletamine; Morphinans: Dextrallorphan • Dextromethorphan • Dextrorphan • Methorphan (Racemethorphan) • Morphan (Racemorphan); Others: 2-MDP • 8A-PDHQ • Aptiganel • Dexoxadrol • Dizocilpine (MK-801) • Etoxadrol • Ibogaine • Midafotel • NEFA • Nitrous Oxide • Noribogaine • Perzinfotel • Remacemide • Selfotel • Xenon Deliriants mAChR antagonists 3-Quinuclidinyl benzilate • Atropine • Benactyzine • Benzatropine • Benzydamine • Biperiden • Brompheniramine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • Chlorpheniramine • Chloropyramine • Clemastine • CS-27349 • Cyclizine • Cyproheptadine • Dicyclomine (Dicycloverine) • Dimenhydrinate • Diphenhydramine • Ditran • Doxylamine • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Flavoxate • Hydroxyzine • Hyoscyamine • Meclizine • Myristicin • N-Ethyl-3-piperidyl benzilate • N-Methyl-3-piperidyl benzilate • Pyrilamine • Orphenadrine • Oxybutynin • Pheniramine • Phenyltoloxamine • Procyclidine • Promethazine • Scopolamine (Hyoscine) • Tolterodine • Trihexyphenidyl • Tripelennamine • Triprolidine • WIN-2299 Miscellaneous Cannabinoids CB1R agonists Cannabinol • CP-47,497 • CP-55,244 • CP-55,940 • DMHP • HU-210 • JWH-018 • JWH-030 • JWH-073 • JWH-081 • JWH-200 • JWH-250 • Nabilone • Nabitan • Nantradol • Parahexyl • THC (Dronabinol) • WIN-55,212-2 D2R agonists Apomorphine • Bromocriptine • Cabergoline • Lisuride • Memantine • Pergolide • Piribedil • Pramipexole • Ropinirole • Rotigotine * Also indirect D2 agonists such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa). GABAAR agonists Eszopiclone • Gaboxadol • Ibotenic Acid • Muscimol • Zolpidem • Zopiclone Inhalants Mixed MOA Butane • Chloroform • Diethyl Ether (Ether) • Enflurane • Freon • Gasoline (Petrol) • Kerosene (Paraffin) • Propane κOR agonists 2-EMSB • 2-MMSB • Alazocine • Bremazocine • Butorphanol • Cyclazocine • Cyprenorphine • Dextrallorphan • Dezocine • Enadoline • Herkinorin • HZ-2 • Ibogaine • Ketazocine • Metazocine • Nalbuphine • Nalorphine • Noribogaine • Pentazocine • Phenazocine • Salvinorin A • Spiradoline • Tifluadom • U-50,488 • U-69,593 σR agonists Dextrallorphan • Dextromethorphan • Dextrorphan • Noscapine (Narcotine) Others Efavirenz • Glaucine • Isoaminile v · d · eCholinergics  Receptor ligands mAChR Agonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B • AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine • 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 • Suberylcholine • 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 • Anisodamine • Anisodine • Atropine • Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 • Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate • Darifenacin • DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine (Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-031,120 • Ipratropium • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl Benzilate • N-Methyl-3-Piperidyl Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID • PD-102,807 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) • Solifenacin • Telenzepine • Tiotropium • Tolterodine • Trihexyphenidyl • Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Xanomeline • Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine, chlorpheniramine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine/pyrilamine, phenindamine, pheniramine, tripelennamine, triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, doxepin, trimipramine, etc) • Tetracyclic Antidepressants (Amoxapine, maprotiline, etc) • Typical Antipsychotics (Chlorpromazine, thioridazine, etc) • Atypical Antipsychotics (Clozapine, olanzapine, quetiapine, etc) nAChR Agonists: 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 • AR-R17779 • Butyrylcholine • Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium • Epibatidine • Epiboxidine • Ethanol • Ethoxysebacylcholine • EVP-4473 • EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y • SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 • TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 • Varenicline • WAY-317,538 • XY-4083 Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Amantadine • Anatruxonium • Atracurium • Bupropion (Amfebutamone) • Chandonium • Chlorisondamine • Cisatracurium • Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan • Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine (Metocurine) • Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Isoflurane • Ketamine • Kynurenic acid • Laudexium (Laudolissin) • Levacetylmethadol • Malouetine • Mecamylamine • Memantine • Methadone • Methorphan (Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium • Morphanol (Racemorphanol) • Neramexane • Nitrous Oxide • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin • Suxamethonium (Succinylcholine) • Thiocolchicoside • Toxiferine • Trimethaphan • Tropeinium • Tubocurarine • Vecuronium • Xenon  Reuptake inhibitors Plasmalemmal CHT Inhibitors Hemicholinium-3 (Hemicholine; HC3) • Triethylcholine Vesicular VAChT Inhibitors Vesamicol  Enzyme inhibitors Anabolism ChAT inhibitors 1-(-Benzoylethyl)pyridinium • 2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole • 4-(1-Naphthylvinyl)pyridine • Acetylseco hemicholinium-3 • Acryloylcholine • AF64A • B115 • BETA • CM-54,903 • N,N-Dimethylaminoethylacrylate • N,N-Dimethylaminoethylchloroacetate Catabolism AChE inhibitors Reversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb • Carbaryl • Carbendazim • Carbetamide • Carbofuran • Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb • Fenobucarb • Fenoxycarb • Formetanate • Furadan • Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl • Phenmedipham • Pinmicarb • Pirimicarb • Propamocarb • Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine • Phenserine • Physostigmine • Pyridostigmine • Rivastigmine; Others: Acotiamide • Ambenonium • Donepezil • Edrophonium • Galantamine • Huperzine A • Minaprine • Tacrine • Zanapezil Irreversible: Organophosphates: Acephate • Azinphos-methyl • Bensulide • Cadusafos • Chlorethoxyfos • Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl • Coumaphos • Cyclosarin (GF) • Demeton • Demeton-S-Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl fluorophosphate (Guthion) • Diisopropylphosphate • Dimethoate • Dioxathion • Disulfoton • EA-3148 • Echothiophate • Ethion • Ethoprop • Fenamiphos • Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate • Isoxathion • Malaoxon • Malathion • Methamidophos • Methidathion • Metrifonate • Mevinphos • Monocrotophos • Naled • Novichok agent • Omethoate • Oxydemeton-Methyl • Paraoxon • Parathion • Parathion-Methyl • Phorate • Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-Methyl • Sarin (GB) • Soman (GD) • Tabun (GA) • Temefos • Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE • VG • VM • VR • VX; Others: Demecarium • Onchidal (Onchidella binneyi) BChE inhibitors * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.  Others Precursors Choline (Lecithin) • Citicoline • Cyprodenate • Dimethylethanolamine (DMAE, deanol) • Glycerophosphocholine • Meclofenoxate (Centrophenoxine) • Phosphatidylcholine • Phosphatidylethanolamine • Phosphorylcholine • Pirisudanol Cofactors Acetic acid • Acetylcarnitine • Acetyl-coA • Vitamin B5 (Pantethine, Pantetheine, Panthenol) Others Acetylcholine releasing agents: α-Latrotoxin • β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime • Obidoxime • Pralidoxime