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Chloroform, or trichloromethane, is an organic compound with formula CHCl3. It is a colorless, sweet-smelling, dense liquid that is produced on a large scale as a precursor to PTFE. It is also a precursor to various refrigerants.[4] It is one of the four chloromethanes and a trihalomethane.

Contents

1 Structure 2 Natural occurrence 3 History 4 Production

4.1 Deuterochloroform 4.2 Inadvertent formation of chloroform

5 Uses

5.1 Solvent 5.2 Reagent 5.3 Anesthetic 5.4 Criminal use

6 Safety

6.1 Exposure 6.2 Pharmacology 6.3 Conversion to phosgene 6.4 Regulation

7 References 8 External links

Structure[edit] The molecule adopts tetrahedral molecular geometry with C3v symmetry. Natural occurrence[edit] The total global flux of chloroform through the environment is approximately 7005660000000000000♠660000 tonnes per year,[5] and about 90% of emissions are natural in origin. Many kinds of seaweed produce chloroform, and fungi are believed to produce chloroform in soil.[6] Chloroform
Chloroform
volatilizes readily from soil and surface water and undergoes degradation in air to produce phosgene, dichloromethane, formyl chloride, carbon monoxide, carbon dioxide, and hydrogen chloride. Its half-life in air ranges from 55 to 620 days. Biodegradation in water and soil is slow. Chloroform
Chloroform
does not significantly bioaccumulate in aquatic organisms.[7] History[edit] Chloroform
Chloroform
was synthesized independently by several investigators circa 1831:

Moldenhawer, a German pharmacist from Frankfurt an der Oder, appears to have produced chloroform in 1830 by mixing chlorinated lime (calcium hypochlorite) with ethanol; however, he mistook it for Chloräther (chloric ether, 1,2-dichloroethane).[8][9] Samuel Guthrie, an American physician from Sackets Harbor, New York, also appears to have produced chloroform in 1831 by reacting chlorinated lime with ethanol, as well as noting its anaesthetic properties; however, he also believed that he had prepared chloric ether.[10][11][12] Justus von Liebig
Justus von Liebig
carried out the alkaline cleavage of chloral.[13][14] Eugène Soubeiran
Eugène Soubeiran
obtained the compound by the action of chlorine bleach on both ethanol and acetone.[15] In 1834, French chemist Jean-Baptiste Dumas
Jean-Baptiste Dumas
determined chloroform's empirical formula and named it.[16] In 1835, Dumas prepared the substance by the alkaline cleavage of trichloroacetic acid. Regnault prepared chloroform by chlorination of chloromethane. In 1842, Robert Mortimer Glover in London discovered the anaesthetic qualities of chloroform on laboratory animals.[17] In 1847, Scottish obstetrician James Y. Simpson
James Y. Simpson
was the first to demonstrate the anaesthetic properties of chloroform on humans and helped to popularise the drug for use in medicine.[18] By the 1850s, chloroform was being produced on a commercial basis by using the Liebig procedure, which retained its importance until the 1960s. Today, chloroform — along with dichloromethane — is prepared exclusively and on a massive scale by the chlorination of methane and chloromethane.[4]

Production[edit] In industry, chloroform is produced by heating a mixture of chlorine and either chloromethane or methane.[4] At 400–500 °C, a free radical halogenation occurs, converting these precursors to progressively more chlorinated compounds:

CH4 + Cl2 → CH3Cl + HCl CH3Cl + Cl2 → CH2Cl2 + HCl CH2Cl2 + Cl2 → CHCl3 + HCl

Chloroform
Chloroform
undergoes further chlorination to yield carbon tetrachloride (CCl4):

CHCl3 + Cl2 → CCl4 + HCl

The output of this process is a mixture of the four chloromethanes (chloromethane, dichloromethane, chloroform, and carbon tetrachloride), which can then be separated by distillation.[4] Chloroform
Chloroform
may also be produced on a small scale via the haloform reaction between acetone and sodium hypochlorite:

3 NaClO + (CH3)2CO → CHCl3 + 2 NaOH + NaOCOCH3

Deuterochloroform[edit] Main article: Deuterated chloroform Deuterated chloroform
Deuterated chloroform
is an isotopologue of chloroform with a single deuterium atom. CDCl3 is a common solvent used in NMR spectroscopy. Deuterochloroform is produced by the haloform reaction,[citation needed] the reaction of acetone (or ethanol) with sodium hypochlorite or calcium hypochlorite.[4] The haloform process is now obsolete for the production of ordinary chloroform. Deuterochloroform can be prepared by the reaction of sodium deuteroxide with chloral hydrate.[19][20] Inadvertent formation of chloroform[edit] The haloform reaction can also occur inadvertently in domestic settings. Bleaching
Bleaching
with hypochlorite generates halogenated compounds in side reactions; chloroform is the main byproduct.[21] Sodium hypochlorite solution (chlorine bleach) mixed with common household liquids such as acetone, butanone, methyl ethyl ketone, ethanol, or isopropyl alcohol can produce some chloroform, in addition to other compounds such as chloroacetone or dichloroacetone. Uses[edit] In terms of scale, the most important reaction of chloroform is with hydrogen fluoride to give monochlorodifluoromethane (CFC-22), a precursor in the production of polytetrafluoroethylene (Teflon):[4]

CHCl3 + 2 HF → CHClF2 + 2 HCl

The reaction is conducted in the presence of a catalytic amount of mixed antimony halides. Chlorodifluoromethane
Chlorodifluoromethane
is then converted into tetrafluoroethylene, the main precursor to Teflon. Before the Montreal Protocol, chlorodifluoromethane (designated as R-22) was also a popular refrigerant. Solvent[edit] The hydrogen attached to carbon in chloroform participates in hydrogen bonding.[22][23] Worldwide, chloroform is also used in pesticide formulations, as a solvent for fats, oils, rubber, alkaloids, waxes, gutta-percha, and resins, as a cleansing agent, grain fumigant, in fire extinguishers, and in the rubber industry.[7][24] CDCl3 is a common solvent used in NMR spectroscopy. Reagent[edit] As a reagent, chloroform serves as a source of the dichlorocarbene CCl2 group.[25] It reacts with aqueous sodium hydroxide usually in the presence of a phase transfer catalyst to produce dichlorocarbene, CCl2.[26][27] This reagent effects ortho-formylation of activated aromatic rings such as phenols, producing aryl aldehydes in a reaction known as the Reimer–Tiemann reaction. Alternatively, the carbene can be trapped by an alkene to form a cyclopropane derivative. In the Kharasch addition, chloroform forms the CHCl2 free radical in addition to alkenes. Anesthetic[edit]

Antique bottles of chloroform

The anaesthetic qualities of chloroform were first described in 1842 in a thesis by Robert Mortimer Glover which won the Harveian Medal for that year. Glover also undertook practical experiments on dogs to prove his theories. Glover further refined his theories and presented them in the thesis for his doctorate at the University of Edinburgh
University of Edinburgh
in the summer of 1847. James Y. Simpson
James Y. Simpson
was one of the persons required to read the thesis. Simpson later claimed to have never read the thesis and to have come to his conclusions independently. On 4 November 1847, the Scottish obstetrician James Young Simpson first used the anesthetic qualities of chloroform on a pair of humans—two guests at his dinner party. This was done as an entertainment and not as a medical procedure.[28] A few days later, during the course of a dental procedure in Edinburgh, Francis Brodie Imlach
Francis Brodie Imlach
became the first person to use chloroform on a patient in a clinical context.[29] In May 1848 Robert Halliday Gunning
Robert Halliday Gunning
made a presentation to the Medico-Chirurgical Society of Edinburgh
Edinburgh
following a series of laboratory experiments on rabbits which confirmed Glover's findings and also refuted Simpson's claims of originality. However, a knighthood for Simpson, and massive media coverage of the wonders of chloroform ensured that Simpson's reputation remained high, whilst the laboratory experiments proving the dangers of chloroform were largely ignored. Gunning, who rose to be one of the richest persons in Britain, endowed some 13 university scholarships under the names of other scientists rather than his own name. Although he considered Simpson a charlatan, one of these prizes is named the Simpson Prize for Obstetrics. It is, however, probably a strange reverse compliment, as arguably any Simpson prize in the wider public eye should be a prize for anaesthesia. By not calling it this he effectively snubbed Simpson whilst at the same time appearing to honour him.[30] The use of chloroform during surgery expanded rapidly thereafter in Europe. In the 1850s, chloroform was used during the birth of Queen Victoria's last two children.[31] In the United States, chloroform began to replace ether as an anesthetic at the beginning of the 20th century; however, it was quickly abandoned in favor of ether upon discovery of its toxicity, especially its tendency to cause fatal cardiac arrhythmia analogous to what is now termed "sudden sniffer's death". Some people used chloroform as a recreational drug or to attempt suicide.[32] One possible mechanism of action for chloroform is that it increases movement of potassium ions through certain types of potassium channels in nerve cells.[33] Chloroform
Chloroform
could also be mixed with other anesthetic agents such as ether to make C.E. mixture, or ether and alcohol to make A.C.E. mixture. In 1848, Hannah Greener, a 15-year-old girl who was having an infected toenail removed, died after being given the anesthetic.[34] Her autopsy establishing the cause of death was undertaken by John Fife assisted by Robert Mortimer Glover.[17] A number of physically fit patients died after inhaling it. However, in 1848 John Snow developed an inhaler that regulated the dosage and so successfully reduced the number of deaths.[35] The opponents and supporters of chloroform were mainly at odds with the question of whether the complications were solely due to respiratory disturbance or whether chloroform had a specific effect on the heart. Between 1864 and 1910 numerous commissions in Britain studied chloroform, but failed to come to any clear conclusions. It was only in 1911 that Levy proved in experiments with animals that chloroform can cause cardiac fibrillation. The reservations about chloroform could not halt its soaring popularity. Between about 1865 and 1920, chloroform was used in 80 to 95% of all narcoses performed in the UK and the German-speaking countries. In America, however, there was less enthusiasm for chloroform narcosis. In Germany, the first comprehensive surveys of the fatality rate during anesthesia were made by Gurlt between 1890 and 1897. In 1934, Killian gathered all the statistics compiled until then and found that the chances of suffering fatal complications under ether were between 1:14,000 and 1:28,000, whereas under chloroform the chances were between 1:3,000 and 1:6,000. The rise of gas anesthesia using nitrous oxide, improved equipment for administering anesthetics and the discovery of hexobarbital in 1932 led to the gradual decline of chloroform narcosis.[36] Criminal use[edit] Chloroform
Chloroform
has been reputed to be used by criminals to knock out, daze or even murder their victims. Joseph Harris was charged in 1894 with using chloroform to rob people.[37] Serial killer
Serial killer
H. H. Holmes
H. H. Holmes
used chloroform overdoses to kill his female victims. In September 1900, chloroform was also implicated in the murder of the American businessman William Marsh Rice, the namesake of the institution now known as Rice University. Chloroform
Chloroform
was also deemed to be a factor in the alleged murder of a woman in 1991 when she was asphyxiated while sleeping.[38] In a 2007 plea bargain a man confessed to using stun guns and chloroform to sexually assault minors.[39] Use of chloroform as an incapacitating agent has become widely recognized, bordering on clichéd, due to the popularity of crime fiction authors having criminals use chloroform-soaked rags to render victims unconscious. However, it is nearly impossible to incapacitate someone using chloroform in this manner.[40] It takes at least five minutes of inhaling an item soaked in chloroform to render a person unconscious. Most criminal cases involving chloroform also involve another drug being co-administered, such as alcohol or diazepam, or the victim being found to have been complicit in its administration. After a person has lost consciousness due to chloroform inhalation, a continuous volume must be administered and the chin must be supported in order to keep the tongue from obstructing the airway, a difficult procedure typically requiring the skills of an anesthesiologist. In 1865 as a direct result of the criminal reputation chloroform had gained, medical journal The Lancet
The Lancet
offered a "permanent scientific reputation" to anyone who could demonstrate "instantaneous insensibility" using chloroform.[41] Safety[edit] Exposure[edit] Chloroform
Chloroform
is known to form as a by-product of water chlorination along with a range of other disinfection by-products and as such is commonly present in municipal tap water and swimming pools. Reported ranges vary considerably but are generally below the current health standard for total trihalomethanes of 100μg/l.[42] Nonetheless the presence of chloroform in drinking water at any concentration is considered controversial by some.[citation needed] Historically chloroform exposure may well have been higher due its common use as an anesthetic, as an ingredient in cough syrups, and as a constituent of tobacco smoke where p,p'-DDT had previously been used as a fumigant.[43] Pharmacology[edit] It is well absorbed, metabolized, and eliminated rapidly by mammals after oral, inhalation, or dermal exposure. Accidental splashing into the eyes has caused irritation.[7] Prolonged dermal exposure can result in the development of sores as a result of defatting. Elimination is primarily from lungs in the form of chloroform and carbon dioxide; less than 1% is excreted in urine.[24] Chloroform
Chloroform
is metabolized in the liver by the cytochrome P-450 enzymes, by oxidation to chloromethanol and by reduction to the dichloromethyl free radical. Other metabolites of chloroform include hydrochloric acid and digluathionyl dithiocarbonate, with carbon dioxide as the predominant end product of metabolism.[44] Chloroform
Chloroform
causes depression of the central nervous system (CNS), ultimately producing deep coma and respiratory center depression.[44] When ingested, chloroform caused symptoms similar to those seen following inhalation. Serious illness has followed ingestion of 7.5 g (0.26 oz). The mean lethal oral dose for an adult is estimated to be about 45 g (1.6 oz).[7] The anesthetic use of chloroform has been discontinued because it caused deaths due to respiratory failure and cardiac arrhythmias. Following chloroform-induced anesthesia, some patients suffered nausea, vomiting, hyperthermia, jaundice, and coma due to hepatic dysfunction. At autopsy, liver necrosis and degeneration have been observed.[7] Chloroform
Chloroform
has induced liver tumors in mice and kidney tumors in mice and rats.[7] The hepatotoxicity and nephrotoxicity of chloroform is thought to be due largely to phosgene.[44] Conversion to phosgene[edit] During prolonged storage in the presence of oxygen, chloroform converts slowly to phosgene (COCl2), releasing HCl
HCl
in the process.[45]

2 CHCl3 + O2 → 2 COCl2 + 2 HCl

To prevent accidents, commercial chloroform is stabilized with ethanol or amylene, but samples that have been recovered or dried no longer contain any stabilizer. Amylene has been found ineffective, and the phosgene can affect analytes in samples, lipids, and nucleic acids dissolved in or extracted with chloroform.[46] Phosgene
Phosgene
and HCl
HCl
can be removed from chloroform by washing with saturated aqueous carbonate solutions, such as sodium bicarbonate. This procedure is simple and results in harmless products. Phosgene
Phosgene
reacts with water to form carbon dioxide and HCl,[47] and the carbonate salt neutralizes the resulting acid. Suspected samples can be tested for phosgene using filter paper (treated with 5% diphenylamine, 5% dimethylaminobenzaldehyde in ethanol, and then dried), which turns yellow in phosgene vapor. There are several colorimetric and fluorometric reagents for phosgene, and it can also be quantified with mass spectrometry. Regulation[edit] It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[48] References[edit]

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 661. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The retained names ‘bromoform’ for HCBr3, ‘chloroform’ for HCCl3, and ‘iodoform’ for HCI3 are acceptable in general nomenclature. Preferred IUPAC names are substitutive names.  ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0127". National Institute for Occupational Safety and Health (NIOSH).  ^ a b "Chloroform". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).  ^ a b c d e f Rossberg, M.; et al. (2005), "Chlorinated Hydrocarbons", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a06_233.pub2  ^ Gribble, Gordon W. (2004). "Natural Organohalogens: A New Frontier for Medicinal Agents?". Journal of Chemical Education. 81 (10): 1441. Bibcode:2004JChEd..81.1441G. doi:10.1021/ed081p1441.  ^ Cappelletti, M. (2012). "Microbial degradation of chloroform". Applied Microbiology and Biotechnology. 96 (6): 1936. doi:10.1007/s00253-012-4494-1.  ^ a b c d e f Chloroform
Chloroform
(PDF), CICAD, 58, World Health Organization, 2004  ^ Moldenhawer (1830). "Verfahren den Spiritus von dem Fuselöl auf leichte Weise zu befreien" [Procedure for freeing ethanol of fusel oil in an easy way]. Magazin für Pharmacie. 8 (31): 222–227.  ^ Defalque, Ray J.; Wright, A. J. (2000). "Was chloroform produced before 1831?". Anesthesiology. 92 (1): 290–291. doi:10.1097/00000542-200001000-00060. PMID 10638939.  ^ Guthrie, Samuel (1832). "New mode of preparing a spirituous solution of chloric ether". The American Journal of Science and Arts. 21: 64–65 and 405–408.  ^ Guthrie, Ossian (1887). Memoirs of Dr. Samuel Guthrie, and the History of the Discovery of Chloroform. Chicago: George K. Hazlitt & Co.  ^ Stratmann, Linda (2003). "Chapter 2". Chloroform: The Quest for Oblivion. Stroud: Sutton Publishing. ISBN 9780752499314.  ^ Liebig, Justus von (1831). "Ueber die Zersetzung des Alkohols durch Chlor" [On the decomposition of alcohol by chlorine]. Annalen der Physik und Chemie. 99 (11): 444. Bibcode:1831AnP....99..444L. doi:10.1002/andp.18310991111.  ^ Liebig, Justus von (1832). "Ueber die Verbindungen, welche durch die Einwirkung des Chlors auf Alkohol, Aether, ölbildendes Gas
Gas
und Essiggeist entstehen" [On the compounds which arise by the reaction of chlorine with alcohol, ether, oil-forming gas, and spirit of vinegar]. Annalen der Physik und Chemie. 100 (2): 243–295. Bibcode:1832AnP...100..243L. doi:10.1002/andp.18321000206.  On pages 259–265, Liebig describes Chlorkohlenstoff ("carbon chloride", chloroform), but on p. 264, Liebig incorrectly states that the empirical formula of chloroform is C2Cl5. ^ Soubeiran, Eugène (1831). "Recherches sur quelques combinaisons du chlore" [Investigations into some compounds of chlorine]. Annales de Chemie et de Physique (série II). 48: 113–157. 

Reprinted in Soubeiran, Eugène (1831). "Recherches sur quelques combinaisons du chlore" [Investigations on some compounds of chlorine]. Journal de pharmacie et des sciences accessoires. 17: 657–672.  Reprinted in Soubeiran, Eugène (1832). "Suite des recherches sur quelques combinaisons du chlore" [Continuation of investigations on some compounds of chlorine]. Journal de pharmacie et des sciences accessoires. 18: 1–24. 

^ Dumas, J.-B. (1834). "Récherches rélative à l'action du chlore sur l'alcool" [Experiments regarding the action of chlorine on alcohol]. L'Institut, journal général des sociétés et travaux scientifiques de la France et de l'étranger. 2: 106–108 and 112–115. 

Reprinted in Dumas, J.-B. (1834). "Untersuchung über die Wirkung des Chlors auf den Alkohol" [Investigation of the action of chlorine on alcohol]. Annalen der Physik und Chemie. 107 (42): 657–673. Bibcode:1834AnP...107..657D. doi:10.1002/andp.18341074202.  On p. 653, Dumas states chloroform's empirical formula:

"Es scheint mir also erweisen, dass die von mir analysirte Substance, … zur Formel hat: C2H2Cl6." (Thus it seems to me to show that the substance [that was] analyzed by me … has as [its empirical] formula: C2H2Cl6.) [Note: The coefficients of his empirical formula must be halved.]

Dumas then notes that chloroform's simple empirical formula resembles that of formic acid. Furthermore, if chloroform is boiled with potassium hydroxide, one of the products is potassium formate. On p. 654, Dumas names chloroform:

"Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen." (This caused me to bestow this substance with the name "chloroform" [i.e., formyl chloride or chloride of formic acid].)

Reprinted in Dumas, J.-B. (1835). "Ueber die Wirkung des Chlors auf den Alkohol" [On the action of chlorine on alcohol]. Annalen der Pharmacie. 16 (2): 164–171. doi:10.1002/jlac.18350160213. 

^ a b Defalque, R. J.; Wright, A. J. (2004). "The short, tragic life of Robert M. Glover" (PDF). Anaesthesia. 59 (4): 394–400. doi:10.1111/j.1365-2044.2004.03671.x. PMID 15023112.  ^ "Sir James Young Simpson". Encyclopædia Britannica. Retrieved 23 August 2013.  ^ Breuer, F. W (1935). "Chloroform-d (Deuteriochloroform)1". Journal of the American Chemical Society. 57 (11): 2236–2237. doi:10.1021/ja01314a058.  ^ Kluger, Ronald (1964). "A Convenient Preparation of Chloroform-d1". The Journal of Organic Chemistry. 29 (7): 2045–2046. doi:10.1021/jo01030a526.  ^ Süss, Hans Ulrich (2005), "Bleaching", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH  ^ Wiley, G. R.; Miller, S. I. (1972). "Thermodynamic parameters for hydrogen bonding of chloroform with Lewis bases in cyclohexane. Proton magnetic resonance study". Journal of the American Chemical Society. 94 (10): 3287–3293. doi:10.1021/ja00765a001.  ^ Kwak, K.; Rosenfeld, D. E.; Chung, J. K.; Fayer, M. D. (2008). "Solute-solvent complex switching dynamics of chloroform between acetone and dimethylsulfoxide-two-dimensional IR chemical exchange spectroscopy". The Journal of Physical Chemistry B. 112 (44): 13906–13915. doi:10.1021/jp806035w. PMC 2646412 . PMID 18855462.  ^ a b Leikin, Jerrold B.; Paloucek, Frank P., eds. (2008). "Chloroform". Poisoning and Toxicology Handbook (4th ed.). Informa. p. 774.  ^ Srebnik, M.; Laloë, E. (2001). "Chloroform". Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis. Wiley. doi:10.1002/047084289X.rc105. ISBN 0471936235.  ^ Vogel, E.; Klug, W.; Breuer (1988). "1,6-Methano[10]annulene". Organic Syntheses. ; Collective Volume, 6, p. 731  ^ Gokel, G. W.; Widera, R. P.; Weber, W. P. (1988). "Phase-Transfer Hofmann Carbylamine Reaction: tert-Butyl Isocyanide". Organic Syntheses. ; Collective Volume, 6, p. 232  ^ Gordon, H. Laing (November 2002). Sir James Young Simpson
James Young Simpson
and Chloroform
Chloroform
(1811–1870). Minerva Group. pp. 106–109. ISBN 978-1-4102-0291-8. Retrieved 11 November 2011.  ^ Dingwall (April 2004). "A pioneering history: dentistry and the Royal College of Surgeons of Edinburgh" (PDF). historyofdentistry.co.uk. Archived from the original (PDF) on 1 February 2013.  ^ https://www.royalsoced.org.uk/cms/files/research_awards/prizes/prize_lists/gunning_victoria_history.pdf ^ "Anesthesia and Queen Victoria". ph.ucla.edu. Retrieved 13 August 2012.  ^ Martin, William (3 July 1886). "A Case of Chloroform
Chloroform
Poisoning; Recovery". British Medical Journal. 2 (1331): 16–17. doi:10.1136/bmj.2.1331.16-a. PMC 2257365 . PMID 20751619.  ^ Patel, Amanda J.; Honoré, Eric; Lesage, Florian; Fink, Michel; Romey, Georges; Lazdunski, Michel (May 1999). "Inhalational anesthetics activate two-pore-domain background K+ channels". Nature Neuroscience. 2 (5): 422–426. doi:10.1038/8084. PMID 10321245.  ^ Knight, Paul R., III; Bacon, Douglas R. (2002). "An Unexplained Death: Hannah Greener and Chloroform". Anesthesiology. 96 (5): 1250–1253. doi:10.1097/00000542-200205000-00030. PMID 11981167.  ^ Snow, John (1858). "On Chloroform
Chloroform
and Other Anaesthetics and Their Action and Administration". pp. 82–85.  ^ Wawersik, J. (1997). "History of chloroform anesthesia". Anesthesiology and Reanimation. 22 (6): 144–152. PMID 9487785.  ^ "Knock-out and Chloroform". The Philadelphia Record. 9 February 1894. Retrieved 31 March 2011.  ^ " Chloroform
Chloroform
case retrial underway". Record-Journal. 7 July 1993. Retrieved 31 March 2011.  ^ "Man admits to raping friends' daughters". USA Today. 6 November 2007. Retrieved 31 March 2011.  ^ Payne, J. P. (July 1998). "The criminal use of chloroform". Anaesthesia. 53 (7): 685–690. doi:10.1046/j.1365-2044.1998.528-az0572.x.  ^ "Medical Annotation: Chloroform
Chloroform
amongst Thieves". The Lancet. 2 (2200): 490–491. 1865. doi:10.1016/s0140-6736(02)58434-8.  ^ Nieuwenhuijsen, MJ; Toledano, MB; Elliott, P (8 August 2000). "Uptake of chlorination disinfection by-products; a review and a discussion of its implications for exposure assessment in epidemiological studies". Journal of exposure analysis and environmental epidemiology. 10 (6 Pt 1): 586–99. doi:10.1038/sj.jea.7500139. PMID 11140442.  ^ Yin-Tak Woo, David Y. Lai, Joseph C. Arcos Aliphatic and Polyhalogenated Carcinogens: Structural Bases and Biological ^ a b c Fan, Anna M. (2005). "Chloroform". Encyclopedia of Toxicology. 1 (2nd ed.). Elsevier. pp. 561–565.  ^ " Chloroform
Chloroform
and Phosgene, Chemical Hygiene and Safety". Earlham College. Retrieved 17 August 2017.  ^ Turk, Eric (2 March 1998). " Phosgene
Phosgene
from Chloroform". Chemical & Engineering News. 76 (9): 6. doi:10.1021/cen-v076n009.p006.  ^ "phosgene (chemical compound)". Encyclopædia Britannica. Retrieved 16 August 2013.  ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved 29 October 2011. 

External links[edit]

Wikimedia Commons has media related to Chloroform.

Chloroform
Chloroform
"The Molecular Lifesaver" An article at Oxford University providing facts about chloroform. Concise International Chemical Assessment Document 58 IARC Summaries & Evaluations: Vol. 1 (1972), Vol. 20 (1979), Suppl. 7 (1987), Vol. 73 (1999) International Chemical Safety Card 0027 "NIOSH Pocket Guide to Chemical Hazards #0127". National Institute for Occupational Safety and Health (NIOSH).  NIST Standard Reference Database Story on Chloroform
Chloroform
from BBC's The Material World (28 July 2005) Sudden Sniffer's Death Syndrome article at Carolinas Poison Center Calculation of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of chloroform ChemSub Online: Chloroform
Chloroform
– Methane, trichloro-

v t e

Halomethanes

Monosubstituted

CH3F CH3Cl CH3Br CH3I

Disubstituted

CH2F2 CH2ClF CH2BrF CH2FI CH2Cl2 CH2BrCl CH2ClI CH2Br2 CH2BrI CH2I2

Trisubstituted

CHF3 CHClF2 CHBrF2 CHF2I CHCl2F C*HBrClF C*HClFI CHBr2F C*HBrFI CHFI2 CHCl3 CHBrCl2 CHCl2I CHBr2Cl C*HBrClI CHClI2 CHBr3 CHBr2I CHBrI2 CHI3

Tetrasubstituted

CF4 CClF3 CBrF3 CF3I CCl2F2 CBrClF2 CClF2I CBr2F2 CBrF2I CF2I2 CCl3F CBrCl2F CCl2FI CBr2ClF C*BrClFI CClFI2 CBr3F CBr2FI CBrFI2 CFI3 CCl4 CBrCl3 CCl3I CBr2Cl2 CBrCl2I CCl2I2 CBr3Cl CBr2ClI CBrClI2 CClI3 CBr4 CBr3I CBr2I2 CBrI3 CI4 CAt4

* Chiral compound.

v t e

General anesthetics (N01A)

Inhalational

Chloroethane
Chloroethane
(ethyl chloride)‡ Chloroform‡ Cyclopropane‡ Desflurane Diethyl ether‡ Enflurane Ethylene‡ Fluroxene‡ Halothane# Isoflurane# Methoxyflurane Methoxypropane‡ Nitrous oxide# Sevoflurane Trichloroethylene‡ Vinyl ether‡ Xenon

Injection

Phenols

Fospropofol Propofol#

Opioids

Morphine Oxycodone Anileridine‡ Embutramide‡ Fentanyl Alfentanil Phenoperidine Remifentanil÷ Sufentanil

Arylcyclohexylamines

Esketamine Ketamine# Phencyclidine‡ Tiletamine

Neuroactive steroids

Alfadolone Alfaxalone Hydroxydione

Others

Propanidid‡

#WHO-EM ‡Withdrawn from market Clinical trials:

†Phase III §Never to phase III

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

Pharmacodynamics

v t e

GABAA receptor
GABAA receptor
positive modulators

Alcohols

Brometone Butanol Chloralodol Chlorobutanol
Chlorobutanol
(cloretone) Ethanol
Ethanol
(alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol

Barbiturates

(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital

Benzodiazepines

2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam
Triflunordazepam
(Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam

Carbamates

Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate

Flavonoids

6-Methylapigenin Ampelopsin
Ampelopsin
(dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin

Imidazoles

Etomidate Metomidate Propoxate

Kava
Kava
constituents

10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin

Monoureides

Acecarbromal Apronal
Apronal
(apronalide) Bromisoval Carbromal Capuride Ectylurea

Neuroactive steroids

Acebrochol Allopregnanolone
Allopregnanolone
(brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Pregnanolone
Pregnanolone
(eltanolone) Progesterone Renanolone SAGE-105 SAGE-217 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC

Nonbenzodiazepines

β-Carbolines: Abecarnil Gedocarnil Harmane SL-651,498 ZK-93423

Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone

Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem

Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon

Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil
Lirequinil
(Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684

Phenols

Fospropofol Propofol Thymol

Piperidinediones

Glutethimide Methyprylon Piperidione Pyrithyldione

Pyrazolopyridines

Cartazolate Etazolate ICI-190,622 Tracazolate

Quinazolinones

Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164

Volatiles/gases

Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral
Chloral
betaine Chloral
Chloral
hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether

Others/unsorted

3-Hydroxybutanal α-EMTBL AA-29504 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate
Menthyl isovalerate
(validolum) Monastrol Niacin Nicotinamide
Nicotinamide
(niacinamide) Org 25,435 Phenytoin Propanidid Retigabine
Retigabine
(ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)

Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205

See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

v t e

Ionotropic glutamate receptor
Ionotropic glutamate receptor
modulators

AMPAR

Agonists: Main site agonists: 5-Fluorowillardiine Acromelic acid (acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam Cyclothiazide CX-516 CX-546 CX-614 Farampator
Farampator
(CX-691, ORG-24448) CX-717 CX-1739 CX-1942 Diazoxide Hydrochlorothiazide
Hydrochlorothiazide
(HCTZ) IDRA-21 LY-392098 LY-395153 LY-404187 LY-451646 LY-503430 Mibampator
Mibampator
(LY-451395) Nooglutyl ORG-26576 Oxiracetam PEPA PF-04958242 Piracetam Pramiracetam S-18986 Tulrampator
Tulrampator
(S-47445, CX-1632)

Antagonists: ACEA-1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel
Fanapanel
(MPQX) GAMS Kaitocephalin Kynurenic acid Kynurenine Licostinel
Licostinel
(ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates
Barbiturates
(e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol
Ethanol
(alcohol) Evans blue GYKI-52466 GYKI-53655 Halothane Irampanel Isoflurane Perampanel Pregnenolone
Pregnenolone
sulfate Sevoflurane Talampanel; Unknown/unsorted antagonists: Minocycline

KAR

Agonists: Main site agonists: 5-Bromowillardiine 5-Iodowillardiine Acromelic acid (acromelate) AMPA ATPA Domoic acid Glutamate Ibotenic acid Kainic acid LY-339434 Proline Quisqualic acid SYM-2081; Positive allosteric modulators: Cyclothiazide Diazoxide Enflurane Halothane Isoflurane

Antagonists: ACEA-1011 CNQX Dasolampanel DNQX GAMS Kaitocephalin Kynurenic acid Licostinel
Licostinel
(ACEA-1021) LY-382884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302; Negative allosteric modulators: Barbiturates
Barbiturates
(e.g., pentobarbital, sodium thiopental) Enflurane Ethanol
Ethanol
(alcohol) Evans blue NS-3763 Pregnenolone
Pregnenolone
sulfate

NMDAR

Agonists: Main site agonists: AMAA Aspartate Glutamate Homocysteic acid
Homocysteic acid
(L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine; Glycine
Glycine
site agonists: β-Fluoro-D-alanine ACBD ACC (ACPC) ACPD AK-51 Apimostinel
Apimostinel
(NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine Milacemide Neboglamine
Neboglamine
(nebostinel) Rapastinel
Rapastinel
(GLYX-13) Sarcosine; Polyamine site agonists: Neomycin Spermidine Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol DHEA (prasterone) DHEA sulfate
DHEA sulfate
(prasterone sulfate) Epipregnanolone sulfate Pregnenolone
Pregnenolone
sulfate SAGE-201 SAGE-301 SAGE-718

Antagonists: Competitive antagonists: AP5
AP5
(APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP Kaitocephalin LY-233053 LY-235959 LY-274614 MDL-100453 Midafotel
Midafotel
(d-CPPene) NPC-12626 NPC-17742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel; Glycine
Glycine
site antagonists: 4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC ACEA-1011 ACEA-1328 Apimostinel
Apimostinel
(NRX-1074) AV-101 Carisoprodol CGP-39653 CNQX D-Cycloserine DNQX Felbamate Gavestinel GV-196771 Harkoseride Kynurenic acid Kynurenine L-689560 L-701324 Licostinel
Licostinel
(ACEA-1021) LU-73068 MDL-105519 Meprobamate MRZ 2/576 PNQX Rapastinel
Rapastinel
(GLYX-13) ZD-9379; Polyamine site antagonists: Arcaine Co 101676 Diaminopropane Diethylenetriamine Huperzine A Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Alazocine
Alazocine
(SKF-10047) Amantadine Aptiganel Argiotoxin-636 Arketamine ARL-12495 ARL-15896-AR ARL-16247 Budipine Coronaridine Delucemine
Delucemine
(NPS-1506) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan Levomilnacipran Levorphanol Loperamide Memantine Methadone Methorphan Methoxetamine Methoxphenidine Milnacipran Morphanol NEFA Neramexane Nitromemantine Noribogaine Norketamine Orphenadrine PCPr PD-137889 Pethidine
Pethidine
(meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol; Ifenprodil (NR2B) site antagonists: Besonprodil Buphenine
Buphenine
(nylidrin) CO-101244 (PD-174494) Eliprodil Haloperidol Isoxsuprine Radiprodil (RGH-896) Rislenemdaz
Rislenemdaz
(CERC-301, MK-0657) Ro 8-4304 Ro 25-6981 Safaprodil Traxoprodil
Traxoprodil
(CP-101606); NR2A-selective antagonists: MPX-004 MPX-007 TCN-201 TCN-213; Cations: Hydrogen Magnesium Zinc; Alcohols/volatile anesthetics/related: Benzene Butane Chloroform Cyclopropane Desflurane Diethyl ether Enflurane Ethanol
Ethanol
(alcohol) Halothane Hexanol Isoflurane Methoxyflurane Nitrous oxide Octanol Sevoflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Urethane Xenon Xylene; Unknown/unsorted antagonists: ARR-15896 Bumetanide Caroverine Conantokin D-αAA Dexanabinol Flufenamic acid Flupirtine FPL-12495 FR-115427 Furosemide Hodgkinsine Ipenoxazone (MLV-6976) MDL-27266 Metaphit Minocycline MPEP Niflumic acid Pentamidine Pentamidine
Pentamidine
isethionate Piretanide Psychotridine Transcrocetin
Transcrocetin
(saffron)

See also: Receptor/signaling modulators Metabotropic glutamate receptor modulators Glutamate
Glutamate
metabolism/transport modulators

v t e

Glycine
Glycine
receptor modulators

Receptor (ligands)

GlyR

Agonists: β-Alanine β-ABA (BABA) β-AIBA Caesium D-Alanine D-Serine GABA Glycine Hypotaurine Ivermectin L-Alanine L-Proline L-Serine L-Threonine MDL-27531 Milacemide Picolinic acid Propofol Quisqualamine Sarcosine Taurine

Positive modulators: Alcohols (e.g., brometone, chlorobutanol (chloretone), ethanol (alcohol), tert-butanol (2M2P), tribromoethanol, trichloroethanol, trifluoroethanol) Alkylbenzene sulfonate Anandamide Barbiturates
Barbiturates
(e.g., pentobarbital, sodium thiopental) Chlormethiazole D12-116 Dihydropyridines (e.g., nicardipine) Etomidate Ginseng
Ginseng
constituents (e.g., ginsenosides (e.g., ginsenoside-Rf)) Glutamic acid
Glutamic acid
(glutamate) Ivermectin Ketamine Neuroactive steroids (e.g., alfaxolone, pregnenolone (eltanolone), pregnenolone acetate, minaxolone, ORG-20599) Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g., atropine, bemesetron, cocaine, LY-278584, tropisetron, zatosetron) Volatiles/gases (e.g., chloral hydrate, chloroform, desflurane, diethyl ether (ether), enflurane, halothane, isoflurane, methoxyflurane, sevoflurane, toluene, trichloroethane (methyl chloroform), trichloroethylene) Xenon Zinc

Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol
Gaboxadol
(THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g., 4-hydroxyquinoline, 4-hydroxyquinoline-3-carboxylic acid, 5,7-CIQA, 7-CIQ, 7-TFQ, 7-TFQA) RU-5135 Sinomenine Strychnine Thiocolchicoside Tutin

Negative modulators: Amiloride Benzodiazepines (e.g., bromazepam, clonazepam, diazepam, flunitrazepam, flurazepam) Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g., nicardipine, nifedipine, nitrendipine) Furosemide Genistein Ginkgo constituents (e.g., bilobalide, ginkgolides (e.g., ginkgolide A, ginkgolide B, ginkgolide C, ginkgolide J, ginkgolide M)) Imipramine NBQX Neuroactive steroids (e.g., 3α-androsterone sulfate, 3β-androsterone sulfate, deoxycorticosterone, DHEA sulfate, pregnenolone sulfate, progesterone) Opioids (e.g., codeine, dextromethorphan, dextrorphan, levomethadone, levorphanol, morphine, oripavine, pethidine, thebaine) Picrotoxin
Picrotoxin
(i.e., picrotin and picrotoxinin) PMBA Riluzole Tropeines (e.g., bemesetron, LY-278584, tropisetron, zatosetron) Verapamil Zinc

NMDAR

See here instead.

Transporter (blockers)

GlyT1

ACPPB ALX-1393 ALX-5407 (NFPS) AMG-747 ASP2535 Bitopertin
Bitopertin
(RG1678/RO4917838) CP-802079 Ethanol
Ethanol
(alcohol) Glycyldodecylamide GSK1018921 LY-2365109 ORG-24598 ORG-25935
ORG-25935
(SCH-900435) PF-02545920 PF-03463275 PF-04958242 Sarcosine SSR-103,800 SSR-504,734

GlyT2

Amoxapine Ethanol
Ethanol
(alcohol) NAGly Opiranserin (VVZ-149) ORG-25543 VVZ-368

See also Receptor/signaling modulators GABA receptor modulators GABAA receptor
GABAA receptor
positive modulators Ionotropic glutamate receptor
Ionotropic glutamate receptor
modulators

v t e

Chloroform
Chloroform
committees and commissions

1847

( Chloroform
Chloroform
first used)

Antique bottles of chloroform

1864

Chloroform
Chloroform
Committee

Royal Medico-Chirurgical Society

See also: Clover bag

1877

The Glasgow Committee on Anæsthetics

British Medical Association

1888

First Hyderabad Commissions

Surgeon-Major Lawrie of the Bengal Medical Service
Bengal Medical Service
appointed by the Nizam: Mahbub Ali Khan, Asaf Jah VI

See also: Lawrie's Apparatus

1889

Second Hyderabad Commission (Surgeon-Major Lawrie with T. Lauder Brunton FRS of St. Bartholomew's Hospital)

1891

British Medical Association
British Medical Association
Anæsthetics Committee

British Medical Association

1893

The Lancet
The Lancet
commissioned Dudley Buxton to implement a questionnaire to report deaths, the method of induction and the clinical stance of chloroform.

1901

The Special
Special
Chloroform Committee
Chloroform Committee
of the British Medical Association

British Medical Association

1912

American Medical Association
American Medical Association
Committee on Anæsthesia (American Medical Association) - ban chloroform

The list shown in this table is referenced.to view its references see: Template: Chloroform
Chloroform
committees and commissions.

Authority control

LCCN: sh85024563 GN

.

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