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Chloral hydrate

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1178:. However, chloral hydrate products, licensed for short-term management of severe insomnia, are available in the United Kingdom. Chloral hydrate was voluntarily removed from the market by all manufacturers in the United States in 2012. Prior to that, chloral hydrate may have been sold as a "legacy" or "grandfathered" drug;" that is, a drug that existed prior to the time certain FDA regulations took effect and therefore, some pharmaceutical companies have argued, has never required FDA approval. New drugs did not have to be approved for safety until Congress passed the Federal Food, Drug, and Cosmetic Act (the "FD&C Act") in 1938. Further, a new drug did not have to be proven effective until 1962, when Congress amended the Act. Manufacturers contend that such "legacy drugs", by virtue of the fact that they have been prescribed for decades, have gained a history of safety and efficacy. 474: 323: 42: 99: 1734:. However, chloral hydrate was quite polar but nonetheless a potent hypnotic. Overton was unable to explain this mystery. Thus, chloral hydrate remained one of the major and persistent exceptions to this breakthrough discovery in pharmacology. This anomaly was eventually resolved in 1948, when Claude Bernard's experiment was repeated. While chloral hydrate was converted to a different metabolite than chloroform, it was found that it was converted into the more 897: 1583:, a pharmaceutical developed during the 1950s that was marketed as both a sedative and a hypnotic under the trade name Placidyl. In 1999, Abbott, the sole manufacturer of the drug in the United States at the time, decided to discontinue the product. After Abbott ceased production, the drug remained available for about a year. Despite the fact that it could have been manufactured generically, no other company in the United States chose to do so. 892: 1277: 33: 3922: 1858:
She put out her hand and measured the soothing drops into a glass; but as she did so, she knew they would be powerless against the supernatural lucidity of her brain. She had long since raised the dose to its highest limit, but to-night she felt she must increase it. She knew she took a slight risk
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family, chloral hydrate began to disappear from use among those with means. It remained common in asylums and hospitals until the Second World War as it was quite cheap. Chloral hydrate had some other important advantages that kept it in use for five decades despite the existence of more advanced
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began experiments on animals, followed by humans. While a state of general anesthesia could be achieved, the technique never caught on because its administration was more complex and less safe than the oral administration of chloral hydrate, and less safe for intravenous use than later general
1694:. It was the safest available sedative until the middle of the twentieth century, and thus was particularly favored for children. It also left patients much more refreshed after a deep sleep than more recently invented sedatives. Its frequency of use made it an early and regular feature in 2568: 1389:
for 4-hour exposure of 440 mg/m. Long-term use of chloral hydrate is associated with a rapid development of tolerance to its effects and possible addiction as well as adverse effects including rashes, gastric discomfort and severe kidney, heart, and liver failure.
1877:(1853–1910) used the drug for a period after 1893 to relieve what may have been a mix of depression and unspecified illnesses. He was reported by his doctor to have been taking one bottle per day during July 1894 although this was reduced after this time. 1421:
concentrations of chloral hydrate and/or trichloroethanol, its major active metabolite, may be measured to confirm a diagnosis of poisoning in hospitalized patients or to aid in the forensic investigation of fatalities. Accidental
1778:(better known by their original brand names Nembutal and Seconal, respectively) were synthesized. Chloral hydrate was still prescribed, although its predominance as a sedative and a hypnotic was largely eclipsed by barbiturates. 1742:. This metabolite fit much better with the Meyer–Overton correlation than chloral had. Prior to this, it had not been demonstrated that general anesthetics could undergo chemical changes to exert their action in the body. 905: 872: 1969:(1933–2015) abused chloral hydrate in 1965 as a depressed insomniac. He found himself taking fifteen times the usual dose of chloral hydrate every night before he eventually ran out, causing violent withdrawal symptoms. 1949:(1844–1900) regularly used chloral hydrate in the years leading up to his nervous breakdown, according to Lou Salome and other associates. Whether the drug contributed to his insanity is a point of controversy. 1963:
overdose in 1862. He had a mental breakdown in 1872. He lived out the last ten years of his life addicted to chloral and alcohol, in part to mask the pain of botched surgery to an enlarged testicle in 1877.
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in Germany in the 1870s. Over time it was replaced by safer and more effective alternatives but it remained in usage in the United States until at least the 1970s. It sometimes finds usage as a laboratory
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Because of its status as a regulated substance, chloral hydrate can be difficult to obtain. This has led to chloral hydrate being replaced by alternative reagents in microscopy procedures.
1997:, is largely a fictionalised account of an episode Waugh himself experienced as a result of excessive use of chloral in combination with bromide and alcohol. Waugh's friend and biographer 967: 1677:
and the homes of those socially refined enough to avoid asylums. Upper- and middle-class women, well-represented in the latter category, were particularly susceptible to chloral hydrate
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Chloral hydrate is soluble in both water and ethanol, readily forming concentrated solutions. A solution of chloral hydrate in ethanol called "knockout drops" was used to prepare a
8204: 717: 9362: 9128: 8172: 3954: 2828: 1523:, which is responsible for secondary physiological and psychological effects. The metabolite of chloral hydrate exerts its pharmacological properties via enhancing the 5726: 5564: 2433: 1174:
and is on the FDA list of unapproved drugs that are still prescribed by clinicians. Usage of the drug as a sedative or hypnotic may carry some risk given the lack of
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o' Nolan, Daniel; Perry, Miranda L.; Zaworotko, Michael J. (2016). "Chloral Hydrate Polymorphs and Cocrystal Revisited: Solving Two Pharmaceutical Cold Cases".
1340: 836: 5580: 1840:! I should be careful not to let it grow into a habit. No I shall take none to-night! I have thought of Lucy, and I shall not dishonor her by mixing the two. 523: 9351: 5557: 1715:
in the body but also the first to measure the concentration of a particular pharmaceutical in the blood. The results were inconclusive. In 1899 and 1901
2005:'s demise under the effects of excessive use of chloral in his 1928 biography of the artist "is a fairly exact description of how life ended in 1966". 8197: 1197:
but is not considered acceptable for anesthesia or euthanasia of small animals due to adverse effects. It is also still used as a sedative prior to
7920: 2963: 2908:"Rising incidence of hospital-reported drug-facilitated sexual assault in a large urban community in Canada. Retrospective population-based study" 1991:(1903–1966), insomniac for much of his adult life, for which "in later life ... he became so deleteriously dependent on chloral". Waugh's novel, 3734: 1283:
Moreover, chloral hydrate is used as a reagent for the deprotection of acetals, dithioacetals and tetrahydropyranyl ethers in organic solvents.
3894: 2541:"Chloral Hydrate as a Water Carrier for the Efficient Deprotection of Acetals, Dithioacetals, and Tetrahydropyranyl Ethers in Organic Solvents" 1724: 3947: 3904: 3668: 3637: 3552: 2668:"Pyrrole Alkaloids with Potential Cancer Chemopreventive Activity Isolated from a Goji Berry-Contaminated Commercial Sample of African Mango" 2197: 2137: 8827: 1430:
has been used successfully to accelerate clearance of the drug in poisoning victims. It is listed as having a "conditional risk" of causing
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Chloral hydrate is a starting point for the synthesis of other organic compounds. It is the starting material for the production of
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Das Chloralhydrat : ein neues Hypnoticum und Anaestheticum und dessen Anwendung in der Medicin; eine Arzneimittel-Untersuchung
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Gauillard, J.; Cheref, S.; Vacherontrystram, M. N.; J. C., Martin (May–June 2002). "Chloral hydrate: a hypnotic best forgotten?".
3940: 1287: 1889:(1869–1951) was given chloral hydrate as a boy for sleep problems by a physician named Lizart. Gide states in his autobiography 2753: 1155: 821: 3033:"Ueber die Verbindungen, welche durch die Einwirkung des Chlors auf Alkohol, Aether, ölbildendes Gas und Essiggeist entstehen" 2826:
Jira, Reinhard; Kopp, Erwin; McKusick, Blaine C.; Röderer, Gerhard; Bosch, Axel; Fleischmann, Gerald. "Chloroacetaldehydes".
1658:, manufactured and marketed by the German pharmaceutical industry. Historically, chloral hydrate was utilized primarily as a 9067: 2801: 2058:
per litre (μg/L) but concentrations are normally found to be below 10 μg/L. Levels are generally found to be higher in
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Kales, Anthony (1 September 1970). "Hypnotic Drugs and Their Effectiveness: All-night EEG Studies of Insomniac Subjects".
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began to promote its use to calm anxiety, especially when it caused insomnia. Chloral hydrate had certain advantages over
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and clearing (macerating) properties of small specimens (especially advantageous if specimens require observation with
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Chloral hydrate was routinely administered in gram quantities. Prolonged exposure to its vapors is unhealthy, with an
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I cannot but think of Lucy, and how different things might have been. If I don't sleep at once, chloral, the modern
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and as a sedative before minor medical or dental treatment. It was largely displaced in the mid-20th century by
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Chloral hydrate was also a significant object of study in various early pharmacological experiments. In 1875,
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in doing so; she remembered the chemist's warning. If sleep came at all, it might be a sleep without waking.
1374:. Whether tissue or spores react to this reagent is vital for the correct identification of some mushrooms. 738: 5430: 3035:[On compounds that arise by the reaction of chlorine with alcohol, oil-forming gas , and acetone]. 1901:(1842–1910), psychologist and philosopher, used the drug for insomnia and sedation due to chronic neurosis. 318: 9434: 8993: 8899: 8783: 8709: 8586: 8422: 8262: 5766: 5317: 5256: 5070: 4030: 2002: 1952: 1739: 1659: 1540: 1489: 1198: 1138: 789: 41: 8773: 6872: 6857: 1208:
In therapeutic doses for insomnia, chloral hydrate is effective within 20 to 60 minutes. In humans it is
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McGregor, M. J.; Ericksen, J.; Ronald, L. A.; Janssen, P. A.; Van Vliet, A.; Schulzer, M. (2004).
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Meadows, Michelle (January–February 2007). "The FDA Takes Action Against Unapproved Drugs".
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for this application, as it worked quickly without injection and had a consistent strength.
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tried to determine if chloral hydrate exerted its action through a metabolic conversion to
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and requires a physician's prescription. Its properties have sometimes led to its use as a
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Li, J.; Pan, L.; Naman, C. B.; Deng, Y.; Chai, H.; Keller, W. J.; Kinghorn, A. D. (2014).
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in 1832 at the University of Giessen. Liebig discovered the molecule when a chlorination (
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Vardanyan, R.S.; Hruby, V.J. (2006). "Soporific Agents (Hypnotics and Sedative Drugs)".
1933:, became addicted in the years after her husband's death and was committed to an asylum. 1034: 473: 322: 240: 9296: 9198: 8868: 8788: 8622: 8397: 8355: 8119: 7948: 7857: 7724: 7719: 7143: 6031: 5936: 5811: 5776: 5771: 5657: 5622: 5243: 5171: 5057: 4968: 4918: 4862: 4833: 4822: 4806: 4702: 4183: 4128: 4025: 4010: 3980: 3347: 3322: 3112:
Butler, Thomas C. (1970). "The Introduction of Chloral Hydrate into Medical Practice".
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Baxter, Mark G.; Murphy, Kathy L.; Taylor, Polly M.; Wolfensohn, Sarah E. (July 2009).
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Chloral Hydrate: A new hypnotic and anaesthetic and its use in medicine; A drug study
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Gawron, O.; Draus, F. (1958). "Kinetic Evidence for Reaction of Chloralate Ion with
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are present. It has been detected in drinking water at concentrations of up to 100
2043: 1988: 1982: 1966: 1920: 1775: 1623: 1536: 1427: 1410: 1276: 1090: 947: 728: 723: 8257: 3456: 2837: 2776: 2556: 2365: 2349:"Chloral Hydrate Is Not Acceptable for Anesthesia or Euthanasia of Small Animals" 2348: 394: 9306: 9223: 9089: 9031: 9023: 8913: 8768: 8689: 8679: 8626: 8576: 8475: 8460: 8432: 8303: 8134: 8069: 8064: 8034: 8014: 7769: 7749: 7699: 7522: 7504: 7499: 7489: 7466: 7461: 7428: 7350: 7191: 7158: 7148: 7004: 6988: 6892: 6775: 6692: 6672: 6662: 6632: 6597: 6549: 6539: 6499: 6494: 6469: 6454: 6414: 6404: 6339: 6309: 6259: 6204: 6179: 6159: 6154: 6119: 6016: 5971: 5926: 5906: 5871: 5846: 5741: 5718: 5642: 5612: 5523: 5467: 5462: 5418: 5392: 5350: 5327: 5312: 5271: 5217: 5085: 5031: 4981: 4948: 4933: 4893: 4754: 4749: 4744: 4615: 4597: 4587: 4516: 4496: 4458: 4334: 4271: 4266: 4211: 4196: 4168: 4133: 4118: 4053: 4040: 4005: 2512: 2476:"NTP Technical Report on the Toxicity and Metabolism Studies of Chloral Hydrate" 2051: 1802: 1789: 1691: 1686: 1655: 1426:
of young children undergoing simple dental or surgical procedures has occurred.
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and trichloroethanol glucuronide by erythrocytes and plasma esterases and into
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procedures, as it is one of the few available sedatives that does not suppress
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Takahashi, Yasuo; Onodera, Sukeo; Morita, Masatoshi; Terao, Yoshiyasu (2003).
2085: 2039: 1908: 1810: 1735: 1731: 1712: 1708: 1497: 1493: 1398: 1328: 1209: 775: 704: 640: 567: 271: 32: 3932: 3395: 3299: 3264: 3229: 3194: 3048: 3005: 2374: 1606:," originally referred specifically to adding chloral hydrate to a person's ( 933: 9291: 9248: 9233: 9228: 9099: 9043: 9039: 8932: 8863: 8803: 8743: 8738: 8704: 8614: 8610: 8551: 8541: 8520: 8466: 8370: 8337: 8092: 8044: 8039: 8024: 7982: 7977: 7935: 7930: 7925: 7883: 7779: 7764: 7704: 7689: 7674: 7494: 7405: 7360: 7325: 7315: 7285: 7280: 7265: 7239: 7201: 7196: 7173: 7168: 7153: 7059: 7054: 6935: 6813: 6803: 6795: 6730: 6707: 6687: 6682: 6652: 6637: 6607: 6589: 6579: 6574: 6569: 6564: 6544: 6529: 6524: 6514: 6509: 6504: 6474: 6449: 6399: 6384: 6379: 6364: 6349: 6329: 6324: 6314: 6304: 6299: 6294: 6214: 6209: 6184: 6114: 6094: 6064: 5986: 5921: 5851: 5841: 5806: 5703: 5607: 5528: 5322: 5212: 5179: 5114: 5026: 4991: 4943: 4786: 4739: 4546: 4531: 4521: 4511: 4420: 4382: 4372: 4364: 4349: 4306: 4296: 4291: 4261: 4216: 4153: 4088: 3098: 2603: 2312:
Tariq, Syed H.; Pulisetty, Shailaja (2008). "Pharmacotherapy for Insomnia".
2189: 2055: 1904: 1678: 1651: 1320: 1308: 1249: 1244:, which is produced by the distillation of a mixture of chloral hydrate and 1059: 810: 441: 3403: 3356: 3307: 2941: 2892: 2734:(8th ed.). Foster City, CA: Biomedical Publications. pp. 259–261. 2701: 2652: 2460: 2382: 2333: 2264: 3921: 3243:
Cuadrado, Fernando F.; Alston, Theodore A. (October 2016). "Book Review".
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Chloral hydrate was used as one of the earliest synthetic drugs to treat
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A History of Psychiatry: From the era of the asylum to the age of Prozac
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Alston, Theodore A. (July 2016). "Noteworthy Chemistry of Chloroform".
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that "all my later weaknesses of will or memory I attribute to him."
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Except where otherwise noted, data are given for materials in their
3858:"Summary statement - 12.20 Chloral hydrate (trichloroacetaldehyde)" 3586:
Gone from the Promised Land: Jonestown in American Cultural History
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Before Prozac: The troubled history of mood disorders in psychiatry
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Chloral hydrate is also an ingredient used for Hoyer's solution, a
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Villani, Thomas S.; Koroch, Adolfina R.; Simon, James E. (2013).
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Mohammed M.S. Jan, MBChB, FRCP (C); Marilou F. Aquino, EEG Tech.
1654:. It was the first of a long line of sedatives, most notably the 9104: 8976: 8649: 6823: 4000: 2398:"The use of chloral hydrate in pediatric electroencephalography" 1406: 1324: 1316: 1312: 991: 588: 360: 8186: 5553: 3936: 1638:
in 1861, but described in detail and published only in 1869 by
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making this drug difficult to use. Higher doses can depress
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for microscopic observation of diverse plant types such as
1232:. Tolerance to the drug develops after a few days of use. 1939:(1926–1962) died from an overdose of chloral hydrate and 1181:
Chloral hydrate was used for the short-term treatment of
3372:"A History of Intravenous Anesthesia in War (1656–1988)" 2011:(1923–1953) died from a combination of chloral hydrate, 1193:. It was also formerly used in veterinary medicine as a 843: 830: 816:
Bile, feces, urine (various metabolites not unchanged)
9115: 5373: 2992:[On the degradation of alcohol by chlorine]. 1618:
Chloral hydrate was first synthesized by the chemist
9272: 9159: 9142: 9113: 8240: 8223: 7808: 7576: 7513: 7480: 7447: 7419: 7133: 6954: 6911: 6822: 6794: 6706: 6588: 6030: 5717: 5593: 5411: 5364: 5336: 5303: 5283: 5229: 5170: 5158: 5101: 5043: 4967: 4904: 4892: 4821: 4669: 4606: 4573: 4555: 4487: 4434: 4391: 4363: 4305: 4182: 4039: 3991: 3979: 2863:"Sleep circuitry and the hypnotic mechanism of GABA 1267:to give a condensation product which cyclicizes in 1745:Chloral hydrate was the first hypnotic to be used 623:98 °C (208 °F; 371 K) (decomposes) 8132:Unsorted benzodiazepine site positive modulators: 3432:. Drug Enforcement Administration. Archived from 2025:(1877-1909), a prominent lesbian poet during the 1286:The compound can be crystallized in a variety of 1259:. In this synthesis, chloral hydrate reacts with 3846:. West Virginia Division of Culture and History. 3509:"HM King Chulalongkorn's 1897 Journey to Europe" 3168: 3166: 3164: 1979:" with chloral hydrate as the "major component". 393: 3074: 3072: 3070: 2990:"Ueber die Zersetzung des Alkohols durch Chlor" 2732:Disposition of Toxic Drugs and Chemicals in Man 1723:respectively made the major discovery that the 1662:. In 1869, German physician and pharmacologist 1137:(trichloroacetaldehyde) by the addition of one 183: 3370:Roberts, Matthew; Jagdish, S. (January 2016). 2829:Ullmann's Encyclopedia of Industrial Chemistry 2719:(3rd ed.). New York: Oxford. p. 238. 2211: 2209: 2029:, abused chloral hydrate for much of her life. 1555:symptoms. The chemical can potentiate various 1527:complex and therefore is similar in action to 1354:Chloral hydrate is an ingredient used to make 1335:. An advantage of this medium includes a high 9395:GABAA receptor positive allosteric modulators 9274: 9161: 8198: 5565: 4977:Serotonin antagonists and reuptake inhibitors 3948: 1575:Chloral hydrate is structurally and somewhat 1341:differential interference contrast microscopy 1154:Chloral hydrate has not been approved by the 8: 3511:. Archived from the original on 1 March 2021 2432:: CS1 maint: multiple names: authors list ( 1770:under the brand name Luminal. In the 1930s, 1362:that is used to identify certain species of 5581: 5366: 2485:. National Toxicology Program. p. 10. 2157:-Nitrophenyl Acetate in Aqueous Solution". 1591:In the United States, chloral hydrate is a 1393:Acute overdosage is often characterized by 9156: 8237: 8205: 8191: 8183: 5572: 5558: 5550: 5167: 4901: 3988: 3955: 3941: 3933: 3735:"Smith died from accidental drug overdose" 3176:The Worst of Evils: The fight against pain 2715:Gelder, M.; Mayou, R.; Geddes, J. (2005). 2672:Journal of Agricultural and Food Chemistry 1907:in 1978 involved the communal drinking of 472: 321: 279: 20: 3757:. Oxford: Oxford University Press. 1999. 3346: 2931: 2882: 2795: 2691: 2642: 2539:Chandrasekhar, S.; Shrinidhi, A. (2014). 2364: 1727:of a drug was strongly correlated to its 497:InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H 429: 9363:Ionotropic glutamate receptor modulators 8242: 3543:Brando, Marlon; Lindsey, Robert (1994). 2159:Journal of the American Chemical Society 1929:(1818–1882), wife of American president 1831: 1827: 1610:) drink without the person's knowledge. 1476: 1472: 1468: 1464: 1460: 1456: 1116: 1101: 558: 554: 507:InChI=1/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H 3589:. Transaction Publishers. p. 282. 2112: 2050:of water when organic residues such as 1673:The compound achieved wide use in both 1646:clarified that the chloral hydrate was 528: 493: 468: 299: 3522: 2425: 312: 9385:Acetaldehyde dehydrogenase inhibitors 9120:Tooltip N-Methyl-D-aspartate receptor 3896:Crossroads: A Southern Culture Annual 3829: 3817: 3715:from the original on 5 September 2015 2756:from the original on 16 November 2018 2571:from the original on 20 February 2022 2186:CRC Handbook of Chemistry and Physics 2001:observed that Waugh's description of 1766:. In 1912, Bayer introduced the drug 1220:in 4 to 5 days. It has a very narrow 613:57 °C (135 °F; 330 K) 500:Key: RNFNDJAIBTYOQL-UHFFFAOYSA-N 259: 239: 7: 8812:4-hydroxyquinoline-3-carboxylic acid 8670:4-Phenyl-4-formyl-N-methylpiperidine 8173:GABA metabolism/transport modulators 3870:from the original on 21 October 2013 3625:Marilyn: The Passion and the Paradox 2511:Marvel, C. S.; Hiers, G. S. (1941). 2492:from the original on 23 October 2011 2230:10.1001/archpsyc.1970.01750030034006 727: 8635:trichloroethane (methyl chloroform) 7790:Trichloroethane (methyl chloroform) 3782:. Sinclair-Stevenson. p. 140. 3410:from the original on 29 August 2021 3114:Bulletin of the History of Medicine 2289:. Electronic Medicines Compendium. 1488:takes place and chloral hydrate is 510:Key: RNFNDJAIBTYOQL-UHFFFAOYAY 384: 368: 16:Chemical sedative and hypnotic drug 9239:Pesampator (BIIB-104, PF-04958242) 6853:11-Methoxy-12-hydroxydehydrokavain 3603:from the original on 12 March 2020 2966:from the original on 23 March 2021 2871:Journal of Clinical Sleep Medicine 2807:from the original on 22 March 2021 2746:"CredibleMeds :: Quicksearch" 1905:The Jonestown mass murder-suicides 1749:as a general anesthetic. In 1871, 1255:Notably, it is used to synthesize 1133:and precursor. It is derived from 14: 7600:Acetylglycinamide chloral hydrate 4682:Acetylglycinamide chloral hydrate 3489:from the original on 18 July 2018 3455:Stoker, Bram (28 February 1897). 2912:Canadian Journal of Public Health 2293:from the original on 7 March 2018 1442:Chloral hydrate is produced from 1327:). Other ingredients may include 128:Trichloroacetaldehyde monohydrate 3920: 3703:Sacks, Oliver (27 August 2012). 3659:. Cooper Square Press. pp.  3055:from the original on 28 May 2020 3012:from the original on 27 May 2020 2483:Toxicity Report Series Number 59 2130:10.1016/B978-044452166-8/50004-2 1801:, one of its characters, Doctor 1401:, slow and irregular breathing, 1275: 895: 890: 97: 8020:Menthyl isovalerate (validolum) 3461:. New York Grosset & Dunlap 1513:Chloral hydrate is metabolized 1298: 1071:(at 25 °C , 100 kPa). 6969:Allopregnanolone (brexanolone) 3497:– via www.gutenberg.org. 3327:Bulletin of Anesthesia History 3321:Krasowski, Matthew D. (2003). 2623:Applications in Plant Sciences 2218:Archives of General Psychiatry 1754:anesthetics were found to be. 1681:. After the 1904 invention of 116:2,2,2-Trichloroethane-1,1-diol 1: 9338:Receptor/signaling modulators 9279:Tooltip Glycine transporter 2 9189:Bitopertin (RG1678/RO4917838) 9166:Tooltip Glycine transporter 1 8165:Receptor/signaling modulators 6721:Ampelopsin (dihydromyricetin) 3863:. World Health Organization. 3807:. Penguin Books. p. 124. 3656:Marilyn Monroe: The Biography 3469:– via Internet Archive. 3376:Journal of Anesthesia History 3339:10.1016/s1522-8649(03)50031-2 3280:Journal of Anesthesia History 3245:Journal of Anesthesia History 2861:Lu, J.; Greco, M. A. (2006). 2838:10.1002/14356007.a06_527.pub2 2314:Clinics in Geriatric Medicine 2287:"EMC Search: chloral hydrate" 1994:The Ordeal of Gilbert Pinfold 1271:to give the target compound: 839:(Other controlled substances) 9356:receptor positive modulators 7915:ergoloid (dihydroergotoxine) 7000:anabolic-androgenic steroids 5782:Butabarbital/Secbutabarbital 5587:receptor positive modulators 3570:If It Die...An Autobiography 2557:10.1080/00397911.2013.876652 2366:10.1097/aln.0b013e3181a8617e 2122:Synthesis of Essential Drugs 1883:(1920–1966), American actor. 1634:properties were observed by 1626:) reaction was performed on 1366:. The other ingredients are 6555:Triflunordazepam (Ro5-2904) 5208:Tetracyclic antidepressants 5022:Tetracyclic antidepressants 3899:. Mercer University Press. 3844:Hank's Lost Charleston Show 3803:Sykes, Christopher (1977). 3214:. Oxford University Press. 2592:Crystal Growth & Design 1805:, recorded his use and his 1005:or concentration (LD, LC): 27: 9461: 8394:chlorobutanol (chloretone) 6883:5,6,7,8-Tetrahydroyangonin 3754:A Dictionary of scientists 3547:. New York: Random House. 3388:10.1016/j.janh.2015.10.007 3292:10.1016/j.janh.2016.04.008 3257:10.1016/j.janh.2016.01.004 2527:, vol. 1, p. 327 2326:10.1016/j.cger.2007.08.009 1977:combined drug intoxication 1725:general anaesthetic action 9445:IARC Group 2A carcinogens 9430:Trichloromethyl compounds 9400:Glycine receptor agonists 9329: 8509:pregnenolone (eltanolone) 8486:Glutamic acid (glutamate) 8158: 7075:Pregnanolone (eltanolone) 5618:Chlorobutanol (cloretone) 5185:Tricyclic antidepressants 4999:Tricyclic antidepressants 3805:Evelyn Waugh: A Biography 3780:Evelyn Waugh: A Biography 3778:Hastings, Selina (1994). 3545:Songs my mother taught me 3529:: CS1 maint: unfit URL ( 3179:. Yale University Press. 3173:Dormandy, Thomas (2006). 3147:Liebreich, Oskar (1869). 2784:Journal of Health Science 2184:Lide, D. R., ed. (2005). 1120:. It was first used as a 1065: 1040: 1001: 871: 866: 753: 710: 691: 593:Aromatic, slightly acrid 539: 519: 484: 167: 122: 110: 105: 96: 26: 9345:GABA receptor modulators 8247:Tooltip Glycine receptor 8169:GABA receptor modulators 8079:sulfonmethane (sulfonal) 4770:Sulfonmethane (sulfonal) 3208:Shorter, Edward (2009). 3079:Shorter, Edward (1998). 3049:10.1002/jlac.18320010203 3006:10.1002/jlac.18320010109 2545:Synthetic Communications 1484:In basic conditions the 942:Precautionary statements 8990:3β-androsterone sulfate 8986:3α-androsterone sulfate 5257:Atypical antipsychotics 5071:Atypical antipsychotics 3628:. Bloomsbury. pp.  2960:The New York Daily News 2832:. Weinheim: Wiley-VCH. 2604:10.1021/acs.cgd.6b00032 1539:. It can be moderately 1397:, vomiting, confusion, 1349: 1299:Hoyer's mounting medium 9234:ORG-25935 (SCH-900435) 8423:Alkylbenzene sulfonate 8055:Retigabine (ezogabine) 7331:Lirequinil (Ro41-3696) 6898:7,8-Dihydromethysticin 6888:5,6-Dehydromethysticin 5767:Benzylbutylbarbiturate 5431:Chlorophenylalkyldiols 5239:Typical antipsychotics 5053:Typical antipsychotics 3653:Spoto, Donald (2001). 3583:Hall, John R. (1987). 3157:]. Berlin: Müller. 3031:Justus Liebig (1832). 2956:"Attacked by the Gang" 1953:Dante Gabriel Rossetti 1861: 1842: 1740:2,2,2-trichloroethanol 1660:psychiatric medication 1547:use is known to cause 1248:, which serves as the 45: 36: 9307:Opiranserin (VVZ-149) 8607:diethyl ether (ether) 3684:Cate, Curtis (2005). 3622:Banner, Lois (2012). 3037:Annalen der Pharmacie 2994:Annalen der Pharmacie 2474:Beland, Frederick A. 2253:FDA Consumer Magazine 2038:It is, together with 1975:(1967–2007) died of " 1856: 1844:In the conclusion of 1818: 1450:in acidic solution. 44: 35: 9002:pregnenolone sulfate 8982:Neuroactive steroids 8940:constituents (e.g., 8900:Cyanotriphenylborate 8861:Negative modulators: 8784:N,N-Dimethylmuscimol 8710:Cyanotriphenylborate 8547:Tetrahydrocannabinol 8513:pregnenolone acetate 8501:Neuroactive steroids 8474:constituents (e.g., 8383:Positive modulators: 8110:constituents (e.g., 7894:Deuterated etifoxine 6956:Neuroactive steroids 6926:Apronal (apronalide) 6778:constituents (e.g., 6395:N-Desalkylflurazepam 5388:Gabapentin enacarbil 4436:Neuroactive steroids 4406:Apronal (apronalide) 3929:at Wikimedia Commons 2635:10.3732/apps.1300016 2091:Disulfiram-like drug 1596:controlled substance 1236:In organic synthesis 1218:trichloroacetic acid 1212:within 7 hours into 1189:and subsequently by 799:Biological half-life 112:Preferred IUPAC name 8994:deoxycorticosterone 8774:N-Methylbicuculline 7903:dihydroergocryptine 7215:Pyrazolopyrimidines 6873:5,6-Dihydroyangonin 6858:7,8-Dihydroyangonin 6045:3-Hydroxyphenazepam 5887:Methylphenobarbital 3893:Olson, Ted (2004). 3686:Friedrich Nietzsche 2962:. 25 October 2008. 2730:Baselt, R. (2008). 2455:(3 Pt 1): 200–204. 2171:10.1021/ja01553a018 2076:Chloral cyanohydrin 1947:Friedrich Nietzsche 1915:, chloral hydrate, 1758:Society and culture 1685:, the first of the 1577:pharmacodynamically 1432:torsades de pointes 1294:Botany and mycology 746:Oral syrup, rectal 630:Solubility in water 575: g·mol 221:Beilstein Reference 23: 9204:Glycyldodecylamide 8808:4-hydroxyquinoline 8779:N-Methylstrychnine 7997:4-O-methylhonokiol 7660:Dichloralphenazone 7558:Methylmethaqualone 7135:Nonbenzodiazepines 6848:Desmethoxyyangonin 6843:11-Hydroxyyangonin 6838:11-Methoxyyangonin 6833:10-Methoxyyangonin 6220:Ethyl carfluzepate 5822:Cyclopentobarbital 5453:Diethylpropanediol 4735:Dichloralphenazone 4651:Methylmethaqualone 4489:Nonbenzodiazepines 4016:Diethylpropanediol 3690:The Overlook Press 2924:10.1007/BF03403990 2884:10.5664/jcsm.26527 2124:. pp. 57–68. 1851:The House of Mirth 1751:Pierre-Cyprien Oré 1533:nonbenzodiazepines 1403:cardiac arrhythmia 1222:therapeutic window 1195:general anesthetic 1172:medical indication 1075:Infobox references 1041:Related compounds 1023:1100 mg/kg (oral) 847:: Unscheduled 46: 37: 21: 9372: 9371: 9325: 9324: 9297:Ethanol (alcohol) 9199:Ethanol (alcohol) 9153: 9138: 9137: 8759:Isonipecotic acid 8665:2-Nitrostrychnine 8660:2-Aminostrychnine 8639:trichloroethylene 8441:sodium thiopental 8398:ethanol (alcohol) 8340: 8332: 8324: 8316: 8288: 8280: 8234: 8180: 8179: 8140:MRK-409 (MK-0343) 7911:dihydroergotamine 7854:potassium bromide 7848:compounds (e.g., 7795:Trichloroethylene 7563:Nitromethaqualone 7482:Pyrazolopyridines 6984:3α-Androstanediol 6878:7,8-Dihydrokavain 6230:Ethyl loflazepate 6007:Thiotetrabarbital 5623:Ethanol (alcohol) 5547: 5546: 5299: 5298: 5097: 5096: 4817: 4816: 4698:Potassium bromide 4656:Nitromethaqualone 4164:Thiotetrabarbital 4011:Ethanol (alcohol) 3925:Media related to 3906:978-0-86554-866-4 3741:on 31 March 2007. 3688:. Woodstock, NY: 3670:978-0-8154-1183-3 3639:978-1-40883-133-5 3553:978-0-09-943691-1 3430:"Chloral Hydrate" 2684:10.1021/jf500802x 2678:(22): 5054–5060. 2551:(13): 1904–1913. 2525:Collected Volumes 2518:Organic Syntheses 2414:on 18 August 2011 2199:978-0-8493-0484-2 2192:. pp. 3–98. 2188:(85th ed.). 2165:(20): 5392–5394. 2139:978-0-444-52166-8 1999:Christopher Sykes 1973:Anna Nicole Smith 1927:Mary Todd Lincoln 1807:molecular formula 1650:as opposed to an 1620:Justus von Liebig 1604:slipping a mickey 1486:haloform reaction 1083:Chemical compound 1081: 1080: 1047:Related compounds 1029:Safety data sheet 920:Hazard statements 855: 846: 834: 699:Crystal structure 453:CompTox Dashboard 209:Interactive image 153:Novo-Chlorhydrate 92: 91: 9452: 9280: 9276: 9167: 9163: 9157: 9147: 9121: 9117: 9020:dextromethorphan 8910:Dihydropyridines 8849:Thiocolchicoside 8799:Pseudostrychnine 8739:Gaboxadol (THIP) 8733:anandamide (AEA) 8725:Endocannabinoids 8457:Dihydropyridines 8417:trifluoroethanol 8413:trichloroethanol 8338: 8330: 8322: 8314: 8286: 8278: 8248: 8244: 8238: 8228: 8214:Glycine receptor 8207: 8200: 8193: 8184: 7899:Dihydroergolines 7816:3-Hydroxybutanal 7449:Piperidinediones 7182:Imidazopyridines 6716:6-Methylapigenin 6648:Hydroxyphenamate 6520:SH-053-R-CH3-2′F 6225:Ethyl dirazepate 6105:Chlordiazepoxide 5997:Thiobutabarbital 5709:Trifluoroethanol 5699:Trichloroethanol 5689:-Pentanol (2M2B) 5583: 5574: 5567: 5560: 5551: 5472:muscle relaxants 5375: 5372: 5168: 4902: 4839:4-Fluorophenibut 4575:Piperidinediones 4449:Allopregnanolone 4031:Trichloroethanol 3989: 3957: 3950: 3943: 3934: 3924: 3910: 3880: 3879: 3877: 3875: 3869: 3862: 3854: 3848: 3847: 3839: 3833: 3827: 3821: 3815: 3809: 3808: 3800: 3794: 3793: 3775: 3769: 3768: 3749: 3743: 3742: 3737:. Archived from 3731: 3725: 3724: 3722: 3720: 3705:"Altered States" 3700: 3694: 3693: 3681: 3675: 3674: 3650: 3644: 3643: 3619: 3613: 3612: 3610: 3608: 3580: 3574: 3573: 3562: 3556: 3541: 3535: 3534: 3528: 3520: 3518: 3516: 3505: 3499: 3498: 3496: 3494: 3477: 3471: 3470: 3468: 3466: 3452: 3446: 3445: 3443: 3441: 3426: 3420: 3419: 3417: 3415: 3367: 3361: 3360: 3350: 3318: 3312: 3311: 3275: 3269: 3268: 3240: 3234: 3233: 3205: 3199: 3198: 3170: 3159: 3158: 3144: 3138: 3137: 3109: 3103: 3102: 3076: 3065: 3064: 3062: 3060: 3028: 3022: 3021: 3019: 3017: 2982: 2976: 2975: 2973: 2971: 2952: 2946: 2945: 2935: 2903: 2897: 2896: 2886: 2858: 2852: 2851: 2823: 2817: 2816: 2814: 2812: 2806: 2799: 2797:10.1248/jhs.49.1 2781: 2772: 2766: 2765: 2763: 2761: 2750:Crediblemeds.org 2742: 2736: 2735: 2727: 2721: 2720: 2712: 2706: 2705: 2695: 2663: 2657: 2656: 2646: 2614: 2608: 2607: 2598:(4): 2211–2217. 2587: 2581: 2580: 2578: 2576: 2536: 2530: 2528: 2521: 2508: 2502: 2501: 2499: 2497: 2491: 2480: 2471: 2465: 2464: 2444: 2438: 2437: 2431: 2423: 2421: 2419: 2413: 2407:. Archived from 2402: 2393: 2387: 2386: 2368: 2344: 2338: 2337: 2309: 2303: 2302: 2300: 2298: 2283: 2277: 2276: 2248: 2242: 2241: 2213: 2204: 2203: 2181: 2175: 2174: 2150: 2144: 2143: 2117: 2096:Trichloroethanol 1957:Elizabeth Siddal 1881:Montgomery Clift 1839: 1794:epistolary novel 1717:Hans Horst Meyer 1697:The Merck Manual 1521:trichloroethanol 1509:Pharmacodynamics 1480: 1368:potassium iodide 1360:aqueous solution 1356:Melzer's reagent 1350:Melzer's reagent 1337:refractive index 1279: 1214:trichloroethanol 1131:chemical reagent 1119: 997: 993: 989: 985: 981: 977: 973: 969: 965: 961: 957: 953: 949: 935: 931: 927: 899: 894: 853: 850: 845: 842: 832: 829: 790:trichloroethanol 755:Pharmacokinetics 731: 645:Very soluble in 583:Colorless solid 574: 561: 547:Chemical formula 531:ClC(Cl)(Cl)C(O)O 477: 476: 461: 459: 433: 397: 386: 372: 350:Gmelin Reference 333: 325: 314: 303: 283: 263: 243: 211: 187: 101: 81: 71: 61: 51: 28: 24: 22:Chloral hydrate 9460: 9459: 9455: 9454: 9453: 9451: 9450: 9449: 9420:Organochlorides 9375: 9374: 9373: 9368: 9355: 9321: 9278: 9268: 9179:ALX-5407 (NFPS) 9165: 9146: 9134: 9119: 9109: 8869:Benzodiazepines 8754:Isobutyric acid 8595:chloral hydrate 8447:Chlormethiazole 8409:tribromoethanol 8405:-butanol (2M2P) 8246: 8227: 8219: 8211: 8181: 8176: 8154: 8112:isovaleric acid 8075:Sulfonylalkanes 7973:Hopantenic acid 7957:tolfenamic acid 7945:flufenamic acid 7907:dihydroergosine 7850:lithium bromide 7809:Others/unsorted 7804: 7665:Dichloromethane 7640:Chloral hydrate 7635:Chloral betaine 7572: 7509: 7476: 7443: 7415: 7144:Cyclopyrrolones 7129: 7035:Etiocholanolone 6950: 6907: 6868:5-Hydroxykavain 6818: 6790: 6702: 6584: 6032:Benzodiazepines 6026: 5837:Ethallobarbital 5832:Enallylpropymal 5713: 5694:Tribromoethanol 5681:-Butanol (2M2P) 5627:alcoholic drink 5589: 5586: 5578: 5548: 5543: 5407: 5370: 5360: 5332: 5295: 5279: 5225: 5172:Antidepressants 5163: 5154: 5125:Dexmedetomidine 5106: 5093: 5039: 4969:Antidepressants 4963: 4924:Diphenhydramine 4897: 4888: 4826: 4813: 4802:Isovaleric acid 4765:Sulfonylalkanes 4720:Chloral hydrate 4715:Chloral betaine 4693:Lithium bromide 4665: 4602: 4569: 4551: 4483: 4430: 4387: 4359: 4301: 4184:Benzodiazepines 4178: 4084:Ethallobarbital 4035: 3984: 3975: 3961: 3927:Chloral hydrate 3917: 3907: 3892: 3884: 3883: 3873: 3871: 3867: 3860: 3856: 3855: 3851: 3841: 3840: 3836: 3828: 3824: 3816: 3812: 3802: 3801: 3797: 3790: 3777: 3776: 3772: 3765: 3751: 3750: 3746: 3733: 3732: 3728: 3718: 3716: 3702: 3701: 3697: 3683: 3682: 3678: 3671: 3652: 3651: 3647: 3640: 3621: 3620: 3616: 3606: 3604: 3597: 3582: 3581: 3577: 3564: 3563: 3559: 3542: 3538: 3521: 3514: 3512: 3507: 3506: 3502: 3492: 3490: 3479: 3478: 3474: 3464: 3462: 3454: 3453: 3449: 3439: 3437: 3428: 3427: 3423: 3413: 3411: 3369: 3368: 3364: 3320: 3319: 3315: 3277: 3276: 3272: 3242: 3241: 3237: 3222: 3207: 3206: 3202: 3187: 3172: 3171: 3162: 3146: 3145: 3141: 3111: 3110: 3106: 3091: 3078: 3077: 3068: 3058: 3056: 3030: 3029: 3025: 3015: 3013: 2984: 2983: 2979: 2969: 2967: 2954: 2953: 2949: 2905: 2904: 2900: 2866: 2860: 2859: 2855: 2848: 2825: 2824: 2820: 2810: 2808: 2804: 2779: 2774: 2773: 2769: 2759: 2757: 2744: 2743: 2739: 2729: 2728: 2724: 2714: 2713: 2709: 2665: 2664: 2660: 2616: 2615: 2611: 2589: 2588: 2584: 2574: 2572: 2538: 2537: 2533: 2523: 2510: 2509: 2505: 2495: 2493: 2489: 2478: 2473: 2472: 2468: 2446: 2445: 2441: 2424: 2417: 2415: 2411: 2400: 2395: 2394: 2390: 2346: 2345: 2341: 2311: 2310: 2306: 2296: 2294: 2285: 2284: 2280: 2250: 2249: 2245: 2215: 2214: 2207: 2200: 2183: 2182: 2178: 2152: 2151: 2147: 2140: 2119: 2118: 2114: 2104: 2072: 2036: 1931:Abraham Lincoln 1866: 1837: 1833: 1829: 1825: 1760: 1664:Oscar Liebreich 1640:Oscar Liebreich 1636:Rudolf Buchheim 1616: 1602:. The phrase, " 1589: 1529:benzodiazepines 1511: 1506: 1478: 1474: 1470: 1466: 1462: 1458: 1454: 1440: 1387: 1380: 1352: 1305:mounting medium 1301: 1296: 1238: 1191:benzodiazepines 1176:clinical trials 1152: 1147: 1118: 1103: 1097: 1087:Chloral hydrate 1084: 1077: 1072: 1048: 1020: 1014: 944: 922: 908: 887: 862: 813: 801: 778: 766: 764:Bioavailability 743: 740: 720: 701: 683: 635:660 g/(100 ml) 632: 572: 560: 556: 552: 549: 535: 532: 527: 526: 515: 512: 511: 508: 502: 501: 498: 492: 491: 480: 462: 455: 436: 416: 400: 387: 375: 352: 343: 306: 286: 266: 246: 223: 214: 201: 190: 177: 163: 162: 132:Chlorali hydras 118: 117: 88: 87: 79: 77: 69: 67: 59: 57: 49: 17: 12: 11: 5: 9458: 9456: 9448: 9447: 9442: 9437: 9432: 9427: 9422: 9417: 9412: 9407: 9402: 9397: 9392: 9387: 9377: 9376: 9370: 9369: 9367: 9366: 9359: 9353: 9348: 9341: 9334: 9330: 9327: 9326: 9323: 9322: 9320: 9319: 9314: 9309: 9304: 9299: 9294: 9289: 9283: 9281: 9270: 9269: 9267: 9266: 9261: 9256: 9251: 9246: 9241: 9236: 9231: 9226: 9221: 9216: 9211: 9206: 9201: 9196: 9191: 9186: 9181: 9176: 9170: 9168: 9154: 9140: 9139: 9136: 9135: 9133: 9132: 9124: 9122: 9111: 9110: 9108: 9107: 9102: 9097: 9075: 9070: 9065: 9051: 9009: 8979: 8974: 8969: 8935: 8930: 8925: 8907: 8902: 8897: 8892: 8866: 8857: 8856: 8851: 8846: 8841: 8836: 8831: 8801: 8796: 8791: 8789:Nipecotic acid 8786: 8781: 8776: 8771: 8766: 8761: 8756: 8751: 8746: 8741: 8736: 8722: 8717: 8712: 8707: 8702: 8697: 8692: 8687: 8682: 8677: 8672: 8667: 8662: 8653: 8652: 8647: 8642: 8623:methoxyflurane 8584: 8554: 8549: 8544: 8539: 8534: 8529: 8524: 8498: 8493: 8488: 8483: 8480:ginsenoside-Rf 8469: 8464: 8454: 8449: 8444: 8430: 8425: 8420: 8379: 8378: 8373: 8368: 8363: 8358: 8356:Picolinic acid 8353: 8348: 8343: 8335: 8327: 8319: 8311: 8306: 8301: 8296: 8291: 8283: 8275: 8270: 8265: 8260: 8251: 8249: 8235: 8221: 8220: 8212: 8210: 8209: 8202: 8195: 8187: 8178: 8177: 8159: 8156: 8155: 8153: 8152: 8147: 8142: 8137: 8128: 8127: 8120:valerenic acid 8105: 8100: 8090: 8072: 8067: 8062: 8057: 8052: 8047: 8042: 8037: 8032: 8027: 8022: 8017: 8012: 7990: 7985: 7980: 7975: 7970: 7965: 7960: 7949:mefenamic acid 7938: 7933: 7928: 7923: 7918: 7896: 7891: 7886: 7881: 7876: 7871: 7866: 7861: 7858:sodium bromide 7843: 7833: 7828: 7823: 7818: 7812: 7810: 7806: 7805: 7803: 7802: 7797: 7792: 7787: 7782: 7777: 7772: 7767: 7762: 7757: 7752: 7747: 7742: 7737: 7732: 7727: 7725:Methoxypropane 7722: 7720:Methoxyflurane 7717: 7712: 7707: 7702: 7697: 7692: 7687: 7682: 7680:Ethyl chloride 7677: 7672: 7667: 7662: 7657: 7652: 7647: 7642: 7637: 7632: 7627: 7622: 7617: 7612: 7607: 7602: 7597: 7592: 7586: 7584: 7574: 7573: 7571: 7570: 7565: 7560: 7555: 7550: 7545: 7540: 7535: 7530: 7525: 7519: 7517: 7515:Quinazolinones 7511: 7510: 7508: 7507: 7502: 7497: 7492: 7486: 7484: 7478: 7477: 7475: 7474: 7469: 7464: 7459: 7453: 7451: 7445: 7444: 7442: 7441: 7436: 7431: 7425: 7423: 7417: 7416: 7414: 7413: 7408: 7403: 7398: 7393: 7388: 7383: 7378: 7373: 7368: 7363: 7358: 7353: 7348: 7343: 7338: 7333: 7328: 7323: 7318: 7313: 7308: 7303: 7298: 7293: 7288: 7283: 7278: 7273: 7268: 7258: 7257: 7252: 7247: 7242: 7237: 7232: 7227: 7222: 7210: 7209: 7204: 7199: 7194: 7189: 7177: 7176: 7171: 7166: 7161: 7156: 7151: 7139: 7137: 7131: 7130: 7128: 7127: 7122: 7117: 7112: 7107: 7102: 7097: 7092: 7087: 7082: 7077: 7072: 7067: 7062: 7057: 7052: 7047: 7042: 7037: 7032: 7027: 7022: 7017: 7012: 7007: 7002: 6996: 6991: 6986: 6981: 6976: 6971: 6966: 6960: 6958: 6952: 6951: 6949: 6948: 6943: 6938: 6933: 6928: 6923: 6917: 6915: 6909: 6908: 6906: 6905: 6900: 6895: 6890: 6885: 6880: 6875: 6870: 6865: 6860: 6855: 6850: 6845: 6840: 6835: 6829: 6827: 6820: 6819: 6817: 6816: 6811: 6806: 6800: 6798: 6792: 6791: 6789: 6788: 6783: 6773: 6768: 6763: 6758: 6753: 6748: 6743: 6738: 6733: 6728: 6723: 6718: 6712: 6710: 6704: 6703: 6701: 6700: 6695: 6690: 6685: 6680: 6675: 6670: 6665: 6660: 6655: 6650: 6645: 6640: 6635: 6630: 6625: 6620: 6615: 6610: 6605: 6600: 6594: 6592: 6586: 6585: 6583: 6582: 6577: 6572: 6567: 6562: 6557: 6552: 6547: 6542: 6537: 6532: 6527: 6522: 6517: 6512: 6507: 6502: 6497: 6492: 6487: 6482: 6477: 6472: 6467: 6462: 6457: 6452: 6447: 6442: 6437: 6432: 6427: 6422: 6417: 6412: 6407: 6402: 6397: 6392: 6387: 6382: 6377: 6372: 6367: 6362: 6357: 6352: 6347: 6342: 6337: 6332: 6327: 6322: 6317: 6312: 6307: 6302: 6297: 6292: 6287: 6282: 6277: 6272: 6267: 6262: 6257: 6252: 6247: 6242: 6237: 6232: 6227: 6222: 6217: 6212: 6207: 6202: 6197: 6192: 6187: 6182: 6177: 6172: 6167: 6162: 6157: 6152: 6147: 6142: 6137: 6132: 6127: 6122: 6117: 6112: 6107: 6102: 6097: 6092: 6087: 6082: 6077: 6072: 6067: 6062: 6057: 6052: 6047: 6042: 6036: 6034: 6028: 6027: 6025: 6024: 6019: 6014: 6009: 6004: 5999: 5994: 5989: 5984: 5979: 5974: 5969: 5964: 5959: 5954: 5949: 5944: 5939: 5937:Propylbarbital 5934: 5929: 5924: 5919: 5914: 5909: 5904: 5899: 5894: 5889: 5884: 5879: 5874: 5869: 5864: 5859: 5854: 5849: 5844: 5839: 5834: 5829: 5824: 5819: 5814: 5812:Crotylbarbital 5809: 5804: 5799: 5794: 5789: 5784: 5779: 5777:Brophebarbital 5774: 5772:Brallobarbital 5769: 5764: 5759: 5754: 5749: 5744: 5739: 5734: 5729: 5723: 5721: 5715: 5714: 5712: 5711: 5706: 5701: 5696: 5691: 5683: 5675: 5670: 5665: 5660: 5658:Methylpentynol 5655: 5650: 5645: 5640: 5635: 5630: 5620: 5615: 5610: 5605: 5599: 5597: 5591: 5590: 5584: 5579: 5577: 5576: 5569: 5562: 5554: 5545: 5544: 5542: 5541: 5536: 5531: 5526: 5521: 5519:Passion flower 5516: 5506: 5501: 5500: 5499: 5494: 5489: 5484: 5479: 5465: 5460: 5455: 5450: 5449: 5448: 5443: 5438: 5428: 5427: 5426: 5415: 5413: 5409: 5408: 5406: 5405: 5400: 5395: 5390: 5385: 5379: 5377: 5368: 5362: 5361: 5359: 5358: 5353: 5348: 5342: 5340: 5334: 5333: 5331: 5330: 5325: 5320: 5315: 5309: 5307: 5301: 5300: 5297: 5296: 5294: 5293: 5287: 5285: 5281: 5280: 5278: 5277: 5276: 5275: 5269: 5264: 5254: 5253: 5252: 5246: 5244:Chlorpromazine 5235: 5233: 5231:Antipsychotics 5227: 5226: 5224: 5223: 5222: 5221: 5215: 5205: 5204: 5203: 5197: 5192: 5182: 5176: 5174: 5165: 5161: 5156: 5155: 5153: 5152: 5147: 5142: 5137: 5132: 5127: 5122: 5117: 5111: 5109: 5104: 5099: 5098: 5095: 5094: 5092: 5091: 5090: 5089: 5083: 5078: 5068: 5067: 5066: 5060: 5058:Chlorpromazine 5049: 5047: 5045:Antipsychotics 5041: 5040: 5038: 5037: 5036: 5035: 5029: 5019: 5018: 5017: 5011: 5006: 4996: 4995: 4994: 4989: 4984: 4973: 4971: 4965: 4964: 4962: 4961: 4956: 4951: 4946: 4941: 4936: 4931: 4926: 4921: 4919:Cyproheptadine 4916: 4910: 4908: 4906:Antihistamines 4899: 4895: 4890: 4889: 4887: 4886: 4881: 4876: 4871: 4866: 4863:sodium oxybate 4856: 4851: 4846: 4841: 4836: 4834:1,4-Butanediol 4830: 4828: 4824: 4819: 4818: 4815: 4814: 4812: 4811: 4810: 4809: 4807:Valerenic acid 4804: 4799: 4789: 4784: 4783: 4782: 4777: 4772: 4762: 4757: 4752: 4747: 4742: 4737: 4732: 4727: 4722: 4717: 4712: 4707: 4706: 4705: 4703:Sodium bromide 4700: 4695: 4684: 4679: 4673: 4671: 4667: 4666: 4664: 4663: 4658: 4653: 4648: 4643: 4638: 4633: 4628: 4623: 4618: 4612: 4610: 4608:Quinazolinones 4604: 4603: 4601: 4600: 4595: 4590: 4585: 4579: 4577: 4571: 4570: 4568: 4567: 4561: 4559: 4553: 4552: 4550: 4549: 4544: 4539: 4534: 4529: 4524: 4519: 4514: 4509: 4504: 4499: 4493: 4491: 4485: 4484: 4482: 4481: 4476: 4471: 4466: 4461: 4456: 4451: 4446: 4440: 4438: 4432: 4431: 4429: 4428: 4423: 4418: 4413: 4408: 4403: 4397: 4395: 4389: 4388: 4386: 4385: 4380: 4375: 4369: 4367: 4361: 4360: 4358: 4357: 4352: 4347: 4342: 4337: 4332: 4327: 4322: 4317: 4311: 4309: 4303: 4302: 4300: 4299: 4294: 4289: 4284: 4279: 4274: 4269: 4264: 4259: 4254: 4249: 4244: 4239: 4234: 4229: 4224: 4219: 4214: 4209: 4204: 4199: 4194: 4188: 4186: 4180: 4179: 4177: 4176: 4171: 4166: 4161: 4156: 4151: 4146: 4141: 4136: 4131: 4129:Propylbarbital 4126: 4121: 4116: 4111: 4106: 4101: 4096: 4091: 4086: 4081: 4076: 4071: 4066: 4061: 4056: 4051: 4045: 4043: 4037: 4036: 4034: 4033: 4028: 4026:Methylpentynol 4023: 4018: 4013: 4008: 4003: 3997: 3995: 3986: 3982: 3977: 3976: 3962: 3960: 3959: 3952: 3945: 3937: 3931: 3930: 3916: 3915:External links 3913: 3912: 3911: 3905: 3882: 3881: 3849: 3834: 3822: 3810: 3795: 3788: 3770: 3763: 3744: 3726: 3709:The New Yorker 3695: 3692:. p. 453. 3676: 3669: 3645: 3638: 3614: 3595: 3575: 3557: 3536: 3500: 3482:House of Mirth 3472: 3447: 3436:on 11 May 2012 3421: 3362: 3313: 3270: 3251:(4): 153–155. 3235: 3220: 3200: 3186:978-0300113228 3185: 3160: 3139: 3120:(2): 168–172. 3104: 3090:978-0471245315 3089: 3066: 3043:(2): 182–230. 3023: 2986:Liebig, Justus 2977: 2947: 2918:(6): 441–445. 2898: 2877:(2): S19–S26. 2864: 2853: 2847:978-3527306732 2846: 2818: 2767: 2737: 2722: 2707: 2658: 2629:(5): 1300016. 2609: 2582: 2531: 2503: 2466: 2439: 2405:Jcc.kau.edu.sa 2388: 2359:(1): 209–210. 2353:Anesthesiology 2339: 2304: 2278: 2243: 2224:(3): 226–232. 2205: 2198: 2176: 2145: 2138: 2111: 2110: 2103: 2100: 2099: 2098: 2093: 2088: 2083: 2078: 2071: 2068: 2035: 2032: 2031: 2030: 2020: 2006: 2003:D. G. Rossetti 1986: 1980: 1970: 1964: 1950: 1944: 1937:Marilyn Monroe 1934: 1924: 1911:poisoned with 1902: 1896: 1884: 1878: 1865: 1862: 1848:'s 1905 novel 1835: 1759: 1756: 1721:Ernest Overton 1705:Claude Bernard 1644:Claude Bernard 1615: 1612: 1600:date rape drug 1588: 1585: 1559:and is weakly 1557:anticoagulants 1510: 1507: 1505: 1502: 1482: 1481: 1439: 1436: 1385: 1379: 1376: 1351: 1348: 1300: 1297: 1295: 1292: 1281: 1280: 1237: 1234: 1230:blood pressure 1168:European Union 1151: 1148: 1146: 1143: 1082: 1079: 1078: 1073: 1069:standard state 1066: 1063: 1062: 1049: 1046: 1043: 1042: 1038: 1037: 1032: 1025: 1024: 1021: 1012: 1010: 1007: 1006: 999: 998: 968:P305+P351+P338 945: 940: 937: 936: 923: 918: 915: 914: 909: 904: 901: 900: 888: 883: 880: 879: 869: 868: 864: 863: 861: 860: 848: 840: 826: 824: 818: 817: 814: 809: 806: 805: 802: 797: 794: 793: 788:(converted to 779: 774: 771: 770: 769:Well absorbed 767: 762: 759: 758: 751: 750: 744: 741:administration 737: 734: 733: 721: 716: 713: 712: 708: 707: 702: 697: 694: 693: 689: 688: 685: 681: 671: 670: 667: 658: 657: 643: 637: 636: 633: 628: 625: 624: 621: 615: 614: 611: 605: 604: 601: 595: 594: 591: 585: 584: 581: 577: 576: 570: 564: 563: 550: 545: 542: 541: 537: 536: 534: 533: 530: 522: 521: 520: 517: 516: 514: 513: 509: 506: 505: 503: 499: 496: 495: 487: 486: 485: 482: 481: 479: 478: 465: 463: 451: 448: 447: 444: 438: 437: 435: 434: 426: 424: 418: 417: 415: 414: 410: 408: 402: 401: 399: 398: 390: 388: 380: 377: 376: 374: 373: 365: 363: 357: 356: 353: 348: 345: 344: 342: 341: 337: 335: 327: 326: 316: 308: 307: 305: 304: 296: 294: 288: 287: 285: 284: 276: 274: 268: 267: 265: 264: 256: 254: 248: 247: 245: 244: 236: 234: 228: 227: 224: 219: 216: 215: 213: 212: 204: 202: 195: 192: 191: 189: 188: 180: 178: 173: 170: 169: 165: 164: 161: 160: 157: 154: 151: 148: 145: 142: 139: 134: 129: 125: 124: 120: 119: 115: 114: 108: 107: 103: 102: 94: 93: 90: 89: 78: 68: 58: 48: 47: 38: 15: 13: 10: 9: 6: 4: 3: 2: 9457: 9446: 9443: 9441: 9438: 9436: 9435:Geminal diols 9433: 9431: 9428: 9426: 9423: 9421: 9418: 9416: 9413: 9411: 9408: 9406: 9403: 9401: 9398: 9396: 9393: 9391: 9388: 9386: 9383: 9382: 9380: 9365: 9364: 9360: 9358: 9357: 9349: 9347: 9346: 9342: 9340: 9339: 9335: 9332: 9331: 9328: 9318: 9315: 9313: 9310: 9308: 9305: 9303: 9300: 9298: 9295: 9293: 9290: 9288: 9285: 9284: 9282: 9277: 9271: 9265: 9262: 9260: 9257: 9255: 9252: 9250: 9247: 9245: 9242: 9240: 9237: 9235: 9232: 9230: 9227: 9225: 9222: 9220: 9217: 9215: 9212: 9210: 9207: 9205: 9202: 9200: 9197: 9195: 9192: 9190: 9187: 9185: 9182: 9180: 9177: 9175: 9172: 9171: 9169: 9164: 9158: 9155: 9151: 9145: 9141: 9130: 9126: 9125: 9123: 9118: 9112: 9106: 9103: 9101: 9098: 9095: 9091: 9087: 9083: 9079: 9076: 9074: 9071: 9069: 9066: 9063: 9059: 9055: 9052: 9049: 9045: 9041: 9037: 9033: 9029: 9028:levomethadone 9025: 9021: 9017: 9013: 9010: 9007: 9003: 8999: 8995: 8991: 8987: 8983: 8980: 8978: 8975: 8973: 8970: 8967: 8963: 8959: 8955: 8951: 8947: 8943: 8939: 8936: 8934: 8931: 8929: 8926: 8923: 8919: 8915: 8911: 8908: 8906: 8903: 8901: 8898: 8896: 8893: 8890: 8886: 8885:flunitrazepam 8882: 8878: 8874: 8870: 8867: 8865: 8862: 8859: 8858: 8855: 8852: 8850: 8847: 8845: 8842: 8840: 8837: 8835: 8832: 8829: 8825: 8821: 8817: 8813: 8809: 8805: 8802: 8800: 8797: 8795: 8792: 8790: 8787: 8785: 8782: 8780: 8777: 8775: 8772: 8770: 8767: 8765: 8764:Isostrychnine 8762: 8760: 8757: 8755: 8752: 8750: 8747: 8745: 8742: 8740: 8737: 8734: 8730: 8726: 8723: 8721: 8718: 8716: 8713: 8711: 8708: 8706: 8703: 8701: 8698: 8696: 8693: 8691: 8688: 8686: 8683: 8681: 8678: 8676: 8673: 8671: 8668: 8666: 8663: 8661: 8658: 8655: 8654: 8651: 8648: 8646: 8643: 8640: 8636: 8632: 8628: 8624: 8620: 8616: 8612: 8608: 8604: 8600: 8596: 8592: 8588: 8585: 8582: 8578: 8574: 8570: 8566: 8562: 8558: 8555: 8553: 8550: 8548: 8545: 8543: 8540: 8538: 8535: 8533: 8530: 8528: 8527:Nitrous oxide 8525: 8522: 8518: 8514: 8510: 8506: 8502: 8499: 8497: 8494: 8492: 8489: 8487: 8484: 8481: 8477: 8473: 8470: 8468: 8465: 8462: 8458: 8455: 8453: 8450: 8448: 8445: 8442: 8438: 8437:pentobarbital 8434: 8431: 8429: 8426: 8424: 8421: 8418: 8414: 8410: 8406: 8404: 8399: 8395: 8391: 8387: 8384: 8381: 8380: 8377: 8374: 8372: 8369: 8367: 8366:Quisqualamine 8364: 8362: 8359: 8357: 8354: 8352: 8349: 8347: 8344: 8342: 8336: 8334: 8328: 8326: 8320: 8318: 8312: 8310: 8307: 8305: 8302: 8300: 8297: 8295: 8292: 8290: 8284: 8282: 8276: 8274: 8271: 8269: 8266: 8264: 8261: 8259: 8256: 8253: 8252: 8250: 8245: 8239: 8236: 8232: 8226: 8222: 8218: 8215: 8208: 8203: 8201: 8196: 8194: 8189: 8188: 8185: 8175: 8174: 8170: 8166: 8163: 8157: 8151: 8148: 8146: 8143: 8141: 8138: 8136: 8133: 8130: 8129: 8125: 8121: 8117: 8116:isovaleramide 8113: 8109: 8106: 8104: 8101: 8098: 8094: 8091: 8088: 8084: 8080: 8076: 8073: 8071: 8068: 8066: 8063: 8061: 8058: 8056: 8053: 8051: 8048: 8046: 8043: 8041: 8038: 8036: 8033: 8031: 8028: 8026: 8023: 8021: 8018: 8016: 8013: 8010: 8006: 8002: 7998: 7994: 7991: 7989: 7986: 7984: 7981: 7979: 7976: 7974: 7971: 7969: 7966: 7964: 7961: 7958: 7954: 7953:niflumic acid 7950: 7946: 7942: 7939: 7937: 7934: 7932: 7929: 7927: 7924: 7922: 7919: 7916: 7912: 7908: 7904: 7900: 7897: 7895: 7892: 7890: 7887: 7885: 7882: 7880: 7879:Clomethiazole 7877: 7875: 7874:Chlormezanone 7872: 7870: 7867: 7865: 7864:Carbamazepine 7862: 7859: 7855: 7851: 7847: 7844: 7841: 7837: 7834: 7832: 7829: 7827: 7824: 7822: 7819: 7817: 7814: 7813: 7811: 7807: 7801: 7798: 7796: 7793: 7791: 7788: 7786: 7783: 7781: 7778: 7776: 7773: 7771: 7768: 7766: 7763: 7761: 7758: 7756: 7753: 7751: 7748: 7746: 7743: 7741: 7740:Nitrous oxide 7738: 7736: 7733: 7731: 7728: 7726: 7723: 7721: 7718: 7716: 7713: 7711: 7708: 7706: 7703: 7701: 7698: 7696: 7693: 7691: 7688: 7686: 7683: 7681: 7678: 7676: 7673: 7671: 7670:Diethyl ether 7668: 7666: 7663: 7661: 7658: 7656: 7653: 7651: 7648: 7646: 7643: 7641: 7638: 7636: 7633: 7631: 7628: 7626: 7623: 7621: 7618: 7616: 7613: 7611: 7608: 7606: 7603: 7601: 7598: 7596: 7593: 7591: 7588: 7587: 7585: 7583: 7579: 7575: 7569: 7566: 7564: 7561: 7559: 7556: 7554: 7551: 7549: 7546: 7544: 7541: 7539: 7536: 7534: 7531: 7529: 7526: 7524: 7521: 7520: 7518: 7516: 7512: 7506: 7503: 7501: 7498: 7496: 7493: 7491: 7488: 7487: 7485: 7483: 7479: 7473: 7472:Pyrithyldione 7470: 7468: 7465: 7463: 7460: 7458: 7455: 7454: 7452: 7450: 7446: 7440: 7437: 7435: 7432: 7430: 7427: 7426: 7424: 7422: 7418: 7412: 7409: 7407: 7404: 7402: 7399: 7397: 7394: 7392: 7389: 7387: 7384: 7382: 7379: 7377: 7374: 7372: 7369: 7367: 7364: 7362: 7359: 7357: 7354: 7352: 7349: 7347: 7344: 7342: 7339: 7337: 7334: 7332: 7329: 7327: 7324: 7322: 7319: 7317: 7314: 7312: 7309: 7307: 7304: 7302: 7299: 7297: 7294: 7292: 7289: 7287: 7284: 7282: 7279: 7277: 7274: 7272: 7269: 7267: 7263: 7260: 7259: 7256: 7253: 7251: 7248: 7246: 7243: 7241: 7238: 7236: 7233: 7231: 7228: 7226: 7223: 7221: 7217: 7216: 7212: 7211: 7208: 7205: 7203: 7200: 7198: 7195: 7193: 7190: 7188: 7184: 7183: 7179: 7178: 7175: 7172: 7170: 7167: 7165: 7162: 7160: 7157: 7155: 7152: 7150: 7146: 7145: 7141: 7140: 7138: 7136: 7132: 7126: 7123: 7121: 7118: 7116: 7113: 7111: 7108: 7106: 7103: 7101: 7098: 7096: 7093: 7091: 7088: 7086: 7083: 7081: 7078: 7076: 7073: 7071: 7068: 7066: 7063: 7061: 7058: 7056: 7053: 7051: 7048: 7046: 7043: 7041: 7038: 7036: 7033: 7031: 7028: 7026: 7023: 7021: 7018: 7016: 7013: 7011: 7008: 7006: 7003: 7001: 6997: 6995: 6992: 6990: 6987: 6985: 6982: 6980: 6977: 6975: 6972: 6970: 6967: 6965: 6962: 6961: 6959: 6957: 6953: 6947: 6944: 6942: 6939: 6937: 6934: 6932: 6929: 6927: 6924: 6922: 6919: 6918: 6916: 6914: 6910: 6904: 6901: 6899: 6896: 6894: 6891: 6889: 6886: 6884: 6881: 6879: 6876: 6874: 6871: 6869: 6866: 6864: 6861: 6859: 6856: 6854: 6851: 6849: 6846: 6844: 6841: 6839: 6836: 6834: 6831: 6830: 6828: 6825: 6821: 6815: 6812: 6810: 6807: 6805: 6802: 6801: 6799: 6797: 6793: 6787: 6784: 6781: 6777: 6774: 6772: 6769: 6767: 6764: 6762: 6759: 6757: 6754: 6752: 6749: 6747: 6744: 6742: 6739: 6737: 6734: 6732: 6729: 6727: 6724: 6722: 6719: 6717: 6714: 6713: 6711: 6709: 6705: 6699: 6696: 6694: 6691: 6689: 6686: 6684: 6681: 6679: 6678:Phenprobamate 6676: 6674: 6671: 6669: 6666: 6664: 6661: 6659: 6656: 6654: 6651: 6649: 6646: 6644: 6643:Hexapropymate 6641: 6639: 6636: 6634: 6631: 6629: 6626: 6624: 6621: 6619: 6618:Difebarbamate 6616: 6614: 6611: 6609: 6606: 6604: 6601: 6599: 6596: 6595: 6593: 6591: 6587: 6581: 6578: 6576: 6573: 6571: 6568: 6566: 6563: 6561: 6558: 6556: 6553: 6551: 6548: 6546: 6543: 6541: 6538: 6536: 6533: 6531: 6528: 6526: 6523: 6521: 6518: 6516: 6513: 6511: 6508: 6506: 6503: 6501: 6498: 6496: 6493: 6491: 6488: 6486: 6483: 6481: 6478: 6476: 6473: 6471: 6468: 6466: 6463: 6461: 6458: 6456: 6453: 6451: 6448: 6446: 6443: 6441: 6438: 6436: 6433: 6431: 6430:Nortetrazepam 6428: 6426: 6423: 6421: 6418: 6416: 6413: 6411: 6408: 6406: 6403: 6401: 6398: 6396: 6393: 6391: 6388: 6386: 6383: 6381: 6378: 6376: 6373: 6371: 6368: 6366: 6363: 6361: 6358: 6356: 6353: 6351: 6348: 6346: 6343: 6341: 6338: 6336: 6333: 6331: 6328: 6326: 6323: 6321: 6318: 6316: 6313: 6311: 6308: 6306: 6303: 6301: 6298: 6296: 6293: 6291: 6290:Flutoprazepam 6288: 6286: 6283: 6281: 6278: 6276: 6273: 6271: 6270:Flunitrazolam 6268: 6266: 6265:Flunitrazepam 6263: 6261: 6258: 6256: 6255:Flubromazolam 6253: 6251: 6250:Flubromazepam 6248: 6246: 6243: 6241: 6238: 6236: 6233: 6231: 6228: 6226: 6223: 6221: 6218: 6216: 6213: 6211: 6208: 6206: 6203: 6201: 6198: 6196: 6193: 6191: 6188: 6186: 6183: 6181: 6178: 6176: 6173: 6171: 6168: 6166: 6163: 6161: 6158: 6156: 6153: 6151: 6150:Cloniprazepam 6148: 6146: 6143: 6141: 6138: 6136: 6133: 6131: 6128: 6126: 6123: 6121: 6118: 6116: 6113: 6111: 6108: 6106: 6103: 6101: 6098: 6096: 6093: 6091: 6088: 6086: 6083: 6081: 6078: 6076: 6073: 6071: 6068: 6066: 6063: 6061: 6058: 6056: 6053: 6051: 6048: 6046: 6043: 6041: 6040:2-Oxoquazepam 6038: 6037: 6035: 6033: 6029: 6023: 6020: 6018: 6015: 6013: 6010: 6008: 6005: 6003: 6000: 5998: 5995: 5993: 5990: 5988: 5985: 5983: 5982:Thialbarbital 5980: 5978: 5977:Tetrabarbital 5975: 5973: 5970: 5968: 5965: 5963: 5962:Spirobarbital 5960: 5958: 5955: 5953: 5950: 5948: 5945: 5943: 5942:Proxibarbital 5940: 5938: 5935: 5933: 5932:Propallylonal 5930: 5928: 5925: 5923: 5920: 5918: 5915: 5913: 5912:Phenobarbital 5910: 5908: 5905: 5903: 5902:Pentobarbital 5900: 5898: 5895: 5893: 5892:Narcobarbital 5890: 5888: 5885: 5883: 5880: 5878: 5875: 5873: 5870: 5868: 5865: 5863: 5860: 5858: 5857:Heptobarbital 5855: 5853: 5850: 5848: 5845: 5843: 5840: 5838: 5835: 5833: 5830: 5828: 5827:Difebarbamate 5825: 5823: 5820: 5818: 5817:Cyclobarbital 5815: 5813: 5810: 5808: 5805: 5803: 5800: 5798: 5795: 5793: 5790: 5788: 5785: 5783: 5780: 5778: 5775: 5773: 5770: 5768: 5765: 5763: 5762:Benzobarbital 5760: 5758: 5755: 5753: 5750: 5748: 5745: 5743: 5740: 5738: 5735: 5733: 5730: 5728: 5725: 5724: 5722: 5720: 5716: 5710: 5707: 5705: 5702: 5700: 5697: 5695: 5692: 5690: 5688: 5684: 5682: 5680: 5676: 5674: 5671: 5669: 5666: 5664: 5661: 5659: 5656: 5654: 5651: 5649: 5646: 5644: 5641: 5639: 5636: 5634: 5633:Ethchlorvynol 5631: 5628: 5624: 5621: 5619: 5616: 5614: 5611: 5609: 5606: 5604: 5601: 5600: 5598: 5596: 5592: 5588: 5575: 5570: 5568: 5563: 5561: 5556: 5555: 5552: 5540: 5537: 5535: 5532: 5530: 5527: 5525: 5522: 5520: 5517: 5514: 5510: 5507: 5505: 5502: 5498: 5497:Methocarbamol 5495: 5493: 5490: 5488: 5487:Mephenoxalone 5485: 5483: 5480: 5478: 5477:Chlorphenesin 5475: 5474: 5473: 5469: 5466: 5464: 5461: 5459: 5456: 5454: 5451: 5447: 5446:Phenaglycodol 5444: 5442: 5439: 5437: 5434: 5433: 5432: 5429: 5425: 5422: 5421: 5420: 5417: 5416: 5414: 5410: 5404: 5401: 5399: 5396: 5394: 5391: 5389: 5386: 5384: 5381: 5380: 5378: 5376: 5363: 5357: 5354: 5352: 5349: 5347: 5344: 5343: 5341: 5339: 5335: 5329: 5326: 5324: 5321: 5319: 5316: 5314: 5311: 5310: 5308: 5306: 5302: 5292: 5289: 5288: 5286: 5282: 5273: 5270: 5268: 5265: 5263: 5260: 5259: 5258: 5255: 5250: 5247: 5245: 5242: 5241: 5240: 5237: 5236: 5234: 5232: 5228: 5219: 5216: 5214: 5211: 5210: 5209: 5206: 5201: 5198: 5196: 5193: 5191: 5190:Amitriptyline 5188: 5187: 5186: 5183: 5181: 5178: 5177: 5175: 5173: 5169: 5166: 5164: 5157: 5151: 5148: 5146: 5143: 5141: 5138: 5136: 5133: 5131: 5128: 5126: 5123: 5121: 5118: 5116: 5113: 5112: 5110: 5108: 5100: 5087: 5084: 5082: 5079: 5077: 5074: 5073: 5072: 5069: 5064: 5061: 5059: 5056: 5055: 5054: 5051: 5050: 5048: 5046: 5042: 5033: 5030: 5028: 5025: 5024: 5023: 5020: 5015: 5012: 5010: 5007: 5005: 5004:Amitriptyline 5002: 5001: 5000: 4997: 4993: 4990: 4988: 4985: 4983: 4980: 4979: 4978: 4975: 4974: 4972: 4970: 4966: 4960: 4957: 4955: 4952: 4950: 4947: 4945: 4942: 4940: 4939:Methapyrilene 4937: 4935: 4932: 4930: 4927: 4925: 4922: 4920: 4917: 4915: 4912: 4911: 4909: 4907: 4903: 4900: 4898: 4891: 4885: 4882: 4880: 4877: 4875: 4872: 4870: 4867: 4864: 4860: 4857: 4855: 4852: 4850: 4847: 4845: 4844:Aceburic acid 4842: 4840: 4837: 4835: 4832: 4831: 4829: 4827: 4820: 4808: 4805: 4803: 4800: 4798: 4797:Isovaleramide 4795: 4794: 4793: 4792:Sesquiterpene 4790: 4788: 4785: 4781: 4778: 4776: 4773: 4771: 4768: 4767: 4766: 4763: 4761: 4758: 4756: 4753: 4751: 4748: 4746: 4743: 4741: 4738: 4736: 4733: 4731: 4730:Clomethiazole 4728: 4726: 4723: 4721: 4718: 4716: 4713: 4711: 4708: 4704: 4701: 4699: 4696: 4694: 4691: 4690: 4688: 4685: 4683: 4680: 4678: 4675: 4674: 4672: 4668: 4662: 4659: 4657: 4654: 4652: 4649: 4647: 4644: 4642: 4639: 4637: 4634: 4632: 4629: 4627: 4624: 4622: 4619: 4617: 4614: 4613: 4611: 4609: 4605: 4599: 4596: 4594: 4593:Pyrithyldione 4591: 4589: 4586: 4584: 4581: 4580: 4578: 4576: 4572: 4566: 4563: 4562: 4560: 4558: 4554: 4548: 4545: 4543: 4540: 4538: 4535: 4533: 4530: 4528: 4525: 4523: 4520: 4518: 4515: 4513: 4510: 4508: 4505: 4503: 4500: 4498: 4495: 4494: 4492: 4490: 4486: 4480: 4477: 4475: 4472: 4470: 4467: 4465: 4462: 4460: 4457: 4455: 4452: 4450: 4447: 4445: 4442: 4441: 4439: 4437: 4433: 4427: 4424: 4422: 4419: 4417: 4414: 4412: 4409: 4407: 4404: 4402: 4399: 4398: 4396: 4394: 4390: 4384: 4381: 4379: 4376: 4374: 4371: 4370: 4368: 4366: 4362: 4356: 4353: 4351: 4348: 4346: 4345:Phenprobamate 4343: 4341: 4340:Methocarbamol 4338: 4336: 4333: 4331: 4330:Hexapropymate 4328: 4326: 4323: 4321: 4318: 4316: 4313: 4312: 4310: 4308: 4304: 4298: 4295: 4293: 4290: 4288: 4285: 4283: 4280: 4278: 4275: 4273: 4270: 4268: 4265: 4263: 4260: 4258: 4255: 4253: 4250: 4248: 4247:Flutoprazepam 4245: 4243: 4240: 4238: 4235: 4233: 4232:Flunitrazepam 4230: 4228: 4227:Flunitrazolam 4225: 4223: 4222:Flubromazolam 4220: 4218: 4215: 4213: 4210: 4208: 4205: 4203: 4200: 4198: 4195: 4193: 4190: 4189: 4187: 4185: 4181: 4175: 4172: 4170: 4167: 4165: 4162: 4160: 4157: 4155: 4152: 4150: 4147: 4145: 4142: 4140: 4137: 4135: 4132: 4130: 4127: 4125: 4124:Phenobarbital 4122: 4120: 4117: 4115: 4114:Pentobarbital 4112: 4110: 4109:Narcobarbital 4107: 4105: 4102: 4100: 4099:Mephobarbital 4097: 4095: 4092: 4090: 4087: 4085: 4082: 4080: 4079:Cyclobarbital 4077: 4075: 4072: 4070: 4067: 4065: 4062: 4060: 4057: 4055: 4052: 4050: 4047: 4046: 4044: 4042: 4038: 4032: 4029: 4027: 4024: 4022: 4021:Ethchlorvynol 4019: 4017: 4014: 4012: 4009: 4007: 4004: 4002: 3999: 3998: 3996: 3994: 3990: 3987: 3985: 3978: 3973: 3969: 3965: 3958: 3953: 3951: 3946: 3944: 3939: 3938: 3935: 3928: 3923: 3919: 3918: 3914: 3908: 3902: 3898: 3897: 3891: 3890: 3889: 3888: 3866: 3859: 3853: 3850: 3845: 3842:Lilly, John. 3838: 3835: 3832:, p. 298 3831: 3826: 3823: 3820:, p. 296 3819: 3814: 3811: 3806: 3799: 3796: 3791: 3789:1-85619-223-7 3785: 3781: 3774: 3771: 3766: 3764:9780192800862 3760: 3756: 3755: 3748: 3745: 3740: 3736: 3730: 3727: 3714: 3710: 3706: 3699: 3696: 3691: 3687: 3680: 3677: 3672: 3666: 3662: 3658: 3657: 3649: 3646: 3641: 3635: 3631: 3627: 3626: 3618: 3615: 3602: 3598: 3596:9780887388019 3592: 3588: 3587: 3579: 3576: 3571: 3567: 3561: 3558: 3554: 3550: 3546: 3540: 3537: 3532: 3526: 3510: 3504: 3501: 3488: 3485:. June 1995. 3484: 3483: 3476: 3473: 3460: 3459: 3451: 3448: 3435: 3431: 3425: 3422: 3409: 3405: 3401: 3397: 3393: 3389: 3385: 3381: 3377: 3373: 3366: 3363: 3358: 3354: 3349: 3344: 3340: 3336: 3332: 3328: 3324: 3317: 3314: 3309: 3305: 3301: 3297: 3293: 3289: 3285: 3281: 3274: 3271: 3266: 3262: 3258: 3254: 3250: 3246: 3239: 3236: 3231: 3227: 3223: 3221:9780195368741 3217: 3213: 3212: 3204: 3201: 3196: 3192: 3188: 3182: 3178: 3177: 3169: 3167: 3165: 3161: 3156: 3152: 3151: 3143: 3140: 3135: 3131: 3127: 3123: 3119: 3115: 3108: 3105: 3100: 3096: 3092: 3086: 3082: 3075: 3073: 3071: 3067: 3054: 3050: 3046: 3042: 3038: 3034: 3027: 3024: 3011: 3007: 3003: 2999: 2995: 2991: 2987: 2981: 2978: 2965: 2961: 2957: 2951: 2948: 2943: 2939: 2934: 2929: 2925: 2921: 2917: 2913: 2909: 2902: 2899: 2894: 2890: 2885: 2880: 2876: 2872: 2868: 2857: 2854: 2849: 2843: 2839: 2835: 2831: 2830: 2822: 2819: 2803: 2798: 2793: 2789: 2785: 2778: 2771: 2768: 2755: 2751: 2747: 2741: 2738: 2733: 2726: 2723: 2718: 2711: 2708: 2703: 2699: 2694: 2689: 2685: 2681: 2677: 2673: 2669: 2662: 2659: 2654: 2650: 2645: 2640: 2636: 2632: 2628: 2624: 2620: 2613: 2610: 2605: 2601: 2597: 2593: 2586: 2583: 2570: 2566: 2562: 2558: 2554: 2550: 2546: 2542: 2535: 2532: 2526: 2520: 2519: 2514: 2507: 2504: 2488: 2484: 2477: 2470: 2467: 2462: 2458: 2454: 2450: 2443: 2440: 2435: 2429: 2410: 2406: 2399: 2392: 2389: 2384: 2380: 2376: 2372: 2367: 2362: 2358: 2354: 2350: 2343: 2340: 2335: 2331: 2327: 2323: 2320:(1): 93–105. 2319: 2315: 2308: 2305: 2292: 2288: 2282: 2279: 2274: 2270: 2266: 2262: 2258: 2254: 2247: 2244: 2239: 2235: 2231: 2227: 2223: 2219: 2212: 2210: 2206: 2201: 2195: 2191: 2187: 2180: 2177: 2172: 2168: 2164: 2160: 2156: 2149: 2146: 2141: 2135: 2131: 2127: 2123: 2116: 2113: 2109: 2108: 2101: 2097: 2094: 2092: 2089: 2087: 2084: 2082: 2081:Chlorobutanol 2079: 2077: 2074: 2073: 2069: 2067: 2065: 2061: 2060:surface water 2057: 2053: 2049: 2045: 2041: 2034:Environmental 2033: 2028: 2024: 2021: 2018: 2014: 2010: 2009:Hank Williams 2007: 2004: 2000: 1996: 1995: 1990: 1987: 1984: 1981: 1978: 1974: 1971: 1968: 1965: 1962: 1958: 1954: 1951: 1948: 1945: 1942: 1941:pentobarbital 1938: 1935: 1932: 1928: 1925: 1922: 1918: 1914: 1910: 1906: 1903: 1900: 1899:William James 1897: 1894: 1893: 1888: 1885: 1882: 1879: 1876: 1872: 1871:Chulalongkorn 1868: 1867: 1864:Notable users 1863: 1860: 1855: 1853: 1852: 1847: 1846:Edith Wharton 1841: 1823: 1817: 1815: 1812: 1808: 1804: 1800: 1799: 1795: 1791: 1786: 1784: 1779: 1777: 1773: 1772:pentobarbital 1769: 1768:phenobarbital 1765: 1757: 1755: 1752: 1748: 1747:intravenously 1743: 1741: 1737: 1733: 1730: 1726: 1722: 1718: 1714: 1710: 1706: 1701: 1699: 1698: 1693: 1688: 1684: 1680: 1676: 1671: 1669: 1665: 1661: 1657: 1653: 1649: 1645: 1641: 1637: 1633: 1629: 1625: 1621: 1613: 1611: 1609: 1605: 1601: 1597: 1594: 1586: 1584: 1582: 1581:ethchlorvynol 1578: 1573: 1571: 1567: 1566: 1562: 1558: 1554: 1550: 1546: 1542: 1538: 1534: 1530: 1526: 1525:GABA receptor 1522: 1518: 1517: 1508: 1503: 1501: 1499: 1495: 1491: 1487: 1453: 1452: 1451: 1449: 1445: 1437: 1435: 1433: 1429: 1425: 1420: 1416: 1412: 1408: 1404: 1400: 1396: 1391: 1388: 1377: 1375: 1373: 1369: 1365: 1361: 1357: 1347: 1344: 1342: 1338: 1334: 1330: 1326: 1322: 1318: 1314: 1310: 1306: 1293: 1291: 1289: 1284: 1278: 1274: 1273: 1272: 1270: 1269:sulfuric acid 1266: 1265:hydroxylamine 1262: 1258: 1253: 1251: 1247: 1246:sulfuric acid 1243: 1235: 1233: 1231: 1227: 1223: 1219: 1215: 1211: 1206: 1204: 1200: 1196: 1192: 1188: 1184: 1179: 1177: 1173: 1169: 1165: 1161: 1160:United States 1157: 1149: 1144: 1142: 1140: 1136: 1132: 1127: 1123: 1114: 1110: 1106: 1100: 1096: 1092: 1088: 1076: 1070: 1064: 1061: 1057: 1056:chlorobutanol 1053: 1050: 1045: 1044: 1039: 1036: 1035:External MSDS 1033: 1030: 1027: 1026: 1022: 1018: 1009: 1008: 1004: 1000: 946: 943: 939: 938: 924: 921: 917: 916: 913: 910: 907: 903: 902: 898: 893: 889: 886: 882: 881: 877: 875: 870: 865: 859: 849: 841: 838: 828: 827: 825: 823: 820: 819: 815: 812: 808: 807: 803: 800: 796: 795: 791: 787: 783: 780: 777: 773: 772: 768: 765: 761: 760: 756: 752: 749: 745: 742: 736: 735: 730: 725: 722: 719: 715: 714: 711:Pharmacology 709: 706: 703: 700: 696: 695: 690: 686: 680: 676: 673: 672: 668: 666: 665: 660: 659: 656: 652: 648: 644: 642: 639: 638: 634: 631: 627: 626: 622: 620: 619:Boiling point 617: 616: 612: 610: 609:Melting point 607: 606: 602: 600: 597: 596: 592: 590: 587: 586: 582: 579: 578: 571: 569: 566: 565: 551: 548: 544: 543: 538: 529: 525: 518: 504: 494: 490: 483: 475: 471: 470:DTXSID7020261 467: 466: 464: 454: 450: 449: 445: 443: 440: 439: 432: 428: 427: 425: 423: 420: 419: 412: 411: 409: 407: 404: 403: 396: 392: 391: 389: 383: 379: 378: 371: 367: 366: 364: 362: 359: 358: 354: 351: 347: 346: 339: 338: 336: 334: 329: 328: 324: 320: 317: 315: 313:ECHA InfoCard 310: 309: 302: 298: 297: 295: 293: 290: 289: 282: 278: 277: 275: 273: 270: 269: 262: 258: 257: 255: 253: 250: 249: 242: 238: 237: 235: 233: 230: 229: 225: 222: 218: 217: 210: 206: 205: 203: 199: 194: 193: 186: 182: 181: 179: 176: 172: 171: 166: 158: 155: 152: 149: 146: 143: 140: 138: 135: 133: 130: 127: 126: 121: 113: 109: 104: 100: 95: 85: 75: 65: 55: 43: 39: 34: 30: 29: 25: 19: 9361: 9350: 9343: 9336: 9062:picrotoxinin 9006:progesterone 8998:DHEA sulfate 8966:ginkgolide M 8962:ginkgolide J 8958:ginkgolide C 8954:ginkgolide B 8950:ginkgolide A 8922:nitrendipine 8860: 8657:Antagonists: 8656: 8594: 8532:Penicillin G 8476:ginsenosides 8433:Barbiturates 8402: 8382: 8263:β-ABA (BABA) 8254: 8161: 8160: 8131: 7988:Lavender oil 7730:Nitric oxide 7650:Cryofluorane 7639: 7595:Acetophenone 7553:Methaqualone 7548:Mecloqualone 7543:Mebroqualone 7533:Diproqualone 7528:Cloroqualone 7457:Glutethimide 7261: 7213: 7180: 7142: 7115:Testosterone 7080:Progesterone 7045:Hydroxydione 6994:Androsterone 6921:Acecarbromal 6826:constituents 6613:Cyclarbamate 6603:Carisoprodol 6375:Metaclazepam 6370:Menitrazepam 6360:Meclonazepam 6355:Lormetazepam 6285:Flutemazepam 6110:Ciclotizolam 6100:Carburazepam 5992:Thiobarbital 5952:Secobarbital 5917:Phetharbital 5897:Nealbarbital 5882:Methohexital 5867:Hexobarbital 5802:Butallylonal 5797:Butobarbital 5752:Barbexaclone 5747:Aprobarbital 5732:Allobarbital 5719:Barbiturates 5686: 5678: 5668:Petrichloral 5539:Valnoctamide 5441:Metaglycodol 5436:Fenpentadiol 5346:Daridorexant 5249:Thioridazine 5200:Trimipramine 5135:Medetomidine 5063:Thioridazine 5014:Trimipramine 4959:Propiomazine 4954:Promethazine 4760:Petrichloral 4745:Kavalactones 4719: 4677:Acetophenone 4646:Methaqualone 4641:Mecloqualone 4636:Mebroqualone 4626:Diproqualone 4621:Cloroqualone 4583:Glutethimide 4479:Progesterone 4469:Hydroxydione 4401:Acecarbromal 4315:Carisoprodol 4257:Lormetazepam 4242:Flutemazepam 4144:Secobarbital 4104:Methohexital 4094:Hexobarbital 4074:Butobarbital 4069:Butabarbital 4059:Aprobarbital 4049:Allobarbital 4041:Barbiturates 3895: 3886: 3885: 3872:. Retrieved 3852: 3843: 3837: 3825: 3813: 3804: 3798: 3779: 3773: 3753: 3747: 3739:the original 3729: 3717:. Retrieved 3708: 3698: 3685: 3679: 3655: 3648: 3624: 3617: 3605:. Retrieved 3585: 3578: 3569: 3560: 3544: 3539: 3513:. Retrieved 3503: 3491:. Retrieved 3481: 3475: 3463:. Retrieved 3457: 3450: 3438:. Retrieved 3434:the original 3424: 3412:. Retrieved 3382:(1): 13–21. 3379: 3375: 3365: 3330: 3326: 3316: 3286:(3): 85–88. 3283: 3279: 3273: 3248: 3244: 3238: 3210: 3203: 3175: 3154: 3149: 3142: 3117: 3113: 3107: 3080: 3059:24 September 3057:. Retrieved 3040: 3036: 3026: 3016:24 September 3014:. Retrieved 3000:(1): 31–32. 2997: 2993: 2980: 2968:. Retrieved 2959: 2950: 2915: 2911: 2901: 2874: 2870: 2856: 2827: 2821: 2809:. Retrieved 2787: 2783: 2770: 2758:. Retrieved 2749: 2740: 2731: 2725: 2716: 2710: 2675: 2671: 2661: 2626: 2622: 2612: 2595: 2591: 2585: 2573:. Retrieved 2548: 2544: 2534: 2524: 2516: 2506: 2494:. Retrieved 2482: 2469: 2452: 2448: 2442: 2416:. Retrieved 2409:the original 2404: 2391: 2356: 2352: 2342: 2317: 2313: 2307: 2295:. Retrieved 2281: 2256: 2252: 2246: 2221: 2217: 2185: 2179: 2162: 2158: 2154: 2148: 2121: 2115: 2106: 2105: 2064:ground water 2048:chlorination 2044:side-product 2037: 2027:Belle Époque 2023:Renée Vivien 1992: 1989:Evelyn Waugh 1983:John Tyndall 1967:Oliver Sacks 1921:promethazine 1892:If It Die... 1890: 1857: 1849: 1843: 1819: 1811:phonographic 1796: 1787: 1780: 1776:secobarbital 1761: 1744: 1702: 1695: 1692:barbiturates 1672: 1656:barbiturates 1624:halogenation 1617: 1590: 1587:Legal status 1574: 1569: 1563: 1537:barbiturates 1514: 1512: 1504:Pharmacology 1483: 1441: 1428:Hemodialysis 1392: 1381: 1353: 1345: 1323:(especially 1319:, and small 1302: 1285: 1282: 1254: 1239: 1207: 1205:discharges. 1203:epileptiform 1187:barbiturates 1180: 1153: 1091:geminal diol 1086: 1085: 1002: 911: 873: 822:Legal status 678: 663: 603:1.9081 g/cm 406:RTECS number 261:ChEMBL455917 168:Identifiers 136: 131: 123:Other names 18: 9259:SSR-504,734 9254:SSR-103,800 9244:PF-03463275 9224:Mardepodect 9144:Transporter 9090:tropisetron 9032:levorphanol 9024:dextrorphan 8946:ginkgolides 8914:nicardipine 8769:Laudanosine 8690:Cacotheline 8680:Bicuculline 8627:sevoflurane 8577:tropisetron 8461:nicardipine 8304:Hypotaurine 8070:Stiripentol 8065:Seproxetine 8035:Niacinamide 8015:Loreclezole 7836:Avermectins 7800:Vinyl ether 7770:Sevoflurane 7750:Paraldehyde 7700:Halopropane 7523:Afloqualone 7505:Tracazolate 7500:ICI-190,622 7490:Cartazolate 7467:Piperidione 7462:Methyprylon 7429:Fospropofol 7351:Pipequaline 7159:Pazinaclone 7149:Eszopiclone 7005:Cholesterol 6989:Androstenol 6913:Monoureides 6893:Methysticin 6693:Tetrabamate 6673:Pentabamate 6663:Meprobamate 6633:Febarbamate 6598:Carisbamate 6550:Triflubazam 6540:Tolufazepam 6500:Rilmazafone 6495:Remimazolam 6470:Proflazepam 6455:Pivoxazepam 6415:Nitrazepate 6405:Nimetazepam 6340:Lopirazepam 6310:Haloxazolam 6260:Fludiazepam 6205:Doxefazepam 6180:Delorazepam 6160:Clotiazepam 6155:Clorazepate 6120:Cinolazepam 6017:Vinbarbital 5972:Tetrabamate 5927:Probarbital 5907:Phenallymal 5872:Metharbital 5847:Febarbamate 5742:Amobarbital 5643:Isopropanol 5613:Chloralodol 5524:Scopolamine 5468:Guaifenesin 5463:Fenadiazole 5419:Cannabidiol 5393:Mirogabalin 5351:Lemborexant 5328:Tasimelteon 5313:Agomelatine 5272:Risperidone 5218:Mirtazapine 5107:-Adrenergic 5086:Risperidone 5032:Mirtazapine 4982:Etoperidone 4949:Pheniramine 4934:Hydroxyzine 4755:Paraldehyde 4750:Loreclezole 4616:Afloqualone 4598:Piperidione 4588:Methyprylon 4517:Pazinaclone 4497:Eszopiclone 4459:Alphaxolone 4454:Alphadolone 4393:Monoureides 4335:Meprobamate 4272:Nitemazepam 4267:Nimetazepam 4212:Doxefazepam 4197:Cinolazepam 4169:Vinbarbital 4134:Proxibarbal 4119:Phenallymal 4054:Amobarbital 4006:Chloralodol 3719:2 September 3566:Gide, André 3515:20 February 3465:28 February 3414:20 February 3333:(3): 1–24. 2970:20 February 2811:20 February 2760:15 November 2575:11 December 2418:15 November 2259:(1): 34–5. 2052:humic acids 1943:(Nembutal). 1803:John Seward 1790:Bram Stoker 1783:Mickey Finn 1687:barbiturate 1593:schedule IV 1579:similar to 1399:convulsions 1226:respiration 1210:metabolized 1017:median dose 1003:Lethal dose 906:Signal word 858:Schedule IV 804:8–10 hours 748:suppository 687:9.66, 11.0 651:ethyl ether 580:Appearance 540:Properties 319:100.005.562 241:CHEBI:28142 141:Aquachloral 137:Tradenames: 9379:Categories 9264:Tilapertin 9219:LY-2365109 9214:Iclepertin 9209:GSK1018921 9094:zatosetron 9082:bemesetron 9054:Picrotoxin 8972:Imipramine 8942:bilobalide 8928:Furosemide 8918:nifedipine 8889:flurazepam 8877:clonazepam 8873:bromazepam 8844:Strychnine 8839:Sinomenine 8804:Quinolines 8794:Pitrazepin 8715:Dendrobine 8700:Colchicine 8619:isoflurane 8603:desflurane 8599:chloroform 8581:zatosetron 8565:bemesetron 8517:minaxolone 8505:alfaxolone 8491:Ivermectin 8428:Anandamide 8351:Milacemide 8341:-Threonine 8309:Ivermectin 8217:modulators 8103:Topiramate 8093:Terpenoids 8050:Propanidid 8040:Org 25,435 7968:Flupirtine 7963:Fluoxetine 7869:Chloralose 7840:ivermectin 7745:Norflurane 7710:Isoflurane 7655:Desflurane 7645:Chloroform 7605:Aliflurane 7538:Etaqualone 7366:SB-205,384 7296:CP-615,003 7291:CL-218,872 7245:Panadiplon 7235:Lorediplon 7164:Suproclone 7125:Zuranolone 7085:Renanolone 7070:Posovolone 7050:Minaxolone 7040:Ganaxolone 6979:Alfaxalone 6974:Alfadolone 6964:Acebrochol 6931:Bromisoval 6809:Metomidate 6796:Imidazoles 6756:Hispidulin 6708:Flavonoids 6668:Nisobamate 6658:Mebutamate 6628:Ethinamate 6623:Emylcamate 6590:Carbamates 6560:Tuclazepam 6535:Tetrazepam 6490:Reclazepam 6465:Premazepam 6445:Phenazepam 6425:Nordazepam 6420:Nitrazolam 6410:Nitrazepam 6390:Motrazepam 6345:Loprazolam 6335:Lofendazam 6320:Imidazenil 6280:Flutazolam 6275:Flurazepam 6245:Fletazepam 6200:Dimdazenil 6195:Diclazepam 6175:Cyprazepam 6165:Cloxazolam 6145:Clonazolam 6140:Clonazepam 6130:Climazolam 6090:Brotizolam 6085:Bromazolam 6080:Bromazepam 6075:Bretazenil 6070:Bentazepam 6060:Arfendazam 6055:Alprazolam 6050:Adinazolam 6022:Vinylbital 6002:Thiopental 5877:Methitural 5792:Buthalital 5787:Butalbital 5638:Isobutanol 5492:Metaxalone 5482:Mephenesin 5403:Pregabalin 5383:Gabapentin 5356:Suvorexant 5291:Niaprazine 5267:Quetiapine 5262:Olanzapine 5145:Tizanidine 5140:Romifidine 5130:Lofexidine 5120:Detomidine 5081:Quetiapine 5076:Olanzapine 4987:Nefazodone 4929:Doxylamine 4914:Captodiame 4725:Chloralose 4689:compounds 4631:Etaqualone 4527:Suproclone 4507:Lirequinil 4474:Minaxolone 4464:Eltanolone 4444:Acebrochol 4411:Bromisoval 4378:Metomidate 4365:Imidazoles 4325:Ethinamate 4320:Emylcamate 4307:Carbamates 4282:Nitrazolam 4277:Nitrazepam 4252:Loprazolam 4237:Flurazepam 4207:Clonazolam 4202:Climazolam 4192:Brotizolam 4174:Vinylbital 4159:Thiopental 3830:Olson 2004 3818:Olson 2004 2717:Psychiatry 2102:References 2086:Chloroform 2056:micrograms 2042:, a minor 2040:chloroform 1909:Flavor Aid 1887:André Gide 1736:lipophilic 1732:solubility 1713:metabolite 1709:chloroform 1553:withdrawal 1549:dependency 1498:chloroform 1494:hydrolysis 1490:decomposed 1438:Production 1424:overdosage 1329:gum arabic 1321:arthropods 1309:bryophytes 1288:polymorphs 1141:of water. 1139:equivalent 885:Pictograms 776:Metabolism 705:Monoclinic 692:Structure 641:Solubility 568:Molar mass 431:418M5916WG 272:ChemSpider 196:3D model ( 175:CAS Number 144:Chloradorm 9440:Jonestown 9415:Sedatives 9410:Hypnotics 9390:Aldehydes 9312:ORG-25543 9292:Amoxapine 9249:Sarcosine 9229:ORG-24598 9194:CP-802079 9100:Verapamil 9086:LY-278584 9078:Tropeines 9044:pethidine 9040:oripavine 8933:Genistein 8864:Amiloride 8744:Gelsemine 8720:Diaboline 8705:Colubrine 8615:halothane 8611:enflurane 8587:Volatiles 8573:LY-278584 8557:Tropeines 8552:Triclofos 8542:Tamoxifen 8521:ORG-20599 8467:Etomidate 8390:brometone 8371:Sarcosine 8346:MDL-27531 8258:β-Alanine 8255:Agonists: 8162:See also: 8124:valerenol 8045:Phenytoin 8025:Monastrol 7983:Lanthanum 7978:KRM-II-81 7941:Fenamates 7936:Etifoxine 7931:Etazepine 7926:Efavirenz 7884:Darigabat 7780:Teflurane 7765:Roflurane 7760:Propylene 7705:Halothane 7690:Fluroxene 7675:Enflurane 7578:Volatiles 7495:Etazolate 7406:Viqualine 7361:RWJ-51204 7326:L-838,417 7316:Imepitoin 7286:CGS-20625 7281:CGS-13767 7266:Adipiplon 7240:Ocinaplon 7202:Saripidem 7197:Necopidem 7174:Zopiclone 7169:Suriclone 7154:Pagoclone 7060:ORG-21465 7055:ORG-20599 6946:Ectylurea 6936:Carbromal 6814:Propoxate 6804:Etomidate 6731:Baicalein 6688:Styramate 6683:Procymate 6653:Lorbamate 6638:Felbamate 6608:Clocental 6580:Zomebazam 6575:Zolazepam 6570:Zapizolam 6565:Uldazepam 6545:Triazolam 6530:Temazepam 6525:Sulazepam 6515:Ro48-8684 6510:Ro48-6791 6505:Ripazepam 6475:Pyrazolam 6450:Pinazepam 6400:Nifoxipam 6385:Midazolam 6380:Mexazolam 6365:Medazepam 6350:Lorazepam 6330:Ketazolam 6325:Irazepine 6315:Iclazepam 6305:Halazepam 6300:Gidazepam 6295:Fosazepam 6215:Estazolam 6210:Elfazepam 6185:Demoxepam 6115:Cinazepam 6095:Camazepam 6065:Avizafone 5987:Thiamylal 5922:Primidone 5852:Heptabarb 5842:Eterobarb 5807:Carbubarb 5704:Triclofos 5603:Brometone 5529:Trazodone 5470:-related 5323:Ramelteon 5318:Melatonin 5305:Melatonin 5213:Mianserin 5180:Trazodone 5115:Clonidine 5027:Mianserin 4992:Trazodone 4944:Perlapine 4787:Triclofos 4740:Gaboxadol 4547:Zopiclone 4532:Suriclone 4522:Saripidem 4512:Necopidem 4426:Ectylurea 4421:Carbromal 4383:Propoxate 4373:Etomidate 4350:Procymate 4297:Triazolam 4292:Temazepam 4262:Midazolam 4217:Estazolam 4154:Thiamylal 4089:Heptabarb 3968:sedatives 3964:Hypnotics 3607:3 October 3568:(2001) . 3396:2352-4529 3300:2352-4529 3265:2352-4529 3230:299368559 3195:878623979 3083:. Wiley. 2449:Encephale 2375:0003-3022 2190:CRC Press 1788:In 1897, 1738:molecule 1679:addiction 1652:analgesic 1608:alcoholic 1561:mutagenic 1541:addictive 1250:desiccant 1093:with the 1060:Triclofos 984:P337+P313 980:P332+P313 964:P302+P352 960:P301+P310 876:labelling 811:Excretion 739:Routes of 442:UN number 340:206-117-5 332:EC Number 147:Chloratol 9425:Prodrugs 9405:Hydrates 9333:See also 9287:ALX-1393 9150:blockers 9131:instead. 9073:Riluzole 9058:picrotin 9048:thebaine 9036:morphine 8905:Daidzein 8895:Corymine 8881:diazepam 8816:5,7-CIQA 8749:iso-THAZ 8695:Caffeine 8561:atropine 8537:Propofol 8496:Ketamine 8386:Alcohols 8361:Propofol 8325:-Proline 8317:-Alanine 8281:-Alanine 8225:Receptor 8150:TCS-1205 8145:TCS-1105 8135:α-Pinene 8108:Valerian 8083:tetronal 8060:Safranal 8009:obovatol 8005:magnolol 8001:honokiol 7831:Alogabat 7826:AA-29504 7775:Synthane 7735:Nitrogen 7715:Kerosine 7695:Gasoline 7685:Ethylene 7625:Centalun 7620:Butylene 7434:Propofol 7396:U-89843A 7376:TGSC01AA 7346:NS-11394 7311:GBLD-345 7276:CGS-9896 7271:CGS-8216 7255:Zaleplon 7250:Taniplon 7230:Indiplon 7225:Fasiplon 7220:Divaplon 7207:Zolpidem 7110:SAGE-872 7105:SAGE-689 7100:SAGE-516 7095:SAGE-324 7090:SAGE-105 6998:Certain 6941:Capuride 6903:Yangonin 6780:baicalin 6776:Skullcap 6766:Luteolin 6741:Catechin 6736:Baicalin 6726:Apigenin 6698:Tybamate 6485:Quazepam 6480:QH-II-66 6460:Prazepam 6440:Oxazolam 6435:Oxazepam 6235:Etizolam 6190:Diazepam 6170:CP-1414S 6135:Clobazam 6125:Clazolam 6012:Valofane 5967:Talbutal 5957:Sigmodal 5862:Hexethal 5757:Barbital 5737:Alphenal 5727:(-)-DMBB 5673:Propanol 5663:Pentanol 5653:Methanol 5595:Alcohols 5513:morphine 5504:Midaflur 5424:Cannabis 5398:Phenibut 5150:Xylazine 4879:Phenibut 4849:Baclofen 4775:Tetronal 4710:Centalun 4565:Propofol 4542:Zolpidem 4537:Zaleplon 4502:Indiplon 4416:Capuride 4355:Tybamate 4287:Quazepam 4149:Talbutal 4064:Barbital 3993:Alcohols 3874:14 March 3865:Archived 3713:Archived 3601:Archived 3525:cite web 3487:Archived 3408:Archived 3404:26898141 3357:17494361 3308:27480474 3126:44450759 3099:60169541 3053:Archived 3010:Archived 2988:(1832). 2964:Archived 2942:15622794 2893:17557503 2802:Archived 2790:(1): 3. 2754:Archived 2702:24792835 2653:25202549 2569:Archived 2565:94886591 2513:"Isatin" 2496:14 March 2487:Archived 2461:12091779 2428:cite web 2383:19546703 2334:18035234 2291:Archived 2273:37097870 2265:17342837 2070:See also 2062:than in 2013:morphine 1961:laudanum 1913:diazepam 1875:Thailand 1834:O·H 1822:Morpheus 1764:insomnia 1683:barbital 1668:morphine 1648:hypnotic 1632:sedative 1565:in vitro 1496:to form 1475:C−CH(OH) 1444:chlorine 1333:glycerol 1183:insomnia 1170:for any 1162:nor the 1150:Hypnotic 1126:hypnotic 1122:sedative 867:Hazards 837:Class C1 732:) 718:ATC code 413:FM875000 292:DrugBank 226:1698497 185:302-17-0 84:Hydrogen 64:Chlorine 9317:VVZ-368 9184:ASP2535 9080:(e.g., 9056:(i.e., 9016:codeine 9014:(e.g., 9012:Opioids 8984:(e.g., 8948:(e.g., 8912:(e.g., 8871:(e.g., 8834:RU-5135 8806:(e.g., 8727:(e.g., 8685:Brucine 8631:toluene 8593:(e.g., 8569:cocaine 8559:(e.g., 8503:(e.g., 8478:(e.g., 8472:Ginseng 8459:(e.g., 8452:D12-116 8435:(e.g., 8388:(e.g., 8376:Taurine 8333:-Serine 8299:Glycine 8289:-Serine 8273:Caesium 8231:ligands 8097:borneol 8095:(e.g., 8087:trional 8077:(e.g., 7995:(e.g., 7993:Lignans 7943:(e.g., 7901:(e.g., 7846:Bromide 7838:(e.g., 7821:α-EMTBL 7785:Toluene 7755:Propane 7630:Chloral 7610:Benzene 7590:Acetone 7421:Phenols 7411:Y-23684 7401:U-90042 7386:TPA-023 7371:SX-3228 7356:ROD-188 7341:NS-2710 7336:NS-2664 7321:JM-1232 7306:ELB-139 7301:CTP-354 7187:Alpidem 6786:Wogonin 6761:Linarin 6240:FG-8205 5947:Reposal 5648:Menthol 5608:Butanol 5511:(e.g., 5509:Opioids 5458:Evoxine 5195:Doxepin 5009:Doxepin 4884:Tolibut 4780:Trional 4687:Bromide 4557:Phenols 4139:Reposal 3887:Sources 3661:580–583 3630:411–412 3458:Dracula 3440:27 June 3348:2701367 3134:4914358 2933:6975915 2693:4047925 2644:4105042 2297:6 March 2238:4318151 2046:of the 2017:whiskey 1959:from a 1917:cyanide 1809:in his 1798:Dracula 1675:asylums 1628:ethanol 1614:History 1570:in vivo 1545:chronic 1516:in vivo 1479:+ 5 HCl 1448:ethanol 1261:aniline 1242:chloral 1166:in the 1158:in the 1135:chloral 1095:formula 1052:Chloral 782:Hepatic 726: ( 724:N05CC01 675:Acidity 655:ethanol 647:benzene 599:Density 562: 382:PubChem 355:101369 301:DB01563 159:Somnote 8938:Ginkgo 8828:7-TFQA 8675:αEMBTL 8268:β-AIBA 8030:Niacin 7615:Butane 7568:SL-164 7439:Thymol 7381:TP-003 7262:Others 7065:P1-185 7025:5β-DHP 7020:5α-DHP 7015:3α-DHP 6863:Kavain 6771:Rc-OMe 5412:Others 5338:Orexin 5284:Others 5274:, etc. 5251:, etc. 5220:, etc. 5202:, etc. 5088:, etc. 5065:, etc. 5034:, etc. 5016:, etc. 4670:Others 4661:SL-164 3903:  3786:  3761:  3667:  3636:  3593:  3551:  3493:2 July 3402:  3394:  3355:  3345:  3306:  3298:  3263:  3228:  3218:  3193:  3183:  3132:  3124:  3097:  3087:  2940:  2930:  2891:  2867:drugs" 2844:  2700:  2690:  2651:  2641:  2563:  2459:  2381:  2373:  2332:  2271:  2263:  2236:  2196:  2136:  1919:, and 1630:. Its 1471:O → Cl 1467:OH + H 1411:plasma 1409:. The 1405:, and 1395:nausea 1378:Safety 1372:iodine 1370:, and 1257:isatin 1031:(SDS) 912:Danger 856: 835: 573:165.39 557:CH(OH) 524:SMILES 370:D00265 252:ChEMBL 156:Somnos 150:Noctec 106:Names 82:  80:  74:Oxygen 72:  70:  62:  60:  54:Carbon 52:  50:  9302:NAGly 9275:GlyT2 9174:ACPPB 9162:GlyT1 9116:NMDAR 8854:Tutin 8824:7-TFQ 8820:7-CIQ 8645:Xenon 8591:gases 7889:DEABL 7582:gases 7391:TP-13 7120:THDOC 7010:DHDOC 5534:UMB68 4854:GABOB 3868:(PDF) 3861:(PDF) 3153:[ 3122:JSTOR 2805:(PDF) 2780:(PDF) 2561:S2CID 2490:(PDF) 2479:(PDF) 2412:(PDF) 2401:(PDF) 2269:S2CID 2107:Notes 1869:King 1814:diary 1729:lipid 1543:, as 1419:blood 1415:serum 1364:fungi 1358:, an 1325:mites 1317:seeds 1313:ferns 1089:is a 786:renal 669:0.99 489:InChI 446:2811 232:ChEBI 198:JSmol 9352:GABA 9129:here 9127:See 9105:Zinc 9068:PMBA 9060:and 8977:NBQX 8729:2-AG 8650:Zinc 8403:tert 8294:GABA 8243:GlyR 7192:DS-1 6824:Kava 6751:EGCG 5687:tert 5679:tert 5582:GABA 5374:VDCC 5160:5-HT 4823:GABA 4001:2M2B 3981:GABA 3972:N05C 3901:ISBN 3876:2013 3784:ISBN 3759:ISBN 3721:2015 3665:ISBN 3634:ISBN 3609:2017 3591:ISBN 3549:ISBN 3531:link 3517:2022 3495:2018 3467:2018 3442:2018 3416:2022 3400:PMID 3392:ISSN 3353:PMID 3304:PMID 3296:ISSN 3261:ISSN 3226:OCLC 3216:ISBN 3191:OCLC 3181:ISBN 3130:PMID 3095:OCLC 3085:ISBN 3061:2016 3018:2016 2972:2022 2938:PMID 2889:PMID 2842:ISBN 2813:2022 2762:2018 2698:PMID 2649:PMID 2577:2021 2498:2013 2457:PMID 2434:link 2420:2018 2379:PMID 2371:ISSN 2330:PMID 2299:2018 2261:PMID 2234:PMID 2194:ISBN 2134:ISBN 2015:and 1774:and 1719:and 1568:and 1551:and 1535:and 1459:+ CH 1455:4 Cl 1446:and 1407:coma 1331:and 1263:and 1228:and 1145:Uses 1124:and 996:P501 992:P405 988:P362 976:P330 972:P321 956:P280 952:P270 948:P264 934:H319 930:H315 926:H301 784:and 662:log 589:Odor 422:UNII 395:2707 361:KEGG 281:2606 66:, Cl 7921:DS2 7030:DHT 6746:EGC 4874:GVL 4869:GBL 4859:GHB 3384:doi 3343:PMC 3335:doi 3288:doi 3253:doi 3045:doi 3002:doi 2928:PMC 2920:doi 2879:doi 2834:doi 2792:doi 2688:PMC 2680:doi 2639:PMC 2631:doi 2600:doi 2553:doi 2361:doi 2357:111 2322:doi 2226:doi 2167:doi 2126:doi 1873:of 1830:HCl 1792:'s 1519:to 1492:by 1417:or 1343:). 1199:EEG 1164:EMA 1156:FDA 874:GHS 729:WHO 553:CCl 458:EPA 385:CID 86:, H 76:, O 56:, C 9381:: 9092:, 9088:, 9084:, 9046:, 9042:, 9038:, 9034:, 9030:, 9026:, 9022:, 9018:, 9004:, 9000:, 8996:, 8992:, 8988:, 8968:)) 8964:, 8960:, 8956:, 8952:, 8944:, 8920:, 8916:, 8887:, 8883:, 8879:, 8875:, 8826:, 8822:, 8818:, 8814:, 8810:, 8731:, 8637:, 8633:, 8629:, 8625:, 8621:, 8617:, 8613:, 8609:, 8605:, 8601:, 8597:, 8579:, 8575:, 8571:, 8567:, 8563:, 8519:, 8515:, 8511:, 8507:, 8482:)) 8439:, 8415:, 8411:, 8407:, 8400:, 8396:, 8392:, 8171:• 8167:• 8122:, 8118:, 8114:, 8085:, 8081:, 8007:, 8003:, 7999:, 7955:, 7951:, 7947:, 7913:, 7909:, 7905:, 7856:, 7852:, 7264:: 7218:: 7185:: 7147:: 5162:2A 3711:. 3707:. 3663:. 3632:. 3599:. 3527:}} 3523:{{ 3406:. 3398:. 3390:. 3378:. 3374:. 3351:. 3341:. 3331:21 3329:. 3325:. 3302:. 3294:. 3282:. 3259:. 3247:. 3224:. 3189:. 3163:^ 3128:. 3118:44 3116:. 3093:. 3069:^ 3051:. 3039:. 3008:. 2996:. 2958:. 2936:. 2926:. 2916:95 2914:. 2910:. 2887:. 2873:. 2869:. 2840:. 2800:. 2788:49 2786:. 2782:. 2752:. 2748:. 2696:. 2686:. 2676:62 2674:. 2670:. 2647:. 2637:. 2625:. 2621:. 2596:16 2594:. 2567:. 2559:. 2549:44 2547:. 2543:. 2522:; 2515:. 2481:. 2453:28 2451:. 2430:}} 2426:{{ 2403:. 2377:. 2369:. 2355:. 2351:. 2328:. 2318:24 2316:. 2267:. 2257:41 2255:. 2232:. 2222:23 2220:. 2208:^ 2163:80 2161:. 2132:. 2066:. 1824:— 1816:: 1785:. 1700:. 1572:. 1531:, 1500:. 1463:CH 1434:. 1413:, 1386:50 1384:LD 1315:, 1311:, 1290:. 1252:. 1115:H) 1107:−C 1099:Cl 1058:, 1054:, 1013:50 1011:LD 994:, 990:, 986:, 982:, 978:, 974:, 970:, 966:, 962:, 958:, 954:, 950:, 932:, 928:, 878:: 852:US 844:CA 831:BR 792:) 757:: 684:) 677:(p 653:, 649:, 9354:A 9152:) 9148:( 9096:) 9064:) 9050:) 9008:) 8924:) 8891:) 8830:) 8735:) 8641:) 8589:/ 8583:) 8523:) 8463:) 8443:) 8419:) 8339:L 8331:L 8323:L 8315:L 8287:D 8279:D 8233:) 8229:( 8206:e 8199:t 8192:v 8126:) 8099:) 8089:) 8011:) 7959:) 7917:) 7860:) 7842:) 7580:/ 6782:) 5629:) 5625:( 5585:A 5573:e 5566:t 5559:v 5515:) 5371:δ 5369:2 5367:α 5105:2 5103:α 4896:1 4894:H 4865:) 4861:( 4825:B 3983:A 3974:) 3970:( 3966:/ 3956:e 3949:t 3942:v 3909:. 3878:. 3792:. 3767:. 3723:. 3673:. 3642:. 3611:. 3555:. 3533:) 3519:. 3444:. 3418:. 3386:: 3380:2 3359:. 3337:: 3310:. 3290:: 3284:2 3267:. 3255:: 3249:2 3232:. 3197:. 3136:. 3101:. 3063:. 3047:: 3041:1 3020:. 3004:: 2998:1 2974:. 2944:. 2922:: 2895:. 2881:: 2875:2 2865:A 2850:. 2836:: 2815:. 2794:: 2764:. 2704:. 2682:: 2655:. 2633:: 2627:1 2606:. 2602:: 2579:. 2555:: 2529:. 2500:. 2463:. 2436:) 2422:. 2385:. 2363:: 2336:. 2324:: 2301:. 2275:. 2240:. 2228:: 2202:. 2173:. 2169:: 2155:p 2142:. 2128:: 2019:. 1923:. 1838:O 1836:2 1832:3 1828:2 1826:C 1477:2 1473:3 1469:2 1465:2 1461:3 1457:2 1117:2 1113:O 1111:( 1109:H 1105:C 1102:3 1019:) 1015:( 854:: 833:: 682:a 679:K 664:P 559:2 555:3 460:) 456:( 200:)

Index



Carbon
Chlorine
Oxygen
Hydrogen

Preferred IUPAC name
CAS Number
302-17-0
JSmol
Interactive image
Beilstein Reference
ChEBI
CHEBI:28142
ChEMBL
ChEMBL455917
ChemSpider
2606
DrugBank
DB01563
ECHA InfoCard
100.005.562
Edit this at Wikidata
EC Number
Gmelin Reference
KEGG
D00265
PubChem
2707

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