Knowledge

γ-Butyrolactone

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Ashland, BASF, and Miami Chemical. Lyondell reportedly stopped commercial sales of this product due to increasingly tight regulations and liabilities but still makes it for internal and downstream production use. To purchase this chemical requires special DEA license and end use certificate approved and a site audit by DEA.
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For those users who do report withdrawal symptoms upon quitting the use of GHB or GBL, symptoms seem to depend on the dosage and the length of time the drug was used. Light to moderate users often experience insomnia and sleep-related problems, whereas heavy, prolonged use can cause severe withdrawal
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GBL is a dangerous drug controlled under Schedule 1 of the Dangerous Drugs Ordinance, Cap.134 (with exemption clause at Paragraph 16D). Any person who is found to have in his possession of it not in accordance with this Ordinance can be liable, on conviction upon indictment, a fine of HK$ 1,000,000
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GBL is not listed in the narcotics law, but its distribution is controlled. Possession is not illegal, but may be punished according to the Medicines Act, when intended to be sold for human consumption or synthesis of GHB. In recent years, an increase of GBL consumption has been observed due to the
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if intended for human consumption. Sales and distribution of this product for industrial use is tightly regulated and requires quantity tracing, lock and key storage and 24 hour surveillance and is limited to a very few suppliers who have appropriate DEA registrations and as of 2021 included only
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GBL is a Controlled Substance under Schedule VI of the "Controlled Drugs and Substances Act" in Canada. Schedule VI of the "Controlled Drugs and Substances Act" requires vendors to collect information regarding purchases of GBL. The Act also prohibits the import and export of GBL into or out of
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Frequent use of GHB or GBL, even when taken long-term and in moderate doses, does not appear to cause significant physical dependency in the majority of its users. In many people, quitting or temporarily abstaining from use of the drugs is achieved with minimal or no difficulty. However, when
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GBL is not classified as a drug but as a health-endangering substance. Legislation entering into force on 1 April 2011 made it possible to handle narcotics for industrial purposes and enabled GBL and 1,4-Butanediol to be classified as controlled substances. As of 2023 there are penalties for
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GBL is not classified as a drug but as a health-endangering substance. Although recently passed legislation to enter into force on 1 April 2011 will make it possible to handle narcotics for industrial purposes will enable GBL and 1,4-Butanediol to be classified as controlled substances.
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Canada classifying it as either an indictable offense punishable with up to 10 years in prison or an offense punishable on summary conviction liable to imprisonment for up to eighteen months. It is not illegal for an individual to possess GBL in Canada.
1590:: GBL is unlike GHB not listed in the narcotics law, but its distribution is controlled. Possession is not illegal but may be punished according to the Medicines Act, when intended to be sold for human consumption or synthesis of GHB. 1485:
consumed in excessive amounts with a high frequency of dosing, physical and psychological dependence can develop. Management of GBL dependence involves considering the person's age, comorbidity and the pharmacological pathways of GBL.
1955:"A Change to the Misuse of Drugs Act 1971 : Control of GBL, 1,4-BD, BZP and related piperazine compounds, a further group of anabolic steroids and 2 non-steroidal agents, synthetic cannabinoid receptor agonists and oripavine" 1139: 740: 707: 1442:
GBL has a distinctive taste and odor, described as being comparable to stale water, synthetic melon aroma or burnt plastic. This differs significantly from GHB, which is described as having a decidedly "salty" taste.
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GHB and GBL users can adopt a '24/7' dosing regime. This is where the user has become tolerant to the effects of the drug, increasing the dosage and frequency of dosage simply to avoid withdrawal symptoms.
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If taken undiluted by mouth, GBL can cause esophageal and gastro-intestinal irritation. It is possible for oral ingestion of GBL to cause nausea and other similar problems, possibly more so than with GHB.
1608:: GBL has been classified as a psychotropic substance since 22 February 2012. Its trafficking is limited, and non-licensed selling, buying or any other use is punishable by imprisonment up to 20 years. 2502:
van Nieuwenhuijzen PS, McGregor, IS (1 August 2009). "Sedative and hypothermic effects of gamma-hydroxybutyrate (GHB) in rats alone and in combination with other drugs: assessment using biotelemetry".
1343:(lactonase) enzymes, found in the blood. Animals which lack these enzymes exhibit no effect from GBL. GBL is more lipophilic (fat soluble) than GHB, and so is absorbed faster and has higher 798: 7075: 2477: 2175: 6869: 5591: 1446:
Due to the fact that those with limited chemistry knowledge can make GBL with easy-to-get precursors, it has become quite popular among young people in French nightclubs.
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and may be present in similar products. The concentration detected was approximately 5 μg/mL and was easily observed using a simple extraction technique followed by
1758:[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). 1466:
the increased sedation and risk of vomiting results in a high risk of fatality. Many harm reduction organisations suggest never mixing the two drugs as a result.
1347:. Because of these pharmacokinetic differences, GBL tends to be more potent and faster-acting than GHB, but has a shorter duration; whereas the related compound 841: 4046: 1625:, except where a person does so knowing or believing that they will be used for the purpose of human ingestion. Otherwise it is a class B controlled substance. 977: 1621:
Because of their legitimate uses, regulation 4B of the 2001 regulations makes it lawful to import, export, produce, supply, offer to supply or possess GBL and
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Elliott S, Burgess V (2005). "The presence of gamma-hydroxybutyric acid (GHB) and gamma-butyrolactone (GBL) in alcoholic and non-alcoholic beverages".
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which increases sleep related growth hormone (GH) secretion, GBL was sold as a nutritional supplement after the scheduling of GHB, under the names
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Hong M, Chen EY (2015). "Completely recyclable biopolymers with linear and cyclic topologies via ring-opening polymerization of γ-butyrolactone".
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Hong M, Chen EX (2016). "Towards Truly Sustainable Polymers: A Metal-Free Recyclable Polyester from Biorenewable Non-Strained γ-Butyrolactone".
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GBL has been found in extracts from samples of unadulterated wines. This finding indicates that GBL is a naturally occurring component in some
2755:"LAW AND JUSTICE LEGISLATION AMENDMENT (SERIOUS DRUG OFFENCES AND OTHER MEASURES) ACT 2005 NO. 129, 2005 - SCHEDULE 1 - Serious drug offences" 6839: 4634: 3017: 2538: 2373: 2220: 1706: 6350: 7540: 5557: 5416: 1119: 2729: 6904: 6355: 2996: 1509:, the common form, so doses are measured in the single milliliter range, either taken all at once or sipped over the course of a night. 6977: 2413:
Galloway G, Frederick-Osborne S, Seymour R, Contini S, Smith D (2000). "Abuse and therapeutic potential of gamma-hydroxybutyric acid".
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Teiber J, Draganov D, Du B (2003). "Lactonase and lactonizing activities of human serum paraoxonase (PON1) and rabbit serum PON3".
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GBL is classified as a drug. A license is mandatory for the manufacture, processing, reworking, importing, distribution of GBL.
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There have been news reports of several deaths associated with GBL, usually in combination with alcohol or other depressants.
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as the organic solvent. It is frequently mixed with a small ratio of ethylene glycol, "9:1" being common, to vary internal
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analysis. GBL can be found in cheese flavorings but typically results in a content of 0.0002% GBL in the final foodstuff.
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a NIDA Neuroscience Consortium and OSPC "Cutting Edge" colloquium (27 June 2000 at the Doubletree hotel, Rockville, MD)
2290:"Simultaneous stimulation of slow-wave sleep and growth hormone secretion by gamma-hydroxybutyrate in normal young Men" 1268:
Gamma-Butyrolactone is used as a chemical solvent and a cleaning agent, for example in paint stripping or for cleaning
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Vose J, Tighe T, Schwartz M, Buel E (2001). "Detection of gamma-butyrolactone (GBL) as a natural component in wine".
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The yield of this process is approximately 95%. The purification takes place with a liquid-gas-phase extraction.
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To bypass GHB restriction laws, home synthesis kits were introduced to transform GBL and/or 1,4-B into GHB.
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Wolfgang Schwarz, Jürgen Schossig, Roland Rossbacher, Rolf Pinkos, Hartmut Höke (2019). "Butyrolactone".
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Santos C, Olmedo RE (2017). "Sedative-Hypnotic Drug Withdrawal Syndrome: Recognition And Treatment".
2639:"[Gamma-hydroxybutyric acid (GHB): more than a date rape drug, a potentially addictive drug]" 1253: 1215: 1189: 565: 58: 6215: 3834: 2288:
Van Cauter E, Plat L, Scharf MB, Leproult R, Cespedes S, l'Hermite-Balériaux M, Copinschi G (1997).
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at a temperature of 180–300 °C and atmospheric pressure in the presence of a copper catalyst.
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Karila L, Novarin J, Megarbane B, Cottencin O, Dally S, Lowenstein W, Reynaud M (1 October 2009).
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Metsger L, Bittner S (March 2000). "Autocatalytic Oxidation of Ethers with Sodium Bromate".
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Weak characteristic odor, comparable to stale water, synthetic melon aroma or burnt plastic
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of butyrolactone gives polybutyrolactone. The resulting reverts to the monomer by thermal
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It has been used as a solvent in various laboratory experiments, e.g., the preparation of
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controlled chemical. As a GHB analog, it is also treated as a controlled substance under
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GBL is not active in its own right; its mechanism of action stems from its identity as a
2888:(in Simplified Chinese). The State Council - The People's Republic of China. 7 June 2021 1536:
Please help update this article to reflect recent events or newly available information.
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GHB has biphasic effects, a euphoric effect at low doses (the reason for the term
1069: 2210: 1843: 1256:. It is claimed that poly(GBL) is competitive with commercial biomaterial poly(4- 768: 300: 7409: 7334: 7269: 7108: 7045: 6952: 6894: 6804: 6674: 6665: 6625: 6420: 6280: 6275: 6264: 6260: 6210: 6200: 6087: 6072: 6054: 5949: 5915: 5772: 5722: 5702: 5652: 5301: 5145: 5095: 4903: 4593: 4537: 4532: 4488: 4462: 4420: 4397: 4382: 4341: 4287: 4155: 4101: 4051: 4018: 4003: 3963: 3824: 3819: 3814: 3685: 3667: 3657: 3586: 3566: 3528: 3404: 3341: 3336: 3281: 3266: 3238: 3203: 3188: 3123: 3110: 3075: 1677: 1340: 1303: 1061: 937: 917: 867: 588: 7294: 7204: 7113: 7103: 6962: 6779: 6769: 6754: 6749: 6744: 6711: 6690: 6660: 6595: 6575: 6569: 6471: 6438: 6432: 6424: 6325: 6320: 6315: 6300: 6252: 6225: 6190: 6165: 6024: 6019: 6013: 5960: 5909: 5905: 5792: 5647: 5510: 5500: 5467: 5457: 5306: 5223: 5208: 5203: 5193: 5125: 4953: 4588: 4561: 4551: 4472: 4452: 4425: 4360: 4336: 4331: 4214: 4209: 4199: 4189: 4150: 4145: 4056: 3998: 3983: 3794: 3700: 3596: 3576: 3543: 3533: 3523: 3513: 3480: 3462: 3447: 3394: 3389: 3351: 3346: 3321: 3306: 3276: 3271: 3261: 3243: 2654: 1178: 1099: 559: 470: 245: 185: 3002: 2662: 2638: 2390:"USDOJ: U.S. Department of Justice Archive National Drug Intelligence Center" 1851: 7429: 7424: 7414: 7374: 7319: 7304: 7284: 7279: 7264: 7060: 7030: 6937: 6917: 6912: 6764: 6686: 6620: 6590: 6561: 6491: 6476: 6443: 6410: 6174: 6150: 6108: 6100: 6059: 6049: 6033: 6029: 6005: 5990: 5985: 5945: 5862: 5847: 5812: 5802: 5787: 5762: 5742: 5697: 5505: 5350: 5291: 5198: 5135: 5120: 4948: 4832: 4598: 4392: 4282: 4249: 4184: 4096: 4061: 4013: 3856: 3809: 3616: 3601: 3591: 3581: 3490: 3452: 3442: 3434: 3419: 3376: 3366: 3361: 3331: 3286: 3223: 3158: 2612: 664: 5569: 2715: 2670: 2523: 2434: 2257: 2136: 2128: 2099: 1937: 1902: 1859: 4619: 2794:"Consolidated federal laws of Canada, Controlled Drugs and Substances Act" 2323: 7419: 7349: 7339: 7299: 7274: 7214: 7117: 7025: 6899: 6829: 6784: 6715: 6655: 6640: 6555: 6516: 6415: 6295: 6204: 6144: 6124: 6116: 6009: 5995: 5979: 5929: 5827: 5817: 5797: 5767: 5751: 5642: 5515: 5472: 5213: 5100: 4845: 4827: 4582: 4573: 4467: 4219: 3948: 3918: 3844: 3779: 3634: 3611: 3606: 3571: 3424: 3356: 3218: 3133: 3037: 3033: 2616: 1438:
FDA warning against products containing GHB and its prodrugs, such as GBL
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Butyrolactone, with its wide liquid range, chemical stability, and high
1214:. In acidic water, a mixture of the lactone and acid forms exists in an 214: 7324: 7309: 7219: 7132: 6859: 6819: 6814: 6739: 6650: 6630: 6546: 6375: 6370: 6195: 5935: 5851: 5832: 5667: 5462: 5429: 5286: 4850: 4527: 4264: 4078: 3953: 3849: 3756: 3475: 3208: 2091: 1405: 1381: 1328: 1219: 1174: 1080: 584: 580: 576: 501: 287: 2305: 1894: 1505:
A milliliter of pure GBL metabolizes to the equivalent 1.65 g of
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possessing, selling or driving under the influence of the substance.
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Except where otherwise noted, data are given for materials in their
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Schep LJ, Knudsen K, Slaughter RJ, Vale JA, Mégarbane B (2012).
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In the laboratory, it may also be obtained via the oxidation of
1115: 1065: 491: 266: 5573: 4623: 3006: 2685:"GHB addiction, GHB physical n psychological dependency levels" 1283: 1130:γ-Butyrolactone is produced industrially by dehydrogenation of 1064:, colorless, water-miscible liquid with a weak, characteristic 6244: 1516: 1280:. It is also used as a solvent in lotions and some polymers. 5417: 353: 6840: 2964:"Information Bulletin: GHB Analogs; GBL, BD, GHV, and GVL" 2539:"Coroner's 'Russian roulette' warning over GBL party drug" 825: 2338:"Erowid GHB vault: FDA Warning about Gamma Butyrlactone" 1584:
GBL was classified as a proscribed substance from 2007.
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Gamma-Hydroxybutyric acid § Sports and athletics
1232:. When treated with a non-nucleophilic base, such as 5028: 7164: 7155: 6838: 5622: 5613: 5481: 5443: 5415: 5359: 5336: 5319: 5254:
Tooltip Vesicular inhibitory amino acid transporter
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Tooltip Sodium-coupled monocarboxylate transporters
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Boca Raton, FL: CRC Press. 1290:is an herbicide produced from butyrolactone. 5601: 4436: 7161: 6849:Tooltip γ-Aminobutyric acid A-rho receptor 5619: 5592: 5578: 5570: 5333: 5023: 4677: 4642: 4628: 4620: 4237: 3971: 3058: 3025: 3011: 3003: 2204: 2202: 368: 235: 193: 28: 2886:"国务院办公厅关于同意将α-苯乙酰乙酸甲酯等6种物质列入易制毒化学品品种目录的函" 2613:"GBL drug death identified by UK doctors" 2313: 1786: 1784: 1782: 1780: 1323:gamma-hydroxybutyrate § Pharmacology 335: 1056: 1052: 5366:Tooltip 4-Hydroxybutyrate dehydrogenase 5343:Tooltip Succinic semialdehyde reductase 2116:Angewandte Chemie International Edition 2051: 2049: 2034:"Sandmeyer Reaction of GABA to GBL/GHB" 1669: 1472:Gamma-Butyrolactone is often used as a 424: 389: 364: 213: 7174:Tooltip γ-Aminobutyric acid B receptor 5632:Tooltip γ-Aminobutyric acid A receptor 4987:Tooltip γ-Aminobutyric acid B receptor 2936:"UK Statutory Instrument 2011 No. 448" 2858:"Webwinkels gestopt met handel in GBL" 2215:. John Wiley & Sons. p. 386. 1988: 1977: 886:455 °C (851 °F; 728 K) 542:204 °C (399 °F; 477 K) 226: 1698:CRC Handbook of Chemistry and Physics 1396:, until they were banned by the FDA. 1339:GBL is rapidly converted into GHB by 1157:. An alternative route proceeds from 396:Key: YEJRWHAVMIAJKC-UHFFFAOYSA-N 393:InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2 173: 153: 7: 7479:GABA metabolism/transport modulators 5033:Tooltip Monocarboxylate transporters 4682: 2990:"The paint stripper drug that kills" 1288:2-Methyl-4-chlorophenoxybutyric acid 403:InChI=1/C4H6O2/c5-4-2-1-3-6-4/h1-3H2 5875:Positive modulators (abridged; see 2908:"Główny Inspektorat Farmaceutyczny" 2769:"GHB - Alcohol and Drug Foundation" 406:Key: YEJRWHAVMIAJKC-UHFFFAOYAC 290: 274: 1495:Benzodiazepine withdrawal syndrome 25: 7410:Homotaurine (tramiprosate, 3-APS) 6908:-Chloroacetylcytosine arabinoside 5703:Homotaurine (tramiprosate, 3-APS) 3752:Acetylglycinamide chloral hydrate 2537:Edwards, Richard (23 July 2009). 2294:Journal of Clinical Investigation 1578:and to imprisonment for 7 years. 1102:with effects similar to those of 88:gamma-Hydroxybutyric acid lactone 2516:10.1016/j.drugalcdep.2009.03.004 1521: 1153:(THF), for example with aqueous 1138: 997: 926:>5640 mg/kg (dermal, rabbit) 730: 725: 454: 44: 35: 7536:Drug-facilitated sexual assault 6702:Pentylenetetrazol (pentetrazol) 4825:Positive allosteric modulators: 2611:Casciani D (23 December 2009). 1930:10.1016/j.forsciint.2005.02.014 1766:from the original on 2023-08-03 1380:Due to its property of being a 993:(at 25 °C , 100 kPa). 5488:Tooltip Aldehyde dehydrogenase 1918:Forensic Science International 689:Occupational safety and health 460: 448: 1: 7461:Receptor/signaling modulators 6616:Isopregnanolone (sepranolone) 5551:Glutamate receptor modulators 5537:Receptor/signaling modulators 5468:Fomepizole (4-methylpyrazole) 5450:Tooltip Alcohol dehydrogenase 2427:10.1016/S0741-8329(99)00090-7 2250:10.1016/S0006-2952(03)00401-5 2020:10.1016/S0040-4020(00)00098-3 1803:10.1002/14356007.a04_495.pub2 1185:conditions, for example in a 1090:(GHB) and is often used as a 86:4-Hydroxybutyric acid lactone 7472:receptor positive modulators 5980:ergoloid (dihydroergotoxine) 2992:. BBC News. October 7, 2005. 2362:Meyer J, Quenzer LF (2005). 2056:Micu A (December 12, 2015). 1883:Journal of Forensic Sciences 1844:10.3109/15563650.2012.702218 1480:Addictiveness and dependence 7541:Neurotransmitter precursors 5558:Glycine receptor modulators 4711:Aceburic acid (GHB acetate) 4278:Tetracyclic antidepressants 4092:Tetracyclic antidepressants 2866:(in Dutch). 9 December 2013 2504:Drug and Alcohol Dependence 2212:Forensic Chemistry Handbook 2209:Kobilinsky L (2011-11-29). 1695:Lide DR, ed. (2009-06-03). 1250:ring-opening polymerization 906:or concentration (LD, LC): 7557: 6671:Nonsteroidal antiandrogens 2792:Branch LS (May 19, 2023). 2484:(in French). 17 April 2018 1594:People's Republic of China 1373: 1320: 1311:methylammonium lead halide 7452: 5528: 4255:Tricyclic antidepressants 4069:Tricyclic antidepressants 2655:10.1016/j.lpm.2009.05.017 1641:Controlled Substances Act 1530:This section needs to be 1276:, and with ammonia gives 1079:In humans, GBL acts as a 987: 944:>2.68 mg/kg (rat, 4h) 902: 706: 686: 681: 435: 415: 380: 93: 69: 57: 52: 43: 34: 6220:sulfonmethane (sulfonal) 5544:GABA receptor modulators 3840:Sulfonmethane (sulfonal) 2838:(in Dutch). 19 July 2019 2368:. Sinauer. p. 370. 2238:Biochemical Pharmacology 1762:(published 2023-04-04). 1234:lithium diisopropylamide 1126:Production and synthesis 777:Precautionary statements 7516:GABAB receptor agonists 4327:Atypical antipsychotics 4141:Atypical antipsychotics 2798:laws-lois.justice.gc.ca 2395:. Usdoj.gov. 2012-06-15 1797:. Weinheim: Wiley-VCH. 1760:Diário Oficial da União 1300:electrolytic capacitors 1230:1,6-Dioxecane-2,7-dione 1223:poly(4-hydroxybutyrate) 7099:5α-Dihydroprogesterone 6646:Morphine-3-glucuronide 6306:Hyenachin (mellitoxin) 6191:Retigabine (ezogabine) 4501:Chlorophenylalkyldiols 4309:Typical antipsychotics 4123:Typical antipsychotics 2588:. GMFA. Archived from 2129:10.1002/anie.201601092 1987:Cite journal requires 1631:GBL is regulated as a 1439: 1431: 1370:Nutritional supplement 1366: 1291: 1163:diazonium intermediate 1096:central nervous system 1074:N-methyl-2-pyrrolidone 924:1540 mg/kg (oral, rat) 836: 7521:GHB receptor agonists 6487:Chlorophenylsilatrane 5374:α-Ketoisocaproic acid 1734:"gamma-Butyrolactone" 1437: 1429: 1358:Metabolic pathway of 1357: 1286: 1068:. It is the simplest 835: 7437:Negative modulators: 7317:Positive modulators: 7210:Arbaclofen placarbil 7096:Negative modulators: 6945:Positive modulators: 6730:Pregnenolone sulfate 6366:17-Phenylandrostenol 6348:Negative modulators: 6233:constituents (e.g., 6203:constituents (e.g., 6065:Neuroactive steroids 6042:constituents (e.g., 5778:Neuroactive steroids 4687:Tooltip GHB receptor 4458:Gabapentin enacarbil 3506:Neuroactive steroids 3476:Apronal (apronalide) 1571:prohibition of GHB. 1493:symptoms similar to 1212:-hydroxybutyric acid 1088:-hydroxybutyric acid 980:(Psychoactive drugs) 938:median concentration 818:(fire diamond) 702:Toxic and flammable 59:Preferred IUPAC name 7026:Gabazine (SR-95531) 7016:CGP-36742 (SGS-742) 6724:dihydropicrotoxinin 6449:Bicyclic phosphates 6361:11-Ketoprogesterone 6296:Gabazine (SR-95531) 6121:pyrazolopyrimidines 4846:Gabazine (SR-95531) 1832:Clinical Toxicology 1296:dielectric constant 549:Solubility in water 478: g·mol 31: 18:Gamma-Butyrolactone 6547:FG-7142 (ZK-31906) 6093:Nonbenzodiazepines 5209:Mesalazine (5-ASA) 5116:Phenylpyruvic acid 4746:GHV (4-methyl-GHB) 4523:Diethylpropanediol 3805:Dichloralphenazone 3721:Methylmethaqualone 3559:Nonbenzodiazepines 3086:Diethylpropanediol 2092:10.1038/nchem.2391 1659:Succinic anhydride 1440: 1432: 1430:Jugs of seized GBL 1367: 1292: 1020:Infobox references 837: 29: 7488: 7487: 7448: 7447: 7370:2-Hydroxysaclofen 7151: 7150: 7041:Isonipecotic acid 6406:Anabolic steroids 6376:α5IA (LS-193,268) 6286:Dihydrosecurinine 6171:Pyrazolopyridines 5940:potassium bromide 5938:compounds (e.g., 5901:Anabolic steroids 5879:for a full list): 5733:Isonipecotic acid 5567: 5566: 5524: 5523: 5406: 5330: 5315: 5314: 5041:α-Ketoisocaproate 5020: 5005: 5004: 4858:Unknown/unsorted: 4674: 4617: 4616: 4369: 4368: 4167: 4166: 3887: 3886: 3768:Potassium bromide 3726:Nitromethaqualone 3234:Thiotetrabarbital 3081:Ethanol (alcohol) 2691:on July 26, 2010. 2649:(10): 1526–1538. 2375:978-0-87893-534-5 2306:10.1172/JCI119587 2222:978-0-471-73954-8 2123:(13): 4188–4193. 2014:(13): 1905–1910. 1895:10.1520/JFS15116J 1708:978-1-4200-9084-0 1551: 1550: 1400:Recreational drug 1092:recreational drug 1049:with the formula 1028:Chemical compound 1026: 1025: 975: 956:Fisher Scientific 950:Safety data sheet 755:Hazard statements 655:1.435, 1.4341 (20 486:Colorless liquid 349:CompTox Dashboard 135:Interactive image 16:(Redirected from 7548: 7195:4-Fluorophenibut 7175: 7171: 7162: 7031:Gaboxadol (THIP) 6948:Allopregnanolone 6850: 6846: 6581:Fluoroquinolones 6336:Thiocolchicoside 6156:Piperidinediones 6113:imidazopyridines 6069:allopregnanolone 5976:Dihydroergolines 5891:drinking alcohol 5782:allopregnanolone 5698:Gaboxadol (THIP) 5633: 5629: 5620: 5603: 5594: 5587: 5580: 5571: 5489: 5485: 5451: 5447: 5423: 5419: 5407:-Glucuronic acid 5404: 5367: 5363: 5344: 5340: 5334: 5324: 5255: 5251: 5172: 5168: 5151:Sodium valproate 5046:Acetoacetic acid 5034: 5030: 5024: 5014: 4988: 4984: 4944:Prochlorperazine 4688: 4684: 4678: 4668: 4653: 4644: 4637: 4630: 4621: 4542:muscle relaxants 4445: 4442: 4238: 3972: 3909:4-Fluorophenibut 3645:Piperidinediones 3519:Allopregnanolone 3101:Trichloroethanol 3059: 3027: 3020: 3013: 3004: 2997:"All About GHB," 2993: 2972: 2971: 2960: 2954: 2953: 2946: 2940: 2939: 2932: 2926: 2925: 2918: 2912: 2911: 2904: 2898: 2897: 2895: 2893: 2882: 2876: 2875: 2873: 2871: 2854: 2848: 2847: 2845: 2843: 2826: 2820: 2819: 2808: 2802: 2801: 2789: 2783: 2782: 2780: 2779: 2765: 2759: 2758: 2751: 2745: 2744: 2742: 2741: 2732:. Archived from 2726: 2720: 2719: 2699: 2693: 2692: 2687:. Archived from 2681: 2675: 2674: 2634: 2628: 2627: 2625: 2623: 2608: 2602: 2601: 2599: 2597: 2582: 2576: 2575: 2573: 2571: 2560: 2554: 2553: 2551: 2549: 2534: 2528: 2527: 2499: 2493: 2492: 2490: 2489: 2474: 2468: 2467: 2465: 2464: 2455:. Archived from 2453:Resident Advisor 2445: 2439: 2438: 2410: 2404: 2403: 2401: 2400: 2394: 2386: 2380: 2379: 2359: 2353: 2352: 2350: 2349: 2334: 2328: 2327: 2317: 2285: 2279: 2278: 2276: 2268: 2262: 2261: 2233: 2227: 2226: 2206: 2197: 2191: 2190: 2188: 2186: 2172: 2166: 2165: 2163: 2161: 2147: 2141: 2140: 2110: 2104: 2103: 2080:Nature Chemistry 2075: 2069: 2068: 2066: 2065: 2053: 2044: 2043: 2041: 2040: 2030: 2024: 2023: 2003: 1997: 1996: 1990: 1985: 1983: 1975: 1973: 1972: 1966: 1960:. Archived from 1959: 1951: 1942: 1941: 1924:(2–3): 289–292. 1913: 1907: 1906: 1889:(5): 1164–1167. 1878: 1872: 1871: 1823: 1817: 1816: 1788: 1775: 1774: 1772: 1771: 1748: 1742: 1741: 1730: 1724: 1723: 1721: 1720: 1711:. Archived from 1692: 1686: 1681:, 12th edition, 1674: 1546: 1543: 1537: 1525: 1524: 1517: 1335:Pharmacokinetics 1198:-hydroxybutyrate 1187:sodium hydroxide 1142: 1094:. GHB acts as a 1070:4-carbon lactone 1059: 1047:organic compound 1010: 1004: 1001: 1000: 973: 970: 898:16% v/v (upper) 896:3.6% v/v (lower) 892:Explosive limits 857: 850: 843: 828: 808: 804: 800: 796: 792: 788: 784: 770: 766: 762: 734: 729: 676: 672: 658: 642:Refractive index 616: 521: 517: 513: 509: 477: 462: 456: 450: 443:Chemical formula 373: 372: 357: 355: 339: 303: 292: 278: 258: 239: 228: 217: 197: 177: 157: 137: 113: 72:Dihydrofuran-2(3 48: 39: 32: 30:γ-Butyrolactone 21: 7556: 7555: 7551: 7550: 7549: 7547: 7546: 7545: 7491: 7490: 7489: 7484: 7471: 7444: 7173: 7170: 7147: 6875:Homohypotaurine 6848: 6844: 6834: 6707:Phenylsilatrane 6249:chloral hydrate 6216:Sulfonylalkanes 6105:cyclopyrrolones 5926:Benzodiazepines 5678:Dihydromuscimol 5631: 5628: 5609: 5598: 5568: 5563: 5520: 5487: 5477: 5449: 5439: 5421: 5411: 5365: 5355: 5342: 5323: 5311: 5253: 5243: 5239:Salicyclic acid 5170: 5160: 5032: 5013: 5001: 4986: 4983: 4973: 4909:azido-BnOPh-GHB 4686: 4667: 4659: 4648: 4618: 4613: 4477: 4440: 4430: 4402: 4365: 4349: 4295: 4242:Antidepressants 4233: 4224: 4195:Dexmedetomidine 4176: 4163: 4109: 4039:Antidepressants 4033: 3994:Diphenhydramine 3967: 3958: 3896: 3883: 3872:Isovaleric acid 3835:Sulfonylalkanes 3790:Chloral hydrate 3785:Chloral betaine 3763:Lithium bromide 3735: 3672: 3639: 3621: 3553: 3500: 3457: 3429: 3371: 3254:Benzodiazepines 3248: 3154:Ethallobarbital 3105: 3054: 3045: 3031: 2988: 2980: 2975: 2968:www.justice.gov 2962: 2961: 2957: 2948: 2947: 2943: 2934: 2933: 2929: 2920: 2919: 2915: 2906: 2905: 2901: 2891: 2889: 2884: 2883: 2879: 2869: 2867: 2856: 2855: 2851: 2841: 2839: 2828: 2827: 2823: 2810: 2809: 2805: 2791: 2790: 2786: 2777: 2775: 2767: 2766: 2762: 2753: 2752: 2748: 2739: 2737: 2728: 2727: 2723: 2704:Emerg Med Pract 2701: 2700: 2696: 2683: 2682: 2678: 2643:Presse Médicale 2636: 2635: 2631: 2621: 2619: 2610: 2609: 2605: 2595: 2593: 2592:on 20 June 2020 2584: 2583: 2579: 2569: 2567: 2566:. London Friend 2562: 2561: 2557: 2547: 2545: 2536: 2535: 2531: 2501: 2500: 2496: 2487: 2485: 2476: 2475: 2471: 2462: 2460: 2447: 2446: 2442: 2412: 2411: 2407: 2398: 2396: 2392: 2388: 2387: 2383: 2376: 2361: 2360: 2356: 2347: 2345: 2336: 2335: 2331: 2287: 2286: 2282: 2274: 2270: 2269: 2265: 2235: 2234: 2230: 2223: 2208: 2207: 2200: 2194: 2184: 2182: 2174: 2173: 2169: 2159: 2157: 2149: 2148: 2144: 2112: 2111: 2107: 2077: 2076: 2072: 2063: 2061: 2055: 2054: 2047: 2038: 2036: 2032: 2031: 2027: 2005: 2004: 2000: 1986: 1976: 1970: 1968: 1964: 1957: 1953: 1952: 1945: 1915: 1914: 1910: 1880: 1879: 1875: 1825: 1824: 1820: 1813: 1790: 1789: 1778: 1769: 1767: 1750: 1749: 1745: 1738:www.chemsrc.com 1732: 1731: 1727: 1718: 1716: 1709: 1694: 1693: 1689: 1675: 1671: 1667: 1650: 1619:United Kingdom: 1547: 1541: 1538: 1535: 1526: 1522: 1515: 1503: 1482: 1452: 1402: 1378: 1372: 1345:bioavailability 1337: 1325: 1319: 1266: 1258:hydroxybutyrate 1246: 1225:as well as the 1171: 1151:tetrahydrofuran 1128: 1112: 1058: 1054: 1050: 1032:γ-Butyrolactone 1029: 1022: 1017: 1016: 1015:  ?) 1006: 1002: 998: 994: 983: 941: 935: 925: 921: 915: 897: 883: 880: 862: 861: 860: 859: 852: 845: 838: 834: 826: 779: 757: 743: 722: 699: 674: 670: 656: 652: 650: 631: 614: 569: 551: 519: 515: 511: 507: 475: 465: 459: 453: 445: 431: 428: 423: 422: 411: 408: 407: 404: 398: 397: 394: 388: 387: 376: 358: 351: 342: 322: 306: 293: 281: 261: 248: 220: 200: 180: 160: 140: 127: 116: 103: 89: 87: 85: 84:4-Butyrolactone 83: 81: 79: 77: 65: 64: 23: 22: 15: 12: 11: 5: 7554: 7552: 7544: 7543: 7538: 7533: 7531:GABA analogues 7528: 7526:Designer drugs 7523: 7518: 7513: 7508: 7506:Gamma-lactones 7503: 7493: 7492: 7486: 7485: 7483: 7482: 7475: 7469: 7464: 7457: 7453: 7450: 7449: 7446: 7445: 7443: 7442: 7433: 7432: 7427: 7422: 7417: 7412: 7407: 7402: 7397: 7392: 7387: 7382: 7377: 7372: 7363: 7362: 7357: 7352: 7347: 7342: 7337: 7332: 7327: 7322: 7313: 7312: 7307: 7302: 7297: 7292: 7290:Sodium oxybate 7287: 7282: 7277: 7272: 7267: 7262: 7257: 7252: 7247: 7242: 7237: 7232: 7227: 7222: 7217: 7212: 7207: 7202: 7197: 7192: 7187: 7185:1,4-Butanediol 7178: 7176: 7168: 7159: 7153: 7152: 7149: 7148: 7146: 7145: 7140: 7135: 7130: 7125: 7111: 7106: 7101: 7092: 7091: 7086: 7078: 7073: 7068: 7063: 7058: 7053: 7048: 7043: 7038: 7033: 7028: 7023: 7018: 7013: 7005: 7000: 6995: 6990: 6985: 6980: 6975: 6966: 6965: 6960: 6955: 6950: 6941: 6940: 6935: 6930: 6925: 6920: 6915: 6910: 6902: 6897: 6892: 6887: 6882: 6877: 6872: 6867: 6862: 6853: 6851: 6842: 6836: 6835: 6833: 6832: 6827: 6822: 6817: 6812: 6807: 6802: 6797: 6792: 6787: 6782: 6777: 6772: 6767: 6762: 6757: 6752: 6747: 6742: 6737: 6732: 6727: 6709: 6704: 6699: 6694: 6668: 6663: 6658: 6653: 6648: 6643: 6638: 6633: 6628: 6623: 6618: 6613: 6608: 6603: 6598: 6593: 6588: 6578: 6573: 6559: 6549: 6544: 6539: 6534: 6529: 6524: 6519: 6514: 6509: 6504: 6499: 6494: 6489: 6484: 6479: 6474: 6469: 6464: 6446: 6441: 6436: 6429:cephalosporins 6418: 6413: 6408: 6403: 6398: 6393: 6388: 6383: 6378: 6373: 6368: 6363: 6358: 6353: 6344: 6343: 6338: 6333: 6328: 6323: 6318: 6313: 6308: 6303: 6298: 6293: 6288: 6283: 6278: 6269: 6268: 6238: 6235:valerenic acid 6228: 6223: 6213: 6208: 6198: 6193: 6188: 6181:Quinazolinones 6178: 6168: 6163: 6153: 6148: 6138: 6133: 6128: 6090: 6085: 6080: 6062: 6057: 6052: 6047: 6037: 6027: 6022: 6017: 6003: 6000:mefenamic acid 5993: 5988: 5983: 5973: 5968: 5963: 5958: 5953: 5943: 5933: 5923: 5913: 5903: 5898: 5884: 5871: 5870: 5865: 5860: 5855: 5845: 5840: 5835: 5830: 5825: 5820: 5815: 5810: 5805: 5800: 5795: 5790: 5785: 5775: 5770: 5765: 5760: 5755: 5745: 5740: 5735: 5730: 5725: 5720: 5715: 5710: 5705: 5700: 5695: 5690: 5685: 5680: 5675: 5670: 5665: 5660: 5650: 5645: 5636: 5634: 5626: 5617: 5611: 5610: 5599: 5597: 5596: 5589: 5582: 5574: 5565: 5564: 5562: 5561: 5554: 5547: 5540: 5533: 5529: 5526: 5525: 5522: 5521: 5519: 5518: 5513: 5508: 5503: 5498: 5492: 5490: 5479: 5478: 5476: 5475: 5470: 5465: 5460: 5454: 5452: 5441: 5440: 5438: 5437: 5435:Phenanthroline 5432: 5426: 5424: 5413: 5412: 5410: 5409: 5397: 5396: 5391: 5389:Salicylic acid 5386: 5381: 5376: 5370: 5368: 5357: 5356: 5354: 5353: 5347: 5345: 5331: 5317: 5316: 5313: 5312: 5310: 5309: 5304: 5299: 5297:Nipecotic acid 5294: 5289: 5284: 5279: 5274: 5269: 5267:Bafilomycin A1 5264: 5258: 5256: 5245: 5244: 5242: 5241: 5236: 5231: 5229:Propionic acid 5226: 5221: 5219:Nicotinic acid 5216: 5211: 5206: 5201: 5196: 5191: 5186: 5181: 5175: 5173: 5162: 5161: 5159: 5158: 5153: 5148: 5143: 5141:Salicylic acid 5138: 5133: 5128: 5123: 5118: 5113: 5108: 5103: 5098: 5093: 5088: 5083: 5078: 5073: 5068: 5063: 5058: 5053: 5048: 5043: 5037: 5035: 5021: 5007: 5006: 5003: 5002: 5000: 4999: 4991: 4989: 4981: 4975: 4974: 4972: 4971: 4966: 4961: 4956: 4951: 4946: 4941: 4936: 4931: 4926: 4921: 4916: 4911: 4906: 4901: 4896: 4891: 4886: 4881: 4876: 4871: 4866: 4854: 4853: 4848: 4836: 4835: 4830: 4818: 4813: 4808: 4803: 4798: 4793: 4788: 4783: 4781:Sodium oxybate 4778: 4773: 4768: 4763: 4758: 4753: 4748: 4743: 4738: 4733: 4728: 4723: 4718: 4713: 4708: 4703: 4691: 4689: 4675: 4661: 4660: 4649: 4647: 4646: 4639: 4632: 4624: 4615: 4614: 4612: 4611: 4606: 4601: 4596: 4591: 4589:Passion flower 4586: 4576: 4571: 4570: 4569: 4564: 4559: 4554: 4549: 4535: 4530: 4525: 4520: 4519: 4518: 4513: 4508: 4498: 4497: 4496: 4485: 4483: 4479: 4478: 4476: 4475: 4470: 4465: 4460: 4455: 4449: 4447: 4438: 4432: 4431: 4429: 4428: 4423: 4418: 4412: 4410: 4404: 4403: 4401: 4400: 4395: 4390: 4385: 4379: 4377: 4371: 4370: 4367: 4366: 4364: 4363: 4357: 4355: 4351: 4350: 4348: 4347: 4346: 4345: 4339: 4334: 4324: 4323: 4322: 4316: 4314:Chlorpromazine 4305: 4303: 4301:Antipsychotics 4297: 4296: 4294: 4293: 4292: 4291: 4285: 4275: 4274: 4273: 4267: 4262: 4252: 4246: 4244: 4235: 4231: 4226: 4225: 4223: 4222: 4217: 4212: 4207: 4202: 4197: 4192: 4187: 4181: 4179: 4174: 4169: 4168: 4165: 4164: 4162: 4161: 4160: 4159: 4153: 4148: 4138: 4137: 4136: 4130: 4128:Chlorpromazine 4119: 4117: 4115:Antipsychotics 4111: 4110: 4108: 4107: 4106: 4105: 4099: 4089: 4088: 4087: 4081: 4076: 4066: 4065: 4064: 4059: 4054: 4043: 4041: 4035: 4034: 4032: 4031: 4026: 4021: 4016: 4011: 4006: 4001: 3996: 3991: 3989:Cyproheptadine 3986: 3980: 3978: 3976:Antihistamines 3969: 3965: 3960: 3959: 3957: 3956: 3951: 3946: 3941: 3936: 3933:sodium oxybate 3926: 3921: 3916: 3911: 3906: 3904:1,4-Butanediol 3900: 3898: 3894: 3889: 3888: 3885: 3884: 3882: 3881: 3880: 3879: 3877:Valerenic acid 3874: 3869: 3859: 3854: 3853: 3852: 3847: 3842: 3832: 3827: 3822: 3817: 3812: 3807: 3802: 3797: 3792: 3787: 3782: 3777: 3776: 3775: 3773:Sodium bromide 3770: 3765: 3754: 3749: 3743: 3741: 3737: 3736: 3734: 3733: 3728: 3723: 3718: 3713: 3708: 3703: 3698: 3693: 3688: 3682: 3680: 3678:Quinazolinones 3674: 3673: 3671: 3670: 3665: 3660: 3655: 3649: 3647: 3641: 3640: 3638: 3637: 3631: 3629: 3623: 3622: 3620: 3619: 3614: 3609: 3604: 3599: 3594: 3589: 3584: 3579: 3574: 3569: 3563: 3561: 3555: 3554: 3552: 3551: 3546: 3541: 3536: 3531: 3526: 3521: 3516: 3510: 3508: 3502: 3501: 3499: 3498: 3493: 3488: 3483: 3478: 3473: 3467: 3465: 3459: 3458: 3456: 3455: 3450: 3445: 3439: 3437: 3431: 3430: 3428: 3427: 3422: 3417: 3412: 3407: 3402: 3397: 3392: 3387: 3381: 3379: 3373: 3372: 3370: 3369: 3364: 3359: 3354: 3349: 3344: 3339: 3334: 3329: 3324: 3319: 3314: 3309: 3304: 3299: 3294: 3289: 3284: 3279: 3274: 3269: 3264: 3258: 3256: 3250: 3249: 3247: 3246: 3241: 3236: 3231: 3226: 3221: 3216: 3211: 3206: 3201: 3199:Propylbarbital 3196: 3191: 3186: 3181: 3176: 3171: 3166: 3161: 3156: 3151: 3146: 3141: 3136: 3131: 3126: 3121: 3115: 3113: 3107: 3106: 3104: 3103: 3098: 3096:Methylpentynol 3093: 3088: 3083: 3078: 3073: 3067: 3065: 3056: 3052: 3047: 3046: 3032: 3030: 3029: 3022: 3015: 3007: 3001: 3000: 2994: 2986: 2979: 2978:External links 2976: 2974: 2973: 2955: 2941: 2927: 2913: 2899: 2877: 2849: 2821: 2816:www.nevo.co.il 2803: 2784: 2760: 2746: 2721: 2694: 2676: 2629: 2603: 2577: 2555: 2529: 2494: 2469: 2440: 2421:(3): 263–269. 2405: 2381: 2374: 2354: 2329: 2300:(3): 745–753. 2280: 2277:. 4 June 2012. 2263: 2244:(6): 887–896. 2228: 2221: 2198: 2192: 2167: 2142: 2105: 2070: 2045: 2025: 1998: 1989:|journal= 1943: 1908: 1873: 1838:(6): 458–470. 1818: 1812:978-3527306732 1811: 1776: 1754:(2023-03-31). 1743: 1725: 1707: 1687: 1668: 1666: 1663: 1662: 1661: 1656: 1654:1,4-Butanediol 1649: 1646: 1629:United States: 1575:Hong Kong SAR: 1549: 1548: 1529: 1527: 1520: 1514: 1511: 1502: 1499: 1481: 1478: 1474:date rape drug 1460:liquid ecstasy 1451: 1448: 1401: 1398: 1374:Main article: 1371: 1368: 1360:1,4-butanediol 1349:1,4-butanediol 1336: 1333: 1321:Main article: 1318: 1315: 1265: 1262: 1245: 1244:Polymerization 1242: 1170: 1167: 1155:sodium bromate 1144: 1143: 1132:1,4-butanediol 1127: 1124: 1111: 1108: 1043:-butyrolactone 1027: 1024: 1023: 1018: 996: 995: 991:standard state 988: 985: 984: 982: 981: 967: 965: 959: 958: 953: 946: 945: 942: 933: 931: 928: 927: 922: 913: 911: 908: 907: 900: 899: 894: 888: 887: 884: 877: 874: 873: 870: 864: 863: 853: 846: 839: 824: 823: 822: 821: 819: 810: 809: 799:P305+P351+P338 780: 775: 772: 771: 758: 753: 750: 749: 744: 739: 736: 735: 723: 718: 715: 714: 704: 703: 700: 697: 694: 693: 684: 683: 679: 678: 667: 661: 660: 653: 648: 640: 637: 636: 633: 629: 619: 618: 611: 609:Vapor pressure 605: 604: 601: 592: 591: 567: 562: 556: 555: 552: 547: 544: 543: 540: 534: 533: 530: 524: 523: 504: 498: 497: 494: 488: 487: 484: 480: 479: 473: 467: 466: 463: 457: 451: 446: 441: 438: 437: 433: 432: 430: 429: 426: 418: 417: 416: 413: 412: 410: 409: 405: 402: 401: 399: 395: 392: 391: 383: 382: 381: 378: 377: 375: 374: 361: 359: 347: 344: 343: 341: 340: 332: 330: 324: 323: 321: 320: 316: 314: 308: 307: 305: 304: 296: 294: 286: 283: 282: 280: 279: 271: 269: 263: 262: 260: 259: 251: 249: 244: 241: 240: 230: 222: 221: 219: 218: 210: 208: 202: 201: 199: 198: 190: 188: 182: 181: 179: 178: 170: 168: 162: 161: 159: 158: 150: 148: 142: 141: 139: 138: 130: 128: 121: 118: 117: 115: 114: 106: 104: 99: 96: 95: 91: 90: 71: 67: 66: 62: 61: 55: 54: 50: 49: 41: 40: 24: 14: 13: 10: 9: 6: 4: 3: 2: 7553: 7542: 7539: 7537: 7534: 7532: 7529: 7527: 7524: 7522: 7519: 7517: 7514: 7512: 7509: 7507: 7504: 7502: 7499: 7498: 7496: 7481: 7480: 7476: 7474: 7473: 7465: 7463: 7462: 7458: 7455: 7454: 7451: 7441: 7438: 7435: 7434: 7431: 7428: 7426: 7423: 7421: 7418: 7416: 7413: 7411: 7408: 7406: 7403: 7401: 7398: 7396: 7393: 7391: 7388: 7386: 7383: 7381: 7378: 7376: 7373: 7371: 7368: 7365: 7364: 7361: 7358: 7356: 7353: 7351: 7348: 7346: 7343: 7341: 7338: 7336: 7333: 7331: 7328: 7326: 7323: 7321: 7318: 7315: 7314: 7311: 7308: 7306: 7303: 7301: 7298: 7296: 7293: 7291: 7288: 7286: 7283: 7281: 7278: 7276: 7273: 7271: 7268: 7266: 7263: 7261: 7258: 7256: 7253: 7251: 7248: 7246: 7243: 7241: 7238: 7236: 7233: 7231: 7228: 7226: 7223: 7221: 7218: 7216: 7213: 7211: 7208: 7206: 7203: 7201: 7200:Aceburic acid 7198: 7196: 7193: 7191: 7188: 7186: 7183: 7180: 7179: 7177: 7172: 7163: 7160: 7158: 7154: 7144: 7141: 7139: 7136: 7134: 7131: 7129: 7126: 7123: 7119: 7115: 7112: 7110: 7107: 7105: 7102: 7100: 7097: 7094: 7093: 7090: 7087: 7085: 7083: 7079: 7077: 7074: 7072: 7069: 7067: 7064: 7062: 7059: 7057: 7054: 7052: 7049: 7047: 7044: 7042: 7039: 7037: 7034: 7032: 7029: 7027: 7024: 7022: 7019: 7017: 7014: 7012: 7010: 7006: 7004: 7001: 6999: 6996: 6994: 6991: 6989: 6986: 6984: 6981: 6979: 6976: 6974: 6971: 6968: 6967: 6964: 6961: 6959: 6956: 6954: 6951: 6949: 6946: 6943: 6942: 6939: 6936: 6934: 6931: 6929: 6926: 6924: 6921: 6919: 6916: 6914: 6911: 6909: 6907: 6903: 6901: 6898: 6896: 6893: 6891: 6890:Ibotenic acid 6888: 6886: 6883: 6881: 6878: 6876: 6873: 6871: 6868: 6866: 6863: 6861: 6858: 6855: 6854: 6852: 6847: 6837: 6831: 6828: 6826: 6823: 6821: 6818: 6816: 6813: 6811: 6808: 6806: 6803: 6801: 6798: 6796: 6793: 6791: 6788: 6786: 6783: 6781: 6778: 6776: 6773: 6771: 6768: 6766: 6763: 6761: 6758: 6756: 6753: 6751: 6748: 6746: 6743: 6741: 6738: 6736: 6735:Propybicyphat 6733: 6731: 6728: 6725: 6721: 6717: 6713: 6710: 6708: 6705: 6703: 6700: 6698: 6697:Oenanthotoxin 6695: 6692: 6688: 6684: 6680: 6676: 6672: 6669: 6667: 6664: 6662: 6659: 6657: 6654: 6652: 6649: 6647: 6644: 6642: 6639: 6637: 6634: 6632: 6629: 6627: 6624: 6622: 6619: 6617: 6614: 6612: 6609: 6607: 6606:Iomazenil (I) 6604: 6602: 6599: 6597: 6594: 6592: 6589: 6586: 6585:ciprofloxacin 6582: 6579: 6577: 6574: 6571: 6567: 6566:amentoflavone 6563: 6560: 6557: 6553: 6550: 6548: 6545: 6543: 6540: 6538: 6535: 6533: 6530: 6528: 6525: 6523: 6520: 6518: 6515: 6513: 6510: 6508: 6505: 6503: 6502:Cyclothiazide 6500: 6498: 6495: 6493: 6490: 6488: 6485: 6483: 6480: 6478: 6475: 6473: 6470: 6468: 6465: 6462: 6458: 6454: 6450: 6447: 6445: 6442: 6440: 6437: 6434: 6430: 6426: 6422: 6419: 6417: 6414: 6412: 6409: 6407: 6404: 6402: 6399: 6397: 6394: 6392: 6389: 6387: 6384: 6382: 6379: 6377: 6374: 6372: 6369: 6367: 6364: 6362: 6359: 6357: 6354: 6352: 6349: 6346: 6345: 6342: 6339: 6337: 6334: 6332: 6329: 6327: 6324: 6322: 6319: 6317: 6314: 6312: 6309: 6307: 6304: 6302: 6299: 6297: 6294: 6292: 6291:Famiraprinium 6289: 6287: 6284: 6282: 6279: 6277: 6274: 6271: 6270: 6266: 6262: 6258: 6257:diethyl ether 6254: 6250: 6246: 6242: 6239: 6236: 6232: 6229: 6227: 6224: 6221: 6217: 6214: 6212: 6209: 6206: 6202: 6199: 6197: 6194: 6192: 6189: 6186: 6182: 6179: 6176: 6172: 6169: 6167: 6164: 6161: 6157: 6154: 6152: 6149: 6146: 6142: 6139: 6137: 6134: 6132: 6131:Norfluoxetine 6129: 6126: 6122: 6118: 6114: 6110: 6106: 6102: 6098: 6094: 6091: 6089: 6086: 6084: 6081: 6078: 6074: 6070: 6066: 6063: 6061: 6058: 6056: 6053: 6051: 6048: 6045: 6041: 6038: 6035: 6031: 6028: 6026: 6023: 6021: 6018: 6015: 6011: 6007: 6004: 6001: 5997: 5994: 5992: 5989: 5987: 5984: 5981: 5977: 5974: 5972: 5971:Clomethiazole 5969: 5967: 5966:Chlormezanone 5964: 5962: 5959: 5957: 5956:Carbamazepine 5954: 5951: 5947: 5944: 5941: 5937: 5934: 5931: 5927: 5924: 5921: 5920:phenobarbital 5917: 5914: 5911: 5907: 5904: 5902: 5899: 5896: 5892: 5888: 5885: 5883: 5880: 5878: 5873: 5872: 5869: 5866: 5864: 5861: 5859: 5856: 5853: 5849: 5846: 5844: 5841: 5839: 5836: 5834: 5831: 5829: 5826: 5824: 5823:Quisqualamine 5821: 5819: 5816: 5814: 5811: 5809: 5806: 5804: 5801: 5799: 5796: 5794: 5791: 5789: 5786: 5783: 5779: 5776: 5774: 5771: 5769: 5766: 5764: 5761: 5759: 5758:Methylglyoxal 5756: 5753: 5749: 5746: 5744: 5741: 5739: 5736: 5734: 5731: 5729: 5726: 5724: 5721: 5719: 5716: 5714: 5711: 5709: 5708:Ibotenic acid 5706: 5704: 5701: 5699: 5696: 5694: 5691: 5689: 5686: 5684: 5681: 5679: 5676: 5674: 5671: 5669: 5666: 5664: 5661: 5658: 5657:phenobarbital 5654: 5651: 5649: 5646: 5644: 5641: 5638: 5637: 5635: 5630: 5621: 5618: 5616: 5612: 5608: 5605: 5595: 5590: 5588: 5583: 5581: 5576: 5575: 5572: 5560: 5559: 5555: 5553: 5552: 5548: 5546: 5545: 5541: 5539: 5538: 5534: 5531: 5530: 5527: 5517: 5514: 5512: 5509: 5507: 5504: 5502: 5499: 5497: 5494: 5493: 5491: 5486: 5480: 5474: 5471: 5469: 5466: 5464: 5461: 5459: 5456: 5455: 5453: 5448: 5442: 5436: 5433: 5431: 5428: 5427: 5425: 5420: 5414: 5408: 5402: 5399: 5398: 5395: 5394:Valproic acid 5392: 5390: 5387: 5385: 5384:Phenylacetate 5382: 5380: 5377: 5375: 5372: 5371: 5369: 5364: 5358: 5352: 5349: 5348: 5346: 5341: 5335: 5332: 5328: 5322: 5318: 5308: 5305: 5303: 5300: 5298: 5295: 5293: 5290: 5288: 5285: 5283: 5280: 5278: 5275: 5273: 5270: 5268: 5265: 5263: 5260: 5259: 5257: 5252: 5246: 5240: 5237: 5235: 5232: 5230: 5227: 5225: 5222: 5220: 5217: 5215: 5212: 5210: 5207: 5205: 5202: 5200: 5197: 5195: 5192: 5190: 5187: 5185: 5182: 5180: 5177: 5176: 5174: 5169: 5163: 5157: 5156:Valproic acid 5154: 5152: 5149: 5147: 5144: 5142: 5139: 5137: 5134: 5132: 5129: 5127: 5124: 5122: 5119: 5117: 5114: 5112: 5109: 5107: 5106:Niflumic acid 5104: 5102: 5099: 5097: 5094: 5092: 5091:Hexanoic acid 5089: 5087: 5084: 5082: 5079: 5077: 5074: 5072: 5069: 5067: 5064: 5062: 5059: 5057: 5054: 5052: 5049: 5047: 5044: 5042: 5039: 5038: 5036: 5031: 5025: 5022: 5018: 5012: 5008: 4997: 4993: 4992: 4990: 4985: 4976: 4970: 4967: 4965: 4962: 4960: 4957: 4955: 4952: 4950: 4947: 4945: 4942: 4940: 4937: 4935: 4934:Levosulpiride 4932: 4930: 4927: 4925: 4922: 4920: 4917: 4915: 4912: 4910: 4907: 4905: 4902: 4900: 4899:4-Phenyl-THCA 4897: 4895: 4892: 4890: 4889:4-Methyl-THCA 4887: 4885: 4882: 4880: 4877: 4875: 4874:3-Methyl-THCA 4872: 4870: 4867: 4865: 4862: 4859: 4856: 4855: 4852: 4849: 4847: 4844: 4841: 4838: 4837: 4834: 4831: 4829: 4826: 4822: 4819: 4817: 4814: 4812: 4809: 4807: 4804: 4802: 4799: 4797: 4794: 4792: 4789: 4787: 4784: 4782: 4779: 4777: 4774: 4772: 4769: 4767: 4764: 4762: 4759: 4757: 4754: 4752: 4749: 4747: 4744: 4742: 4739: 4737: 4734: 4732: 4729: 4727: 4724: 4722: 4719: 4717: 4714: 4712: 4709: 4707: 4704: 4702: 4699: 4696: 4693: 4692: 4690: 4685: 4679: 4676: 4672: 4666: 4662: 4658: 4655: 4645: 4640: 4638: 4633: 4631: 4626: 4625: 4622: 4610: 4607: 4605: 4602: 4600: 4597: 4595: 4592: 4590: 4587: 4584: 4580: 4577: 4575: 4572: 4568: 4567:Methocarbamol 4565: 4563: 4560: 4558: 4557:Mephenoxalone 4555: 4553: 4550: 4548: 4547:Chlorphenesin 4545: 4544: 4543: 4539: 4536: 4534: 4531: 4529: 4526: 4524: 4521: 4517: 4516:Phenaglycodol 4514: 4512: 4509: 4507: 4504: 4503: 4502: 4499: 4495: 4492: 4491: 4490: 4487: 4486: 4484: 4480: 4474: 4471: 4469: 4466: 4464: 4461: 4459: 4456: 4454: 4451: 4450: 4448: 4446: 4433: 4427: 4424: 4422: 4419: 4417: 4414: 4413: 4411: 4409: 4405: 4399: 4396: 4394: 4391: 4389: 4386: 4384: 4381: 4380: 4378: 4376: 4372: 4362: 4359: 4358: 4356: 4352: 4343: 4340: 4338: 4335: 4333: 4330: 4329: 4328: 4325: 4320: 4317: 4315: 4312: 4311: 4310: 4307: 4306: 4304: 4302: 4298: 4289: 4286: 4284: 4281: 4280: 4279: 4276: 4271: 4268: 4266: 4263: 4261: 4260:Amitriptyline 4258: 4257: 4256: 4253: 4251: 4248: 4247: 4245: 4243: 4239: 4236: 4234: 4227: 4221: 4218: 4216: 4213: 4211: 4208: 4206: 4203: 4201: 4198: 4196: 4193: 4191: 4188: 4186: 4183: 4182: 4180: 4178: 4170: 4157: 4154: 4152: 4149: 4147: 4144: 4143: 4142: 4139: 4134: 4131: 4129: 4126: 4125: 4124: 4121: 4120: 4118: 4116: 4112: 4103: 4100: 4098: 4095: 4094: 4093: 4090: 4085: 4082: 4080: 4077: 4075: 4074:Amitriptyline 4072: 4071: 4070: 4067: 4063: 4060: 4058: 4055: 4053: 4050: 4049: 4048: 4045: 4044: 4042: 4040: 4036: 4030: 4027: 4025: 4022: 4020: 4017: 4015: 4012: 4010: 4009:Methapyrilene 4007: 4005: 4002: 4000: 3997: 3995: 3992: 3990: 3987: 3985: 3982: 3981: 3979: 3977: 3973: 3970: 3968: 3961: 3955: 3952: 3950: 3947: 3945: 3942: 3940: 3937: 3934: 3930: 3927: 3925: 3922: 3920: 3917: 3915: 3914:Aceburic acid 3912: 3910: 3907: 3905: 3902: 3901: 3899: 3897: 3890: 3878: 3875: 3873: 3870: 3868: 3867:Isovaleramide 3865: 3864: 3863: 3862:Sesquiterpene 3860: 3858: 3855: 3851: 3848: 3846: 3843: 3841: 3838: 3837: 3836: 3833: 3831: 3828: 3826: 3823: 3821: 3818: 3816: 3813: 3811: 3808: 3806: 3803: 3801: 3800:Clomethiazole 3798: 3796: 3793: 3791: 3788: 3786: 3783: 3781: 3778: 3774: 3771: 3769: 3766: 3764: 3761: 3760: 3758: 3755: 3753: 3750: 3748: 3745: 3744: 3742: 3738: 3732: 3729: 3727: 3724: 3722: 3719: 3717: 3714: 3712: 3709: 3707: 3704: 3702: 3699: 3697: 3694: 3692: 3689: 3687: 3684: 3683: 3681: 3679: 3675: 3669: 3666: 3664: 3663:Pyrithyldione 3661: 3659: 3656: 3654: 3651: 3650: 3648: 3646: 3642: 3636: 3633: 3632: 3630: 3628: 3624: 3618: 3615: 3613: 3610: 3608: 3605: 3603: 3600: 3598: 3595: 3593: 3590: 3588: 3585: 3583: 3580: 3578: 3575: 3573: 3570: 3568: 3565: 3564: 3562: 3560: 3556: 3550: 3547: 3545: 3542: 3540: 3537: 3535: 3532: 3530: 3527: 3525: 3522: 3520: 3517: 3515: 3512: 3511: 3509: 3507: 3503: 3497: 3494: 3492: 3489: 3487: 3484: 3482: 3479: 3477: 3474: 3472: 3469: 3468: 3466: 3464: 3460: 3454: 3451: 3449: 3446: 3444: 3441: 3440: 3438: 3436: 3432: 3426: 3423: 3421: 3418: 3416: 3415:Phenprobamate 3413: 3411: 3410:Methocarbamol 3408: 3406: 3403: 3401: 3400:Hexapropymate 3398: 3396: 3393: 3391: 3388: 3386: 3383: 3382: 3380: 3378: 3374: 3368: 3365: 3363: 3360: 3358: 3355: 3353: 3350: 3348: 3345: 3343: 3340: 3338: 3335: 3333: 3330: 3328: 3325: 3323: 3320: 3318: 3317:Flutoprazepam 3315: 3313: 3310: 3308: 3305: 3303: 3302:Flunitrazepam 3300: 3298: 3297:Flunitrazolam 3295: 3293: 3292:Flubromazolam 3290: 3288: 3285: 3283: 3280: 3278: 3275: 3273: 3270: 3268: 3265: 3263: 3260: 3259: 3257: 3255: 3251: 3245: 3242: 3240: 3237: 3235: 3232: 3230: 3227: 3225: 3222: 3220: 3217: 3215: 3212: 3210: 3207: 3205: 3202: 3200: 3197: 3195: 3194:Phenobarbital 3192: 3190: 3187: 3185: 3184:Pentobarbital 3182: 3180: 3179:Narcobarbital 3177: 3175: 3172: 3170: 3169:Mephobarbital 3167: 3165: 3162: 3160: 3157: 3155: 3152: 3150: 3149:Cyclobarbital 3147: 3145: 3142: 3140: 3137: 3135: 3132: 3130: 3127: 3125: 3122: 3120: 3117: 3116: 3114: 3112: 3108: 3102: 3099: 3097: 3094: 3092: 3091:Ethchlorvynol 3089: 3087: 3084: 3082: 3079: 3077: 3074: 3072: 3069: 3068: 3066: 3064: 3060: 3057: 3055: 3048: 3043: 3039: 3035: 3028: 3023: 3021: 3016: 3014: 3009: 3008: 3005: 2998: 2995: 2991: 2987: 2985: 2984:Erowid on GBL 2982: 2981: 2977: 2969: 2965: 2959: 2956: 2951: 2945: 2942: 2938:. 2011-02-18. 2937: 2931: 2928: 2923: 2917: 2914: 2909: 2903: 2900: 2887: 2881: 2878: 2865: 2864: 2859: 2853: 2850: 2837: 2836: 2831: 2825: 2822: 2817: 2813: 2807: 2804: 2799: 2795: 2788: 2785: 2774: 2770: 2764: 2761: 2756: 2750: 2747: 2736:on 2016-03-19 2735: 2731: 2725: 2722: 2717: 2713: 2709: 2705: 2698: 2695: 2690: 2686: 2680: 2677: 2672: 2668: 2664: 2660: 2656: 2652: 2648: 2644: 2640: 2633: 2630: 2618: 2614: 2607: 2604: 2591: 2587: 2586:"GHB and GBL" 2581: 2578: 2565: 2559: 2556: 2544: 2543:The Telegraph 2540: 2533: 2530: 2525: 2521: 2517: 2513: 2510:(3): 137–47. 2509: 2505: 2498: 2495: 2483: 2479: 2473: 2470: 2459:on 2018-04-20 2458: 2454: 2450: 2444: 2441: 2436: 2432: 2428: 2424: 2420: 2416: 2409: 2406: 2391: 2385: 2382: 2377: 2371: 2367: 2366: 2358: 2355: 2343: 2339: 2333: 2330: 2325: 2321: 2316: 2311: 2307: 2303: 2299: 2295: 2291: 2284: 2281: 2273: 2267: 2264: 2259: 2255: 2251: 2247: 2243: 2239: 2232: 2229: 2224: 2218: 2214: 2213: 2205: 2203: 2199: 2196: 2193: 2181: 2177: 2171: 2168: 2156: 2155:Chemical Book 2152: 2146: 2143: 2138: 2134: 2130: 2126: 2122: 2118: 2117: 2109: 2106: 2101: 2097: 2093: 2089: 2085: 2081: 2074: 2071: 2060:. ZME Science 2059: 2052: 2050: 2046: 2035: 2029: 2026: 2021: 2017: 2013: 2009: 2002: 1999: 1994: 1981: 1967:on 2014-10-06 1963: 1956: 1950: 1948: 1944: 1939: 1935: 1931: 1927: 1923: 1919: 1912: 1909: 1904: 1900: 1896: 1892: 1888: 1884: 1877: 1874: 1869: 1865: 1861: 1857: 1853: 1849: 1845: 1841: 1837: 1833: 1829: 1822: 1819: 1814: 1808: 1804: 1800: 1796: 1795: 1787: 1785: 1783: 1781: 1777: 1765: 1761: 1757: 1753: 1747: 1744: 1739: 1735: 1729: 1726: 1715:on 2011-07-16 1714: 1710: 1704: 1700: 1699: 1691: 1688: 1684: 1680: 1679: 1673: 1670: 1664: 1660: 1657: 1655: 1652: 1651: 1647: 1645: 1642: 1638: 1634: 1630: 1626: 1624: 1620: 1616: 1613: 1609: 1607: 1603: 1601: 1597: 1595: 1591: 1589: 1585: 1583: 1579: 1576: 1572: 1569: 1565: 1562: 1558: 1555: 1545: 1533: 1528: 1519: 1518: 1512: 1510: 1508: 1500: 1498: 1496: 1490: 1486: 1479: 1477: 1475: 1470: 1467: 1465: 1461: 1456: 1449: 1447: 1444: 1436: 1428: 1424: 1421: 1419: 1415: 1411: 1407: 1399: 1397: 1395: 1391: 1387: 1383: 1377: 1369: 1365: 1361: 1356: 1352: 1350: 1346: 1342: 1334: 1332: 1330: 1324: 1316: 1314: 1312: 1307: 1305: 1301: 1298:, is used in 1297: 1289: 1285: 1281: 1279: 1275: 1271: 1263: 1261: 1259: 1255: 1251: 1243: 1241: 1239: 1235: 1231: 1228: 1224: 1221: 1217: 1213: 1211: 1206: 1203: 1199: 1197: 1191: 1188: 1184: 1180: 1176: 1168: 1166: 1164: 1160: 1156: 1152: 1147: 1141: 1137: 1136: 1135: 1133: 1125: 1123: 1121: 1117: 1109: 1107: 1105: 1101: 1097: 1093: 1089: 1087: 1082: 1077: 1075: 1071: 1067: 1063: 1048: 1044: 1042: 1037: 1033: 1021: 1014: 1009: 992: 986: 979: 969: 968: 966: 964: 961: 960: 957: 954: 951: 948: 947: 943: 939: 930: 929: 923: 919: 910: 909: 905: 901: 895: 893: 890: 889: 885: 882: 876: 875: 871: 869: 866: 865: 858: 851: 844: 820: 817: 816: 812: 811: 781: 778: 774: 773: 759: 756: 752: 751: 748: 745: 742: 738: 737: 733: 728: 724: 721: 717: 716: 712: 710: 705: 701: 696: 695: 691: 690: 685: 680: 668: 666: 663: 662: 654: 647: 643: 639: 638: 634: 628: 624: 621: 620: 612: 610: 607: 606: 602: 600: 599: 594: 593: 590: 586: 582: 578: 574: 570: 563: 561: 558: 557: 553: 550: 546: 545: 541: 539: 538:Boiling point 536: 535: 531: 529: 528:Melting point 526: 525: 505: 503: 500: 499: 495: 493: 490: 489: 485: 482: 481: 474: 472: 469: 468: 447: 444: 440: 439: 434: 425: 421: 414: 400: 390: 386: 379: 371: 367: 366:DTXSID6020224 363: 362: 360: 350: 346: 345: 338: 334: 333: 331: 329: 326: 325: 318: 317: 315: 313: 310: 309: 302: 298: 297: 295: 289: 285: 284: 277: 273: 272: 270: 268: 265: 264: 257: 253: 252: 250: 247: 243: 242: 238: 234: 231: 229: 227:ECHA InfoCard 224: 223: 216: 212: 211: 209: 207: 204: 203: 196: 192: 191: 189: 187: 184: 183: 176: 172: 171: 169: 167: 164: 163: 156: 152: 151: 149: 147: 144: 143: 136: 132: 131: 129: 125: 120: 119: 112: 108: 107: 105: 102: 98: 97: 92: 80:Butyrolactone 75: 68: 60: 56: 51: 47: 42: 38: 33: 27: 19: 7477: 7466: 7459: 7436: 7367:Antagonists: 7366: 7316: 7181: 7157:Metabotropic 7128:Pregnanolone 7122:picrotoxinin 7095: 7081: 7008: 6978:(S)-4-ACPBPA 6973:(S)-2-MeGABA 6970:Antagonists: 6969: 6944: 6933:Thiomuscimol 6905: 6856: 6720:picrotoxinin 6683:enzalutamide 6679:bicalutamide 6601:Golexanolone 6497:Cloflubicyne 6347: 6273:Antagonists: 6272: 6185:methaqualone 6160:glutethimide 6136:Petrichloral 6097:β-carbolines 5916:Barbiturates 5874: 5858:Thiomuscimol 5663:Beta-Alanine 5653:Barbiturates 5643:(+)-Catechin 5639: 5556: 5549: 5542: 5535: 5496:Acetaldehyde 5400: 5379:Ethosuximide 5272:Butyric acid 5234:Pyruvic acid 5189:Butyric acid 5179:Benzoic acid 5131:Pyruvic acid 5071:Butyric acid 5061:Benzoic acid 5056:Atorvastatin 4894:4-Phenyl-GHB 4879:4-Benzyl-GHB 4869:3-Methyl-GHB 4860: 4857: 4842: 4840:Antagonists: 4839: 4828:(+)-Catechin 4824: 4725: 4697: 4694: 4609:Valnoctamide 4511:Metaglycodol 4506:Fenpentadiol 4416:Daridorexant 4319:Thioridazine 4270:Trimipramine 4205:Medetomidine 4133:Thioridazine 4084:Trimipramine 4029:Propiomazine 4024:Promethazine 3830:Petrichloral 3815:Kavalactones 3747:Acetophenone 3716:Methaqualone 3711:Mecloqualone 3706:Mebroqualone 3696:Diproqualone 3691:Cloroqualone 3653:Glutethimide 3549:Progesterone 3539:Hydroxydione 3471:Acecarbromal 3385:Carisoprodol 3327:Lormetazepam 3312:Flutemazepam 3214:Secobarbital 3174:Methohexital 3164:Hexobarbital 3144:Butobarbital 3139:Butabarbital 3129:Aprobarbital 3119:Allobarbital 3111:Barbiturates 2967: 2958: 2944: 2930: 2916: 2902: 2890:. Retrieved 2880: 2868:. Retrieved 2861: 2852: 2840:. Retrieved 2833: 2824: 2815: 2806: 2797: 2787: 2776:. Retrieved 2772: 2763: 2749: 2738:. Retrieved 2734:the original 2724: 2707: 2703: 2697: 2689:the original 2679: 2646: 2642: 2632: 2620:. Retrieved 2606: 2594:. Retrieved 2590:the original 2580: 2568:. Retrieved 2558: 2546:. Retrieved 2542: 2532: 2507: 2503: 2497: 2486:. Retrieved 2481: 2472: 2461:. Retrieved 2457:the original 2452: 2443: 2418: 2414: 2408: 2397:. Retrieved 2384: 2364: 2357: 2346:. Retrieved 2344:. 1998-11-21 2332: 2297: 2293: 2283: 2266: 2241: 2237: 2231: 2211: 2195: 2183:. Retrieved 2179: 2170: 2158:. Retrieved 2154: 2145: 2120: 2114: 2108: 2086:(1): 42–49. 2083: 2079: 2073: 2062:. Retrieved 2037:. Retrieved 2028: 2011: 2007: 2001: 1980:cite journal 1969:. Retrieved 1962:the original 1921: 1917: 1911: 1886: 1882: 1876: 1835: 1831: 1821: 1792: 1768:. Retrieved 1746: 1737: 1728: 1717:. Retrieved 1713:the original 1697: 1690: 1682: 1676: 1672: 1628: 1627: 1618: 1617: 1611: 1610: 1605: 1604: 1599: 1598: 1593: 1592: 1587: 1586: 1581: 1580: 1574: 1573: 1567: 1566: 1560: 1559: 1553: 1552: 1542:January 2020 1539: 1531: 1513:Legal status 1504: 1491: 1487: 1483: 1471: 1468: 1459: 1457: 1453: 1445: 1441: 1422: 1403: 1393: 1389: 1379: 1338: 1326: 1317:Pharmacology 1308: 1293: 1267: 1247: 1238:caprolactone 1209: 1195: 1172: 1148: 1145: 1129: 1113: 1104:barbiturates 1085: 1078: 1040: 1039: 1035: 1031: 1030: 963:Legal status 903: 879:Autoignition 814: 746: 708: 698:Main hazards 687: 645: 626: 597: 312:RTECS number 94:Identifiers 73: 70:Other names 63:Oxolan-2-one 26: 7440:Compound 14 7270:Lesogaberan 7109:Loreclezole 7046:Loreclezole 6983:(S)-4-ACPCA 6963:Lanthanides 6953:Alphaxolone 6895:Isoguvacine 6805:Terbequinil 6675:apalutamide 6666:Nicardipine 6626:Laudanosine 6433:carbapenems 6425:penicillins 6281:Coriamyrtin 6276:Bicuculline 6265:sevoflurane 6261:paraldehyde 6211:Stiripentol 6088:Niacinamide 6073:cholesterol 6055:Loreclezole 5950:meprobamate 5906:Avermectins 5773:Nefiracetam 5738:Kojic amine 5728:Isomuscimol 5723:Isoguvacine 5302:Valinomycin 5146:Simvastatin 5096:Lactic acid 5011:Transporter 4904:Amisulpride 4786:T-HCA (GHC) 4716:BDDA (DABD) 4594:Scopolamine 4538:Guaifenesin 4533:Fenadiazole 4489:Cannabidiol 4463:Mirogabalin 4421:Lemborexant 4398:Tasimelteon 4383:Agomelatine 4342:Risperidone 4288:Mirtazapine 4177:-Adrenergic 4156:Risperidone 4102:Mirtazapine 4052:Etoperidone 4019:Pheniramine 4004:Hydroxyzine 3825:Paraldehyde 3820:Loreclezole 3686:Afloqualone 3668:Piperidione 3658:Methyprylon 3587:Pazinaclone 3567:Eszopiclone 3529:Alphaxolone 3524:Alphadolone 3463:Monoureides 3405:Meprobamate 3342:Nitemazepam 3337:Nimetazepam 3282:Doxefazepam 3267:Cinolazepam 3239:Vinbarbital 3204:Proxibarbal 3189:Phenallymal 3124:Amobarbital 3076:Chloralodol 2710:(3): 1–20. 2482:Le Monde.fr 2008:Tetrahedron 1678:Merck Index 1588:Netherlands 1394:Renewtrient 1341:paraoxonase 1304:resistivity 1278:pyrrolidone 1216:equilibrium 1062:hygroscopic 918:median dose 904:Lethal dose 881:temperature 868:Flash point 741:Signal word 692:(OHS/OSH): 613:1.5 kPa (20 589:ethyl ether 564:Soluble in 514:°C), 1.1296 483:Appearance 436:Properties 233:100.002.282 175:ChEMBL95681 155:CHEBI:42639 82:1,4-Lactone 7495:Categories 7295:SKF-97,541 7205:Arbaclofen 7114:Picrotoxin 7104:Bilobalide 6780:Suritozole 6770:Sarmazenil 6755:Ro 19-4603 6750:Ro 15-4513 6745:Radequinil 6712:Picrotoxin 6691:nilutamide 6661:Naltrexone 6596:Furosemide 6576:Flumazenil 6570:oroxylin A 6562:Flavonoids 6542:Etbicyphat 6472:Bilobalide 6439:Basmisanil 6326:Sinomenine 6321:Securinine 6316:Pitrazepin 6301:Hydrastine 6253:chloroform 6226:Topiramate 6166:Propanidid 6030:Imidazoles 6025:Flupirtine 6020:Fluoxetine 6014:hispidulin 6006:Flavonoids 5961:Chloralose 5946:Carbamates 5910:ivermectin 5848:Terpenoids 5793:PF-6372865 5648:Bamaluzole 5615:Ionotropic 5607:modulators 5511:Disulfiram 5501:Cimetidine 5458:Cimetidine 5401:Enhancers: 5327:inhibitors 5307:Vigabatrin 5277:Evans blue 5224:Probenecid 5204:Ketoprofen 5194:Fenoprofen 5126:Probenecid 5051:AR-C155858 4954:Sultopride 4861:Main site: 4843:Main site: 4698:Main site: 4657:modulators 4562:Metaxalone 4552:Mephenesin 4473:Pregabalin 4453:Gabapentin 4426:Suvorexant 4361:Niaprazine 4337:Quetiapine 4332:Olanzapine 4215:Tizanidine 4210:Romifidine 4200:Lofexidine 4190:Detomidine 4151:Quetiapine 4146:Olanzapine 4057:Nefazodone 3999:Doxylamine 3984:Captodiame 3795:Chloralose 3759:compounds 3701:Etaqualone 3597:Suproclone 3577:Lirequinil 3544:Minaxolone 3534:Eltanolone 3514:Acebrochol 3481:Bromisoval 3448:Metomidate 3435:Imidazoles 3395:Ethinamate 3390:Emylcamate 3377:Carbamates 3352:Nitrazolam 3347:Nitrazepam 3322:Loprazolam 3307:Flurazepam 3277:Clonazolam 3272:Climazolam 3262:Brotizolam 3244:Vinylbital 3229:Thiopental 2892:11 October 2870:9 December 2778:2023-07-17 2773:adf.org.au 2740:2010-08-06 2488:2018-04-19 2463:2018-04-19 2399:2014-01-22 2348:2013-10-10 2064:2015-12-13 2039:2018-06-14 1971:2014-03-31 1770:2023-08-16 1719:2011-07-18 1665:References 1637:Schedule I 1554:Australia: 1390:Revivarant 1362:, GBL and 1179:hydrolyzed 1110:Occurrence 1100:depressant 720:Pictograms 560:Solubility 471:Molar mass 337:OL659KIY4X 246:IUPHAR/BPS 186:ChemSpider 122:3D model ( 101:CAS Number 7501:Sedatives 7430:SKF-97541 7425:SCH-50911 7415:Phaclofen 7400:CGP-64213 7395:CGP-55845 7390:CGP-54626 7385:CGP-52432 7380:CGP-46381 7375:CGP-35348 7345:CGP-13501 7320:ADX-71441 7305:Tolgabide 7285:Progabide 7280:Picamilon 7265:Isovaline 7182:Agonists: 7084:-3-ACPBPA 7061:SKF-97541 7011:-3-ACPBPA 6938:Tolgabide 6918:Progabide 6913:Picamilon 6857:Agonists: 6765:RO4938581 6760:RO4882224 6687:flutamide 6621:L-655,708 6591:Flurothyl 6492:Cicutoxin 6477:Bupropion 6444:Bemegride 6421:β-Lactams 6411:Amiloride 6241:Volatiles 6175:etazolate 6151:Phenytoin 6109:zopiclone 6101:abecarnil 6060:Monastrol 6050:Lanthanum 6034:etomidate 5996:Fenamates 5991:Etifoxine 5986:Etazepine 5863:Tolgabide 5813:Progabide 5803:Picamilon 5788:Org 20599 5763:Monastrol 5743:L-838,417 5640:Agonists: 5506:Cyanamide 5351:Quercetin 5292:Nigericin 5262:β-Alanine 5199:Ibuprofen 5136:Quercetin 5121:Phloretin 4949:Sulpiride 4914:BnOPh-GHB 4833:Monastrol 4695:Agonists: 4599:Trazodone 4540:-related 4393:Ramelteon 4388:Melatonin 4375:Melatonin 4283:Mianserin 4250:Trazodone 4185:Clonidine 4097:Mianserin 4062:Trazodone 4014:Perlapine 3857:Triclofos 3810:Gaboxadol 3617:Zopiclone 3602:Suriclone 3592:Saripidem 3582:Necopidem 3496:Ectylurea 3491:Carbromal 3453:Propoxate 3443:Etomidate 3420:Procymate 3367:Triazolam 3362:Temazepam 3332:Midazolam 3287:Estazolam 3224:Thiamylal 3159:Heptabarb 3038:sedatives 3034:Hypnotics 2835:Wetten.nl 2663:2213-0276 2596:18 August 2570:18 August 2564:"GBL/GHB" 1852:1556-3650 1404:GBL is a 1177:, GBL is 1169:Reactions 1060:. It is 803:P403+P233 795:P301+P312 711:labelling 665:Viscosity 554:Miscible 427:O=C1OCCC1 319:LU3500000 7511:Solvents 7456:See also 7420:Saclofen 7355:rac-BHFF 7350:GS-39783 7340:CGP-7930 7300:SL 75102 7275:Phenibut 7230:Gabamide 7215:Baclofen 7118:picrotin 7071:SR-95813 7066:SR-95318 6988:2-MeTACA 6900:Muscimol 6830:ZK-93426 6800:TCS-1105 6785:TB-21007 6716:picrotin 6656:Naloxone 6641:Morphine 6636:MaxiPost 6556:fipronil 6552:Fiproles 6522:(+)-DMBB 6517:Dieldrin 6416:Anisatin 6331:SR-42641 6231:Valerian 6205:baicalin 6201:Skullcap 6145:propofol 6125:zaleplon 6117:zolpidem 6010:apigenin 5930:diazepam 5887:Alcohols 5828:SL-75102 5818:Propofol 5798:Phenibut 5768:Muscimol 5752:honokiol 5718:iso-THIP 5713:iso-THAZ 5688:Gabamide 5604:receptor 5532:See also 5516:Prunetin 5473:Pyrazole 5214:Naproxen 5101:Luteolin 5017:blockers 4998:instead. 4665:Receptor 4654:receptor 4583:morphine 4574:Midaflur 4494:Cannabis 4468:Phenibut 4220:Xylazine 3949:Phenibut 3919:Baclofen 3845:Tetronal 3780:Centalun 3635:Propofol 3612:Zolpidem 3607:Zaleplon 3572:Indiplon 3486:Capuride 3425:Tybamate 3357:Quazepam 3219:Talbutal 3134:Barbital 3063:Alcohols 2716:28186869 2671:19762202 2617:BBC News 2524:19446408 2435:10869868 2258:12963475 2137:26934184 2100:26673263 1938:15939164 1903:11569560 1868:19697449 1860:22746383 1764:Archived 1648:See also 1568:Germany: 1331:of GHB. 1270:graffiti 1254:cracking 1190:solution 978:Class B1 815:NFPA 704 682:Hazards 573:methanol 518:g/mL (20 510:g/mL (15 206:DrugBank 7325:BHF-177 7310:Tolibut 7220:BL-1020 7133:ROD-188 6998:4-ACPAM 6993:3-APMPA 6860:BL-1020 6820:U-93631 6815:Thujone 6740:PWZ-029 6714:(i.e., 6673:(e.g., 6651:MRK-016 6631:Lindane 6583:(e.g., 6564:(e.g., 6554:(e.g., 6423:(e.g., 6401:β-EMGBL 6311:PHP-501 6247:(e.g., 6218:(e.g., 6196:ROD-188 6183:(e.g., 6173:(e.g., 6158:(e.g., 6143:(e.g., 6141:Phenols 6123:(e.g., 6115:(e.g., 6107:(e.g., 6099:(e.g., 6095:(e.g., 6067:(e.g., 6032:(e.g., 6008:(e.g., 5998:(e.g., 5978:(e.g., 5948:(e.g., 5936:Bromide 5928:(e.g., 5918:(e.g., 5908:(e.g., 5889:(e.g., 5882:α-EMTBL 5852:borneol 5850:(e.g., 5833:Taurine 5780:(e.g., 5750:(e.g., 5748:Lignans 5668:BL-1020 5655:(e.g., 5463:Ethanol 5430:Cyanide 5287:Glycine 4939:NCS-400 4851:NCS-382 4776:NCS-435 4771:NCS-356 4671:ligands 4581:(e.g., 4579:Opioids 4528:Evoxine 4265:Doxepin 4079:Doxepin 3954:Tolibut 3850:Trional 3757:Bromide 3627:Phenols 3209:Reposal 2842:19 July 2415:Alcohol 2324:9239423 2185:21 June 2160:21 June 1639:of the 1612:Sweden: 1600:Poland: 1582:Israel: 1561:Canada: 1532:updated 1497:(BWS). 1464:alcohol 1450:Dangers 1406:prodrug 1382:prodrug 1329:prodrug 1220:polymer 1194:sodium 1175:lactone 1081:prodrug 1051:O=CO(CH 1013:what is 1011: ( 623:Acidity 585:benzene 581:acetone 577:ethanol 502:Density 288:PubChem 215:DB04699 111:96-48-0 7360:KK-92A 7190:3-APPA 6958:ATHDOC 6512:DHEA-S 6351:1,3M1B 6083:Niacin 6044:kavain 5321:Enzyme 4969:UMB119 4964:UMB109 4959:UMB108 4884:4-HPBA 4761:HOCPCA 4756:HOCHCA 4701:1,4-BD 4482:Others 4408:Orexin 4354:Others 4344:, etc. 4321:, etc. 4290:, etc. 4272:, etc. 4158:, etc. 4135:, etc. 4104:, etc. 4086:, etc. 3740:Others 3731:SL-164 2863:Emerce 2714:  2669:  2661:  2622:May 1, 2548:May 1, 2522:  2433:  2372:  2342:Erowid 2322:  2315:508244 2312:  2256:  2219:  2180:Medium 2135:  2098:  1936:  1901:  1866:  1858:  1850:  1809:  1752:Anvisa 1705:  1633:List I 1623:1,4-BD 1606:Russia 1202:sodium 1200:, the 1181:under 1161:via a 1098:(CNS) 1045:is an 1008:verify 1005:  976: 952:(SDS) 747:Danger 675:  673:cP (25 671:  657:  615:  603:−0.76 520:  516:  512:  508:  506:1.1286 476:86.090 420:SMILES 276:C01770 166:ChEMBL 53:Names 7250:GHBAL 7235:GABOB 7138:THDOC 7082:trans 7076:TPMPA 7051:P4MPA 7003:4-GBA 6885:GABOB 6611:IPTBO 6461:IPTBO 6396:β-CCP 6391:β-CCM 6386:β-CCE 6381:β-CCB 6341:Tutin 6245:gases 6077:THDOC 5693:GABOB 5362:GHBDH 5250:VIATT 5167:SMCTs 4864:2-HPA 4821:UMB86 4816:UMB73 4811:UMB72 4806:UMB68 4801:UMB66 4796:UMB58 4741:GHBAL 4706:3-HPA 4604:UMB68 3924:GABOB 2393:(PDF) 2275:(PDF) 1965:(PDF) 1958:(PDF) 1864:S2CID 1507:NaGHB 1418:death 1227:dimer 1210:gamma 1196:gamma 1192:into 1183:basic 1173:As a 1120:GC/MS 1116:wines 1086:gamma 1041:gamma 1038:) or 385:InChI 146:ChEBI 124:JSmol 76:)-one 7468:GABA 7405:DAVA 7335:BSPP 7330:BHFF 7225:GABA 7167:GABA 7143:Zinc 7089:ZAPA 7036:I4AA 7021:DAVA 6928:TAMP 6923:TACA 6880:GABA 6870:CAMP 6865:CACA 6841:GABA 6825:Zinc 6810:TETS 6795:TBPS 6790:TBOB 6722:and 6537:EBOB 6532:DMPC 6527:DMCM 6507:DHEA 6482:CHEB 6467:BIDN 6457:TBPO 6453:TBPS 6371:α3IA 6356:3M2B 6040:Kava 5895:2M2B 5877:here 5868:ZAPA 5843:TAMP 5838:TACA 5683:GABA 5673:DAVA 5625:GABA 5602:GABA 5484:ALDH 5282:GABA 5111:NPPB 5086:DIDS 5081:DBDS 5076:CHCA 5029:MCTs 4996:here 4994:See 4980:GABA 4929:GTBL 4683:GHBR 4444:VDCC 4230:5-HT 3893:GABA 3071:2M2B 3051:GABA 3042:N05C 2894:2021 2872:2013 2844:2019 2712:PMID 2667:PMID 2659:ISSN 2624:2012 2598:2014 2572:2014 2550:2012 2520:PMID 2431:PMID 2370:ISBN 2320:PMID 2254:PMID 2217:ISBN 2187:2024 2162:2024 2133:PMID 2096:PMID 1993:help 1934:PMID 1899:PMID 1856:PMID 1848:ISSN 1807:ISBN 1703:ISBN 1683:1632 1501:Dose 1416:and 1414:coma 1392:and 1264:Uses 1248:The 1205:salt 1159:GABA 1083:for 1066:odor 807:P501 791:P280 787:P270 783:P264 769:H336 765:H318 761:H302 677:°C) 659:°C) 635:4.5 617:°C) 596:log 522:°C) 492:Odor 328:UNII 301:7302 267:KEGG 256:5462 195:7029 7260:GVL 7255:GHV 7245:GHB 7240:GBL 7056:P4S 7009:cis 6775:SCS 6119:), 6111:), 6103:), 5808:P4S 5446:ADH 5418:HOT 5339:SSR 5184:BHB 5066:BHB 4924:DVL 4919:DHV 4791:THF 4766:MAB 4751:GVL 4736:GHB 4731:GCL 4726:GBL 4721:EAB 4652:GHB 3944:GVL 3939:GBL 3929:GHB 2651:doi 2512:doi 2508:103 2423:doi 2310:PMC 2302:doi 2298:100 2246:doi 2125:doi 2088:doi 2016:doi 1926:doi 1922:151 1891:doi 1840:doi 1799:doi 1410:GHB 1408:of 1386:GHB 1384:of 1364:GHB 1274:NMP 1207:of 1036:GBL 709:GHS 669:1.7 575:, 566:CCl 354:EPA 291:CID 78:GBL 7497:: 7120:, 6845:-ρ 6718:, 6689:, 6685:, 6681:, 6677:, 6568:, 6459:, 6455:, 6431:, 6427:, 6263:, 6259:, 6255:, 6251:, 6127:)) 6075:, 6071:, 6012:, 5893:, 4823:; 4232:2A 2966:. 2860:. 2832:. 2814:. 2796:. 2771:. 2708:19 2706:. 2665:. 2657:. 2647:38 2645:. 2641:. 2615:. 2541:. 2518:. 2506:. 2480:. 2451:. 2429:. 2419:20 2417:. 2340:. 2318:. 2308:. 2296:. 2292:. 2252:. 2242:66 2240:. 2201:^ 2178:. 2153:. 2131:. 2121:55 2119:. 2094:. 2082:. 2048:^ 2012:56 2010:. 1984:: 1982:}} 1978:{{ 1946:^ 1932:. 1920:. 1897:. 1887:46 1885:. 1862:. 1854:. 1846:. 1836:50 1834:. 1830:. 1805:. 1779:^ 1736:. 1476:. 1420:. 1313:. 1306:. 1165:. 1106:. 1076:. 972:BR 934:50 932:LC 914:50 912:LD 805:, 801:, 797:, 793:, 789:, 785:, 767:, 763:, 713:: 632:) 625:(p 587:, 583:, 579:, 571:, 7470:A 7169:B 7124:) 7116:( 6906:N 6843:A 6726:) 6693:) 6587:) 6572:) 6558:) 6463:) 6451:( 6435:) 6267:) 6243:/ 6237:) 6222:) 6207:) 6187:) 6177:) 6162:) 6147:) 6079:) 6046:) 6036:) 6016:) 6002:) 5982:) 5952:) 5942:) 5932:) 5922:) 5912:) 5897:) 5854:) 5784:) 5754:) 5659:) 5627:A 5593:e 5586:t 5579:v 5405:D 5329:) 5325:( 5019:) 5015:( 4982:B 4673:) 4669:( 4643:e 4636:t 4629:v 4585:) 4441:δ 4439:2 4437:α 4175:2 4173:α 3966:1 3964:H 3935:) 3931:( 3895:B 3053:A 3044:) 3040:( 3036:/ 3026:e 3019:t 3012:v 2970:. 2952:. 2924:. 2910:. 2896:. 2874:. 2846:. 2818:. 2800:. 2781:. 2757:. 2743:. 2718:. 2673:. 2653:: 2626:. 2600:. 2574:. 2552:. 2526:. 2514:: 2491:. 2466:. 2437:. 2425:: 2402:. 2378:. 2351:. 2326:. 2304:: 2260:. 2248:: 2225:. 2189:. 2164:. 2139:. 2127:: 2102:. 2090:: 2084:8 2067:. 2042:. 2022:. 2018:: 1995:) 1991:( 1974:. 1940:. 1928:: 1905:. 1893:: 1870:. 1842:: 1815:. 1801:: 1773:. 1740:. 1722:. 1685:. 1544:) 1540:( 1534:. 1057:3 1055:) 1053:2 1034:( 1003:Y 974:: 940:) 936:( 920:) 916:( 856:1 849:1 842:2 651:) 649:D 646:n 644:( 630:a 627:K 598:P 568:4 464:2 461:O 458:6 455:H 452:4 449:C 356:) 352:( 126:) 74:H 20:)

Index

Gamma-Butyrolactone


Preferred IUPAC name
CAS Number
96-48-0
JSmol
Interactive image
ChEBI
CHEBI:42639
ChEMBL
ChEMBL95681
ChemSpider
7029
DrugBank
DB04699
ECHA InfoCard
100.002.282
Edit this at Wikidata
IUPHAR/BPS
5462
KEGG
C01770
PubChem
7302
RTECS number
UNII
OL659KIY4X
CompTox Dashboard
DTXSID6020224

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