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| butane-1,4-diol |
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| CHEBI:41189 |
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| A butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16°C) with a high boiling point (230°C), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF). |
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This entity has been manually annotated by the ChEBI Team.
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| ChemicalBook:CB71074836, ChemicalBook:CB4452184, eMolecules:483162, ZINC000001599375 |
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Molfile
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more structures >>
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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__93601625573542__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__93601625573542__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41189","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__93601625573542__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"93601625573542","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__93601625573542__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 08261114323D starting HoverWatcher_5 Time for openFile( Marvin 08261114323D 16 15 0 0 0 0 999 V2000 0.5180 0.0000 1.8540 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4150 0.0000 0.6420 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4150 0.0000 -0.6420 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5180 0.0000 -1.8540 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2570 0.0000 3.0530 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2570 0.0000 -3.0530 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1470 0.8900 1.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1470 -0.8900 1.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0440 -0.8900 0.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0440 0.8900 0.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0440 0.8900 -0.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0440 -0.8900 -0.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1470 -0.8900 -1.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1470 0.8900 -1.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3680 0.0000 3.7910 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3680 0.0000 -3.7910 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 5 1 0 0 0 0 1 7 1 0 0 0 0 1 8 1 0 0 0 0 2 3 1 0 0 0 0 2 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 1 0 0 0 0 3 11 1 0 0 0 0 3 12 1 0 0 0 0 4 6 1 0 0 0 0 4 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 M END): 14 ms reading 16 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 16 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| 1,4-Butanediol, also called Butane-1,4-diol (other names include 1,4-B, BD, BDO and 1,4-BD), is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH. It is a colorless viscous liquid first synthesized in 1890 via acidic hydrolysis of N,N'-dinitro-1,4-butanediamine by Dutch chemist Pieter Johannes Dekkers, who called it "tetramethylene glycol". |
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Read full article at Wikipedia
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| InChI=1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2 |
| WERYXYBDKMZEQL-UHFFFAOYSA-N |
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protic solvent
A polar solvent that is capable of acting as a hydron (proton) donor.
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neurotoxin
A poison that interferes with the functions of the nervous system.
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protic solvent
A polar solvent that is capable of acting as a hydron (proton) donor.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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View more via ChEBI Ontology
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Outgoing
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butane-1,4-diol
(CHEBI:41189)
has role
neurotoxin
(CHEBI:50910)
butane-1,4-diol
(CHEBI:41189)
has role
prodrug
(CHEBI:50266)
butane-1,4-diol
(CHEBI:41189)
has role
protic solvent
(CHEBI:48356)
butane-1,4-diol
(CHEBI:41189)
is a
butanediol
(CHEBI:52684)
butane-1,4-diol
(CHEBI:41189)
is a
glycol
(CHEBI:13643)
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Incoming
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1,4-diacetoxybutane
(CHEBI:87345)
has functional parent
butane-1,4-diol
(CHEBI:41189)
busulfan
(CHEBI:28901)
has functional parent
butane-1,4-diol
(CHEBI:41189)
naproxcinod
(CHEBI:76254)
has functional parent
butane-1,4-diol
(CHEBI:41189)
secoisolariciresinol
(CHEBI:67250)
has functional parent
butane-1,4-diol
(CHEBI:41189)
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1,4-BD
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ChemIDplus
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1,4-BUTANEDIOL
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PDBeChem
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1,4-butylene glycol
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ChemIDplus
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1,4-dihydroxybutane
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ChemIDplus
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1,4-tetramethylene glycol
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ChemIDplus
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HO(CH2)4OH
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ChEBI
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HOCH2CH2CH2CH2OH
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ChEBI
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tetramethylene 1,4-diol
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ChemIDplus
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tetramethylene glycol
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ChemIDplus
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110-63-4
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CAS Registry Number
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NIST Chemistry WebBook
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110-63-4
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CAS Registry Number
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ChemIDplus
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1633445
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Reaxys Registry Number
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Reaxys
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Wood DM, Brailsford AD, Dargan PI (2011)
Acute toxicity and withdrawal syndromes related to γ-hydroxybutyrate (GHB) and its analogues γ-butyrolactone (GBL) and 1,4-butanediol (1,4-BD).
Drug testing and analysis 3, 417-425 [PubMed:21548140]
[show Abstract]
Gamma-hydroxybutyrate (GHB) has been used as a recreational drug since the 1990s and over the last few years there has been increasing use of its analogues gamma-butyrolactone (GBL) and to a lesser extent 1,4-butanediol (1,4BD). This review will summarize the literature on the pharmacology of these compounds; the patterns and management of acute toxicity associated with their use; and the clinical patterns of presentation and management of chronic dependency associated with GHB and its analogues. | Yim H, Haselbeck R, Niu W, Pujol-Baxley C, Burgard A, Boldt J, Khandurina J, Trawick JD, Osterhout RE, Stephen R, Estadilla J, Teisan S, Schreyer HB, Andrae S, Yang TH, Lee SY, Burk MJ, Van Dien S (2011)
Metabolic engineering of Escherichia coli for direct production of 1,4-butanediol.
Nature chemical biology 7, 445-452 [PubMed:21602812]
[show Abstract]
1,4-Butanediol (BDO) is an important commodity chemical used to manufacture over 2.5 million tons annually of valuable polymers, and it is currently produced exclusively through feedstocks derived from oil and natural gas. Herein we report what are to our knowledge the first direct biocatalytic routes to BDO from renewable carbohydrate feedstocks, leading to a strain of Escherichia coli capable of producing 18 g l(-1) of this highly reduced, non-natural chemical. A pathway-identification algorithm elucidated multiple pathways for the biosynthesis of BDO from common metabolic intermediates. Guided by a genome-scale metabolic model, we engineered the E. coli host to enhance anaerobic operation of the oxidative tricarboxylic acid cycle, thereby generating reducing power to drive the BDO pathway. The organism produced BDO from glucose, xylose, sucrose and biomass-derived mixed sugar streams. This work demonstrates a systems-based metabolic engineering approach to strain design and development that can enable new bioprocesses for commodity chemicals that are not naturally produced by living cells. | Maytum HC, Francos J, Whatrup DJ, Williams JM (2010)
1,4-Butanediol as a reducing agent in transfer hydrogenation reactions.
Chemistry, an Asian journal 5, 538-542 [PubMed:20112336]
[show Abstract]
1,4-Butanediol is able to deliver two equivalents of H(2) in hydrogen-transfer reactions to ketones, imines, and alkenes. Unlike simple alcohols, which establish equilibrium in the reduction of ketones, 1,4-butanediol acts essentially irreversibly owing to the formation of butyrolactone, which acts as a thermodynamic sink. It is therefore not necessary to use 1,4-butanediol in great excess in order to achieve reduction reactions. In addition, allylic alcohols are reduced to saturated alcohols through an isomerization/reduction sequence using a ruthenium catalyst with 1,4-butanediol as the reducing agent. Imines and alkenes are also reduced under similar conditions. | Ortmann LA, Jaeger MW, James LP, Schexnayder SM (2009)
Coma in a 20-month-old child from an ingestion of a toy containing 1,4-butanediol, a precursor of gamma-hydroxybutyrate.
Pediatric emergency care 25, 758-760 [PubMed:19915428]
[show Abstract]
Ingestion of plastic toys is common in children and usually does not result in harm. We report a case of coma in a 20-month-old child after an ingestion of a toy containing 1,4-butanediol, an industrial solvent used to manufacture plastics. When ingested, 1,4-butanediol is metabolized to gamma-hydroxybutyrate, which can have significant systemic effects including death. Health care providers should suspect the possibility of a toxic component when a presumed nontoxic object causes unusual symptoms. | Wood DM, Warren-Gash C, Ashraf T, Greene SL, Shather Z, Trivedy C, Clarke S, Ramsey J, Holt DW, Dargan PI (2008)
Medical and legal confusion surrounding gamma-hydroxybutyrate (GHB) and its precursors gamma-butyrolactone (GBL) and 1,4-butanediol (1,4BD).
QJM : monthly journal of the Association of Physicians 101, 23-29 [PubMed:18203723]
[show Abstract]
BackgroundGamma-hydroxybutyrate (GHB) is used as a recreational drug, with significant associated morbidity and mortality; it is therefore a class C drug under the Misuse of Drugs Act (1971). However, its precursors gamma-butyrolactone (GBL) and 1,4-butanediol (1,4BD) remain legally available despite having similar clinical effects.AimThe aim of this study was to determine whether the relative proportions of self-reported ingestions of GHB or its precursors GBL and 1,4BD were similar to those seen in analysis of seized drugs.Design and methodsRetrospective review of our clinical toxicology database to identify all cases of self-reported recreational GHB, GBL and 1,4BD use associated with ED presentation in 2006. Additionally all seized substances on people attending local club venues were analysed by a Home Office approved laboratory to identify any illicit substances present.ResultsIn 2006, there were a total of 158 ED presentations, of which 150 (94.9%) and 8 (5.1%) were GHB and GBL self-reported ingestions respectively; 96.8% (153) were recreational use. Of the 418 samples seized, 225 (53.8%) were in liquid form; 85 (37.8%) contained GHB and 140 (62.2%) contained GBL. None of the seized samples contained 1,4BD and there were no self-reported 1,4BD ingestions.ConclusionSelf-reported GHB ingestion was much more common than GBL ingestion, whereas GBL was more commonly found in the seized samples. These differences suggest that GBL use may be more common than previously thought and we suggest that there should be further debate about the legal status of the precursors of GHB. | Maytum HC, Tavassoli B, Williams JM (2007)
Reduction of aldehydes and ketones by transfer hydrogenation with 1,4-butanediol.
Organic letters 9, 4387-4389 [PubMed:17854202]
[show Abstract]
1,4-Butanediol has been used as the hydrogen donor in transfer hydrogenation reactions. The equilibrium is driven by the formation of gamma-butyrolactone, and the diol is therefore not required in excess. | Irwin RD (2006)
A review of evidence leading to the prediction that 1,4-butanediol is not a carcinogen.
Journal of applied toxicology : JAT 26, 72-80 [PubMed:16193534]
[show Abstract]
1,4-Butanediol is an industrial chemical used primarily as an intermediate in the manufacture of other organic chemicals. It has recently been associated with deaths, addiction and withdrawal related to its promotion and use as a dietary supplement. The rapid absorption and conversion of 1,4-butanediol to gamma-hydroxybutyric acid (GHB, or date rape drug) in animals and humans is well documented and is the basis for its abuse potential. A disposition and metabolism study conducted in F344 rats by the National Toxicology Program (NTP) confirmed the rapid conversion of 1-(14)C-1,4-butanediol to (14)CO2. Because of this, the toxicological profile of 1,4-butanediol resembles that of gamma-hydroxybutyric acid. Gamma-hydroxybutyric acid occurs naturally in the brain and peripheral tissues and is converted to succinate and metabolized through the TCA cycle. Although the function of gamma-hydroxybutyric acid in peripheral tissues is not known, the presence of specific high affinity receptors for gamma-hydroxybutyric acid suggests that it functions as a neuromodulator in the brain and neuronal tissue. Gamma-hydroxybutyric acid readily crosses the blood-brain barrier and elicits characteristic neuropharmacologic responses after oral, i.p., or i.v. administration. The same responses are observed after administration of 1,4-butanediol. The cyclic lactone of gamma-hydroxybutyric acid, gamma-butyrolactone, is also rapidly converted to gamma-hydroxybutyric acid by enzymes in the blood and liver in animals and humans, and produces pharmacological effects identical to those produced by 1,4-butanediol and gamma-hydroxybutyric acid. Gamma-butyrolactone was previously evaluated by the NTP in 14-day and 13-week prechronic toxicology studies and in 2-year chronic toxicology and carcinogenesis studies in F344 rats and B6C3F1 mice. No organ specific toxicity occurred. In the carcinogenesis studies there was an equivocal response in male mice based on a marginal increase in the incidence of pheochromocytomas of the adrenal medulla. Because the absence of chronic toxicity and significant carcinogenicity of gamma-hydroxybutyric acid were established in NTP prechronic and chronic studies with gamma-butyrolactone, it is concluded that similar results would be obtained in a 2-year study with 1,4-butanediol, and that 1,4-butanediol is not a carcinogen. | Palmer RB (2004)
Gamma-butyrolactone and 1,4-butanediol: abused analogues of gamma-hydroxybutyrate.
Toxicological reviews 23, 21-31 [PubMed:15298490]
[show Abstract]
gamma-Hydroxybutyrate (GHB) is a GABA-active CNS depressant, commonly used as a drug of abuse. In the early 1990s, the US Drug Enforcement Administration (DEA) warned against the use of GHB and restricted its sale. This diminished availability of GHB caused a shift toward GHB analogues such as gamma-butyrolactone (GBL) and 1,4-butanediol (1,4-BD) as precursors and surrogates. Both GBL and 1,4-BD are metabolically converted to GHB. Furthermore, GBL is commonly used as a starting material for chemical conversion to GHB. As such, the clinical presentation and management of GBL and 1,4-BD intoxication shares a great deal of common ground with that for GHB. This similarity exists not only for acute intoxication but also for withdrawal in those patients with a history of extended high-dose abuse. This review examines the history of GHB analogue abuse as well as the clinical presentation and management of acute intoxication and withdrawal associated with abuse of these compounds. | Irwin RD (1996)
NTP summary report on the metabolism, disposition, and toxicity of 1,4-butanediol (CAS No. 110-63-4).
Toxicity report series1-28, A1-8, B1-5 [PubMed:11803699]
[show Abstract]
1,4-Butanediol is an industrial chemical used in the manufacture of other organic chemicals. It was nominated by the National Cancer Institute and selected for evaluation by the NTP because of high production volume, the potential for worker exposure, the lack of adequate toxicological characterization, and the lack of evaluation for carcinogenic potential. As documented in the scientific literature, 1,4-butanediol is rapidly absorbed and metabolized to gamma-hydroxybutyric acid in animals and humans. A metabolism and disposition study conducted in F344/N rats by the NTP confirmed the rapid and extensive conversion of 1-[14C]-1,4-butanediol to 14CO2. Because of this rapid and extensive conversion, the toxicological profile of 1,4-butanediol reflects that of gamma-hydroxybutyric acid. gamma-Hydroxybutyric acid is a naturally occurring chemical found in the brain and peripheral tissues which is converted to succinate and processed through the tricarboxylic acid cycle. Although the function of gamma-hydroxybutyric acid in peripheral tissues is unknown, in the brain and neuronal tissue it is thought to function as a neuromodulator. gamma-Hydroxybutyric acid readily crosses the blood-brain barrier, and oral, intraperitoneal, or intravenous administration elicits characteristic neuropharmacologic responses. These same responses are observed after administration of 1,4-butanediol. The lactone of gamma-hydroxybutyric acid, gamma-butyrolactone, is also rapidly converted to gamma-hydroxybutyric acid by enzymes in the blood and liver of animals and humans. gamma-Butyrolactone was previously evaluated by the NTP in 14-day and 13-week toxicology studies and 2-year toxicology and carcinogenesis studies in F344/N rats and B6C3F1 mice. No organ-specific toxicity occurred in the toxicology studies. In the carcinogenesis studies, an equivocal response occurred in male mice, based on a marginal increase in the incidence of pheochromocytomas of the renal medulla. Because of the rapid and extensive conversion of gamma-butyrolactone to gamma-hydroxybutyric acid, the evaluation of gamma-butyrolactone was in fact an evaluation of gamma-hydroxybutyric acid. This summary report presents a review of the current literature which documents that both 1,4-butanediol and gamma-butyrolactone are rapidly metabolized to gamma-hydroxybutyric acid, and the pharmacologic and toxicologic responses to these chemicals are due to their metabolic conversion to gamma-hydroxybutyric acid. Because the toxicity and carcinogenicity of gamma-hydroxybutyric acid was fully evaluated in the NTP studies of gamma-butyrolactone, and a lack of organ-specific toxicity or carcinogenic potential was demonstrated, it is concluded that there is a high likelihood that 1,4-butanediol would be negative in a similar set of studies. For these reasons, it is the opinion of the NTP that 1,4-butanediol should be considered not carcinogenic in animals and no further evaluation of 1,4-butanediol is needed at this time. |
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