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1,4-Butanediol: Difference between revisions

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{{headerpanel|{{DepressantOD|GABAergics}}}}
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'''1,4-Butanediol''' ('''1,4-B''', '''butylene glycol,''' or '''BD''') is a thick, colourless liquid which is nearly odorless with a distinct bitter taste. 1,4-Butanediol is used industrially as a solvent and in the manufacture of some types of plastics, elastic fibers and polyurethanes. In organic chemistry, 1,4-butanediol is used for the synthesis of [[GBL|γ-butyrolactone (GBL)]].<ref>http://pubs.acs.org/doi/abs/10.1021/om048983m</ref>
'''1,4-Butanediol''' (also known as '''1,4-B''', '''BDO''', '''BD or 1,4-BD''') is a [[psychoactive class::depressant]] substance and a [[prodrug]] for [[GHB]]. It occurs as a thick, colorless liquid or solid depending on storage temperature (melting point of 20 ℃), and has a distinct bitter-sweet taste.<ref>{{Citation | vauthors=PubChem | title=1,4-Butanediol | url=https://pubchem.ncbi.nlm.nih.gov/compound/8064}}</ref> It is used as a recreational intoxicant with effects similar to [[alcohol]] and [[GHB]].<ref>{{cite journal | vauthors=((Zvosec, D. L.)), ((Smith, S. W.)), ((McCutcheon, J. R.)), ((Spillane, J.)), ((Hall, B. J.)), ((Peacock, E. A.)) | journal=New England Journal of Medicine | title=Adverse Events, Including Death, Associated with the Use of 1,4-Butanediol | volume=344 | issue=2 | pages=87–94 | date=11 January 2001 | url=https://doi.org/10.1056/NEJM200101113440202 | issn=0028-4793 | doi=10.1056/NEJM200101113440202}}</ref> 1 ml of 1,4-butanediol is equivalent to 1.4 g of Na-GHB.


In humans, it acts as a [[psychoactive class::depressant]] and a [[prodrug]] for [[GHB]] where 1ml is equivalent to 1g of GHB. It is used as a recreational intoxicant with effects similar to [[alcohol]].<ref>http://www.nejm.org/doi/full/10.1056/NEJM200101113440202</ref>
1,4-Butanediol is used industrially as a solvent and in the manufacture of some types of plastics, elastic fibers and polyurethanes. In organic chemistry, it is used for the synthesis of [[GBL|γ-butyrolactone (GBL)]].<ref>{{cite journal | vauthors=((Zhao, J.)), ((Hartwig, J. F.)) | journal=Organometallics | title=Acceptorless, Neat, Ruthenium-Catalyzed Dehydrogenative Cyclization of Diols to Lactones | volume=24 | issue=10 | pages=2441–2446 | date=1 May 2005 | url=https://pubs.acs.org/doi/10.1021/om048983m | issn=0276-7333 | doi=10.1021/om048983m}}</ref>


1,4-Butanediol, as well as [[GBL]], will dissolve most types of plastic over time.<ref>https://www.erowid.org/chemicals/14b/14b_storage1.shtml | 1,4-Butanediol & GBL Storage - 1,4-B & GBL May Dissolve Some Plastics by Erowid  (Jul 2001)</ref> For this reason, it is recommended to only transport and store the drug using a glass container, standard gelatin capsules (not vegetarian), or high-density polyethylene plastic (also known as #2 recycled plastic). To check the type of plastic used on a bottle, one can look at the bottom for a number in the triangle shaped recycling label.
1,4-Butanediol, as well as [[GBL]], will dissolve most types of plastic over time.<ref>{{Citation | title=Erowid 1,4-butanediol Vault : Storage : 14b and GBL May Dissolve Some Plastics | url=https://www.erowid.org/chemicals/14b/14b_storage1.shtml |date=2001}}</ref> For this reason, it is recommended to only transport and store the drug using a glass container, standard gelatin capsules (not vegetarian), or high-density polyethylene plastic (also known as #2 recycled plastic). To check the type of plastic used on a bottle, one can look at the bottom for a number in the triangle-shaped recycling label.


[[File:1,4 Butanediol pic.jpg|200px|thumb|Bottle of 1,4 Butanediol.]]
==Chemistry==
==Chemistry==
1,4-Butanediol is classified as a subclass of alcoholic compounds called [[chemical class::diol|diols]]. Diols are named for having two alcohol (OH-) substitutions in their structure. 1,4-Butanediol is comprised of a butane chain of four carbon groups with an alcohol group bound to each terminal carbon of this chain. 1,4-Butanediol is named for these alcohol substitutions, which are located at R<sub>1</sub> and R<sub>4</sub>.
1,4-Butanediol is classified as a subclass of alcoholic compounds called [[chemical class::diol|diols]]. Diols are named for having two alcohol (OH-) substitutions in their structure. 1,4-Butanediol is comprised of a butane chain of four carbon groups with an alcohol group bound to each terminal carbon of this chain. 1,4-Butanediol is named for these alcohol substitutions, which are located at R<sub>1</sub> and R<sub>4</sub>. These alcohol substitutions make 1,4-Butanediol a polar liquid, which explains its good solubility in water.
 
Physically, it is a hygroscopic colorless oily liquid with a barely noticeable characteristic odor. Unlike GHB, 1,4-Butanediol has a distinct taste, described as being repulsive, plastic-like and chemical.


==Pharmacology==
==Pharmacology==
{{Main|GHB#Pharmacology}}
{{Main|GHB#Pharmacology}}
1,4-Butanediol is not active in its own right; its mechanism of action stems from its identity as a prodrug of [[GHB]].<ref>http://onlinelibrary.wiley.com/doi/10.1111/j.1460-9568.2006.05146.x/abstract;jsessionid=D1EC0DE56C54DB2E93F66DEC2CCB2EDD.f02t02</ref>
1,4-Butanediol is not active in its own right; its mechanism of action stems from its identity as a prodrug of [[GHB]].<ref>{{cite journal | vauthors=((Carter, L. P.)), ((Koek, W.)), ((France, C. P.)) | journal=European Journal of Neuroscience | title=Lack of effects of GHB precursors GBL and 1,4-BD following i.c.v. administration in rats: GBL and 1,4-BD after i.p. and i.c.v. administration | volume=24 | issue=9 | pages=2595–2600 | date= November 2006 | url=https://onlinelibrary.wiley.com/doi/10.1111/j.1460-9568.2006.05146.x | issn=0953816X | doi=10.1111/j.1460-9568.2006.05146.x}}</ref>
 
It is converted into GHB in the liver by the enzymes alcohol dehydrogenase and aldehyde dehydrogenase, which is the same enzyme as [[alcohol]].<ref>{{cite journal | title=Gamma-Hydroxybutyrate Toxicity: Practice Essentials, Background, Pathophysiology | date=12 May 2022 | url=https://emedicine.medscape.com/article/820531-overview}}</ref> 1,4-Butanediol is first converted into 4-hydroxybutaldehyde in the liver and is released into the bloodstream before returning to the liver to convert into [[GHB]]. This process results in a much more delayed onset than [[GBL]] or [[GHB]].<ref>{{Citation | vauthors=((Burk, M. J.)), ((Van Dien, S. J.)), ((Burgard, A. P.)), ((Niu, W.)) | title=United States Patent: 8067214 - Compositions and methods for the biosynthesis of 1,4-butanediol and its precursors | url=https://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=8067214.PN.&OS=PN/8067214&RS=PN/8067214}}</ref> 4-hydroxybutaldehyde, even though it is an potentially toxic metabolite, no toxicity identified. Possibly because the very fast metabolism to GHB.<ref>{{cite journal | vauthors=((Irwin, R. D.)) | journal=Journal of applied toxicology: JAT | title=A review of evidence leading to the prediction that 1,4-butanediol is not a carcinogen | volume=26 | issue=1 | pages=72–80 | date= February 2006 | issn=0260-437X | doi=10.1002/jat.1110}}</ref>
 
[[File:GHB Prodrugs metabolic Pathways.png|300px|thumb|left|Metabolic pathways of GBL and 1,4-Butanediol as prodrugs for GHB]]
 
The differing levels of dehydrogenase enzymes can vary between individuals, meaning that, like alcohol, effects can differ greatly between users. In many, this manifests as a slow onset of effects and a higher rate of aldehyde collecting in the bloodstream.{{cn}} Because of these pharmacokinetic differences, 1,4-butanediol tends to be less potent and with a slower onset than GHB but has a longer duration; the related compound [[GBL]] tends to be slightly more potent and faster to take effect but more short-acting than GHB.
 


It is converted into GHB in the liver by the enzymes alcohol dehydrogenase and aldehyde dehydrogenase, which is the same enzyme as [[alcohol]].<ref>http://emedicine.medscape.com/article/820531-overview | Gamma-Hydroxybutyrate Toxicity</ref> 1,4-Butanediol is first converted into 4-hydroxybutaldehyde in the liver and is released into the bloodstream before returning to the liver to convert into [[GHB]]. This process results in a much more delayed onset than [[GBL]] or [[GHB]].<ref>http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=8067214.PN.&OS=PN/8067214&RS=PN/8067214</ref>


The differing levels of dehydrogenase enzymes can vary between individuals, meaning that, like alcohol, effects can differ greatly between users. In many, this manifests as a slow onset of effects and a higher rate of aldehyde collecting in the bloodstream, causing more toxic side effects. Because of these pharmacokinetic differences, 1,4-butanediol tends to be less potent and with a slower onset than GHB but has a longer duration; the related compound [[GBL]] tends to be slightly more potent and faster to take effect but more short-acting than GHB.


==Subjective effects==
==Subjective effects==
[[File:1,4 Butanediol pic.jpg|200px|thumb|Bottle of 1,4 Butanediol.]]
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
{{effects/base
{{effects/base
|{{effects/physical|
|{{effects/physical|
*'''[[Effect::Stimulation]]''' and '''[[Effect::Sedation]]''' - At lower doses, 1,4-butanediol is physically stimulating, encouraging movement and wakefulness. At higher doses, however, it becomes physically sedating, encouraging sleep and lethargy.
 
*'''[[Effect::Stimulation]]''' and '''[[Effect::Sedation]]''' - At lower dosages, 1,4-Butanediol is physically stimulating, encouraging movement and wakefulness. At higher dosages, however, it becomes physically sedating, encouraging sleep and lethargy.
*'''[[Effect::Respiratory depression]]''' - In cases of 1,4-butanediol overdoses, many reportedly experience an abnormal pattern of breathing characterized by progressively deeper and sometimes faster breathing, followed by a gradual decrease that results in a temporary stop in breathing called an apnea.
*'''[[Effect::Physical euphoria|Euphoria]]'''
*'''[[Effect::Physical euphoria|Euphoria]]'''
*'''[[Effect::Nausea]]'''
*'''[[Effect::Nausea]]''' - This effect is more common with 1,4-butanediol than [[GHB]].
*'''[[Effect::Stomach cramps]]'''
*'''[[Effect::Motor control loss]]'''
*'''[[Effect::Motor control loss]]'''
*'''[[Effect::Dizziness]]'''
*'''[[Effect::Dizziness]]'''
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Dehydration]]''' - This effect is related to the hygroscopic nature of 1,4-Butanediol.
*'''[[Effect::Respiratory depression]]''' - Many reportedly experience an abnormal pattern of breathing characterized by progressively deeper and sometimes faster breathing followed by a gradual decrease that results in a temporary stop in breathing called an apnea.
*'''[[Effect::Muscle cramps]]'''
*'''[[Effect::Optical sliding]]'''
*'''[[Effect::Increased salivation]]'''  


}}
}}
|{{effects/cognitive|


|{{effects/cognitive|
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Empathy, love, and sociability enhancement]]''' - Unlike [[alcohol]] which merely increases sociability through [[disinhibition]], 1,4-butanediol presents strong [[entactogenic]] effects which, although weaker than that of [[MDMA]], are still prominent and well-defined.
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Cognitive euphoria]]'''
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - Unlike [[alcohol]] which merely increases sociability through [[Effect::disinhibition]], 1,4-butanediol presents strong [[entactogenic]] effects which are prominent and well defined although weaker than that of [[MDMA]].
*'''[[Effect::Analysis suppression]]'''
*'''[[Effect::Analysis suppression]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Amnesia]]'''
*'''[[Effect::Amnesia]]'''
*'''[[Effect::Cognitive euphoria|Euphoria]]'''
*'''[[Effect::Suggestibility enhancement]]
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased libido]]
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased music appreciation]]'''
}}
}}
}}
}}
===Experience reports===
===Experience reports===
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
* [https://www.erowid.org/experiences/subs/exp_14Butanediol.shtml Erowid Experience Vaults: 1,4-Butanediol]
{{#ask: [[Category:1,4-Butanediol]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here
 
*[https://www.erowid.org/experiences/subs/exp_14Butanediol.shtml Erowid Experience Vaults: 1,4-Butanediol]


==Toxicity and harm potential==
==Toxicity and harm potential==
{{Main|GHB#Toxicity and harm potential}}
{{Main|GHB#Toxicity and harm potential}}
[[File:harmchart.png|thumb|right|300px|Radar plot showing relative physical harm, social harm, and dependence of [[GHB]]<ref>Development of a rational scale to assess the harm of drugs of potential misuse (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0140673607604644</ref>]]
[[File:harmchart.png|thumb|right|300px|Radar plot showing relative physical harm, social harm, and dependence of [[GHB]]<ref>{{cite journal | vauthors=((Nutt, D.)), ((King, L. A.)), ((Saulsbury, W.)), ((Blakemore, C.)) | journal=The Lancet | title=Development of a rational scale to assess the harm of drugs of potential misuse | volume=369 | issue=9566 | pages=1047–1053 | date=24 March 2007 | url=https://www.sciencedirect.com/science/article/pii/S0140673607604644 | issn=0140-6736 | doi=10.1016/S0140-6736(07)60464-4}}</ref>]]
1,4-Butanediol is not active in its own right; its mechanism of action stems from its identity as a prodrug of GHB, meaning that it is rapidly converted into GHB in the body.
1,4-Butanediol is not active in its own right; its mechanism of action stems from its identity as a prodrug of GHB, meaning that it is rapidly converted into GHB in the body.


GHB is considered to be a safe and non-toxic substance when used responsibly or medically. The [[LD50|LD<sub>50</sub>]] is above the active dosage, and there is no danger of acute toxicity when this compound is taken at appropriate dosages. However, it can be dangerous when used as a recreational drug or abused. There have been many negative reports from recreational users who have overdosed, combined GHB with alcohol or other drugs, or accidentally dosed themselves unexpectedly.<ref>https://www.erowid.org/experiences/exp.php?ID=1926 | Erowid. "GHB Overdoses & Poisonings: An Experience with GHB (ID 1926)". Erowid.org. Jun 19, 2000. erowid.org/exp/1926</ref>  
GHB is considered to be a safe and non-toxic substance when used responsibly or medically. The [[LD50|LD<sub>50</sub>]] is above the active dosage, and there is no danger of acute toxicity when this compound is taken at appropriate dosages. However, it can be dangerous when used as a recreational drug or abused. There have been many negative reports from recreational users who have overdosed, combined GHB with alcohol or other drugs, or accidentally dosed themselves unexpectedly.<ref>{{Citation | title=GHB - Erowid Exp - “GHB Overdoses & Poisonings” | url=https://www.erowid.org/experiences/exp.php?ID=1926}}</ref>  


One publication has investigated 226 deaths attributed to GHB.<ref>https://www.ncbi.nlm.nih.gov/pubmed/20825811 | Zvosec DL, Smith SW, Porrata T, Strobl AQ, Dyer JE (2011). "Case series of 226 gamma-hydroxybutyrate-associated deaths: lethal toxicity and trauma". The American Journal of Emergency Medicine 29 (3): 319–32.</ref> Seventy-one deaths (34%) were caused by GHB alone while the other deaths were from [[respiratory depression]] caused by interaction with alcohol or other drugs.
One publication has investigated 226 deaths attributed to GHB.<ref>{{cite journal | vauthors=((Zvosec, D. L.)), ((Smith, S. W.)), ((Porrata, T.)), ((Strobl, A. Q.)), ((Dyer, J. E.)) | journal=The American Journal of Emergency Medicine | title=Case series of 226 γ-hydroxybutyrate-associated deaths: lethal toxicity and trauma | volume=29 | issue=3 | pages=319–332 | date= March 2011 | issn=1532-8171 | doi=10.1016/j.ajem.2009.11.008}}</ref> Seventy-one deaths (34%) were caused by GHB alone while the other deaths were from [[respiratory depression]] caused by interaction with alcohol or other drugs.


To avoid a possible overdose of GHB/1,4-Butanediol, it is important to start with a low dose and work your way up slowly by increasing the dosage in small increments as the [[Toxicity::exact toxic dosage is unknown]].
To avoid a possible overdose of GHB/1,4-Butanediol, it is important to start with a low dose and work your way up slowly by increasing the dosage in small increments as the [[Toxicity::exact toxic dosage is unknown]].
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It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
===Neurotoxicity===
===Neurotoxicity===
In multiple studies, GHB has been found to impair spatial memory, working memory, learning and memory in rats with chronic administration.<ref>Adolescent γ-hydroxybutyric acid exposure decreases cortical N-methyl-d-aspartate receptor and impairs spatial learning (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S009130570400320X</ref><ref>Effects of subchronic administration of gammahydroxybutyrate (GHB) on spatial working memory in rats (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/17296081</ref><ref>γ-Hydroxybutyric Acid–Induced Cognitive Deficits in the Female Adolescent Rat | http://onlinelibrary.wiley.com/doi/10.1196/annals.1432.044/abstract</ref><ref>Neurotoxic effects induced by gammahydroxybutyric acid (GHB) in male rats | http://journals.cambridge.org/action/displayAbstract?fromPage=online&aid=6137924</ref> These effects are associated with decreased NMDA receptor expression in the cerebral cortex and possibly other areas as well.<ref>https://www.ncbi.nlm.nih.gov/pubmed/15582677 (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/15582677</ref>
In multiple studies, GHB has been found to impair spatial memory, working memory, learning and memory in rats with chronic administration.<ref>{{cite journal | vauthors=((Sircar, R.)), ((Basak, A.)) | journal=Pharmacology Biochemistry and Behavior | title=Adolescent γ-hydroxybutyric acid exposure decreases cortical N-methyl-d-aspartate receptor and impairs spatial learning | volume=79 | issue=4 | pages=701–708 | date=1 December 2004 | url=https://www.sciencedirect.com/science/article/pii/S009130570400320X | issn=0091-3057 | doi=10.1016/j.pbb.2004.09.022}}</ref><ref>{{cite journal | vauthors=((García, F. B.)), ((Pedraza, C.)), ((Arias, J. L.)), ((Navarro, J. F.)) | journal=Psicothema | title=[Effects of subchronic administration of gammahydroxybutyrate (GHB) on spatial working memory in rats] | volume=18 | issue=3 | pages=519–524 | date= August 2006 | issn=0214-9915}}</ref><ref>{{cite journal | vauthors=((Sircar, R.)), ((Basak, A.)), ((Sircar, D.)) | journal=Annals of the New York Academy of Sciences | title=γ-Hydroxybutyric Acid-Induced Cognitive Deficits in the Female Adolescent Rat | volume=1139 | issue=1 | pages=386–389 | date= October 2008 | url=http://doi.wiley.com/10.1196/annals.1432.044 | issn=00778923 | doi=10.1196/annals.1432.044}}</ref><ref>{{cite journal | vauthors=((Pedraza, C.)), ((García, F. B.)), ((Navarro, J. F.)) | journal=The International Journal of Neuropsychopharmacology | title=Neurotoxic effects induced by gammahydroxybutyric acid (GHB) in male rats | volume=12 | issue=09 | pages=1165 | date= October 2009 | url=https://academic.oup.com/ijnp/article-lookup/doi/10.1017/S1461145709000157 | issn=1461-1457 | doi=10.1017/S1461145709000157}}</ref> These effects are associated with decreased NMDA receptor expression in the cerebral cortex and possibly other areas as well.<ref>{{cite journal | vauthors=((Sircar, R.)), ((Basak, A.)) | journal=Pharmacology, Biochemistry, and Behavior | title=Adolescent gamma-hydroxybutyric acid exposure decreases cortical N-methyl-D-aspartate receptor and impairs spatial learning | volume=79 | issue=4 | pages=701–708 | date= December 2004 | issn=0091-3057 | doi=10.1016/j.pbb.2004.09.022}}</ref>


One study found that repeated administration of GHB to rats for 15 days drastically reduced the number of neurons and non-neuronal cells within the hippocampus and in the prefrontal cortex. With doses of 10 mg/kg of GHB, they were decreased by 61% in the hippocampus region and 32% in the prefrontal cortex, and with 100 mg/kg, they were decreased by 38% and 9%, respectively. This paper demonstrates contradicting effects on neuronal loss, with lower doses (10 mg/kg) producing the most neurotoxicity, and higher doses (100 mg/kg) producing less.
One study found that repeated administration of GHB to rats for 15 days drastically reduced the number of neurons and non-neuronal cells within the hippocampus and in the prefrontal cortex. With doses of 10 mg/kg of GHB, they were decreased by 61% in the hippocampus region and 32% in the prefrontal cortex, and with 100 mg/kg, they were decreased by 38% and 9%, respectively. This paper demonstrates contradicting effects on neuronal loss, with lower doses (10 mg/kg) producing the most neurotoxicity, and higher doses (100 mg/kg) producing less.
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===Tolerance and addiction potential===
===Tolerance and addiction potential===
[[File:GHBwithdrawal2.png|350px|thumbnail|right|This table compares the withdrawal symptoms of GHB/1,4-Butanediol, [[benzodiazepines]], and [[alcohol]].<ref name="GHB">GHB Withdrawal Syndrome | Texas Commission on Alcohol and Drug Abuse | https://www.erowid.org/chemicals/ghb/ghb_addiction2.pdf</ref>]]
[[File:GHBwithdrawal2.png|350px|thumbnail|right|This table compares the withdrawal symptoms of GHB/1,4-Butanediol, [[benzodiazepines]], and [[alcohol]].<ref name="GHB">GHB Withdrawal Syndrome | Texas Commission on Alcohol and Drug Abuse | https://www.erowid.org/chemicals/ghb/ghb_addiction2.pdf</ref>]]
GHB/1,4-Butanediol is [[Addiction potential::moderately physically and psychologically addictive]]. The frequent use of GHB/1,4-Butanediol can cause withdrawal symptoms similar to those caused by other [[depressants]] such as [[alcohol]] and [[benzodiazepines]] if abruptly discontinued.<ref>Systematic Assessment of Gamma Hydroxybutyrate (GHB) Effects During and After Acute Intoxication (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2759403/</ref><ref>Illicit gamma-hydroxybutyrate (GHB) and pharmaceutical sodium oxybate (Xyrem®): differences in characteristics and misuse (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2713368/</ref> These symptoms seem to depend on the dosage and the length of time the drug was used for. Light to moderate users often experience anxiety, insomnia, sleep-related problems, and tremors whereas heavy use can cause severe withdrawal symptoms like delirium, psychosis, and hallucinations.<ref>https://www.ncbi.nlm.nih.gov/pubmed/11174231 | Gamma-hydroxybutyrate withdrawal syndrome.</ref><ref name="GHB"></ref>
GHB/1,4-Butanediol is [[Addiction potential::moderately physically and psychologically addictive]]. The frequent use of GHB/1,4-Butanediol can cause withdrawal symptoms similar to those caused by other [[depressants]] such as [[alcohol]] and [[benzodiazepines]] if abruptly discontinued.<ref>{{cite journal | vauthors=((Kim, S. Y.)), ((Barker, J. C.)), ((Anderson, I. B.)), ((Dyer, J. E.)), ((Earnest, G.)), ((Blanc, P. D.)) | journal=The American journal on addictions / American Academy of Psychiatrists in Alcoholism and Addictions | title=Systematic Assessment of Gamma Hydroxybutyrate (GHB) Effects During and After Acute Intoxication | volume=17 | issue=4 | pages=312–318 | date= 2008 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2759403/ | issn=1055-0496 | doi=10.1080/10550490802138988}}</ref><ref>{{cite journal | vauthors=((Carter, L. P.)), ((Pardi, D.)), ((Gorsline, J.)), ((Griffiths, R. R.)) | journal=Drug and alcohol dependence | title=Illicit gamma-hydroxybutyrate (GHB) and pharmaceutical sodium oxybate (Xyrem®): differences in characteristics and misuse | volume=104 | issue=1–2 | pages=1–10 | date=1 September 2009 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2713368/ | issn=0376-8716 | doi=10.1016/j.drugalcdep.2009.04.012}}</ref> These symptoms seem to depend on the dosage and the length of time the drug was used for. Light to moderate users often experience anxiety, insomnia, sleep-related problems, and tremors whereas heavy use can cause severe withdrawal symptoms like delirium, psychosis, and hallucinations.<ref>{{cite journal | vauthors=((Dyer, J. E.)), ((Roth, B.)), ((Hyma, B. A.)) | journal=Annals of Emergency Medicine | title=Gamma-hydroxybutyrate withdrawal syndrome | volume=37 | issue=2 | pages=147–153 | date= February 2001 | issn=0196-0644 | doi=10.1067/mem.2001.112985}}</ref><ref name="GHB" />


Although there have been reported fatalities due to GHB/1,4-Butanediol withdrawal, reports are inconclusive and further research is needed.<ref>Gamma-hydroxybutyrate: an emerging drug of abuse that causes physical dependence | http://onlinelibrary.wiley.com/doi/10.1111/j.1360-0443.1997.tb03640.x/abstract</ref>
Although there have been reported fatalities due to GHB/1,4-Butanediol withdrawal, reports are inconclusive and further research is needed.<ref>{{cite journal | vauthors=((Galloway, G. P.)), ((Frederick, S. L.)), ((Staggers, F. E.)), ((Gonzales, M.)), ((Stalcup, S. A.)), ((Smith, D. E.)) | journal=Addiction | title=Gamma-hydroxybutyrate: an emerging drug of abuse that causes physical dependence | volume=92 | issue=1 | pages=89–96 | date= January 1997 | url=https://onlinelibrary.wiley.com/doi/10.1111/j.1360-0443.1997.tb03640.x | issn=09652140 | doi=10.1111/j.1360-0443.1997.tb03640.x}}</ref>


Tolerance will develop to the sedative-hypnotic effects [[Time to full tolerance::within several weeks of continuous use]]. After cessation, the tolerance returns to baseline in [[Time to zero tolerance::7 - 14 days]]. Withdrawal symptoms or rebound symptoms may occur after ceasing usage abruptly following a few weeks or longer of steady dosing, and may necessitate a gradual dose reduction.
Tolerance will develop to the sedative-hypnotic effects [[Time to full tolerance::within several weeks of continuous use]]. After cessation, the tolerance returns to baseline in [[Time to zero tolerance::7 - 14 days]]. Withdrawal symptoms or rebound symptoms may occur after ceasing usage abruptly following a few weeks or longer of steady dosing, and may necessitate a gradual dose reduction.
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===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/GHB}}
{{DangerousInteractions/Depressants}}
{{DangerousInteractions/Depressants}}


==Legal issues==
==Legal status==
*'''United States''': While 1,4-butanediol is not currently scheduled federally in the United States, a number of states have classified it as a controlled substance. Additionally, individuals have been prosecuted for this substance under the Federal Analogue Act as being substantially similar to GHB.<ref>http://cases.justia.com/us-court-of-appeals/F3/312/926/608696/</ref> A federal district court in Chicago ruled that 1,4-butanediol could not be considered an analogue of GHB under federal law, and the Seventh Circuit Court of Appeals upheld that ruling.<ref>United States v. Turcotte, 405 F.3d 515 (7th Cir. 2005) "With specific regard to 1,4-butanediol, the jury has returned a special verdict which states that 1,4-butanediol is not a Schedule I drug analogue, because 1,4-butanediol's chemical structure is not significantly similar to the chemical structure of GHB.</ref>
 
*'''United Kingdom''': In the United Kingdom, 1,4-butanediol was scheduled in December 2009 (along with another GHB precursor, gamma-butyrolactone) as a Class C controlled substance.  
*'''United States''': While 1,4-butanediol is not currently scheduled federally in the United States, a number of states have classified it as a controlled substance. Additionally, individuals have been prosecuted for this substance under the Federal Analogue Act as being substantially similar to GHB.<ref>{{Citation | title=United States of America, Appellee, v. Thomas William Washam, Appellant, 312 F.3d 926 (8th Cir. 2003) | url=https://law.justia.com/cases/federal/appellate-courts/F3/312/926/608696/}}</ref> A federal district court in Chicago ruled that 1,4-butanediol could not be considered an analogue of GHB under federal law, and the Seventh Circuit Court of Appeals upheld that ruling.<ref>United States v. Turcotte, 405 F.3d 515 (7th Cir. 2005) "With specific regard to 1,4-butanediol, the jury has returned a special verdict which states that 1,4-butanediol is not a Schedule I drug analogue, because 1,4-butanediol's chemical structure is not significantly similar to the chemical structure of GHB.</ref>
*'''Germany''': In Germany, the drug is not explicitly illegal, but might also be treated as illegal if used as a drug.  
*'''United Kingdom''': In the United Kingdom, 1,4-butanediol was scheduled in December 2009 (along with another GHB precursor, gamma-butyrolactone) as a Class C controlled substance.
*'''Germany''': 1,4-butanediol is not a controlled substance under the BtMG (Narcotics Act) or the NpSG (New Psychoactive Substances Act).<ref>BtMG | http://www.gesetze-im-internet.de/btmg_1981/BtMG.pdf</ref><ref>NpSG | https://www.gesetze-im-internet.de/npsg/NpSG.pdf</ref> It is legal, as long as it is not sold for human consumption, according to §2 AMG.<ref>{{Citation | title=§ 2 AMG - Einzelnorm | url=https://www.gesetze-im-internet.de/amg_1976/__2.html}}</ref>
*'''Canada''': It is controlled as a Schedule VI precursor in Canada.
*'''Canada''': It is controlled as a Schedule VI precursor in Canada.
*'''Switzerland''': 1,4-Butanediol is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Depressants]]
*[[Depressants]]
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*[[GBL]]
*[[GBL]]
*[[GABA]]
*[[GABA]]
==External links==
==External links==
*[https://en.wikipedia.org/wiki/1,4-Butanediol 1,4-Butanediol (Wikipedia)]
*[https://en.wikipedia.org/wiki/1,4-Butanediol 1,4-Butanediol (Wikipedia)]
*[https://erowid.org/chemicals/14b/ 1,4-Butanediol (Erowid Vault)]
*[https://erowid.org/chemicals/14b/14b.shtml 1,4-Butanediol (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=12266 1,4-Butanediol (Isomer Design)]


==References==
==References==
<references />
<references />
[[Category:Substance]]
[[Category::Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Alkanediol]]
[[Category:Alcohol]]
[[Category:Depressant]]
[[Category:Depressant]]
[[Category:Prodrug]]
[[Category:Prodrug]]
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