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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>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>
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 aldehyde, does not have the same organ toxicity associated with acetaldehyde.<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> One reason could be the very fast metabolism to GHB.
[[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, 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.
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}}
===Physical effects===
*'''[[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.
{{effects/base
|{{effects/physical|
*'''[[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]]'''
===Cognitive effects===
}}
*'''[[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.
|{{effects/cognitive|
*'''[[Effect::Anxiety suppression]]'''
*'''[[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:
[[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 Analog 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 analog 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>
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
1,4-Butanediol (also known as 1,4-B, BDO, BD or 1,4-BD) is a 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.[3] It is used as a recreational intoxicant with effects similar to alcohol and GHB.[4] 1 ml of 1,4-butanediol is equivalent to 1.4 g of Na-GHB.
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 γ-butyrolactone (GBL).[5]
1,4-Butanediol, as well as GBL, will dissolve most types of plastic over time.[6] 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 is classified as a subclass of alcoholic compounds called 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 R1 and R4. 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.
1,4-Butanediol is not active in its own right; its mechanism of action stems from its identity as a prodrug of GHB.[7]
It is converted into GHB in the liver by the enzymes alcohol dehydrogenase and aldehyde dehydrogenase, which is the same enzyme as alcohol.[8] 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.[9] 4-hydroxybutaldehyde, even though it is an aldehyde, does not have the same organ toxicity associated with acetaldehyde.[10] One reason could be the very fast metabolism to GHB.
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, 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
Bottle of 1,4 Butanediol.
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWikicontributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
Physical effects
Stimulation and 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.
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.
Radar plot showing relative physical harm, social harm, and dependence of GHB[11]
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 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.[12]
One publication has investigated 226 deaths attributed to GHB.[13] 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 exact toxic dosage is unknown.
Accidental ingestions of 1,4-Butanediol have also occurred due to inadequate storage methods. If 1,4-Butanediol is put into a clear liquid, glass, or bottle, it can be easily mistaken for water. It is recommended to clearly label your 1,4-Butanediol in writing and dye the liquid with blue food coloring so it no longer resembles a drinkable beverage. It is also recommended to store your 1,4-Butanediol in a container that no one would drink out of.
In multiple studies, GHB has been found to impair spatial memory, working memory, learning and memory in rats with chronic administration.[14][15][16][17] These effects are associated with decreased NMDA receptor expression in the cerebral cortex and possibly other areas as well.[18]
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.
GHB/1,4-Butanediol is 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.[20][21] 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.[22][19]
Although there have been reported fatalities due to GHB/1,4-Butanediol withdrawal, reports are inconclusive and further research is needed.[23]
Tolerance will develop to the sedative-hypnotic effects within several weeks of continuous use. After cessation, the tolerance returns to baseline in 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.
Dangerous interactions
Warning:Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
Dissociatives - This combination can unpredictably potentiate the amnesia, sedation, motor control loss and delusions that can be caused by each other. It may also result in a sudden loss of consciousness accompanied by a dangerous degree of respiratory depression. If nausea or vomiting occurs before consciousness is lost, users should attempt to fall asleep in the recovery position or have a friend move them into it.
Stimulants - Stimulants mask the sedative effect of depressants, which is the main factor most people use to gauge their level of intoxication. Once the stimulant effects wear off, the effects of the depressant will significantly increase, leading to intensified disinhibition, motor control loss, and dangerous black-out states. This combination can also potentially result in severe dehydration if one's fluid intake is not closely monitored. If choosing to combine these substances, one should strictly limit themselves to a pre-set schedule of dosing only a certain amount per hour until a maximum threshold has been reached.
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.[24] 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.[25]
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).[26][27] It is legal, as long as it is not sold for human consumption, according to §2 AMG.[28]
Canada: It is controlled as a Schedule VI precursor in Canada.
Switzerland: 1,4-Butanediol is a controlled substance specifically named under Verzeichnis E.[29]
↑Irwin, R. D. (February 2006). "A review of evidence leading to the prediction that 1,4-butanediol is not a carcinogen". Journal of applied toxicology: JAT. 26 (1): 72–80. doi:10.1002/jat.1110. ISSN0260-437X.
↑Zvosec, D. L., Smith, S. W., Porrata, T., Strobl, A. Q., Dyer, J. E. (March 2011). "Case series of 226 γ-hydroxybutyrate-associated deaths: lethal toxicity and trauma". The American Journal of Emergency Medicine. 29 (3): 319–332. doi:10.1016/j.ajem.2009.11.008. ISSN1532-8171.
↑García, F. B., Pedraza, C., Arias, J. L., Navarro, J. F. (August 2006). "[Effects of subchronic administration of gammahydroxybutyrate (GHB) on spatial working memory in rats]". Psicothema. 18 (3): 519–524. ISSN0214-9915.
↑Dyer, J. E., Roth, B., Hyma, B. A. (February 2001). "Gamma-hydroxybutyrate withdrawal syndrome". Annals of Emergency Medicine. 37 (2): 147–153. doi:10.1067/mem.2001.112985. ISSN0196-0644.
↑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.
