1,4-Butanediol: Difference between revisions

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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 ~~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.~~

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~~, 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.{{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.

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*[https://en.wikipedia.org/wiki/1,4-Butanediol 1,4-Butanediol (Wikipedia)]

*[https://erowid.org/chemicals/14b/14b.shtml 1,4-Butanediol (Erowid Vault)]

*[https://isomerdesign.com/PiHKAL/explore.php?id=12266 1,4-Butanediol (~~TiHKAL /~~ Isomer Design)]

*[https://isomerdesign.com/PiHKAL/explore.php?id=12266 1,4-Butanediol (Isomer Design)]

==References==

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[[Category::Psychoactive substance]]

[[Category:Alkanediol]]

[[Category:Alcohol]]

[[Category:Depressant]]

[[Category:Prodrug]]

@@ Line 18: / Line 18: @@
 ,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 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.
+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, 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.{{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.
@@ Line 121: / Line 121: @@
 *[https://en.wikipedia.org/wiki/1,4-Butanediol 1,4-Butanediol (Wikipedia)]
 *[https://erowid.org/chemicals/14b/14b.shtml 1,4-Butanediol (Erowid Vault)]
-*[https://isomerdesign.com/PiHKAL/explore.php?id=12266 1,4-Butanediol (TiHKAL / Isomer Design)]
+*[https://isomerdesign.com/PiHKAL/explore.php?id=12266 1,4-Butanediol (Isomer Design)]
 ==References==
@@ Line 127: / Line 127: @@
 [[Category::Psychoactive substance]]
 [[Category:Alkanediol]]
+[[Category:Alcohol]]
 [[Category:Depressant]]
 [[Category:Prodrug]]
 {{#set:Featured=true}}