GABA analogue: Difference between revisions
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[[Image:Gamma-Aminobuttersäure - gamma-aminobutyric acid.svg|right|thumb|300px|γ-Aminobutyric acid (GABA)]] |
[[Image:Gamma-Aminobuttersäure - gamma-aminobutyric acid.svg|right|thumb|300px|γ-Aminobutyric acid (GABA)]] |
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{{short_description|Class of drugs}} |
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A '''GABA analogue''' is a compound which is an [[structural analog|analogue]] or [[chemical derivative|derivative]] of the neurotransmitter [[gamma-Aminobutyric acid]] (GABA) (the [[IUPAC]] of which is 4-aminobutanoic acid). |
A '''GABA analogue''' is a compound which is an [[structural analog|analogue]] or [[chemical derivative|derivative]] of the neurotransmitter [[gamma-Aminobutyric acid]] (GABA) (the [[IUPAC]] of which is 4-aminobutanoic acid). |
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Many GABA analogues are used as [[drug]]s, especially as [[anticonvulsant]]s, [[sedative]]s, and [[anxiolytic]]s |
Many GABA analogues are used as [[drug]]s, especially as [[anticonvulsant]]s, [[sedative]]s, and [[anxiolytic]]s. |
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==List of GABA analogues== |
==List of GABA analogues== |
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** Derivatives: [[butyrate]] (butanoate), [[sodium butyrate]], [[methyl butyrate]], [[ethyl butyrate]], [[butyl butyrate]], [[pentyl butyrate]] |
** Derivatives: [[butyrate]] (butanoate), [[sodium butyrate]], [[methyl butyrate]], [[ethyl butyrate]], [[butyl butyrate]], [[pentyl butyrate]] |
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* [[Valeric acid]] (pentanoic acid) – constituent of valerian; has an unpleasant odor and fruity flavor and esters are used as additives |
* [[Valeric acid]] (pentanoic acid) – constituent of valerian; has an unpleasant odor and fruity flavor and esters are used as additives |
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** Derivatives: [[valerate]] (pentanoate), [[methyl valerate]], [[ethyl valerate]], [[pentyl valerate]] |
** Derivatives: [[Valeric acid#Valerate salts and esters|valerate]] (pentanoate), [[methyl valerate]], [[ethyl valerate]], [[pentyl valerate]] |
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* [[Isovaleric acid]] (isopentanoic acid/3-methylbutanoic acid) – constituent of [[Valeriana officinalis|valerian]]; has anticonvulsant effects; [[positive allosteric modulator|PAM]] of the [[GABAA receptor|GABA<sub>A</sub> receptor]] |
* [[Isovaleric acid]] (isopentanoic acid/3-methylbutanoic acid) – constituent of [[Valeriana officinalis|valerian]]; has anticonvulsant effects; [[positive allosteric modulator|PAM]] of the [[GABAA receptor|GABA<sub>A</sub> receptor]] |
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** Derivatives: [[isovalerate]] (isopentanoate/3-methylbutanoate), [[menthyl isovalerate]] (validolum) – used as an anxiolytic and sedative in [[Russia]] |
** Derivatives: [[isovalerate]] (isopentanoate/3-methylbutanoate), [[menthyl isovalerate]] (validolum) – used as an anxiolytic and sedative in [[Russia]] |
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===β-Substituted=== |
===β-Substituted=== |
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* [[GABOB]] (β-hydroxy-GABA) – anticonvulsant; [[GABA receptor agonist]] |
* [[GABOB]] (β-hydroxy-GABA) – anticonvulsant; [[GABA receptor agonist]] |
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* [[Pregabalin]] (β-isobutyl-GABA) – [[analgesic]], [[anticonvulsant |
* [[Pregabalin]] (β-isobutyl-GABA) – [[analgesic]], [[anticonvulsant]], and [[anxiolytic]]; potent inhibitor of [[Voltage-dependent calcium channel#α2δ Subunit|α<sub>2</sub>δ subunit]]-containing [[voltage-gated calcium channel|VGCC]]s. |
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* [[Phenibut]] (β-phenyl-GABA) – sedative and anxiolytic from Russia; inhibitor of [[Voltage-dependent calcium channel#α2δ Subunit|α<sub>2</sub>δ subunit]]-containing [[voltage-gated calcium channel|VGCC]]s and, to a lesser extent, GABA<sub>B</sub> receptor agonist. |
* [[Phenibut]] (β-phenyl-GABA) – sedative and anxiolytic from Russia; inhibitor of [[Voltage-dependent calcium channel#α2δ Subunit|α<sub>2</sub>δ subunit]]-containing [[voltage-gated calcium channel|VGCC]]s and, to a lesser extent, GABA<sub>B</sub> receptor agonist. |
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* [[Baclofen]] (β-(4-chlorophenyl)-GABA) – [[antispasmodic]] drug; potent GABA<sub>B</sub> receptor agonist, weak inhibitor of α<sub>2</sub>δ subunit-containing VGCCs |
* [[Baclofen]] (β-(4-chlorophenyl)-GABA) – [[antispasmodic]] drug; potent GABA<sub>B</sub> receptor agonist, weak inhibitor of α<sub>2</sub>δ subunit-containing VGCCs |
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* [[Saclofen]] (sulfonobaclofen) – GABA<sub>B</sub> receptor antagonist |
* [[Saclofen]] (sulfonobaclofen) – GABA<sub>B</sub> receptor antagonist |
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===Cyclized=== |
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* [[Arecaidine]] – constituent of [[areca nuts]]; GABA reuptake inhibitor |
* [[Arecaidine]] – constituent of [[areca nuts]]; GABA reuptake inhibitor |
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* [[Gabaculine]] – [[neurotoxin]]; GABA-T inhibitor and [[GABA reuptake inhibitor]] |
* [[Gabaculine]] – [[neurotoxin]]; GABA-T inhibitor and [[GABA reuptake inhibitor]] |
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* [[N-Anisoyl-GABA]] – major active metabolite of the nootropic [[aniracetam]] |
* [[N-Anisoyl-GABA]] – major active metabolite of the nootropic [[aniracetam]] |
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* [[NCS-382]] – antagonist of the GHB receptor |
* [[NCS-382]] – antagonist of the GHB receptor |
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* [[Piracetam]] and other [[racetam]]s<ref name="WerryAman2013">{{cite book|author1=John Scott Werry|author2=Michael G. Aman|title= |
* [[Piracetam]] and other [[racetam]]s<ref name="WerryAman2013">{{cite book|author1=John Scott Werry|author2=Michael G. Aman|title=Practitioner's Guide to Psychoactive Drugs for Children and Adolescents|url=https://books.google.com/books?id=k_2fBwAAQBAJ&pg=PA415|date=29 June 2013|publisher=Springer Science & Business Media|isbn=978-1-4899-0086-9|pages=415–}}</ref> – nootropics |
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* [[Pivagabine]] (N-pivaloyl-GABA) – [[antidepressant]]/anxiolytic drug; [[corticotropin-releasing factor|CRF]] inhibitor |
* [[Pivagabine]] (N-pivaloyl-GABA) – [[antidepressant]]/anxiolytic drug; [[corticotropin-releasing factor|CRF]] inhibitor |
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* [[Vigabatrin]] (y-vinyl-GABA) – anticonvulsant; GABA-T inhibitor |
* [[Vigabatrin]] (y-vinyl-GABA) – anticonvulsant; GABA-T inhibitor |
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{{Channel blockers}} |
{{Channel blockers}} |
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[[Category:GABA analogues]] |
[[Category:GABA analogues| ]] |
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[[Category:GABA receptor agonists]] |
[[Category:GABA receptor agonists]] |
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Latest revision as of 04:40, 27 January 2024
A GABA analogue is a compound which is an analogue or derivative of the neurotransmitter gamma-Aminobutyric acid (GABA) (the IUPAC of which is 4-aminobutanoic acid).
Many GABA analogues are used as drugs, especially as anticonvulsants, sedatives, and anxiolytics.
List of GABA analogues
[edit]Deaminated
[edit]- Butyric acid (butanoic acid) – histone deacetylase inhibitor and full agonist of free fatty acid receptor 2, free fatty acid receptor 3, and niacin receptor 1
- Derivatives: butyrate (butanoate), sodium butyrate, methyl butyrate, ethyl butyrate, butyl butyrate, pentyl butyrate
- Valeric acid (pentanoic acid) – constituent of valerian; has an unpleasant odor and fruity flavor and esters are used as additives
- Derivatives: valerate (pentanoate), methyl valerate, ethyl valerate, pentyl valerate
- Isovaleric acid (isopentanoic acid/3-methylbutanoic acid) – constituent of valerian; has anticonvulsant effects; PAM of the GABAA receptor
- Derivatives: isovalerate (isopentanoate/3-methylbutanoate), menthyl isovalerate (validolum) – used as an anxiolytic and sedative in Russia
- Isovaleramide (isopentamide/3-methylbutanamide) – constituent of valerian; has anxiolytic and sedative effects; PAM of the GABAA receptor
- Valproic acid (2-propylpentanoic acid) – anticonvulsant/mood stabilizer; inhibitor of HDAC, SSADH, and GABA-T, blocker of VDSCs and GABA reuptake, AR/PR antagonist
- Derivatives: sodium valproate, valproate semisodium, divalproex sodium, valproate pivoxil
- Valpromide (2-propylpentanamide) – anticonvulsant; same mechanism of action as valproic acid, plus inhibitor of epoxide hydrolase
- Valnoctamide (2-ethyl-3-methylpentanamide) – anticonvulsant; similar mechanism of action to valproic acid; structural isomer of valpromide
3- or 4-Hydroxylated
[edit]- 3-Hydroxybutanal – synthetic hypnotic and sedative drug
- GHB (γ-hydroxybutyric acid) – neurotransmitter, drug of abuse; agonist of GHB receptor and GABAB receptor
- Derivatives: sodium oxybate (sodium γ-hydroxybutanoate) – used to treat narcolepsy; same mechanism of action as GHB
- Aceburic acid (γ-hydroxybutyric acid acetate) – synthetic prodrug to GHB
- GBL (γ-hydroxybutyric acid lactone) – metabolic intermediate and prodrug to GHB
- GHBAL (γ-hydroxybutyraldehyde or γ-hydroxybutanal) – metabolic intermediate and prodrug to GHB
- GHV (γ-hydroxyvaleric acid) – designer drug; analogue of GHB with similar effects
- GVL (γ-valerolactone) – designer drug; prodrug to GHV
- T-HCA/GHC (γ-hydroxycrotonic acid) – neurotransmitter; GHB receptor agonist
- GCL (γ-crotonolactone) – prodrug to T-HCA/GHC
- HOCPCA (3-hydroxycyclopent-1-enecarboxylic acid) – synthetic GHB receptor agonist
- UMB68 (γ-hydroxy-γ-methylpentanoic acid) – synthetic GHB receptor agonist
β-Substituted
[edit]- GABOB (β-hydroxy-GABA) – anticonvulsant; GABA receptor agonist
- Pregabalin (β-isobutyl-GABA) – analgesic, anticonvulsant, and anxiolytic; potent inhibitor of α2δ subunit-containing VGCCs.
- Phenibut (β-phenyl-GABA) – sedative and anxiolytic from Russia; inhibitor of α2δ subunit-containing VGCCs and, to a lesser extent, GABAB receptor agonist.
- Baclofen (β-(4-chlorophenyl)-GABA) – antispasmodic drug; potent GABAB receptor agonist, weak inhibitor of α2δ subunit-containing VGCCs
- Tolibut (β-(4-methylphenyl)-GABA) – analgesic, tranquilizing, and neuroprotective drug
- Phaclofen (phosphonobaclofen) – GABAB receptor antagonist
- Saclofen (sulfonobaclofen) – GABAB receptor antagonist
Cyclized
[edit]- Arecaidine – constituent of areca nuts; GABA reuptake inhibitor
- Gabaculine – neurotoxin; GABA-T inhibitor and GABA reuptake inhibitor
- Gabapentin – anticonvulsant; inhibitor of α2δ subunit-containing VGCCs
- Gabapentin enacarbil – used for the treatment of restless legs syndrome and postherpetic neuralgia; same mechanism of action as gabapentin
- Gaboxadol – GABAA receptor agonist
- Guvacine – constituent of areca nuts; GABA reuptake inhibitor
- Isoguvacine – GABAA receptor agonist
- Isonipecotic acid – GABAA receptor partial agonist
- Muscimol – constituent of Amanita muscaria mushrooms; GABAA receptor agonist
- Nipecotic acid – used in scientific research; GABA reuptake inhibitor
GABA prodrugs
[edit]- L-Glutamine – endogenous precursor of GABA and glutamate
- N-Isonicotinoyl-GABA – structural isomer of picamilon
- Picamilon (N-nicotinoyl-GABA) – dietary supplement and prescription drug in Russia
- Progabide (complex structure) – anticonvulsant
- Tolgabide (complex structure) – anticonvulsant
Others/miscellaneous
[edit]- 1,4-Butanediol – metabolic intermediate and prodrug to GHB
- 3-Methyl-GABA – GABA-T activator
- AABA/homoalanine (α-aminobutyric acid) – used by nonribosomal peptide synthetases
- BABA (β-aminobutyric acid) – known for its ability to induce plant disease resistance
- DAVA (δ-aminopentanoic acid) – GABA receptor agonist
- Gabamide (γ-aminobutanamide) – GABA receptor agonist
- Gabazine (SR-95531) – antagonist of the GABAA and GHB receptors
- GAVA (γ-aminopentanoic acid) – GABA reuptake inhibitor
- Glufimet (dimethyl 3-phenylglutamate hydrochloride) – experimental drug related to phenibut
- Glutamic acid (glutamate) – neurotransmitter
- Homotaurine (tramiprosate) – GABAA receptor agonist, GABAB receptor antagonist
- Hopantenic acid (N-pantoyl-GABA) – central nervous system depressant used in Russia
- Isovaline – peripherally selective agonist of the GABAB receptor
- Lesogaberan (AZD-3355) – agonist of the GABAB receptor
- N-Anisoyl-GABA – major active metabolite of the nootropic aniracetam
- NCS-382 – antagonist of the GHB receptor
- Piracetam and other racetams[1] – nootropics
- Pivagabine (N-pivaloyl-GABA) – antidepressant/anxiolytic drug; CRF inhibitor
- Vigabatrin (y-vinyl-GABA) – anticonvulsant; GABA-T inhibitor
See also
[edit]- Bamaluzole
- Bicuculline
- Deramciclane
- Ethanol
- Fengabine
- Gabapentinoid
- Loreclezole
- Propofol
- Retigabine/ezogabine
- Tiagabine
- Valerenic acid
References
[edit] | This article needs additional citations for verification. (January 2017) |
- ^ John Scott Werry; Michael G. Aman (29 June 2013). Practitioner's Guide to Psychoactive Drugs for Children and Adolescents. Springer Science & Business Media. pp. 415–. ISBN 978-1-4899-0086-9.