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GABA analogue

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GABA analogue

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).

Contents

Many GABA analogues are used as drugs, especially as anticonvulsants, sedatives, and anxiolytics

Deaminated

  • Butyric acid (butanoic acid) – agonist of Free fatty acid receptor 2, Free fatty acid receptor 3, and Niacin receptor 1, and HDAC inhibitor
  • Derivatives: butyrate (butanoate), sodium butyrate, methyl butyrate, ethyl butyrate, butyl butyrate, pentyl butyrate
  • Valeric acid (pentanoic acid) – constituent of valerian; has a pleasant 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

  • 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

  • GABOB (β-hydroxy-GABA) – anticonvulsant; GABA receptor agonist
  • Pregabalin (β-isobutyl-GABA) – analgesic, anticonvulsant, anxiolytic, and drug of abuse; 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

    • Aromatized

  • 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

  • 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

  • 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
  • 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 – nootropics
  • Pivagabine (N-pivaloyl-GABA) – antidepressant/anxiolytic drug; CRF inhibitor
  • Vigabatrin (y-vinyl-GABA) – anticonvulsant; GABA-T inhibitor

    • References

    GABA analogue Wikipedia
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