GABA analogue

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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

Video GABA analogue

List of GABA analogues

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 GABA_A 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 GABA_A 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 (?-hydroxybutyric acid) - neurotransmitter, drug of abuse; agonist of GHB receptor and GABA_B receptor
  • Derivatives: sodium oxybate (sodium ?-hydroxybutanoate) - used to treat narcolepsy; same mechanism of action as GHB
• Aceburic acid (?-hydroxybutyric acid acetate) - synthetic prodrug to GHB
• GBL (?-hydroxybutyric acid lactone) - metabolic intermediate and prodrug to GHB
• GHBAL (?-hydroxybutyraldehyde or ?-hydroxybutanal) - metabolic intermediate and prodrug to GHB
• GHV (?-hydroxyvaleric acid) - designer drug; analogue of GHB with similar effects
• GVL (?-valerolactone) - designer drug; prodrug to GHV
• T-HCA/GHC (?-hydroxycrotonic acid) - neurotransmitter; GHB receptor agonist
• GCL (?-crotonolactone) - prodrug to T-HCA/GHC
• HOCPCA (3-hydroxycyclopent-1-enecarboxylic acid) - synthetic GHB receptor agonist
• UMB68 (?-hydroxy-?-methylpentanoic acid) - synthetic GHB receptor agonist

?-Substituted

• GABOB (?-hydroxy-GABA) - anticonvulsant; GABA receptor agonist
• Pregabalin (?-isobutyl-GABA) - analgesic, anticonvulsant, anxiolytic, and drug of abuse; potent inhibitor of ?₂? subunit-containing VGCCs.
• Phenibut (?-phenyl-GABA) - sedative and anxiolytic from Russia; inhibitor of ?₂? subunit-containing VGCCs and, to a lesser extent, GABA_B receptor agonist.
• Baclofen (?-(4-chlorophenyl)-GABA) - antispasmodic drug; potent GABA_B receptor agonist, weak inhibitor of ?₂? subunit-containing VGCCs
• Tolibut (?-(4-methylphenyl)-GABA) - analgesic, tranquilizing, and neuroprotective drug
• Phaclofen (phosphonobaclofen) - GABA_B receptor antagonist
• Saclofen (sulfonobaclofen) - GABA_B receptor antagonist

Aromatized

• Arecaidine - constituent of areca nuts; GABA reuptake inhibitor
• Gabaculine - neurotoxin; GABA-T inhibitor and GABA reuptake inhibitor
• Gabapentin - anticonvulsant; inhibitor of ?₂? subunit-containing VGCCs
  • Gabapentin enacarbil - used for the treatment of restless legs syndrome and postherpetic neuralgia; same mechanism of action as gabapentin
• Gaboxadol - GABA_A receptor agonist
• Guvacine - constituent of areca nuts; GABA reuptake inhibitor
• Isoguvacine - GABA_A receptor agonist
• Isonipecotic acid - GABA_A receptor partial agonist
• Muscimol - constituent of Amanita muscaria mushrooms; GABA_A 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 (?-aminobutyric acid) - used by nonribosomal peptide synthetases
• BABA (?-aminobutyric acid) - known for its ability to induce plant disease resistance
• DAVA (?-aminopentanoic acid) - GABA receptor agonist
• Gabamide (?-aminobutanamide) - GABA receptor agonist
• Gabazine (SR-95531) - antagonist of the GABA_A and GHB receptors
• GAVA (?-aminopentanoic acid) - GABA reuptake inhibitor
• Glutamic acid (glutamate) - neurotransmitter
• Homotaurine (tramiprosate) - GABA_A receptor agonist, GABA_B receptor antagonist
• Hopantenic acid (N-pantoyl-GABA) - central nervous system depressant used in Russia
• Isovaline - peripherally selective agonist of the GABA_B receptor
• Lesogaberan (AZD-3355) - agonist of the GABA_B 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

Maps GABA analogue

See also

• Bamaluzole
• Bicuculline
• Deramciclane
• Ethanol
• Fengabine
• Gabapentinoid
• Loreclezole
• Propofol
• Retigabine/ezogabine
• Tiagabine
• Valerenic acid

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References

Source of article : Wikipedia