GABA analogue

γ-Aminobutyric acid (GABA)

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

Deaminated

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 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 (γ-hydroxybutyric acid) – neurotransmitter, drug of abuse; agonist of GHB receptor and GABA_B 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, GABA_B receptor agonist.
Baclofen (β-(4-chlorophenyl)-GABA) – antispasmodic drug; potent GABA_B receptor agonist, weak inhibitor of α₂δ subunit-containing VGCCs
Tolibut (β-(4-methylphenyl)-GABA) – analgesic, tranquilizing, and neuroprotective drug
Phaclofen (phosphonobaclofen) – GABA_B receptor antagonist
Saclofen (sulfonobaclofen) – GABA_B receptor antagonist

Cyclized

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 – 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 (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 GABA_A 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) – 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^[1] – nootropics
Pivagabine (N-pivaloyl-GABA) – antidepressant/anxiolytic drug; CRF inhibitor
Vigabatrin (y-vinyl-GABA) – anticonvulsant; GABA-T inhibitor

References

↑ 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.

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[WerryAman2013-1] 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.

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