# 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).
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, and anxiolytic; potent inhibitor of α$_2$δ subunit-containing VGCCs.
* Phenibut (β-phenyl-GABA) – sedative and anxiolytic from Russia; GABA$_B$ receptor agonist, and to a lesser extent inhibitor of α$_2$δ subunit-containing VGCCs.
* Baclofen (β-(4-chlorophenyl)-GABA) – antispasmodic drug; potent GABA$_B$ receptor agonist, weak inhibitor of α$_2$δ 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 α$_2$δ 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 – nootropics
* Pivagabine (N-pivaloyl-GABA) – antidepressant/anxiolytic drug; CRF inhibitor
* Vigabatrin (y-vinyl-GABA) – anticonvulsant; GABA-T inhibitor