A GABA analogue is a compound which is an analogue or

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

of the neurotransmitter

gamma-Aminobutyric acid GABA (gamma-aminobutyric acid, γ-aminobutyric acid) is the chief inhibitory neurotransmitter in the developmentally mature mammalian central nervous system. Its principal role is reducing neuronal excitability throughout the nervous system. GA ...

(GABA) (the

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

of which is 4-aminobutanoic acid). Many GABA analogues are used as

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

s, especially as

anticonvulsant Anticonvulsants (also known as antiepileptic drugs, antiseizure drugs, or anti-seizure medications (ASM)) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also used in the treatme ...

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or Psychomotor agitation, excitement. They are central nervous system (CNS) Depressant, depressants and interact with brain activity, causing its decelera ...

s, and

anxiolytic An anxiolytic (; also antipanic or anti-anxiety agent) is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxie ...

List of GABA analogues

Deaminated

Butyric acid Butyric acid (; from , meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula . It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid (2-met ...

(butanoic acid) –

histone deacetylase inhibitor Histone deacetylase inhibitors (HDAC inhibitors, HDACi, HDIs) are chemical compounds that enzyme inhibitor, inhibit histone deacetylases. Since acetylation of histones, deacetylation of histones produces transcriptionally silenced heterochromatin ...

and

full agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the agoni ...

of free fatty acid receptor 2, free fatty acid receptor 3, and niacin receptor 1 ** Derivatives:

butyrate The conjugate acids are in :Carboxylic acids. {{Commons category, Carboxylate ions, Carboxylate anions Carbon compounds Anions ...

(butanoate), sodium butyrate,

methyl butyrate Methyl butyrate, also known under the systematic name methyl butanoate, is the methyl ester of butyric acid. Like most esters, it has a fruity odor, in this case resembling apples or pineapples. At room temperature, it is a colorless liquid with ...

, ethyl butyrate, butyl butyrate, pentyl butyrate *

Valeric acid Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula . Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant '' Valeriana offici ...

(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 Russia, or the Russian Federation, is a country spanning Eastern Europe and North Asia. It is the list of countries and dependencies by area, largest country in the world, and extends across Time in Russia, eleven time zones, sharing Borders ...

* 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 A mood stabilizer is a psychiatric medication used to treat mood disorders characterized by intense and sustained mood shifts, such as bipolar disorder and the bipolar type of schizoaffective disorder. Uses Mood stabilizers are best known for t ...

;

inhibitor Inhibitor or inhibition may refer to: Biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotransmi ...

of HDAC, SSADH, and GABA-T, blocker of VDSCs and GABA reuptake, AR/ PR

antagonist An antagonist is a character in a story who is presented as the main enemy or rival of the protagonist and is often depicted as a villain.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 A hypnotic (from Ancient Greek, Greek ''Hypnos'', sleep), also known as a somnifacient or soporific, and commonly known as sleeping pills, are a class of psychoactive drugs whose primary function is to sleep induction, induce sleep and to trea ...

and

drug * GHB (γ-hydroxybutyric acid) –

neurotransmitter A neurotransmitter is a signaling molecule secreted by a neuron to affect another cell across a Chemical synapse, synapse. The cell receiving the signal, or target cell, may be another neuron, but could also be a gland or muscle cell. Neurotra ...

, drug of abuse; agonist of GHB receptor and GABA_B receptor ** Derivatives:

sodium oxybate Sodium is a chemical element; it has symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable isotope ...

(sodium γ-hydroxybutanoate) – used to treat

narcolepsy Narcolepsy is a chronic neurological disorder that impairs the ability to regulate sleep–wake cycles, and specifically impacts REM (rapid eye movement) sleep. The symptoms of narcolepsy include excessive daytime sleepiness (EDS), sleep-r ...

; same

mechanism of action In pharmacology, the term mechanism of action (MOA) refers to the specific biochemical Drug interaction, interaction through which a Medication, drug substance produces its pharmacological effect. A mechanism of action usually includes mention o ...

as GHB * Aceburic acid (γ-hydroxybutyric acid acetate) – synthetic

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

to GHB * GBL (γ-hydroxybutyric acid lactone) –

metabolic intermediate Metabolic intermediates are compounds produced during the conversion of substrates (starting molecules) into final products in biochemical reactions within cells. Although these intermediates are of relatively minor direct importance to cell ...

and prodrug to GHB * GHBAL (γ-hydroxybutyraldehyde or γ-hydroxybutanal) – metabolic intermediate and prodrug to GHB * GHV (γ-hydroxyvaleric acid) –

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...

; 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 A GABA receptor agonist is a drug that is an agonist for one or more of the GABA receptors, producing typically sedative effects, and may also cause other effects such as anxiolytic, anticonvulsant, and muscle relaxant effects. There are three r ...

Pregabalin Pregabalin, sold under the brand name Lyrica among others, is an anticonvulsant, analgesic, and anxiolytic amino acid medication used to treat epilepsy, neuropathic pain, fibromyalgia, restless legs syndrome, opioid withdrawal, generalized anx ...

(β-isobutyl-GABA) –

analgesic An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...

, and

; potent inhibitor of α₂δ subunit-containing VGCCs. *

Phenibut Phenibut, sold under the brand name Anvifen among others, is a central nervous system (CNS) depressant with anxiolytic effects, and is used to treat anxiety, insomnia, and for a variety of other indications. It is usually taken oral administrat ...

(β-phenyl-GABA) – sedative and anxiolytic from Russia; GABA_B receptor agonist, and to a lesser extent inhibitor of α₂δ subunit-containing VGCCs. * Baclofen (β-(4-chlorophenyl)-GABA) –

antispasmodic An antispasmodic (synonym: spasmolytic) is a pharmaceutical drug or other agent that suppresses muscle spasms. Smooth muscle spasm One type of antispasmodics is used for smooth muscle relaxation, especially in tubular organs of the gastrointestina ...

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 Arecaidine is a bio-active alkaloid in areca nuts. It is a competitive GABA reuptake inhibitor. Lime is said to hydrolyse arecoline to arecaidine References

{{GABA metabolism and transport modulators Piperidine alkaloids Beta-Amino acid ...

– constituent of areca nuts; GABA reuptake inhibitor * Gabaculine –

neurotoxin Neurotoxins are toxins that are destructive to nervous tissue, nerve tissue (causing neurotoxicity). Neurotoxins are an extensive class of exogenous chemical neurological insult (medical), insultsSpencer 2000 that can adversely affect function ...

; GABA-T inhibitor and GABA reuptake inhibitor *

Gabapentin Gabapentin, sold under the brand name Neurontin among others, is an anticonvulsant medication primarily used to treat neuropathic pain and also for partial seizures of epilepsy. It is a commonly used medication for the treatment of neuropath ...

– anticonvulsant; inhibitor of α₂δ subunit-containing VGCCs **

Gabapentin enacarbil Gabapentin enacarbil (Horizant () (), Regnite (in Japan)) is an anticonvulsant and analgesic drug of the gabapentinoid class, and a prodrug to gabapentin. It was designed for increased oral bioavailability over gabapentin, and human trials showed ...

– used for the treatment of

restless legs syndrome Restless legs syndrome (RLS), also known as Willis–Ekbom disease (WED), is a neurological disorder, usually chronic, that causes an overwhelming urge to move one's legs. There is often an unpleasant feeling in the legs that improves temporaril ...

and

postherpetic neuralgia Postherpetic neuralgia (PHN) is neuropathic pain that occurs due to damage to a peripheral nerve caused by the reactivation of the varicella zoster virus ( herpes zoster, also known as shingles). PHN is defined as pain in a dermatomal distributi ...

; 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 In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

* Muscimol – constituent of ''

Amanita muscaria ''Amanita muscaria'', commonly known as the fly agaric or fly amanita, is a basidiomycete fungus of the genus ''Amanita''. It is a large white-lamella (mycology), gilled, white-spotted mushroom typically featuring a bright red cap covered with ...

'' mushrooms; GABA_A receptor agonist * Nipecotic acid – used in

scientific research The scientific method is an empirical method for acquiring knowledge that has been referred to while doing science since at least the 17th century. Historically, it was developed through the centuries from the ancient and medieval world. The ...

; GABA reuptake inhibitor

GABA prodrugs

* L-Glutamine – endogenous precursor of GABA and

glutamate Glutamic acid (symbol Glu or E; known as glutamate in its anionic form) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a Essential amino acid, non-essential nutrient for humans, meaning that ...

* 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 Nonribosomal peptides (NRP) are a class of peptide secondary metabolites, usually produced by microorganisms like bacterium, bacteria and fungi. Nonribosomal peptides are also found in higher organisms, such as nudibranchs, but are thought to be ma ...

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 Glutamic acid (symbol Glu or E; known as glutamate in its anionic form) is an α- amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a non-essential nutrient for humans, meaning that the human body can ...

(glutamate) – neurotransmitter * Homotaurine (tramiprosate) – GABA_A receptor agonist, GABA_B receptor antagonist *

Hopantenic acid Hopantenic acid (homopantothenic acid), also known as N-pantoyl-GABA, is a central nervous system depressant. Formulated as the calcium salt (chemistry), salt, it is used as a pharmaceutical drug in the Russian Federation for a variety of neurolo ...

(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 Piracetam is a drug that has efficacy in cognitive disorders, vertigo, cortical myoclonus, dyslexia, and sickle cell anemia; sources differ on its usefulness for dementia. Piracetam is sold as a medication in many European countries. Piracetam ...

and other racetams – nootropics * Pivagabine (N-pivaloyl-GABA) –

antidepressant Antidepressants are a class of medications used to treat major depressive disorder, anxiety disorders, chronic pain, and addiction. Common side effects of antidepressants include Xerostomia, dry mouth, weight gain, dizziness, headaches, akathi ...

/anxiolytic drug; CRF inhibitor * Vigabatrin (y-vinyl-GABA) – anticonvulsant; GABA-T inhibitor

References

{{Channel blockers GABA receptor agonists