γ-Aminobutyric acid (GABA)
Short description: Class of drugs
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
- 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 GABAA receptor
- 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
- 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 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
Cyclized
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
- Glufimet (dimethyl 3-phenylglutamate hydrochloride) – experimental drug related to phenibut
- 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[1] – nootropics
- Pivagabine (N-pivaloyl-GABA) – antidepressant/anxiolytic drug; CRF inhibitor
- Vigabatrin (y-vinyl-GABA) – anticonvulsant; GABA-T inhibitor
See also
References
{{Navbox
| name = GABA receptor modulators
| title = GABA receptor modulators
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- Positive modulators (abridged; see here for a full list): α-EMTBL
- Alcohols (e.g., ethanol)
- Anabolic steroids
- Avermectins (e.g., ivermectin)
- Barbiturates (e.g., phenobarbital)
- Benzodiazepines (e.g., diazepam)
- Bromide compounds (e.g., potassium bromide)
- Carbamates (e.g., meprobamate)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- Dihydroergolines (e.g., ergoloid (dihydroergotoxine))
- Etazepine
- Etifoxine
- Fenamates (e.g., mefenamic acid)
- Flavonoids (e.g., apigenin, hispidulin)
- Fluoxetine
- Flupirtine
- Imidazoles (e.g., etomidate)
- Kava constituents (e.g., kavain)<!--PMID: 9776662-->
- Lanthanum
- Loreclezole
- Monastrol
- Neuroactive steroids (e.g., allopregnanolone, [[Chemistry:Cholecholesterol]], THDOC)
- Niacin
- Nicotinamide (niacinamide)
- Nonbenzodiazepines (e.g., β-carbolines (e.g., [[abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon))
- Norfluoxetine
- Petrichloral
- Phenols (e.g., propofol)
- Phenytoin
- Piperidinediones (e.g., glutethimide)
- Propanidid
- Pyrazolopyridines (e.g., etazolate)
- Quinazolinones (e.g., methaqualone)
- Retigabine (ezogabine)
- ROD-188
- Skullcap constituents (e.g., baicalin)
- Stiripentol
- Sulfonylalkanes (e.g., sulfonmethane (sulfonal))
- Topiramate
- Valerian constituents (e.g., valerenic acid)
- Volatiles/gases (e.g., chloral hydrate, chloroform, [[Chemistry:Diethyl diethyl ether, Parparaldehyde]], sevoflurane)
- Negative modulators: 1,3M1B
- 3M2B
- 11-Ketoprogesterone
- 17-Phenylandrostenol
- α5IA (LS-193,268)
- β-CCB
- β-CCE
- β-CCM
- β-CCP
- β-EMGBL
- Anabolic steroids
- Amiloride
- Anisatin
- β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
- Basmisanil
- Bemegride
- Bicyclic phosphates (TBPS, TBPO, IPTBO)
- BIDN
- Bilobalide
- Bupropion
- CHEB
- Chlorophenylsilatrane
- Cicutoxin
- Cloflubicyne
- Cyclothiazide
- DHEA
- DHEA-S
- Dieldrin
- (+)-DMBB
- DMCM
- DMPC
- EBOB
- Etbicyphat
- FG-7142 (ZK-31906)
- Fiproles (e.g., fipronil)
- Flavonoids (e.g., amentoflavone, oroxylin A)
- Flumazenil
- Fluoroquinolones (e.g., ciprofloxacin)
- Flurothyl
- Furosemide
- Golexanolone
- Iomazenil (123I)
- IPTBO
- Isopregnanolone (sepranolone)
- L-655,708
- Laudanosine
- Leptazol
- Lindane
- MaxiPost
- Morphine
- Morphine-3-glucuronide
- MRK-016
- Naloxone
- Naltrexone
- Nicardipine
- Nonsteroidal antiandrogens (e.g., [[apalutamide, [[Chemistry:Bicalutbicalutamide, Enzalutenzalutamide, Chemistry:Flutamide|flut]]amide]], nilutamide)
- Oenanthotoxin
- Pentylenetetrazol (pentetrazol)
- Phenylsilatrane
- Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
- Pregnenolone sulfate
- Propybicyphat
- PWZ-029
- Radequinil
- Ro 15-4513
- Ro 19-4603
- RO4882224
- RO4938581
- Sarmazenil
- SCS
- Suritozole
- TB-21007
- TBOB
- TBPS
- TCS-1105
- Terbequinil
- TETS
- Thujone
- U-93631
- Zinc
- ZK-93426
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| group2 = Metabotropic
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