Chemistry:GABA analogue

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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

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

  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. https://books.google.com/books?id=k_2fBwAAQBAJ&pg=PA415. 

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See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators

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