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11-SEPTEMBER-2008 13:54:10 - aminobutyric acid Gamma-aminobutyric acid IUPAC name 4-aminobutanoic acid Identifiers CAS number 56-12-2 PubChem 119 MeSH gamma-Aminobutyric+Acid SMILES CCC=OOCN ChemSpider ID 116 Properties Molecular formula C4H9NO2 Molar mass 103.12 g/mol Melting point 203°C Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Gamma-aminobutyric acid GABA is the chief inhibitory neurotransmitter in the mammalian central nervous system. It plays an important role in regulating neuronal excitability throughout the nervous system. GABA is also directly responsible for the regulation of muscle tone. GABA behaves primarily as an excitatory neurotransmitter in insect species. Although some GABA can be found in pancreatic islet cells and kidney, there are no significant amounts of GABA in mammalian tissues other than the tissues of the nervous system.citation needed In spastic cerebral palsy in humans, GABA cannot be absorbed properly by the damaged nerve rootlets corresponding to affected muscles, which leads to hypertonia in those muscles. Disrupted GABAergic signaling has been implicated in numerous and varied neurological and psychiatric pathologies including movement and anxiety disorders, epilepsy, schizophrenia, and addiction. Contents 1 Function 2 Structure and conformation 3 History 4 Synthesis 5 Pharmacology 6 See also 7 References 8 External links Function In vertebrates, GABA acts at inhibitory synapses in the brain by binding to specific transmembrane receptors in the plasma membrane of both pre- and postsynaptic neuronal processes. This binding causes the opening of ion channels to allow the flow of either negatively-charged chloride ions into the cell or positively-charged potassium ions out of the cell. This action results in a negative change in the transmembrane potential, usually causing hyperpolarization. Three general classes of GABA receptor are known: GABAA and GABAC ionotropic receptors, which are ion channels themselves, and GABAB metabotropic receptors, which are G protein-coupled receptors that open ion channels via intermediaries G proteins. Neurons that produce GABA as their output are called GABAergic neurons, and have chiefly inhibitory action at receptors in the adult vertebrate. Medium Spiny Cells are a typical example of inhibitory CNS GABAergic cells. In hippocampus and neocortex of the mammalian brain, GABA has primarily excitatory effects early in development, and is in fact the major excitatory neurotransmitter in many regions of the brain prior to the maturation of glutamate synapses - See developing cortex. GABA exhibits excitatory actions in insects, mediating muscle activation at synapses between nerves and muscle cells, and also the stimulation of certain glands. Whether GABA is excitatory or inhibitory depends on the direction into or out of the cell and magnitude of the ionic currents controlled by the GABAA receptor. When net positive ionic current is directed into the cell, GABA is excitatory, when the net positive current is directed out of the cell, GABA is inhibitory. A developmental switch in the molecular machinery controlling the polarity of this current is responsible for the changes in the functional role of GABA between the neonatal and adult stages. That is to say, GABA's role changes from excitatory to inhibitory as the brain develops into adulthood. Structure and conformation GABA is found mostly as a zwitterion, that is, with the carboxyl group deprotonated and the amino group protonated. Its conformation depends on its environment. In the gas phase, a highly folded conformation is strongly favored due to the electrostatic attraction between the two functional groups. The stabilization is about 50 kcal/mol, according to quantum chemistry calculations. In the solid state, a more extended conformation is found, with a trans conformation at the amino end and a gauche conformation at the carboxyl end. This is due to the packing interactions with the neighboring molecules. In solution, five different conformations, some folded and some extended are found as a result of solvation effects. The conformational flexibility of GABA is important for its biological function, as it has been found to bind to different receptors with different conformations. Many GABA analogues with pharmaceutical applications have more rigid structures in order to control the binding better.12 History Gamma-aminobutyric acid was first synthesized in 1883, and was first known only as a plant and microbe metabolic product. In 1950, however, GABA was discovered to be an integral part of the mammalian central nervous system.3 Synthesis Organisms synthesize GABA from glutamate using the enzyme L-glutamic acid decarboxylase and pyridoxal phosphate as a cofactor. It is worth noting that this process converts the principal excitatory neurotransmitter glutamate into the principal inhibitory one GABA. Pharmacology Drugs that act as agonists of GABA receptors known as GABA analogues or GABAergic drugs or increase the available amount of GABA typically have relaxing, anti-anxiety and anti-convulsive effects. Many of the substances below are known to cause anterograde amnesia and retrograde amnesia. GABA has been purported to increase the amount of the Human Growth Hormone. The results of those studies have been seldom replicated, and have recently been in question since it is unknown whether GABA can pass the blood-brain barrier. Drugs that affect GABA receptors: alcohol ethanol456 avermectins-doramectin, selamectin, ivermectin barbiturates bicucullines - GABA antagonist benzodiazepines7 baclofen baicalin and baicalein from skullcap scutellaria lateriflora carbamazepines8 cyclopyrrolone derivatives such as zopiclone7 fluoroquinolones gabazine SR-95531 gamma-Hydroxybutyric acid GHB9 gamma-amino-beta-hydroxybutyric acid imidazopyridine derivatives such as zolpidem kavalactones10 meprobamate muscimol manganese modafinil phenytoin picamilon picrotoxin progabide propofol phenibut pyrazolopyrimidine derivatives such as zaleplon thujone-GABA antagonist Valerian extract Drugs that affect GABA in other ways: tiagabine-potentiates by inhibiting uptake into neurons and glia vigabatrin-potentiates by inhibiting GABA-T, preventing GABA breakdown valproate-potentiates by inhibiting GABA-T tetanospasmin-primary toxin of tetanus bacteria, blocks release of GABA hyperforin-inhibits the reuptake of GABA See also Spastic diplegia, a GABA deficiency neuromuscular neuropathology References ^ Devashis Majumdar and Sephali Guha. Conformation, electrostatic potential and pharmacophoric pattern of GABA gamma-aminobutyric acid and several GABA inhibitors. Journal of Molecular Structure: THEOCHEM 1988, 180, 125-140. doi:10.1016/0166-12808880084-8 ^ Anne-Marie Sapse. Molecular Orbital Calculations for Amino Acids and Peptides. Birkhäuser, 2000. ISBN 0817638938. ^ Roth, Robert J.; Cooper, Jack R.; Bloom, Floyd E. 2003. The Biochemical Basis of Neuropharmacology. Oxford Oxfordshire: Oxford University Press, 416 pages. ISBN 0-19-514008-7. ^ Dzitoyeva S, Dimitrijevic N, Manev H 2003. Gamma-aminobutyric acid B receptor 1 mediates behavior-impairing actions of alcohol in Drosophila: adult RNA interference and pharmacological evidence. Proc. Natl. Acad. Sci. U.S.A. 100 9: 5485-90. doi:10.1073/pnas.0830111100. PMID 12692303. ^ Mihic SJ, Ye Q, Wick MJ, Koltchine VV, Krasowski MD, Finn SE, Mascia MP, Valenzuela CF, Hanson KK, Greenblatt EP, Harris RA, Harrison NL 1997. Sites of alcohol and volatile anaesthetic action on GABAA and glycine receptors. Nature 389 6649: 385-9. doi:10.1038/38738. PMID 9311780. ^ Boehm SL, Ponomarev I, Blednov YA, Harris RA 2006. From gene to behavior and back again: new perspectives on GABAA receptor subunit selectivity of alcohol actions. Adv. Pharmacol. 54: 171-203. doi:10.1016/j.bcp.2004.07.023. PMID 17175815. ^ a b Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996. ^ Granger P, Biton B, Faure C, Vige X, Depoortere H, Graham D, Langer SZ, Scatton B, Avenet P 1995. Modulation of the gamma-aminobutyric acid type A receptor by the antiepileptic drugs carbamazepine and phenytoin. Mol. Pharmacol. 47 6: 1189-96. PMID 7603459. ^ Dimitrijevic N, Dzitoyeva S, Satta R, Imbesi M, Yildiz S, Manev H 2005. Drosophila GABAB receptors are involved in behavioral effects of gamma-hydroxybutyric acid GHB. Eur. J. Pharmacol. 519 3: 246-52. doi:10.1016/j.ejphar.2005.07.016. PMID 16129424. ^ Hunter, A 2006. Kava Piper methysticum back in circulation. Australian Centre for Complementary Medicine 25 7: 529. External links Lydiard B, Pollack MH, Ketter TA, Kisch E, Hettema JM 2001-10-26. GABA. Continuing Medical Education. School of Medicine, Virginia Commonwealth University, Medical College of Virginia Campus VCU, Richmond, VA. Retrieved on 2008-06-20. The role of GABA in the pathogenesis and treatment of anxiety and other neuropsychiatric disorders Retrieved from http://en..org/wiki/Gamma-aminobutyric_acid Categories: Anticonvulsants | Neurotransmitters | Amino acidsHidden categories: All articles with statements | Articles with statements since June 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Dansk Deutsch Español Français Italiano עברית Magyar Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Polski Português РуÑ?Ñ?кий SlovenÄ?ina SlovenÅ¡Ä?ina Suomi Svenska Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 4 September 2008, at 20:01
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