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Theanine: Difference between revisions
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==Chemistry== | ==Chemistry== | ||
Theanine, or N-ethyl-L-glutamine is an amino acid analogue of L-glutamine. Its structure is comprised of a five carbon straight chain carboxylic acid called pentanoic acid, which is bonded to an amino group at R<sub>2</sub>, and an additional ketone group at R<sub>5</sub>. Also substituted at R<sub>5</sub> of the pentanoic group is an ethylamino chain connected at its amino constituent. Theanine is understood to refer to the levorotary enantiomer, which is well documented, rather than the relatively unresearched dextrorotary enantiomer. | |||
==Pharmacology== | ==Pharmacology== | ||
Theanine is structurally similar to the excitatory [[neurotransmitter]] [[glutamate]], and in accordance, binds to glutamate [[receptor]]s, though with much lower affinity in comparison. Specifically, it binds to ionotropic glutamate receptors including the [[AMPA]] and [[kainate]] receptors and, to a lesser extent, the [[NMDA]] receptor.<ref>The neuropharmacology of L-theanine(N-ethyl-L-glutamine): a possible neuroprotective and cognitive enhancing agent (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/17182482</ref><ref>Inhibition by theanine of binding of [3H]AMPA, [3H]kainate, and [3H]MDL 105,519 to glutamate receptors (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/12596867</ref><ref>Neuroprotective effects of theanine and its preventive effects on cognitive dysfunction (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/21477654</ref><ref>Neuroprotective effects of the green tea components theanine and catechins (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/12499631</ref> It acts as an [[antagonist]] of the former two sites<ref>Neuroprotective effects of the green tea components theanine and catechins (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/12499631</ref> and as an [[agonist]] of the latter site.<ref>Behavioral and molecular evidence for psychotropic effects in L-theanine (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/21861094</ref> In addition, it inhibits glutamine transporters and glutamate transporters, and thus acts as [[reuptake inhibitor]] of glutamine and glutamate.<ref>Neuroprotective effects of the green tea components theanine and catechins (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/12499631</ref><ref>Inhibition of glutamate transporter by theanine enhances the therapeutic efficacy of doxorubicin (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/11325559</ref><ref>Theanine and glutamate transporter inhibitors enhance the antitumor efficacy of chemotherapeutic agents (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/14643924</ref> | Theanine is structurally similar to the excitatory [[neurotransmitter]] [[glutamate]], and in accordance, binds to glutamate [[receptor]]s, though with much lower affinity in comparison. Specifically, it binds to ionotropic glutamate receptors including the [[AMPA]] and [[kainate]] receptors and, to a lesser extent, the [[NMDA]] receptor.<ref>The neuropharmacology of L-theanine(N-ethyl-L-glutamine): a possible neuroprotective and cognitive enhancing agent (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/17182482</ref><ref>Inhibition by theanine of binding of [3H]AMPA, [3H]kainate, and [3H]MDL 105,519 to glutamate receptors (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/12596867</ref><ref>Neuroprotective effects of theanine and its preventive effects on cognitive dysfunction (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/21477654</ref><ref>Neuroprotective effects of the green tea components theanine and catechins (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/12499631</ref> It acts as an [[antagonist]] of the former two sites<ref>Neuroprotective effects of the green tea components theanine and catechins (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/12499631</ref> and as an [[agonist]] of the latter site.<ref>Behavioral and molecular evidence for psychotropic effects in L-theanine (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/21861094</ref> In addition, it inhibits glutamine transporters and glutamate transporters, and thus acts as [[reuptake inhibitor]] of glutamine and glutamate.<ref>Neuroprotective effects of the green tea components theanine and catechins (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/12499631</ref><ref>Inhibition of glutamate transporter by theanine enhances the therapeutic efficacy of doxorubicin (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/11325559</ref><ref>Theanine and glutamate transporter inhibitors enhance the antitumor efficacy of chemotherapeutic agents (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/14643924</ref> | ||