Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C7H14N2O3 |
Molecular Weight | 174.1977 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCNC(=O)CC[C@H](N)C(O)=O
InChI
InChIKey=DATAGRPVKZEWHA-YFKPBYRVSA-N
InChI=1S/C7H14N2O3/c1-2-9-6(10)4-3-5(8)7(11)12/h5H,2-4,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1
Molecular Formula | C7H14N2O3 |
Molecular Weight | 174.1977 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
L-Theanine is a relaxing and nondietary amino acid found pretty much exclusively in teas from Camellia sinensis (alongside green tea catechins and caffeine) and is known to promote relaxation without sedation. It appears to be effective at this as well as reducing stress at standard dosages. L-theanine was discovered as a constituent of green tea in 1949 and was approved in Japan in 1964 for unlimited use in all foods, including chocolates, soft drinks, and herb teas, except infant foods. It also provides a unique umami (brothy or savory) taste and flavor to green tea infusion. L-theanine may help relieve stress by inducing a relaxing effect without drowsiness and may also possess immunologic attributes. Theanine may also have effects on the cardiovascular system and play a preventative role in cancer; however, limited clinical information is available to support these claims. L-Theanine and its positive effects on cognitive performance is one of its most important
functions. Because of chemical structure of L-Theanine similar to glutamate it can act as a neurotransmitter
related to memory. In a study made on rats, it was found out that L-Theanine
modulated the serotonin and dopamine levels and increased learning skills with memory. In addition, it is stated that L-Theanine increases neuro - throphine mRNA level by
activating its neuro - transmitter inhibiting system and supports the central nervous system that
helps the development of brain functions. L-Theanine had a positive effect on memory
and had positive effects on the treatment and prevention of Alzheimer. Theanine is an antagonist of the NMDA receptors (albeit with fairly weak efficacy) and can inhibit synaptic release of glutamate via blocking the transporter competitively. Theanine may also reduce glutamate levels, but this is also a fairly weak mechanism requiring a high concentration of theanine.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26192072 | https://examine.com/supplements/theanine/
Curator's Comment: Orally administered L-Theanine supplementation is able to cross the blood brain barier.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24762604 |
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Target ID: CHEMBL2096670 |
24.6 µM [IC50] | ||
Target ID: CHEMBL2109241 |
41.5 µM [IC50] | ||
Target ID: CHEMBL2094124 |
347.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | ZEN THEANINE Approved UseZEN THEANINE is used to provide fast-acting mental relaxation, with its stress reducing effects typically felt within 30 minutes of consumption. |
PubMed
Title | Date | PubMed |
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Theanine production by coupled fermentation with energy transfer employing Pseudomonas taetrolens Y-30 glutamine synthetase and baker's yeast cells. | 2005 Apr |
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Inhibitory activity of a green tea extract and some of its constituents on multidrug resistance-associated protein 2 functionality. | 2005 Feb |
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Toxicity of green tea extracts and their constituents in rat hepatocytes in primary culture. | 2005 Feb |
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Medicinal benefits of green tea: Part I. Review of noncancer health benefits. | 2005 Jun |
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L-theanine . Monograph. | 2005 Jun |
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Pharmacokinetics of theanine enantiomers in rats. | 2005 Mar |
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A novel assay method for theanine synthetase activity by capillary electrophoresis. | 2005 May 5 |
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Effects of theanine on alcohol metabolism and hepatic toxicity. | 2005 Sep |
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Cloning and expression of Pseudomonas taetrolens Y-30 gene encoding glutamine synthetase: an enzyme available for theanine production by coupled fermentation with energy transfer. | 2006 Feb |
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Efficacy of theanine is connected with theanine metabolism by any enzyme, not only drug metabolizing enzymes. | 2006 Feb |
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Pharmacology and therapeutic uses of theanine. | 2006 Jan 1 |
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Inhibitory effect of green coffee bean extract on fat accumulation and body weight gain in mice. | 2006 Mar 17 |
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Multivariate analysis for 1H-NMR spectra of two hundred kinds of tea in the world. | 2006 Oct |
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Expression optimization and biochemical characterization of a recombinant gamma-glutamyltranspeptidase from Escherichia coli novablue. | 2006 Sep |
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Enhancement of antigen-specific immunoglobulin G production in mice by co-administration of L-cystine and L-theanine. | 2007 Dec |
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Spontaneous renal tubular hyperplastic and neoplastic lesions in three Sprague-Dawley rats from a 90-day toxicity study. | 2007 Feb |
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Characterization of theanine-forming enzyme from Methylovorus mays no. 9 in respect to utilization of theanine production. | 2007 Feb |
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Effect of valerian extract preparation (BIM) on the sleep-wake cycle in rats. | 2007 Feb |
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Structure-activity relationships of tea compounds against human cancer cells. | 2007 Jan 24 |
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The deployment of intersensory selective attention: a high-density electrical mapping study of the effects of theanine. | 2007 Jan-Feb |
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Differentiation of green, white, black, Oolong, and Pu-erh teas according to their free amino acids content. | 2007 Jul 25 |
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Source density analysis of the human EEG after ingestion of a drink containing decaffeinated extract of green tea enriched with L-theanine and theogallin. | 2007 Jun-Aug |
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[Determination of amino acids in tea samples by capillary electrophoresis with partition cell and indirect ultraviolet detection]. | 2007 Mar |
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[Effects of theanine and houpu extract in 7-day chick social separation-stress procedure]. | 2007 Oct |
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Involvement of GABA(A) receptors in the neuroprotective effect of theanine on focal cerebral ischemia in mice. | 2007 Oct |
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Theogallin and L-theanine as active ingredients in decaffeinated green tea extract: II. Characterization in the freely moving rat by means of quantitative field potential analysis. | 2007 Oct |
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[Separation and quantification of theanine enantiomers using high performance liquid chromatography coupled with chiral derivatization]. | 2007 Sep |
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Determination of amino acids in tea leaves and beverages using capillary electrophoresis with light-emitting diode-induced fluorescence detection. | 2007 Sep 15 |
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The combined effects of L-theanine and caffeine on cognitive performance and mood. | 2008 Aug |
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Immobilization of Escherichia coli novablue gamma-glutamyltranspeptidase in Ca-alginate-kappa-carrageenan beads. | 2008 Aug |
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Co-administration of l-cystine and l-theanine enhances efficacy of influenza vaccination in elderly persons: nutritional status-dependent immunogenicity. | 2008 Dec |
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Aqueous fish extract increases survival in the mouse model of cytostatic toxicity. | 2008 Dec 4 |
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L-theanine intervention enhances human gammadeltaT lymphocyte function. | 2008 Feb |
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Psychological effects of dietary components of tea: caffeine and L-theanine. | 2008 Feb |
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Cloning and expression of Methylovorus mays No. 9 gene encoding gamma-glutamylmethylamide synthetase: an enzyme usable in theanine formation by coupling with the alcoholic fermentation system of baker's yeast. | 2008 Jan |
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Time for tea: mood, blood pressure and cognitive performance effects of caffeine and theanine administered alone and together. | 2008 Jan |
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Administration of theanine, a unique amino acid in tea leaves, changed feeding-relating components in serum and feeding behavior in rats. | 2008 May |
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Effect of green tea and (-)-epigallocatechin gallate on ethanol-induced toxicity in HepG2 cells. | 2008 May |
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[Determination of hydroxyproline in collagenous proteins by high performance liquid chromatography-mass spectrometry]. | 2008 Sep |
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Effects of theanine on growth of human lung cancer and leukemia cells as well as migration and invasion of human lung cancer cells. | 2009 Apr |
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Rat electropharmacograms of the flavonoids rutin and quercetin in comparison to those of moclobemide and clinically used reference drugs suggest antidepressive and/or neuroprotective action. | 2009 Apr |
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Effects of oral supplementation with cystine and theanine on the immune function of athletes in endurance exercise: randomized, double-blind, placebo-controlled trial. | 2009 Apr 23 |
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Treatment with green tea extract attenuates secondary inflammatory response in an experimental model of spinal cord trauma. | 2009 Aug |
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Bioactive components of tea: cancer, inflammation and behavior. | 2009 Aug |
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l-Theanine, an amino acid in green tea, attenuates beta-amyloid-induced cognitive dysfunction and neurotoxicity: reduction in oxidative damage and inactivation of ERK/p38 kinase and NF-kappaB pathways. | 2009 Dec 1 |
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Tea and health: preventive and therapeutic usefulness in the elderly? | 2009 Jan |
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Impact of two types of Internet-based information on medical students' performance in an Objective Structured Clinical Exam (OSCE). | 2009 Jul |
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Changes in the composition of raw tea leaves from the Korean Yabukida plant during high-temperature processing to pan-fried Kamairi-cha green tea. | 2009 Jun |
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Ethylamine content and theanine biosynthesis in different organs of Camellia sinensis seedlings. | 2009 May-Jun |
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The effect of taurine, a novel biochemical modulator, on the antitumor activity of doxorubicin. | 2009 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/npc/l-theanine.html
Studies reporting an anti-anxiety effect used single doses of theanine 200 to 250 mg.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24762604
Theanine promoted DC secretion of IL-12. IL-12 levels reached (137.4 ± 4.9) pg/ml with theanine at 200 umol/L. However, theanine inhibited the secretion of IL-10 in a dose-dependent manner. IL-10 levels were only (58.4 ± 6.9) pg/ml with theanine at 200 umol/L.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:12:44 GMT 2023
by
admin
on
Fri Dec 15 16:12:44 GMT 2023
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Record UNII |
8021PR16QO
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Record Status |
Validated (UNII)
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Record Version |
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607 (Number of products:983)
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