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
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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Inhibitory effects of theanine and sera from theanine-fed rats on receptor-mediated cancer cell invasion beneath mesothelial-cell monolayers. | 2001 Jul |
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Rapid analysis of amino acids in Japanese green tea by microchip electrophoresis using plastic microchip and fluorescence detection. | 2003 Sep 26 |
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Theanine, a specific glutamate derivative in green tea, reduces the adverse reactions of doxorubicin by changing the glutathione level. | 2004 Aug 30 |
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Simultaneous analysis of theanine, chlorogenic acid, purine alkaloids and catechins in tea samples with the help of multi-dimension information of on-line high performance liquid chromatography/electrospray-mass spectrometry. | 2004 Feb 18 |
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Anti-obesity effects of three major components of green tea, catechins, caffeine and theanine, in mice. | 2004 Jan-Feb |
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Purification and characterization of glutamine synthetase of Pseudomonas taetrolens Y-30: an enzyme usable for production of theanine by coupling with the alcoholic fermentation system of baker's yeast. | 2004 Sep |
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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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The neuropharmacology of L-theanine(N-ethyl-L-glutamine): a possible neuroprotective and cognitive enhancing agent. | 2006 |
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Molecular and sensory studies on the umami taste of Japanese green tea. | 2006 Apr 5 |
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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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A 13-week dietary toxicity and toxicokinetic study with l-theanine in rats. | 2006 Jul |
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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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Green tea increases anti-inflammatory tristetraprolin and decreases pro-inflammatory tumor necrosis factor mRNA levels in rats. | 2007 Jan 5 |
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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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[Determination of amino acids in tea samples by capillary electrophoresis with partition cell and indirect ultraviolet detection]. | 2007 Mar |
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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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Theanine, r-glutamylethylamide, increases neurotransmission concentrations and neurotrophin mRNA levels in the brain during lactation. | 2007 Sep 29 |
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L-theanine, a natural constituent in tea, and its effect on mental state. | 2008 |
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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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Theanine prevents memory impairment induced by repeated cerebral ischemia in rats. | 2008 Jan |
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Protective effect of the green tea component, L-theanine on environmental toxins-induced neuronal cell death. | 2008 Jul |
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Theanine, an ingredient of green tea, inhibits [3H]glutamine transport in neurons and astroglia in rat brain. | 2008 Jun |
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Theanine production by coupled fermentation with energy transfer using gamma-glutamylmethylamide synthetase of Methylovorus mays No. 9. | 2008 May |
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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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Effects of theanine, a unique amino acid in tea leaves, on memory in a rat behavioral test. | 2008 May |
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L-theanine elicits an umami taste with inosine 5'-monophosphate. | 2008 Nov |
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[Determination of hydroxyproline in collagenous proteins by high performance liquid chromatography-mass spectrometry]. | 2008 Sep |
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Determination of theanine, GABA, and other amino acids in green, oolong, black, and Pu-erh teas with dabsylation and high-performance liquid chromatography. | 2008 Sep 10 |
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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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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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The effects of L-theanine on alpha-band oscillatory brain activity during a visuo-spatial attention task. | 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.
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DSLD |
607 (Number of products:983)
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ACTIVE MOIETY