U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of THEANINE

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

HIDE SMILES / InChI
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

Curator's Comment: Orally administered L-Theanine supplementation is able to cross the blood brain barier.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
ZEN THEANINE

Approved Use

ZEN THEANINE is used to provide fast-acting mental relaxation, with its stress reducing effects typically felt within 30 minutes of consumption.
PubMed

PubMed

TitleDatePubMed
Inhibitory effects of theanine and sera from theanine-fed rats on receptor-mediated cancer cell invasion beneath mesothelial-cell monolayers.
2001 Jul
Rapid analysis of amino acids in Japanese green tea by microchip electrophoresis using plastic microchip and fluorescence detection.
2003 Sep 26
Theanine, a specific glutamate derivative in green tea, reduces the adverse reactions of doxorubicin by changing the glutathione level.
2004 Aug 30
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
Anti-obesity effects of three major components of green tea, catechins, caffeine and theanine, in mice.
2004 Jan-Feb
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
Toxicity of green tea extracts and their constituents in rat hepatocytes in primary culture.
2005 Feb
Medicinal benefits of green tea: Part I. Review of noncancer health benefits.
2005 Jun
L-theanine . Monograph.
2005 Jun
Pharmacokinetics of theanine enantiomers in rats.
2005 Mar
The neuropharmacology of L-theanine(N-ethyl-L-glutamine): a possible neuroprotective and cognitive enhancing agent.
2006
Molecular and sensory studies on the umami taste of Japanese green tea.
2006 Apr 5
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
A 13-week dietary toxicity and toxicokinetic study with l-theanine in rats.
2006 Jul
Inhibitory effect of green coffee bean extract on fat accumulation and body weight gain in mice.
2006 Mar 17
Multivariate analysis for 1H-NMR spectra of two hundred kinds of tea in the world.
2006 Oct
Expression optimization and biochemical characterization of a recombinant gamma-glutamyltranspeptidase from Escherichia coli novablue.
2006 Sep
Enhancement of antigen-specific immunoglobulin G production in mice by co-administration of L-cystine and L-theanine.
2007 Dec
Spontaneous renal tubular hyperplastic and neoplastic lesions in three Sprague-Dawley rats from a 90-day toxicity study.
2007 Feb
Characterization of theanine-forming enzyme from Methylovorus mays no. 9 in respect to utilization of theanine production.
2007 Feb
Green tea increases anti-inflammatory tristetraprolin and decreases pro-inflammatory tumor necrosis factor mRNA levels in rats.
2007 Jan 5
Differentiation of green, white, black, Oolong, and Pu-erh teas according to their free amino acids content.
2007 Jul 25
[Determination of amino acids in tea samples by capillary electrophoresis with partition cell and indirect ultraviolet detection].
2007 Mar
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
[Separation and quantification of theanine enantiomers using high performance liquid chromatography coupled with chiral derivatization].
2007 Sep
Determination of amino acids in tea leaves and beverages using capillary electrophoresis with light-emitting diode-induced fluorescence detection.
2007 Sep 15
Theanine, r-glutamylethylamide, increases neurotransmission concentrations and neurotrophin mRNA levels in the brain during lactation.
2007 Sep 29
L-theanine, a natural constituent in tea, and its effect on mental state.
2008
Immobilization of Escherichia coli novablue gamma-glutamyltranspeptidase in Ca-alginate-kappa-carrageenan beads.
2008 Aug
Co-administration of l-cystine and l-theanine enhances efficacy of influenza vaccination in elderly persons: nutritional status-dependent immunogenicity.
2008 Dec
Theanine prevents memory impairment induced by repeated cerebral ischemia in rats.
2008 Jan
Protective effect of the green tea component, L-theanine on environmental toxins-induced neuronal cell death.
2008 Jul
Theanine, an ingredient of green tea, inhibits [3H]glutamine transport in neurons and astroglia in rat brain.
2008 Jun
Theanine production by coupled fermentation with energy transfer using gamma-glutamylmethylamide synthetase of Methylovorus mays No. 9.
2008 May
Administration of theanine, a unique amino acid in tea leaves, changed feeding-relating components in serum and feeding behavior in rats.
2008 May
Effects of theanine, a unique amino acid in tea leaves, on memory in a rat behavioral test.
2008 May
L-theanine elicits an umami taste with inosine 5'-monophosphate.
2008 Nov
[Determination of hydroxyproline in collagenous proteins by high performance liquid chromatography-mass spectrometry].
2008 Sep
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
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
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
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
Treatment with green tea extract attenuates secondary inflammatory response in an experimental model of spinal cord trauma.
2009 Aug
Bioactive components of tea: cancer, inflammation and behavior.
2009 Aug
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
Impact of two types of Internet-based information on medical students' performance in an Objective Structured Clinical Exam (OSCE).
2009 Jul
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
The effects of L-theanine on alpha-band oscillatory brain activity during a visuo-spatial attention task.
2009 Jun
Ethylamine content and theanine biosynthesis in different organs of Camellia sinensis seedlings.
2009 May-Jun
The effect of taurine, a novel biochemical modulator, on the antitumor activity of doxorubicin.
2009 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Studies reporting an anti-anxiety effect used single doses of theanine 200 to 250 mg.
Route of Administration: Oral
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.
Name Type Language
THEANINE
INCI   MI   VANDF   WHO-DD  
INCI  
Official Name English
L-THEANINE [USP-RS]
Common Name English
THEANINE [MI]
Common Name English
N-ETHYL-L-GLUTAMINE
Systematic Name English
Theanine [WHO-DD]
Common Name English
THEANINE [VANDF]
Common Name English
THEANINE [INCI]
Common Name English
THEANINE, L-
Systematic Name English
NSC-21308
Code English
L-THEANINE
USP-RS  
Systematic Name English
Classification Tree Code System Code
DSLD 607 (Number of products:983)
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
221-379-0
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
SMS_ID
100000126208
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
338
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
NSC
21308
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
MESH
C026166
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
NCI_THESAURUS
C87348
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID80184817
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
RXCUI
38022
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY RxNorm
CHEBI
17394
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
CONCEPT Dietary Supplement
RS_ITEM_NUM
1652704
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
WIKIPEDIA
THEANINE
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
EVMPD
SUB33407
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
MERCK INDEX
M10694
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY Merck Index
DAILYMED
8021PR16QO
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
209
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
HSDB
8166
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
EVMPD
SUB33692
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
FDA UNII
8021PR16QO
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
PUBCHEM
439378
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
CHEBI
58128
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
501
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
CAS
3081-61-6
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY
DRUG BANK
DB12444
Created by admin on Wed Jul 05 23:40:11 UTC 2023 , Edited by admin on Wed Jul 05 23:40:11 UTC 2023
PRIMARY