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Details

Stereochemistry ABSOLUTE
Molecular Formula C7H14N2O3
Molecular Weight 174.1979
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THEANINE

SMILES

CCN=C(CC[C@@]([H])(C(=O)O)N)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
Inhibition of glutamate transporter by theanine enhances the therapeutic efficacy of doxorubicin.
2001 Apr 30
Inhibitory effects of theanine and sera from theanine-fed rats on receptor-mediated cancer cell invasion beneath mesothelial-cell monolayers.
2001 Jul
Enhancement of the activity of doxorubicin by inhibition of glutamate transporter.
2001 Sep 15
Neuroprotective effects of the green tea components theanine and catechins.
2002 Dec
Direct determination of free amino acids and sugars in green tea by anion-exchange chromatography with integrated pulsed amperometric detection.
2002 Dec 27
Effect of dihydrokainate on the antitumor activity of doxorubicin.
2002 May 28
[Glutamate transporter mediated increase of antitumor activity by theanine, an amino acid in green tea].
2002 Nov
Rapid analysis of amino acids in Japanese green tea by microchip electrophoresis using plastic microchip and fluorescence detection.
2003 Sep 26
Analysis of derivatized and underivatized theanine enantiomers by high-performance liquid chromatography/atmospheric pressure ionization-mass spectrometry.
2004
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
Effects of theanine on alcohol metabolism and hepatic toxicity.
2005 Sep
The neuropharmacology of L-theanine(N-ethyl-L-glutamine): a possible neuroprotective and cognitive enhancing agent.
2006
Relaxation and immunity enhancement effects of gamma-aminobutyric acid (GABA) administration in humans.
2006
Induction of neutral endopeptidase (NEP) activity of SK-N-SH cells by natural compounds from green tea.
2006 Apr
Molecular and sensory studies on the umami taste of Japanese green tea.
2006 Apr 5
Efficacy of theanine is connected with theanine metabolism by any enzyme, not only drug metabolizing enzymes.
2006 Feb
Pharmacology and therapeutic uses of theanine.
2006 Jan 1
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
The chemopreventive properties of chlorogenic acid reveal a potential new role for the microsomal glucose-6-phosphate translocase in brain tumor progression.
2006 Mar 27
Multivariate analysis for 1H-NMR spectra of two hundred kinds of tea in the world.
2006 Oct
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
[Effects of theanine and houpu extract in 7-day chick social separation-stress procedure].
2007 Oct
A soothing sip of focus. The latest on tea: it might quiet distracted minds.
2007 Oct 8
[Separation and quantification of theanine enantiomers using high performance liquid chromatography coupled with chiral derivatization].
2007 Sep
Theanine, r-glutamylethylamide, increases neurotransmission concentrations and neurotrophin mRNA levels in the brain during lactation.
2007 Sep 29
[The effect of theanine on oxygen-induced retinal neovascularization in the neonatal rat].
2008 Aug
Co-administration of l-cystine and l-theanine enhances efficacy of influenza vaccination in elderly persons: nutritional status-dependent immunogenicity.
2008 Dec
Aqueous fish extract increases survival in the mouse model of cytostatic toxicity.
2008 Dec 4
L-theanine intervention enhances human gammadeltaT lymphocyte function.
2008 Feb
Psychological effects of dietary components of tea: caffeine and L-theanine.
2008 Feb
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
Theanine, an ingredient of green tea, inhibits [3H]glutamine transport in neurons and astroglia in rat brain.
2008 Jun
Effect of green tea and (-)-epigallocatechin gallate on ethanol-induced toxicity in HepG2 cells.
2008 May
L-theanine elicits an umami taste with inosine 5'-monophosphate.
2008 Nov
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
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
Theanine, gamma-glutamylethylamide, a unique amino acid in tea leaves, modulates neurotransmitter concentrations in the brain striatum interstitium in conscious rats.
2009 Jan
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
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 [WHO-DD]
Common Name English
THEANINE [MI]
Common Name English
N-ETHYL-L-GLUTAMINE
Systematic 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 Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
Code System Code Type Description
USP_CATALOG
1652704
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
221-379-0
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
MESH
C026166
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
NCI_THESAURUS
C87348
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
EPA CompTox
3081-61-6
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
RXCUI
38022
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C1505
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
CONCEPT Dietary Supplement
WIKIPEDIA
THEANINE
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
EVMPD
SUB33407
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
MERCK INDEX
M10694
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY Merck Index
HSDB
8166
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
EVMPD
SUB33692
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
FDA UNII
8021PR16QO
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
PUBCHEM
439378
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
CAS
3081-61-6
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY
DRUG BANK
DB12444
Created by admin on Sat Jun 26 14:29:46 UTC 2021 , Edited by admin on Sat Jun 26 14:29:46 UTC 2021
PRIMARY