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 |
---|---|---|---|
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24762604 |
|||
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 |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
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 |
---|---|---|
Theanine, a specific glutamate derivative in green tea, reduces the adverse reactions of doxorubicin by changing the glutathione level. | 2004 Aug 30 |
|
Possible involvement of group I mGluRs in neuroprotective effect of theanine. | 2004 Jul 16 |
|
The acute effects of L-theanine in comparison with alprazolam on anticipatory anxiety in humans. | 2004 Oct |
|
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 |
|
Pu-erh tea supplementation suppresses fatty acid synthase expression in the rat liver through downregulating Akt and JNK signalings as demonstrated in human hepatoma HepG2 cells. | 2005 |
|
Theanine production by coupled fermentation with energy transfer employing Pseudomonas taetrolens Y-30 glutamine synthetase and baker's yeast cells. | 2005 Apr |
|
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 |
|
Pharmacokinetics of theanine enantiomers in rats. | 2005 Mar |
|
A novel assay method for theanine synthetase activity by capillary electrophoresis. | 2005 May 5 |
|
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 |
|
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 |
|
Determination of theanine in commercial tea by liquid chromatography with fluorescence and diode array ultraviolet detection. | 2006 Sep 20 |
|
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 |
|
Effect of valerian extract preparation (BIM) on the sleep-wake cycle in rats. | 2007 Feb |
|
L-Theanine reduces psychological and physiological stress responses. | 2007 Jan |
|
Green tea increases anti-inflammatory tristetraprolin and decreases pro-inflammatory tumor necrosis factor mRNA levels in rats. | 2007 Jan 5 |
|
The deployment of intersensory selective attention: a high-density electrical mapping study of the effects of theanine. | 2007 Jan-Feb |
|
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 |
|
Involvement of GABA(A) receptors in the neuroprotective effect of theanine on focal cerebral ischemia in mice. | 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 |
|
L-theanine, a natural constituent in tea, and its effect on mental state. | 2008 |
|
The combined effects of L-theanine and caffeine on cognitive performance and mood. | 2008 Aug |
|
Immobilization of Escherichia coli novablue gamma-glutamyltranspeptidase in Ca-alginate-kappa-carrageenan beads. | 2008 Aug |
|
L-theanine intervention enhances human gammadeltaT lymphocyte function. | 2008 Feb |
|
The effects of L-theanine, caffeine and their combination on cognition and mood. | 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 |
|
Time for tea: mood, blood pressure and cognitive performance effects of caffeine and theanine administered alone and together. | 2008 Jan |
|
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 production by coupled fermentation with energy transfer using gamma-glutamylmethylamide synthetase of Methylovorus mays No. 9. | 2008 May |
|
Effects of theanine, a unique amino acid in tea leaves, on memory in a rat behavioral test. | 2008 May |
|
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 |
|
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 |
|
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 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 UTC 2023
by
admin
on
Fri Dec 15 16:12:44 UTC 2023
|
Record UNII |
8021PR16QO
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
DSLD |
607 (Number of products:983)
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
221-379-0
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
100000126208
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
338
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
21308
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
C026166
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
C87348
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
DTXSID80184817
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
38022
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | RxNorm | ||
|
17394
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
C1505
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
CONCEPT | Dietary Supplement | ||
|
1652704
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
THEANINE
Created by
admin on Fri Dec 15 16:12:45 UTC 2023 , Edited by admin on Fri Dec 15 16:12:45 UTC 2023
|
PRIMARY | |||
|
SUB33407
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
m10694
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | Merck Index | ||
|
8021PR16QO
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
209
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
8166
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
SUB33692
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
8021PR16QO
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
439378
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
58128
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
501
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
3081-61-6
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY | |||
|
DB12444
Created by
admin on Fri Dec 15 16:12:44 UTC 2023 , Edited by admin on Fri Dec 15 16:12:44 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET -> INHIBITOR |
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |