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
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
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 |
---|---|---|
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
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic 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 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 | ||
---|---|---|---|---|---|
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY