THEANINE

Possibly Marketed Outside US

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 Search

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

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

Description
Sources: https://www.drugs.com/npc/l-theanine.html | https://www.ncbi.nlm.nih.gov/pubmed/26192072 | http://koyumatcha.com/wp/wp-content/uploads/2009/04/what_is_l-theanine.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24762604	Inhibitor 8504
Glutamate receptor ionotropic AMPA 42 Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12596867 \| https://examine.com/supplements/theanine/#ref35	Antagonist 2849	24.6 µM [IC50]
Glutamate receptor ionotropic kainate 24 Target ID: CHEMBL2109241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12596867 \| https://examine.com/supplements/theanine/#ref35	Antagonist 2849	41.5 µM [IC50]
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12596867 \| https://examine.com/supplements/theanine/#ref35	Antagonist 2849	347.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26192072 https://clinicaltrials.gov/ct2/show/NCT00372151 https://www.ncbi.nlm.nih.gov/pubmed/21208586	Primary	Phase III 665	Unknown Approved Use Unknown
Attention deficit hyperactivity disorder 70 Sources: https://clinicaltrials.gov/ct2/show/NCT00291070	Primary	Phase II 1147	Unknown Approved Use Unknown
Anxiety 275 Sources: https://clinicaltrials.gov/ct2/show/NCT00981955 http://overcomingyouranxiety.net/naturalanxietyremedies/theanine-for-anxiety/	Primary	Approved 8583	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.

C_max

Value	Dose	Analyte	Population
24.3 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	THEANINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.8 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	THEANINE red blood cells	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
43.1 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	GLUTAMIC ACID red blood cells	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12.9 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	GLUTAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.1 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	ETHYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
57.1 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	THEANINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
50.5 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	THEANINE red blood cells	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
276 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	GLUTAMIC ACID red blood cells	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
38.9 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	GLUTAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
101 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	ETHYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23096008/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		THEANINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30580081/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/30580081/	Sources: https://pubmed.ncbi.nlm.nih.gov/30580081/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 499 OATP1B3 961 OATP1B1 1079

Drug as perpetrator

Target	Modality	Activity
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15729621/	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDMwMzkxMTMifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDMwMzkxMTMifX0=	yes [Inhibition 10 uM]

PubMed

Title	Date	PubMed
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.	2009-12-01	19766184
The effect of taurine, a novel biochemical modulator, on the antitumor activity of doxorubicin.	2009-09	19721236
Ethylamine content and theanine biosynthesis in different organs of Camellia sinensis seedlings.	2009-08-15	19678543
Treatment with green tea extract attenuates secondary inflammatory response in an experimental model of spinal cord trauma.	2009-08	19337722
Bioactive components of tea: cancer, inflammation and behavior.	2009-08	19258034
Impact of two types of Internet-based information on medical students' performance in an Objective Structured Clinical Exam (OSCE).	2009-07	19157760
Changes in the composition of raw tea leaves from the Korean Yabukida plant during high-temperature processing to pan-fried Kamairi-cha green tea.	2009-06	19646035
The effects of L-theanine on alpha-band oscillatory brain activity during a visuo-spatial attention task.	2009-06	18841456
Effects of oral supplementation with cystine and theanine on the immune function of athletes in endurance exercise: randomized, double-blind, placebo-controlled trial.	2009-04-23	19352043
Effects of theanine on growth of human lung cancer and leukemia cells as well as migration and invasion of human lung cancer cells.	2009-04	19760127
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.	2009-04	19303757
Tea and health: preventive and therapeutic usefulness in the elderly?	2009-01	19057186
Theanine, gamma-glutamylethylamide, a unique amino acid in tea leaves, modulates neurotransmitter concentrations in the brain striatum interstitium in conscious rats.	2009-01	18196445
Aqueous fish extract increases survival in the mouse model of cytostatic toxicity.	2008-12-04	19055794
Co-administration of l-cystine and l-theanine enhances efficacy of influenza vaccination in elderly persons: nutritional status-dependent immunogenicity.	2008-12	19149835
L-theanine elicits an umami taste with inosine 5'-monophosphate.	2008-11	18997398
Determination of theanine, GABA, and other amino acids in green, oolong, black, and Pu-erh teas with dabsylation and high-performance liquid chromatography.	2008-09-10	18652476
[Determination of hydroxyproline in collagenous proteins by high performance liquid chromatography-mass spectrometry].	2008-09	19160759
[The effect of theanine on oxygen-induced retinal neovascularization in the neonatal rat].	2008-08	18767491
The combined effects of L-theanine and caffeine on cognitive performance and mood.	2008-08	18681988
Immobilization of Escherichia coli novablue gamma-glutamyltranspeptidase in Ca-alginate-kappa-carrageenan beads.	2008-08	18483700
Protective effect of the green tea component, L-theanine on environmental toxins-induced neuronal cell death.	2008-07	18452993
Theanine, an ingredient of green tea, inhibits [3H]glutamine transport in neurons and astroglia in rat brain.	2008-06	18293419
Theanine production by coupled fermentation with energy transfer using gamma-glutamylmethylamide synthetase of Methylovorus mays No. 9.	2008-05	18460808
Administration of theanine, a unique amino acid in tea leaves, changed feeding-relating components in serum and feeding behavior in rats.	2008-05	18460793
Effects of theanine, a unique amino acid in tea leaves, on memory in a rat behavioral test.	2008-05	18460792
Altered levels of oxidation and phospholipase C isozyme expression in the brains of theanine-administered rats.	2008-05	18451507
Effect of green tea and (-)-epigallocatechin gallate on ethanol-induced toxicity in HepG2 cells.	2008-05	18350509
L-theanine intervention enhances human gammadeltaT lymphocyte function.	2008-02	18254876
Psychological effects of dietary components of tea: caffeine and L-theanine.	2008-02	18254874
The effects of L-theanine, caffeine and their combination on cognition and mood.	2008-02	18006208
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.	2008-01	18175924
Time for tea: mood, blood pressure and cognitive performance effects of caffeine and theanine administered alone and together.	2008-01	17891480
Theanine prevents memory impairment induced by repeated cerebral ischemia in rats.	2008-01	17705146
L-theanine, a natural constituent in tea, and its effect on mental state.	2008	18296328
Enhancement of antigen-specific immunoglobulin G production in mice by co-administration of L-cystine and L-theanine.	2007-12	18176023
Source density analysis of the human EEG after ingestion of a drink containing decaffeinated extract of green tea enriched with L-theanine and theogallin.	2007-11-21	18019399
A soothing sip of focus. The latest on tea: it might quiet distracted minds.	2007-10-08	17958197
[Effects of theanine and houpu extract in 7-day chick social separation-stress procedure].	2007-10	18161300
Involvement of GABA(A) receptors in the neuroprotective effect of theanine on focal cerebral ischemia in mice.	2007-10	17928735
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.	2007-10	17910815
Theanine, r-glutamylethylamide, increases neurotransmission concentrations and neurotrophin mRNA levels in the brain during lactation.	2007-09-29	17904164
Determination of amino acids in tea leaves and beverages using capillary electrophoresis with light-emitting diode-induced fluorescence detection.	2007-09-15	19073035
[Separation and quantification of theanine enantiomers using high performance liquid chromatography coupled with chiral derivatization].	2007-09	18161325
Theogallin and L-theanine as active ingredients in decaffeinated green tea extract: I. electrophysiological characterization in the rat hippocampus in-vitro.	2007-08	17725856
Differentiation of green, white, black, Oolong, and Pu-erh teas according to their free amino acids content.	2007-07-25	17595106
Effects of green tea fractions on oxygen-induced retinal neovascularization in the neonatal rat.	2007-07	18392105
[Determination of amino acids in tea samples by capillary electrophoresis with partition cell and indirect ultraviolet detection].	2007-03	17580684
Spontaneous renal tubular hyperplastic and neoplastic lesions in three Sprague-Dawley rats from a 90-day toxicity study.	2007-02	17366317
Inhibitory effects of theanine and sera from theanine-fed rats on receptor-mediated cancer cell invasion beneath mesothelial-cell monolayers.	2001-07	19003331

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

In Vitro Use Guide

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 `Mon Mar 31 18:22:00 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:00 GMT 2025`
Record UNII	8021PR16QO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THEANINE

Official Name

English

L-THEANINE

Preferred 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, L-

Systematic Name

English

NSC-21308

Code

English

Classification Tree Code System Code

DSLD

607 (Number of products:983)