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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

Molecular Formula C7H14N2O3
Molecular Weight 174.1977
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
24.6 µM [IC50]
41.5 µM [IC50]
347.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
ZEN THEANINE

Cmax

ValueDoseCo-administeredAnalytePopulation
24.3 μM
100 mg single, oral
THEANINE plasma
Homo sapiens
2.8 μM
100 mg single, oral
THEANINE red blood cells
Homo sapiens
43.1 μM
100 mg single, oral
GLUTAMIC ACID red blood cells
Homo sapiens
12.9 μM
100 mg single, oral
GLUTAMIC ACID plasma
Homo sapiens
6.1 μM
100 mg single, oral
ETHYLAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
57.1 μM × h
100 mg single, oral
THEANINE plasma
Homo sapiens
50.5 μM × h
100 mg single, oral
THEANINE red blood cells
Homo sapiens
276 μM × h
100 mg single, oral
GLUTAMIC ACID red blood cells
Homo sapiens
38.9 μM × h
100 mg single, oral
GLUTAMIC ACID plasma
Homo sapiens
101 μM × h
100 mg single, oral
ETHYLAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.2 h
100 mg single, oral
THEANINE plasma
Homo sapiens

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

PubMed

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
Record UNII
8021PR16QO
Record Status Validated (UNII)
Record Version