theanine

Small moleculeexperimental

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. — NCATS

Clinical trial activity

21 trials · 24 clinical orgs · 0 marketing orgs

Phase 1
4
Phase 2
3
Phase 3
1
Phase 4
2

Earliest trial started Oct 1, 2005 (NCT00291070)

Timeline

2000s

  1. Jan 1, 2005

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2006

    Earliest Phase 3 Sponsor(trial)

2010s

  1. Jan 1, 2018

    Earliest Phase 1 Sponsor(trial)

Indications

Approved for

Mechanism of action

Chemistry & pharmacology

Loading structure…

SMILES

CCNC(=O)CC[C@H](N)C(O)=O
Mol. weight
174.1977 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No

Oral

No

Parenteral

No

Topical

No

Sources

Also known as

  • delta-glutamylethylamide
  • gamma-glutamylethylamide
  • l-glutamic acid-gamma-ethylamide
  • l-theanine
  • l-theanine
  • l-theanine
  • n-ethyl-l-glutamine
  • n-ethyl-l-glutamine
  • theanine
  • theanine
  • theanine
  • theanine, (d)-isomer
  • theanine, (dl)-isomer
  • theanine, (l)-isomer

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07220447Early Phase 1 (Phase 1)Dec 21, 2025City of Hope National Medical Center, National Cancer Institute (NCI)
NCT07004023N/AOct 31, 2025Ethical Naturals, Inc., KGK Science Inc.
NCT07268573N/AAug 1, 2025Sinop University
NCT06889584N/AFeb 15, 2025University of South Carolina
NCT06621797N/AMay 1, 2023Hacettepe University
NCT05808595Phase 2Apr 11, 2023Ethical Naturals, Inc., KGK Science Inc.
NCT05854017N/AFeb 9, 2023Supplement Formulators, Inc.
NCT05450952N/AApr 21, 2022Supplement Formulators, Inc.
NCT05032729N/ANov 6, 2021CQUniversity Australia, PepsiCo
NCT04749745Early Phase 1 (Phase 1)Jun 9, 2020Brown University
NCT04706494Phase 1Feb 2, 2020Ethical Naturals, Inc., KGK Science Inc.
NCT04056650Phase 4Sep 2, 2019Icahn School of Medicine at Mount Sinai
NCT03965819N/AMay 31, 2019KGK Science Inc., LifeSeasons Inc.
NCT03533556Early Phase 1 (Phase 1)May 14, 2018Texas Tech University
NCT02298530N/AMar 31, 2015Unilever, University of London
NCT01851122N/ANov 1, 2011University of Texas at Houston
NCT01361204N/AMay 1, 2011University of Shizuoka
NCT01831986N/AJan 1, 2011Sha'ar Menashe Mental Health Center, Technion University
NCT00981955Phase 4Aug 1, 2009Northumbria University
NCT00372151Phase 3Oct 1, 2006Ben Gurion University, Sha'ar Menashe Mental Health Center, Stanley Medical Research Institute
Showing 20 of 21 trials
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Organizations

Research & Development (24)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
KGK Science Inc.For profit4032019
Ethical Naturals, Inc.For profit3332020
Sha'ar Menashe Mental Health CenterAcademic/Hospital2222006
Supplement Formulators, Inc.For profit2212022
Ben Gurion UniversityAcademic/Hospital1012006
Brown UniversityAcademic/Hospital1112020
City of Hope National Medical CenterAcademic/Hospital1112025
CQUniversity AustraliaAcademic/Hospital1012021
Hacettepe UniversityAcademic/Hospital1112023
Icahn School of Medicine at Mount SinaiAcademic/Hospital1112019
LifeSeasons Inc.For profit1112019
National Cancer Institute (NCI)Government1012025
Northumbria UniversityAcademic/Hospital1112009
PepsiCoFor profit1112021
Sinop UniversityAcademic/Hospital1112025
Stanley Medical Research InstituteAcademic/Hospital1012006
Technion UniversityAcademic/Hospital1012011
Texas Tech UniversityAcademic/Hospital1112018
UnileverFor profit1112015
University of British ColumbiaAcademic/Hospital1112005
24 organizations
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