Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H12N2O2 |
| Molecular Weight | 204.2252 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
InChI
InChIKey=QIVBCDIJIAJPQS-VIFPVBQESA-N
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
| Molecular Formula | C11H12N2O2 |
| Molecular Weight | 204.2252 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugbank.ca/drugs/DB00150Curator's Comment: description was created based on several sources, including
https://www.drugs.com/tryptophan.html
Sources: https://www.drugbank.ca/drugs/DB00150
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/tryptophan.html
Tryptophan is alpha-aminoacid that is used in the biosynthesis of proteins. It is essential aminoacid in humans, meaning the body cannot synthesize and it must be obtained from the diet. Tryptophan is a precursor of serotonin, and as such is sold over the counter in many countries as a dietary supplement for use as an antidepressant, anxiolytic and sleep aid, however application of tryptophan in these indications is not approved by FDA.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1704290
Curator's Comment: Tryptophan is utilized by the brain where it is converted to neuromediator serotonin.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16992614
Curator's Comment: The isolation of tryptophan was first reported by Frederick Hopkins in 1901 through hydrolysis of casein
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map04726 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2271952 |
|||
Target ID: map00380 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2271952 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | OPTIMAX Approved UseOptimax capsules are used only in combination with other anti-depressants when these anti-depressants have been used alone in a patient for a period of time but have not been sufficiently effective. Launch Date2014 |
|||
| Primary | OPTIMAX Approved UseOptimax 500 ing capsules contain L-tryptophan winch is found naturally in animal and plant proteins. L-tryptophan is considered an essential amino acid because our bodies can't make it. It is important for the development and functioning of many organs in the body. After absorbing L-tryptophan from food, our bodies convert it to 5-HTP (5-liydroxytryptophan) and then to serotonin which reduces feelings of anxiety and depression. Launch Date2014 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
717 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6210561/ |
100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
TRYPTOPHAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2538 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6210561/ |
100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
TRYPTOPHAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6210561/ |
100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
TRYPTOPHAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
10 g single, intravenous Highest studied dose |
healthy, 18-40 years |
|
1800 mg 1 times / day multiple, oral Dose: 1800 mg, 1 times / day Route: oral Route: multiple Dose: 1800 mg, 1 times / day Sources: |
healthy, 52 years |
Disc. AE: Eosinophilia myalgia syndrome... AEs leading to discontinuation/dose reduction: Eosinophilia myalgia syndrome (7 patients) Sources: |
1.5 g 2 times / day multiple, oral Dose: 1.5 g, 2 times / day Route: oral Route: multiple Dose: 1.5 g, 2 times / day Sources: |
unhealthy, adult |
Disc. AE: Eosinophilia myalgia syndrome... AEs leading to discontinuation/dose reduction: Eosinophilia myalgia syndrome Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Eosinophilia myalgia syndrome | 7 patients Disc. AE |
1800 mg 1 times / day multiple, oral Dose: 1800 mg, 1 times / day Route: oral Route: multiple Dose: 1800 mg, 1 times / day Sources: |
healthy, 52 years |
| Eosinophilia myalgia syndrome | Disc. AE | 1.5 g 2 times / day multiple, oral Dose: 1.5 g, 2 times / day Route: oral Route: multiple Dose: 1.5 g, 2 times / day Sources: |
unhealthy, adult |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Influence of solvents and leucine configuration at position 5 on tryptophan fluorescence in cyclic enkephalin analogues. | 2001-04-05 |
|
| Reduced brain serotonin activity disrupts prepulse inhibition of the acoustic startle reflex. Effects of 5,7-dihydroxytryptamine and p-chlorophenylalanine. | 2001-04 |
|
| A nonsense mutation in the NDUFS4 gene encoding the 18 kDa (AQDQ) subunit of complex I abolishes assembly and activity of the complex in a patient with Leigh-like syndrome. | 2001-03-01 |
|
| Spectral and metal-binding properties of three single-point tryptophan mutants of the human transferrin N-lobe. | 2001-03-01 |
|
| Src homology 3 domain-dependent interaction of Nck-2 with insulin receptor substrate-1. | 2001-03-01 |
|
| Cooperative binding of inhaled anesthetics and ATP to firefly luciferase. | 2001-03-01 |
|
| Improvement of encapsulation efficiency of water-in-oil-in-water emulsion with hypertonic inner aqueous phase. | 2001-02-24 |
|
| Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition. | 2001-02-23 |
|
| Trp 346 and Leu 352 residues in protective antigen are required for the expression of anthrax lethal toxin activity. | 2001-02-16 |
|
| Hypochlorous acid damages erythrocyte membrane proteins and alters lipid bilayer structure and fluidity. | 2001-02-15 |
|
| Tryptophan glycoconjugate as a novel marker of renal function. | 2001-02-15 |
|
| Kynurenine aminotransferase I activity in human placenta. | 2001-02-15 |
|
| Tryptophan 95, an amino acid residue of the Caprine arthritis encephalitis virus vif protein which is essential for virus replication. | 2001-02-15 |
|
| Engineered antibodies with increased activity to recruit complement. | 2001-02-15 |
|
| N-methyltryptophan oxidase from Escherichia coli: reaction kinetics with N-methyl amino acid and carbinolamine substrates. | 2001-02-06 |
|
| Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli. | 2001-02-06 |
|
| Phosphorescence and optically detected magnetic resonance of HIV-1 nucleocapsid protein complexes with stem-loop sequences of the genomic Psi-recognition element. | 2001-02-06 |
|
| Structural stabilization of [2Fe-2S] ferredoxin from Halobacterium salinarum. | 2001-02-06 |
|
| Orientations of Tyr 21 and Tyr 24 in the capsid of filamentous virus Ff determined by polarized Raman spectroscopy. | 2001-02-06 |
|
| Probing the kinetics of formation of the bacteriophage MS2 translational operator complex: identification of a protein conformer unable to bind RNA. | 2001-02-02 |
|
| Excessive activation of serotonin (5-HT) 1B receptors disrupts the formation of sensory maps in monoamine oxidase a and 5-ht transporter knock-out mice. | 2001-02-01 |
|
| IL-4 and IL-13 regulate the induction of indoleamine 2,3-dioxygenase activity and the control of Toxoplasma gondii replication in human fibroblasts activated with IFN-gamma. | 2001-02 |
|
| Anti-microbial activity and cell binding are controlled by sequence determinants in the anti-microbial peptide PR-39. | 2001-02 |
|
| Contribution of tryptophan residues to the CD spectrum of the extracellular domain of human tissue factor: application in folding studies and prediction of secondary structure. | 2001-02 |
|
| A comparison of kinetic and regulatory properties of the tetrameric and dimeric forms of wild-type and Thr427-->Pro mutant human phenylalanine hydroxylase: contribution of the flexible hinge region Asp425-Gln429 to the tetramerization and cooperative substrate binding. | 2001-02 |
|
| Pumping capacity of bacterial reaction centers and backpressure regulation of energy transduction. | 2001-02 |
|
| Mutagenesis of key residues identifies the connection subdomain of HIV-1 reverse transcriptase as the site of inhibition by heme. | 2001-02 |
|
| The mood-lowering effect of tryptophan depletion: possible explanation for discrepant findings. | 2001-02 |
|
| Interaction of L-tryptophan with alpha-cyclodextrin: studies with calorimetry and proton nuclear magnetic resonance spectroscopy. | 2001-02 |
|
| Increased antibacterial activity of 15-residue murine lactoferricin derivatives. | 2001-02 |
|
| Interaction of pleurocidin and its analogs with phospholipid membrane and their antibacterial activity. | 2001-02 |
|
| Mechanism of porcine pancreatic alpha-amylase. Inhibition of amylose and maltopentaose hydrolysis by alpha-, beta- and gamma-cyclodextrins. | 2001-02 |
|
| Active site characterization of the single endo-polygalacturonase produced by Fusarium moniliforme NCIM 1276. | 2001-02 |
|
| Effects of pressure on the activity and spectroscopic properties of carboxyl proteinases. Apparent correlation of pepstatin-insensitivity and pressure response. | 2001-02 |
|
| Effect of hypothyroidism on pathways for iodothyronine and tryptophan uptake into rat adipocytes. | 2001-02 |
|
| Molecular engineering of myoglobin: the improvement of oxidation activity by replacing Phe-43 with tryptophan. | 2001-01-30 |
|
| Paramecium calmodulin mutants defective in ion channel regulation associate with melittin in the absence of calcium but require it for tertiary collapse. | 2001-01-30 |
|
| Oxidation of human lens recombinant alphaA-crystallin and cysteine-deficient mutants. | 2001-01-26 |
|
| Crystal structures of pristine and oxidatively processed lignin peroxidase expressed in Escherichia coli and of the W171F variant that eliminates the redox active tryptophan 171. Implications for the reaction mechanism. | 2001-01-26 |
|
| A differential scanning calorimetric and 31P NMR spectroscopic study of the effect of transmembrane alpha-helical peptides on the lamellar-reversed hexagonal phase transition of phosphatidylethanolamine model membranes. | 2001-01-23 |
|
| Solution conformation of EcoRI restriction endonuclease changes upon binding of cognate DNA and Mg2+ cofactor. | 2001-01-23 |
|
| Molecular mechanism of stop codon recognition by eRF1: a wobble hypothesis for peptide anticodons. | 2001-01-19 |
|
| Amino acid phosphoramidate monoesters of 3'-azido-3'-deoxythymidine: relationship between antiviral potency and intracellular metabolism. | 2001-01-18 |
|
| Acute tryptophan depletion in schizophrenia. | 2001-01 |
|
| Autofluorescence characteristics of immortalized and carcinogen-transformed human bronchial epithelial cells. | 2001-01 |
|
| Regional changes in kynurenic acid, quinolinic acid, and glial fibrillary acidic protein concentrations in the fetal sheep brain after experimentally induced placental insufficiency. | 2001-01 |
|
| Near-infrared reflectance spectroscopy enables the fast and accurate prediction of the essential amino acid contents in soy, rapeseed meal, sunflower meal, peas, fishmeal, meat meal products, and poultry meal. | 2001-01 |
|
| Tryptophan fluorescence of yeast actin resolved via conserved mutations. | 2001-01 |
|
| Depressive symptoms in hypothyroid disorder with some observations on biochemical correlates. | 2001 |
|
| Mechanisms of biosynthesis of protein-derived redox cofactors. | 2001 |
Patents
Sample Use Guides
As a dietary supplement, tryptophan is administered orally with tryptophan-reach food (turkey, eggs, beans) or as dietary supplements in the form of tablets.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2271952
Tryptophan hydroxylase activity was assayed in a low-speed supernatant fraction of cerebral cortex or midbrain from a single rat. The enzyme preparation contained 2 mM dithiothreitol and had been subjected to gel filtration to remove small molecules. The assay was carried out in the presence of 200 uM L-tryptophan and 50 gM DL-6-methyl-5,6,7,8-tetrahydropterin.
| Substance Class |
Chemical
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| Record UNII |
8DUH1N11BX
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLIC ENZYME -> SUBSTRATE |
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RADIOLIGAND->TARGET |
Used to monitor tryptophan uptake and metabolism
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METABOLIC ENZYME -> INDUCER |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE TOXIC -> PARENT |
Metabolised to indole by gut lactobacilli then to indoxyl sulfate in the liver by cypE1 and a sulfation enzyme.
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
Formed from tryptophanase from gut bacteria.
|
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
Metabolized from indole in the liver.
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PARENT |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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IMPURITY -> PARENT |
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
EP
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||
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IMPURITY -> PARENT |
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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