| Record Information |
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| Version | 2.0 |
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| Creation Date | 2014-08-29 06:35:45 UTC |
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| Update Date | 2018-03-21 17:46:25 UTC |
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| Accession Number | T3D4369 |
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| Identification |
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| Common Name | L-Tryptophan |
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| Class | Small Molecule |
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| Description | Tryptophan is an essential amino acid that is the precursor of both serotonin and melatonin. Melatonin is a hormone that is produced by the pineal gland in animals, which regulates sleep and wakefulness. Serotonin is a brain neurotransmitter, platelet clotting factor, and neurohormone found in organs throughout the body. Metabolism of tryptophan into serotonin requires nutrients such as vitamin B6, niacin, and glutathione. Niacin (also known as vitamin B3) is an important metabolite of tryptophan. It is synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation. There are a number of conditions or diseases that are characterized tryptophan deficiencies. For instance, fructose malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia. Hartnup's disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnup's disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnup's. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan breakdown products (such as kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. The requirement for tryptophan and protein decreases with age. The minimum daily requirement for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ. A cup of low fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg of tryptophan per pound (http://www.dcnutrition.com). Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into serotonin and the resulting serotonin is further metabolized into melatonin by the pineal gland, which promotes sleep. Under certain situations, tryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that causes damage to the brain and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of tryptophan can be found in glutaric aciduria type I (glutaric acidemia type I or GA1). GA1 is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine, and tryptophan. Babies with glutaric acidemia type I are often born with unusually large heads (macrocephaly). Affected individuals may also have difficulty moving and may experience spasms, jerking, rigidity or decreased muscle tone, and muscle weakness. High levels of tryptophan have also been implicated in eosinophilia-myalgia syndrome (EMS), an incurable and sometimes fatal flu-like neurological condition linked to the ingestion of large amounts of L-tryptophan. The risk of developing EMS increases with larger doses of tryptophan and increasing age. Some research suggests that certain genetic polymorphisms may be related to the development of EMS. The presence of eosinophilia is a core feature of EMS, along with unusually severe myalgia (muscle pain). It is thought that both tryptophan and certain unidentified tryptophan contaminants may contribute to EMS (PMID: 1763543). It has also been suggested that excessive tryptophan or elevation of its metabolites could play a role in amplifying some of the pathological features of EMS (PMID: 10721094). This pathological damage is further augmented by metabolites of the kynurenine pathway (a tryptophan degradation pathway). |
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| Compound Type | - Amine
- Amino Acid, Essential
- Animal Toxin
- Antidepressive Agent, Second-Generation
- Dietary Supplement
- Drug
- Food Toxin
- Metabolite
- Micronutrient
- Natural Compound
- Nutraceutical
- Organic Compound
- Supplement
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| Chemical Structure | |
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| Synonyms | | Synonym | | (-)-tryptophan | | (2S)-2-amino-3-(1H-indol-3-yl)propanoate | | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid | | (L)-tryptophan | | (S)-1H-Indole-3-alanine | | (S)-2-Amino-3-(3-indolyl)propionic acid | | (S)-a-Amino-1H-indole-3-propanoate | | (S)-a-Amino-1H-indole-3-propanoic acid | | (S)-a-amino-b-indolepropionate | | (S)-a-amino-b-indolepropionic acid | | (S)-a-Aminoindole-3-propionate | | (S)-a-Aminoindole-3-propionic acid | | (S)-alpha-Amino-1H-indole-3-propanoate | | (S)-alpha-Amino-1H-indole-3-propanoic acid | | (S)-alpha-Amino-beta-(3-indolyl)-propionic acid | | (S)-alpha-amino-beta-indolepropionate | | (S)-alpha-amino-beta-indolepropionic acid | | (S)-alpha-Aminoindole-3-propionate | | (S)-alpha-Aminoindole-3-propionic acid | | (S)-tryptophan | | (S)-α-amino-1H-indole-3-propanoic acid | | 1-beta-3-Indolylalanine | | 1beta-3-Indolylalanine | | 1H-Indole-3-Alanine | | 2-Amino-3-indolylpropanoate | | 2-Amino-3-indolylpropanoic acid | | 3-(1H-Indol-3-yl)-L-Alanine | | 3-Indol-3-ylalanine | | alpha'-Amino-3-indolepropionic acid | | alpha-Aminoindole-3-propionic acid | | Alti-Tryptophan | | Ardeytropin | | H-TRP-oh | | Indole-3-alanine | | Kalma | | L-(-)-Tryptophan | | L-(−)-tryptophan | | L-alpha-Amino-3-indolepropionic acid | | L-alpha-Aminoindole-3-propionic acid | | L-b-3-Indolylalanine | | L-beta-3-Indolylalanine | | L-Tryptofan | | L-Tryptophane | | L-β-3-indolylalanine | | Lopac-T-0254 | | Lyphan | | Optimax | | Pacitron | | Sedanoct | | Triptofano | | Trofan | | Trp | | Tryptacin | | Tryptan | | Tryptophan | | Tryptophane | | Tryptophanum | | W |
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| Chemical Formula | C11H12N2O2 |
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| Average Molecular Mass | 204.225 g/mol |
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| Monoisotopic Mass | 204.090 g/mol |
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| CAS Registry Number | 73-22-3 |
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| IUPAC Name | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid |
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| Traditional Name | L-tryptophan |
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| SMILES | [H][C@](N)(CC1=CNC2=CC=CC=C12)C(O)=O |
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| InChI Identifier | 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 |
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| InChI Key | InChIKey=QIVBCDIJIAJPQS-VIFPVBQESA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Indoles and derivatives |
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| Sub Class | Indolyl carboxylic acids and derivatives |
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| Direct Parent | Indolyl carboxylic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Indolyl carboxylic acid derivative
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- 3-alkylindole
- Indole
- Aralkylamine
- Benzenoid
- Substituted pyrrole
- Heteroaromatic compound
- Pyrrole
- Amino acid or derivatives
- Amino acid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Amine
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Endogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | - Fibroblasts
- Nerve Cells
- Prostate
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| Pathways | |
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| Applications | |
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| Biological Roles | |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 290.5 dec°C | | Boiling Point | Not Available | | Solubility | 1.34E+004 mg/L (at 25°C) | | LogP | -1.06 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-0udi-0190000000-feaec8547634dddcad8c | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-0udi-0390000000-45a6c4fd79081597d44a | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0udi-0290000000-34f7274f31a4cb321a0b | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-0fk9-9270000000-9761607cbe821f87f172 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-001i-0900000000-3faeed7ad32e1755c03c | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-0udi-0290000000-9c57a732e337fade3cb6 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-001i-0900000000-d054a214c1717940989f | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0udi-0290000000-9860799c854e5c9ac1c7 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-0190000000-feaec8547634dddcad8c | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-0390000000-45a6c4fd79081597d44a | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-0290000000-34f7274f31a4cb321a0b | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-QQ (Non-derivatized) | splash10-0udi-3729000000-86129db57aaf1a245f93 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fk9-9270000000-9761607cbe821f87f172 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-001i-0900000000-3faeed7ad32e1755c03c | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udi-0290000000-9c57a732e337fade3cb6 | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0560-4900000000-fa932bc4cffed0ca66b7 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00e9-9560000000-6829a8b2a2096883999f | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0290602010-c09c931538bff74ac400 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0a4i-0900000000-0fed327c2a56f556e04c | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0090000000-98ec1c2c012e58eab924 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-0090000000-fc77784da5d9b288d751 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0290601010-d6f94902c0cf639cb7bc | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0a4i-0900000000-27633a4f7ecfac45c730 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0090000000-ee6cb8392b2e8d644bc1 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0090000000-d81c86eceee1c9824b02 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0udi-0190000000-0e8b883dc8ab06c89d77 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0uxu-2940000000-cb35b9680612e19d8b3a | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-014i-2900000000-7cc592351cc616b1d75f | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-014i-1900000000-987615a0add5eb2c3169 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-014i-1900000000-f150d9d1e19c72d337a8 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0uxr-2960000000-f4c878f3abb1609bb5c5 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0090000000-c73c9b49139319c80b18 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0gb9-0930000000-da94834297fcc5b3d3c5 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-014i-0900000000-94061fd1f6b08445cdf3 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-014i-0900000000-e78172f4f27df232466e | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-014i-0900000000-93406e2cdb79770abc7d | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0udi-0190000000-0e8b883dc8ab06c89d77 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0uxu-2940000000-cb35b9680612e19d8b3a | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-2900000000-5187dac98dbd6834d6ba | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-1900000000-987615a0add5eb2c3169 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-1900000000-174bb4d4390c75ae9a09 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-0900000000-0fed327c2a56f556e04c | JSpectraViewer | MoNA | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | A number of important side reactions occur during the catabolism of tryptophan on the pathway to acetoacetate. The first enzyme of the catabolic pathway is an iron porphyrin oxygenase that opens the indole ring. The latter enzyme is highly inducible, its concentration rising almost 10-fold on a diet high in tryptophan. Kynurenine is the first key branch point intermediate in the pathway. Kynurenine undergoes deamniation in a standard transamination reaction yielding kynurenic acid. Kynurenic acid and metabolites have been shown to act as antiexcitotoxics and anticonvulsives. A second side branch reaction produces anthranilic acid plus alanine. Another equivalent of alanine is produced further along the main catabolic pathway, and it is the production of these alanine residues that allows tryptophan to be classified among the glucogenic and ketogenic amino acids. The second important branch point converts kynurenine into 2-amino-3-carboxymuconic semialdehyde, which has two fates. The main flow of carbon elements from this intermediate is to glutarate. An important side reaction in liver is a transamination and several rearrangements to produce limited amounts of nicotinic acid, which leads to production of a small amount of NAD+ and NADP+. |
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| Metabolism | Hepatic. |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Tryptophan may be useful in increasing serotonin production, promoting healthy sleep, managing depression by enhancing mental and emotional well-being, managing pain tolerance, and managing weight. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Symptoms of overdose include agitation, confusion, diarrhea, fever, overactive reflexes, poor coordination, restlessness, shivering, sweating, talking or acting with excitement you cannot control, trembling or shaking, twitching, and vomiting. |
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| Treatment | Not Available |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB00150 |
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| HMDB ID | HMDB00929 |
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| PubChem Compound ID | 6305 |
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| ChEMBL ID | CHEMBL54976 |
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| ChemSpider ID | 6066 |
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| KEGG ID | C00078 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 16828 |
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| BioCyc ID | TRP |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | TRP |
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| ACToR ID | Not Available |
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| Wikipedia Link | Kalma |
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| References |
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| Synthesis Reference | Sten Vilhelm Gatenbeck, Per Olof Hedman, “Fermentative process for the production of L-tryptophan and its derivatives.” U.S. Patent US3963572, issued April, 1974. |
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| MSDS | Link |
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| General References | - Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. [2472426 ]
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- Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [12297216 ]
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- Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [9849813 ]
- Koskiniemi M, Laakso J, Kuurne T, Laipio M, Harkonen M: Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L-tryptophan administration. Acta Neurol Scand. 1985 Feb;71(2):127-32. [2580417 ]
- Kennedy JS, Gwirtsman HE, Schmidt DE, Johnson BW, Fielstein E, Salomon RM, Shiavi RG, Ebert MH, Parris WC, Loosen PT: Serial cerebrospinal fluid tryptophan and 5-hydroxy indoleacetic acid concentrations in healthy human subjects. Life Sci. 2002 Aug 23;71(14):1703-15. [12137916 ]
- Bender KI, Lutsevich NF, Lutsevich AN, Kupchikov VV: [Endogenous metabolites as modulators of the transport of drugs by serum albumin]. Farmakol Toksikol. 1990 May-Jun;53(3):72-80. [2201566 ]
- Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [8884658 ]
- Heiman-Patterson TD, Bird SJ, Parry GJ, Varga J, Shy ME, Culligan NW, Edelsohn L, Tatarian GT, Heyes MP, Garcia CA, et al.: Peripheral neuropathy associated with eosinophilia-myalgia syndrome. Ann Neurol. 1990 Oct;28(4):522-8. [2174666 ]
- Talbert AM, Tranter GE, Holmes E, Francis PL: Determination of drug-plasma protein binding kinetics and equilibria by chromatographic profiling: exemplification of the method using L-tryptophan and albumin. Anal Chem. 2002 Jan 15;74(2):446-52. [11811421 ]
- Dunner DL, Heiber S, Perel JM: The effect of L-tryptophan administration on the concentration of probenecid in plasma and cerebrospinal fluid in patients. Psychopharmacology (Berl). 1977 Aug 16;53(3):305-8. [408860 ]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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