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L-Tryptophan_Molecular_structure_CAS_73-22-3)
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L-Tryptophan

Catalog No. DB00150 Name DrugBank
CAS Number 73-22-3 Website http://www.ualberta.ca/
M. F. C11H12N2O2 Telephone (780) 492-3111
M. W. 204.22518 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 36

SYNONYMS

IUPAC name
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
IUPAC Traditional name
L-tryptophan
Brand Name
Alti-Tryptophan
Lyphan
Synonyms
2-Amino-3-indolylpropanoic acid
alpha-Amino-beta-(3-indolyl)-propionic acid
Tryptophan
(S)-a-Amino-b-indolepropionic acid
L-(-)-Tryptophan
(-)-Tryptophan
L-Tryptophane
Tryptophane
l-a-Aminoindole-3-propionic acid
l-b-3-Indolylalanine
(S)-a-Amino-1H-indole-3-propanoic acid
(S)-a-Aminoindole-3-propionic acid
3-Indol-3-ylalanine
(S)-Tryptophan

DATABASE IDS

CAS Number 73-22-3
PubChem CID 6305
PubChem SID 46508329

PROPERTIES

Hydrophobicity(logP) -1.3
Solubility Soluble

DETAILS

Description (English)
Item Information
Drug Groups approved; nutraceutical
Description An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. [PubChem]
Indication 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.
Pharmacology Tryptophan is critical for the production of the body's proteins, enzymes and muscle tissue. It is also essential for the production of niacin, the synthesis of the neurotransmitter serotonin and melatonin. Tryptophan supplements can be used as natural relaxants to help relieve insomnia. Tryptophan can also reduce anxiety and depression and has been shown to reduce the intensity of migraine headaches. Other promising indications include the relief of chronic pain, reduction of impulsivity or mania and the treatment of obsessive or compulsive disorders. Tryptophan also appears to help the immune system and can reduce the risk of cardiac spasms. Tryptophan deficiencies may lead to coronary artery spasms. Tryptophan is used as an essential nutrient in infant formulas and intravenous feeding. Tryptophan is marketed as a prescription drug (Tryptan) for those who do not seem to respond well to conventional antidepressants. It may also be used to treat those afflicted with seasonal affective disorder (a winter-onset depression). Tryptopan serves as the precursor for the synthesis of serotonin (5-hydroxytryptamine, 5-HT) and melatonin (N-acetyl-5-methoxytryptamine).
Toxicity Oral rat LD50: > 16 gm/kg. Investigated as a tumorigen, mutagen, reproductive effector. 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.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.

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