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Substance Name: Tryptophan [USAN:INN]
RN: 73-22-3
UNII: 8DUH1N11BX
InChIKey: QIVBCDIJIAJPQS-VIFPVBQESA-N

Note

  • 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.

Molecular Formula

  • C11-H12-N2-O2

Molecular Weight

  • 204.2278
 

Classification Codes

  • Amino Acid
  • Antidepressive Agents
  • Antidepressive Agents, Second-Generation
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Psychotropic Drugs
  • Reproductive Effect
  • Tumor Data

Names and Synonyms

Name of Substance

  • (L)-Tryptophan
  • Tryptophan
  • Tryptophan [USAN:INN]

MeSH Heading

  • Tryptophan

Synonyms

  • (S)-alpha-Amino-1H-indole-3-propanoic acid
  • (S)-alpha-Aminoindole-3-propionic acid
  • (S)-Tryptophan
  • 1-beta-3-Indolylalanine
  • 1beta-3-Indolylalanine
  • 1H-Indole-3-alanine
  • 1H-Indole-3-alanine (VAN)
  • 1H-Indole-3-alanine, (S)-
  • 1H-Indole-3-propanoic acid, alpha-amino-, (S)-
  • 2-Amino-3-indolylpropanoic acid
  • 3-Indol-3-ylalanine
  • AI3-18478
  • Alanine, 3-indol-3-yl-
  • alpha'-Amino-3-indolepropionic acid
  • alpha-Amino-3-indolepropionic acid, L-
  • Ardeytropin
  • CCRIS 617
  • EC 200-795-6
  • EH 121
  • EINECS 200-795-6
  • HSDB 4142
  • Indole-3-alanine
  • Indole-3-propionic acid, alpha-amino-
  • Kalma
  • L-Alanine, 3-(1H-indol-3-yl)-
  • L-alpha-Aminoindole-3-propionic acid
  • L-beta-3-Indolylalanine
  • L-Trp
  • L-Tryptofan
  • L-Tryptophan
  • L-Tryptophane
  • NCI-C01729
  • NSC 13119
  • Optimax
  • Pacitron
  • Propionic acid, 2-amino-3-indol-3-yl-
  • Triptofano
  • Triptofano [Spanish]
  • Trofan
  • TRP
  • Tryptacin
  • Tryptophan
  • tryptophan (H-3)
  • Tryptophan (VAN)
  • Tryptophane
  • Tryptophane [French]
  • Tryptophanum
  • Tryptophanum [Latin]
  • UNII-8DUH1N11BX

Systematic Names

  • L-Tryptophan
  • Tryptophan
  • Tryptophan (VAN)

Superlist Names

  • L-Tryptophan
  • Tryptophan, L-

Registry Numbers

CAS Registry Number

  • 73-22-3

FDA UNII

  • 8DUH1N11BX

Other Registry Numbers

  • 154635-35-5
  • 6912-86-3
  • 80206-30-0

System Generated Number

  • 0000073223

Structure Descriptors

InChI

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

InChIKey

QIVBCDIJIAJPQS-VIFPVBQESA-N

Smiles

N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - domestic LD50 intraperitoneal 2410mg/kg (2410mg/kg)   Drugs in Japan Vol. -, Pg. 744, 1990.
man TDLo oral 300mg/kg (300mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ANTIANXIETY		 British Medical Journal. Vol. 2, Pg. 701, 1976.
man TDLo oral 857mg/kg/30D- (857mg/kg) SKIN AND APPENDAGES (SKIN): OTHER GLANDS: OTHER

MUSCULOSKELETAL: OTHER CHANGES

BLOOD: EOSINOPHILIA		 New England Journal of Medicine. Vol. 322, Pg. 874, 1990.
mouse LD50 intraperitoneal 4800mg/kg (4800mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980.
mouse LDLo oral 15gm/kg (15000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980.
rat LD50 intraperitoneal 1634mg/kg (1634mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Archives of Biochemistry and Biophysics. Vol. 58, Pg. 253, 1955.
rat LD50 oral > 16gm/kg (16000mg/kg) BEHAVIORAL: COMA

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 635, 1980.
rat LDLo unreported 2553mg/kg (2553mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 884, 1973.
women TDLo oral 2700mg/kg/13W (2700mg/kg) BLOOD: EOSINOPHILIA

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI		 Annals of Internal Medicine. Vol. 112, Pg. 301, 1990.
women TDLo oral 3276mg/kg/9W- (3276mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BLOOD: EOSINOPHILIA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 Annals of Internal Medicine. Vol. 112, Pg. 344, 1990.
women TDLo oral 4800mg/kg/34W (4800mg/kg) SKIN AND APPENDAGES (SKIN): OTHER GLANDS: OTHER

BLOOD: EOSINOPHILIA

PERIPHERAL NERVE AND SENSATION: PARESTHESIS		 New England Journal of Medicine. Vol. 322, Pg. 874, 1990.
women TDLo oral 5400mg/kg/134 (5400mg/kg) BLOOD: EOSINOPHILIA

SKIN AND APPENDAGES (SKIN): OTHER GLANDS: OTHER		 New England Journal of Medicine. Vol. 322, Pg. 874, 1990.
women TDLo oral 9gm/kg/22W-I (9000mg/kg) BLOOD: EOSINOPHILIA

LIVER: LIVER FUNCTION TESTS IMPAIRED

BEHAVIORAL: MUSCLE WEAKNESS		 Annals of Internal Medicine. Vol. 112, Pg. 957, 1990.
women TDLo oral 10960mg/kg/20 (10960mg/kg) BLOOD: EOSINOPHILIA

LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

BEHAVIORAL: MUSCLE WEAKNESS		 British Medical Journal. Vol. 301, Pg. 21, 1990.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 290.5 dec deg C   EXP
pKa Dissociation Constant 7.38 (none) 25 EXP
log P (octanol-water) -1.06E+00 (none)   EXP
Water Solubility 1.34E+04 mg/L 25 EXP
Vapor Pressure 2.12E-09 mm Hg 25 EST
Henry's Law Constant 1.98E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.39E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.