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5-hydroxytryptophan
tryptophan, 5-hydroxy-, DL-

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Name:2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
CAS Number: 56-69-9Picture of molecule3D/inchi
Other(deleted CASRN):114-03-4
ECHA EINECS - REACH Pre-Reg:204-039-6
FDA UNII: 9181P3OI6N
Nikkaji Web:J61.742C
Beilstein Number:0088199
MDL:MFCD00005651
XlogP3:-1.20 (est)
Molecular Weight:220.22824000
Formula:C11 H12 N2 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:food additive
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Perfumer and Flavorist:Search
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US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:white crystalline powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 298.00 to 300.00 °C. @ 760.00 mm Hg
Boiling Point: 520.00 to 521.00 °C. @ 760.00 mm Hg (est)
Flash Point: 516.00 °F. TCC ( 268.70 °C. ) (est)
logP (o/w): -0.292 (est)
Soluble in:
 water, 1.00E+04 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
AIDP
5-HTP hydroxytryptophan 98% -101%
Alfa Biotechnology
For experimental / research use only.
5-Hydroxytryptophan 98%
AuNutra® Industries
5-HTP
BOC Sciences
For experimental / research use only.
5-Hydroxy L-Tryptophan >98%
Odor: characteristic
Use: 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN), is a naturally occurring amino acid and chemical precursor for the treatment of depression.
Changsha Organic Herb
5-HTP Griffonia simplicifolia Extract
Jiangyin Healthway
5-HTP 99.0%
New functional food ingredients
Santa Cruz Biotechnology
For experimental / research use only.
5-Hydroxytryptophan ≥98%
Xian Yuensun Biological Technology
5-Hydroxytryptophan, 98%
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 200 mg/kg
National Technical Information Service. Vol. AD277-689

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
food additive
Recommendation for 5-hydroxytryptophan usage levels up to:
 not for fragrance use.
 
Recommendation for 5-hydroxytryptophan flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):56-69-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :144
National Institute of Allergy and Infectious Diseases:Data
2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Chemidplus:0000056699
RTECS:YN7100000 for cas# 56-69-9
 
References:
 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):144
Pubchem (sid):134972916
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C01017
HMDB (The Human Metabolome Database):HMDB00472
Export Tariff Code:2933.90.8000
FDA Listing of Food Additive Status:View
MedlinePlusSupp:View
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
2-amino-3-(5-hydroxy-1H-indol-3-yl)-propionic acid
2-amino-3-(5-hydroxy-1H-indol-3-yl)-propionicacid
2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
2-amino-3-(5-hydroxy-1H-indol-3-yl)propansäure
2-amino-3-(5-hydroxy-1H-indol-3-yl)propionic acid
2-amino-3-(5-hydroxyindol-3-yl)propanoic acid
DL-2-amino-3-[3-(5-hydroxyindole)]propionic acid
5-HTP
DL-5-HTP
5-hydroxy tryptophan
5-hydroxy-DL-tryptophan
(±)-5-hydroxytryptophan
dextro,laevo-5-hydroxytryptophan
DL-5-hydroxytryptophan
5-hydroxytryptophan DL-form
 oxitriptan
DL-pretonine
 tryptophan, 5-hydroxy-
 tryptophan, 5-hydroxy-, DL-
DL-tryptophen, 5-hydroxy- (9CI)
 

Articles:

PubMed:The effects of 5-hydroxytryptophan in combination with different Fatty acids on gastrointestinal functions: a pilot experiment.
PubMed:Serotonergic reinforcement of intestinal barrier function is impaired in irritable bowel syndrome.
PubMed:Quantification of serotonin O-sulphate by LC-MS method in plasma of healthy volunteers.
PubMed:The effect of immunoglobulins and somatic cells on the gravity separation of fat, bacteria, and spores in pasteurized whole milk.
PubMed:Analysis of indole compounds in methanolic extracts from the fruiting bodies of Cantharellus cibarius (the Chanterelle) and from the mycelium of this species cultured in vitro.
PubMed:Heightened serotonin influences contest outcome and enhances expression of high-intensity aggressive behaviors.
PubMed:Male-to-female transfer of 5-hydroxytryptophan glucoside during mating in Zygaena filipendulae (Lepidoptera).
PubMed:Ginsenoside rb1 modulates level of monoamine neurotransmitters in mice frontal cortex and cerebellum in response to immobilization stress.
PubMed:Whole brain monoamine detection and manipulation in a stalk-eyed fly.
PubMed:Synthesis of 2,4-dihydroxychalcone derivatives as potential antidepressant effect.
PubMed:The use of a food supplementation with D-phenylalanine, L-glutamine and L-5-hydroxytriptophan in the alleviation of alcohol withdrawal symptoms.
PubMed:Indole compounds in some culinary-medicinal higher basidiomycetes from Poland.
PubMed:5-hydroxy-L-tryptophan Suppressed Food Intake in Rats Despite an Increase in the Arcuate NPY Expression.
PubMed:Influence of Griffonia simplicifolia on male sexual behavior in rats: behavioral and neurochemical study.
PubMed:Liquid chromatography on a monolithic column microfluidic chip coupled with "three-T" sample injection mode and amperometric detection.
PubMed:5-Hydroxytrytophan inhibits tert-butylhydroperoxide (t-BHP)-induced oxidative damage via the suppression of reactive species (RS) and nuclear factor-kappaB (NF-kappaB) activation on human fibroblast.
PubMed:Griffonia simplicifolia negatively affects sexual behavior in female rats.
PubMed:Sleep disorders in children.
PubMed:Peripheral peptide YY inhibits propulsive colonic motor function through Y2 receptor in conscious mice.
PubMed:Meal ingestion, amino acids and brain neurotransmitters: effects of dietary protein source on serotonin and catecholamine synthesis rates.
PubMed:Characterization of pu-erh tea using chemical and metabolic profiling approaches.
PubMed:Chronic voluntary ethanol intake hypersensitizes 5-HT(1A) autoreceptors in C57BL/6J mice.
PubMed:Repeated administration of fresh garlic increases memory retention in rats.
PubMed:Serotonergic drugs : effects on appetite expression and use for the treatment of obesity.
PubMed:Anxiolytic effect of serotonin depletion in the novelty-induced hypophagia test.
PubMed:Tryptophan enhances ghrelin expression and secretion associated with increased food intake and weight gain in weanling pigs.
PubMed:Alterations in alcohol consumption, withdrawal seizures, and monoamine transmission in rats treated with phentermine and 5-hydroxy-L-tryptophan.
PubMed:Evidence indicating participation of the serotonergic system in controlling feeding behavior in Coturnix japonica (Galliformes: Aves).
PubMed:A reassessment of the role of serotonergic system in the control of feeding behavior.
PubMed:Safety of 5-hydroxy-L-tryptophan.
PubMed:5-Hydroxy-L-tryptophan suppresses food intake in food-deprived and stressed rats.
PubMed:A unique central tryptophan hydroxylase isoform.
PubMed:Systemic 5-hydroxy-L-tryptophan down-regulates the arcuate CART mRNA level in rats.
PubMed:Analysis of optically active compounds using conventional chromatography with a circular dichroism detector.
PubMed:Dwarfism and low insulin-like growth factor-1 due to dopamine depletion in Pts-/- mice rescued by feeding neurotransmitter precursors and H4-biopterin.
PubMed:Gait and Balance Dysfunction in Adults.
PubMed:Serotonin and serotonin 1-A receptors in the failure of ethanol-treated rats to adapt to a repeated stress schedule.
PubMed:A functional food product for the management of weight.
PubMed:Intermittent, chronic fenfluramine administration to rats repeatedly suppresses food intake despite substantial brain serotonin reductions.
PubMed:Oxidation of Free Tryptophan and Tryptophan Residues in Peptides and Proteins.
PubMed:Determination of hydroxytryptophan isomers in gamma-irradiated egg white, chicken meat, and shrimps.
PubMed:Effects of oral 5-hydroxy-tryptophan on energy intake and macronutrient selection in non-insulin dependent diabetic patients.
PubMed:5HT1A receptor antagonists enhance the functional activity of fluoxetine in a mouse model of feeding.
PubMed:Blockade of pre- and post-synaptic 5-HT1A receptors does not modify the effect of fluoxetine or 5-hydroxytryptophan on ethanol and food intake in rats.
PubMed:Effects of food deprivation on midbrain 5-HT1A autoreceptors in Lewis and SHR rats.
PubMed:The weight gain and ultimate adiposity in cafeteria diet-induced obesity is unrelated to the central serotoninergic tonus.
PubMed:1192U90 in animal tests that predict antipsychotic efficacy, anxiolysis, and extrapyramidal side effects.
PubMed:Neuropharmacological studies on Fusarium toxins--II: Total toxin extract from F. oxysporum.
PubMed:Changes in brain neurotransmitters in hypothalamus related to feeding behavior in LEC rat.
PubMed:Food restriction decreases serotonin and its synthesis rate in the hypothalamus.
PubMed:Effect of the i.c.v. injection of 5,7-di-hydroxytryptamine on the aggressive behavior of dominant and submissive pigeons (Columba livia).
PubMed:Effect of subchronic and chronic exposure to 5-hydroxytryptophan (5-HTP) on the aggressive behavior induced by food competition in undernourished dominant and submissive pigeons (Columba livia).
PubMed:Synthesis of dopamine and 5-HT in anatomical regions of the rat's brain is unaffected by sustained infusion of amperozide.
PubMed:Brain tryptophan concentrations and serotonin synthesis remain responsive to food consumption after the ingestion of sequential meals.
PubMed:Serotonergic mechanisms involved in the suppression of feeding by 5-HTP in rats.
PubMed:An eosinophilia-myalgia syndrome related disorder associated with exposure to L-5-hydroxytryptophan.
PubMed:Brain regional serotonin synthesis following adaptation to repeated restraint.
PubMed:[The participation of the endogenous opioid system in regulating the feeding and protective behaviors of the mollusk Lymnaea stagnalis].
PubMed:Melatonin and pineal neurochemicals in steers grazed on endophyte-infected tall fescue: effects of metoclopramide.
PubMed:Effects of tianeptine on 5-HTP- and dextrofenfluramine-induced hypophagia in the rat.
PubMed:LY248686, a new inhibitor of serotonin and norepinephrine uptake.
PubMed:Effects of monoamine precursors on food intake in male rats.
PubMed:Eating behavior and adherence to dietary prescriptions in obese adult subjects treated with 5-hydroxytryptophan.
PubMed:[The neuronal activity of the ventromedial hypothalamus during pharmacological exposures that modulate motivational and emotional states].
PubMed:Protection to glycolysis by a combination of 5-hydroxy-L-tryptophan and 2-aminoethylisothiuronium bromide hydrobromide in lethally irradiated rats.
PubMed:Thermogenic actions of tryptophan in the rat are mediated independently of 5-HT.
PubMed:Food intake and rumen motility in dwarf goats. Effects of some serotonin receptor agonists and antagonists.
PubMed:Involvement of corticotrophin releasing factor (CRF) in the thermogenic and anorexic actions of serotonin (5-HT) and related compounds.
PubMed:Potencies of antagonists indicate that 5-HT1C receptors mediate 1-3(chlorophenyl)piperazine-induced hypophagia.
PubMed:Hypothalamic monoamines and food intake in alcohol-preferring AA and alcohol-avoiding ANA rats.
PubMed:Differential effect of 5-hydroxytryptophan on approach and avoidance behavior in rats.
PubMed:Effect of precursor loading on the synthesis rate and release of dopamine and serotonin in the striatum: a microdialysis study in conscious rats.
PubMed:Effects of 5-hydroxytryptophan on eating behavior and adherence to dietary prescriptions in obese adult subjects.
PubMed:Neuroendocrine measurements in steers grazed on endophyte-infected fescue.
PubMed:Inhibition of human brain aromatic L-amino acid decarboxylase by cooked food-derived 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) and other heterocyclic amines.
PubMed:Effects of serotonin uptake blockers and of 5-hydroxytryptophan on the voluntary consumption of ethanol, water and solid food by UChA and UChB rats.
PubMed:Effect of 5-HTP and ketanserine on the aggressive reaction induced by food competition in dominant and submissive pigeons (Columba livia).
PubMed:Treatment of resistant depression. Review on the efficacy of various biological treatments, specifically in major depression resistant to cyclic antidepressants.
PubMed:Analysis of serotonin, dopamine and their metabolites in the caudate putamen, the suprachiasmatic nucleus and the median raphe nucleus of euthermic and torpid deermice, Peromyscus maniculatus.
PubMed:The effects of intake of lucerne (Medicago sativa L.) and orchard grass (Dactylis glomerata L.) hay on the motility of the forestomach and digesta flow at the abomaso-duodenal junction of the sheep.
PubMed:5-Hydroxytryptophan and carbidopa in spontaneously hypertensive rats.
PubMed:Inhibition of free radical processes by antioxidants--tryptophan and 5-hydroxytryptophan.
PubMed:Modification of quasi-morphine withdrawal with serotonin agonists and antagonists: evidence for a role of serotonin in the expression of opiate withdrawal.
PubMed:The effects of oral 5-hydroxytryptophan administration on feeding behavior in obese adult female subjects.
PubMed:Interaction between opioid agonists or naloxone and 5-HTP on feeding behavior in food-deprived rats.
PubMed:Antagonism by ketanserin of the behavioral effects of quipazine but not l-5-hydroxytryptophan in squirrel monkeys.
PubMed:Neurochemical and behavioural evidence for an agonist action of 1-[2-(4-aminophenyl)ethyl]-4-(3-trifluoromethylphenyl)piperazine (LY 165163) at central 5-HT receptors.
PubMed:Potentiated 5-hydroxytryptophan induced response suppression in rats following chronic reserpine.
PubMed:[Effect of emotional stress on the electrical activity of the jejunum in the dog].
PubMed:5-Hydroxytryptophan and cisapride stimulate propulsive jejunal motility and transit of chyme in dogs.
PubMed:Dissociation of the anorectic actions of 5-HTP and fenfluramine.
PubMed:Effect of mealing on plasma and brain amino acid, and brain monoamine in rats after oral aspartame.
PubMed:The shock probe conflict procedure. A new assay responsive to benzodiazepines, barbiturates and related compounds.
PubMed:Pathological findings in a case of hypoxic myoclonus treated with 5-hydroxytryptophan and a decarboxylase inhibitor.
PubMed:Effects of serotonin receptor agonists and antagonists on schedule-controlled behavior of squirrel monkeys.
PubMed:Comparison of clenbuterol enantiomers using four psychopharmacological tests sensitive to beta-agonists.
PubMed:Nutritional aspects of leprosy.
PubMed:Antihypertensive effects of chronic 5-hydroxytryptamine (5-HT2) receptor blockade with ketanserin in the spontaneously hypertensive rat.
PubMed:Anorexia and brain serotonin: development of tolerance to the effects of fenfluramine and quipazine in rats with serotonin-depleting lesions.
PubMed:Postsynaptic serotonergic blockade following chronic antidepressive treatment with trazodone in an animal model of depression.
PubMed:L-5 HTP available under treatment IND.
PubMed:LCEC monitoring of 5-hydroxyindolic compounds in the cerebrospinal fluid of the rat related to sleep and feeding.
PubMed:Suppression of milk drinking by the combination of fluoxetine and L-5-hydroxytryptophan in rats.
PubMed:Maillard type carbonyl-amine reactions in vivo and their physiological effects.
PubMed:Pre- and postsynaptic serotonergic manipulations in an animal model of depression.
PubMed:Migraine headache: signs and symptoms, biochemistry, and current therapy.
PubMed:Monoamine metabolism in rat brain regions following long term alcohol treatment.
PubMed:Serotonergic influences on food intake: effect of 5-hydroxytryptophan on parameters of feeding behaviour in deprived and free-feeding rats.
PubMed:HPLC determination of biogenic amines in discrete brain areas in food deprived rats.
PubMed:Na+-K+-ATPase activity in the brain cortex of rats ontogenetically malnourished, and treated with serotonin precursors.
PubMed:Effects of various periods of food deprivation on serotonin synthesis in the lateral hypothalamus.
PubMed:para-Chloro-D, L-phenylalanine induced filicidal behavior in the female rat.
PubMed:Behavioral and neurochemical effects of prenatal halothane.
PubMed:[Characteristics of rat training on emotionally varied reinforcement under conditions of an oriented change in the level of brain serotonin and noradrenaline].
PubMed:Appetite stimulant activity of 3-carboxy-10,11-dihydrocyproheptadine.
PubMed:Effects of Lilly 110140, a specific inhibitor of 5-hydroxytryptamine uptake, on food intake and on 5-hydroxytryptophan-induced anorexia. Evidence for serotoninergic inhibition of feeding.
PubMed:Acute reduction of brain serotonin and 5-HIAA following food consumption: correlation with the ratio of serum tryptophan to the sum of competing amino acids.
PubMed:The effect of 5-hydroxytryptophan on food intake and on the anorexic action of amphetamine and fenfluramine.
PubMed:Effects of para-chlorophenylalanine and 5-hydroxytryptophan on alcohol intake in the rat.
PubMed:Effects of dl-para-chlorophenylalanine on sucrose preference and intake: reversal by 5-hydroxytryptophan and 6-methoxy 1,2,3,4,-tetrahydro-beta-carboline.
PubMed:Self-selection of 5-hydroxytryptophan in dl-para-chlorophenylalanine treated rats.
PubMed:Contractile activity of gastric antrum and taenia coli in the unanesthetized monkey.
PubMed:Effect of bile and fat on gastric motility under the influence of various stimulants.
PubMed:[THE EFFECT OF 5-HYDROXYTRYPTOPHEN (SEROTONIN PRECURSOR) ON FOOD-PROCURING CONDITIONED REFLEXES IN RABBITS].
 
Notes:
the immediate precursor in the biosynthesis of serotonin from tryptophan. it is used as an antiepileptic and antidepressant.
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