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Product No: CI3276

DL-5-Hydroxytryptophan, 98%

Name: DL-5-Hydroxytryptophan
Brand: Chempure

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CAS Number

56-69-9

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IUPAC name	2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
inchi	InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)
inchi key	LDCYZAJDBXYCGN-UHFFFAOYSA-N
molecular formula	C11H12N2O3
synonyms	5-hydroxytryptophan 56-69-9 5-Hydroxy-DL-tryptophan DL-5-Hydroxytryptophan 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Compound Description	5-hydroxytryptophan is a tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5. It has a role as a human metabolite and a neurotransmitter. 5-Hydroxytryptophan has been reported in Panaeolus semiovatus and Solanum lycopersicum with data available. 5-Hydroxytryptophan, DL- is a racemic mixture of 5-hydroxytryptophan , a precursor to the neurotransmitter serotonin with anti-depressant, analgesic and appetite-suppressant activities. DL-5-HTP is decarboxylated to serotonin by aromatic-L-amino-acid decarboxylase, and results in increased serotonin levels within the brain. Mediated through serotonin receptors, elevated levels of serotonin causes increased serotonin neurotransmissions, hence leading to release of depression, pain and appetite. 5-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid l-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic l-amino acid decarboxylase , an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumulation of 5-Hydroxy-L-tryptophan in cerebrospinal fluid occurs in Aromatic l-amino acid decarboxylase deficiency , accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinson's patients with severe postural instability and gait disorders. Confirmation of the diagnosis AADC deficiency is then required by enzyme activity measurement or genetic analysis. The amount of endogenous 5-Hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase , indoleamine 2,3-dioxygenase , and tryptophan 2,3-dioxygenase. . 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to depression, the therapeutic administration of 5-Hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system synthesis of serotonin. Supplementation with 5-Hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties. . The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant. See also: Oxitriptan .

Computed Properties

Molecular Weight:	220.22 g/mol
XLogP3:	-1.2
Hydrogen Bond Donor Count:	4
Hydrogen Bond Acceptor Count:	4
Rotatable Bond Count:	3
Exact Mass:	220.08479225 g/mol
Monoisotopic Mass:	220.08479225 g/mol
Topological Polar Surface Area:	99.3 Å²
Heavy Atom Count:	16
Formal Charge:	0
Complexity:	272
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	0
Undefined Atom Stereocenter Count:	1
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Warning
hazard classes and categories	Acute Tox. 4 (100%) Acute Tox. 4 (50%)
precautionary statement codes	P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P305+P351+P338, P317, P330, P337+P317, P370+P378, P403+P235, and P501
hazard statements	H226 (50%): Flammable liquid and vapor [Warning Flammable liquids] H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]

toxicity summary	5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. An accumulation of 5-hydroxy-L-tryptophan in cerebrospinal fluid occurs in aromatic L-amino acid decarboxylase deficiency, accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system synthesis of serotonin. Supplementation with 5-hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties.
symptoms
health effects	Chronically high levels of 5-hydroxytryptophan are associated with Aromatic L-Amino acid Decarboxylase Deficiency.
carcinogen classification	default_key: No indication of carcinogenicity to humans .

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About this item

IUPAC name	2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
inchi	InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)
inchi key	LDCYZAJDBXYCGN-UHFFFAOYSA-N
molecular formula	C11H12N2O3
synonyms	5-hydroxytryptophan 56-69-9 5-Hydroxy-DL-tryptophan DL-5-Hydroxytryptophan 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Compound Description	5-hydroxytryptophan is a tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5. It has a role as a human metabolite and a neurotransmitter. 5-Hydroxytryptophan has been reported in Panaeolus semiovatus and Solanum lycopersicum with data available. 5-Hydroxytryptophan, DL- is a racemic mixture of 5-hydroxytryptophan , a precursor to the neurotransmitter serotonin with anti-depressant, analgesic and appetite-suppressant activities. DL-5-HTP is decarboxylated to serotonin by aromatic-L-amino-acid decarboxylase, and results in increased serotonin levels within the brain. Mediated through serotonin receptors, elevated levels of serotonin causes increased serotonin neurotransmissions, hence leading to release of depression, pain and appetite. 5-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid l-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic l-amino acid decarboxylase , an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumulation of 5-Hydroxy-L-tryptophan in cerebrospinal fluid occurs in Aromatic l-amino acid decarboxylase deficiency , accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinson's patients with severe postural instability and gait disorders. Confirmation of the diagnosis AADC deficiency is then required by enzyme activity measurement or genetic analysis. The amount of endogenous 5-Hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase , indoleamine 2,3-dioxygenase , and tryptophan 2,3-dioxygenase. . 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to depression, the therapeutic administration of 5-Hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system synthesis of serotonin. Supplementation with 5-Hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties. . The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant. See also: Oxitriptan .

Computed Properties

Molecular Weight:	220.22 g/mol
XLogP3:	-1.2
Hydrogen Bond Donor Count:	4
Hydrogen Bond Acceptor Count:	4
Rotatable Bond Count:	3
Exact Mass:	220.08479225 g/mol
Monoisotopic Mass:	220.08479225 g/mol
Topological Polar Surface Area:	99.3 Å²
Heavy Atom Count:	16
Formal Charge:	0
Complexity:	272
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	0
Undefined Atom Stereocenter Count:	1
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Warning
hazard classes and categories	Acute Tox. 4 (100%) Acute Tox. 4 (50%)
precautionary statement codes	P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P305+P351+P338, P317, P330, P337+P317, P370+P378, P403+P235, and P501
hazard statements	H226 (50%): Flammable liquid and vapor [Warning Flammable liquids] H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]

toxicity summary	5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. An accumulation of 5-hydroxy-L-tryptophan in cerebrospinal fluid occurs in aromatic L-amino acid decarboxylase deficiency, accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system synthesis of serotonin. Supplementation with 5-hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties.
symptoms
health effects	Chronically high levels of 5-hydroxytryptophan are associated with Aromatic L-Amino acid Decarboxylase Deficiency.
carcinogen classification	default_key: No indication of carcinogenicity to humans .

Product No: CI3276

DL-5-Hydroxytryptophan, 98%

Product No: CI3276

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

TOXICITY

About this item

Documentation

Certificate of Analysis

Require a Sample Certificate of Analysis (COA) ?

Reviews

Product No: CI3276

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

TOXICITY

Require a Sample Certificate of Analysis (COA) ?