TRYPTOPHAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H12N2O2
Molecular Weight	204.2252
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

InChI

InChIKey=QIVBCDIJIAJPQS-VIFPVBQESA-N

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

HIDE SMILES / InChI

Molecular Formula	C11H12N2O2
Molecular Weight	204.2252
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Tryptophan is alpha-aminoacid that is used in the biosynthesis of proteins. It is essential aminoacid in humans, meaning the body cannot synthesize and it must be obtained from the diet. Tryptophan is a precursor of serotonin, and as such is sold over the counter in many countries as a dietary supplement for use as an antidepressant, anxiolytic and sleep aid, however application of tryptophan in these indications is not approved by FDA.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonergic synapse 2	Substrate 661
Tryptophan metabolism 1	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 235	Primary		Approved 8,429	OPTIMAX
Anxiety 267	Primary		Approved 8,429	OPTIMAX

C_max

Value	Dose	Co-administered	Analyte	Population
717 μM	100 mg/kg single, oral		TRYPTOPHAN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
2538 μM × h	100 mg/kg single, oral		TRYPTOPHAN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h	100 mg/kg single, oral		TRYPTOPHAN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
10 g single, intravenous Highest studied dose	healthy, 18-40 years
1800 mg 1 times / day multiple, oral (mean)	healthy, 52 years n = 7	Disc. AE: Eosinophilia myalgia syndrome...
1.5 g 2 times / day multiple, oral (median)	unhealthy, adult	Disc. AE: Eosinophilia myalgia syndrome...

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AEs

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AE	Significance	Dose	Population
Eosinophilia myalgia syndrome	7 patients Disc. AE	1800 mg 1 times / day multiple, oral (mean)	healthy, 52 years n = 7
Eosinophilia myalgia syndrome	Disc. AE	1.5 g 2 times / day multiple, oral (median)	unhealthy, adult

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-01564	http://www.3bsc.com/index/pro_info.php?id=21776
3B Scientific (Wuhan) Corp	3B3-048371	http://www.3bsc.com/index/pro_info.php?id=85809
AA Blocks	AA003R3R	http://www.aablocks.com/goods/Goods/detail?id=AA003R3R
AHH Chemical co.,ltd	MB-00567	http://www.ahhchemical.com/product/MB-00567.html
AHH Chemical co.,ltd	MT-53335	http://www.ahhchemical.com/product/MT-53335.html

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PubMed

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Title	Date	PubMed
Mechanism of porcine pancreatic alpha-amylase. Inhibition of amylose and maltopentaose hydrolysis by alpha-, beta- and gamma-cyclodextrins.	2001 Feb	11168426
Effects of pressure on the activity and spectroscopic properties of carboxyl proteinases. Apparent correlation of pepstatin-insensitivity and pressure response.	2001 Feb	11168403
Effect of hypothyroidism on pathways for iodothyronine and tryptophan uptake into rat adipocytes.	2001 Feb	11158928
Excessive activation of serotonin (5-HT) 1B receptors disrupts the formation of sensory maps in monoamine oxidase a and 5-ht transporter knock-out mice.	2001 Feb 1	11157075
Tryptophan- and dileucine-based endocytosis signals in the neonatal Fc receptor.	2001 Feb 16	11096078

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Patents

Sample Use Guides

In Vivo Use Guide

As a dietary supplement, tryptophan is administered orally with tryptophan-reach food (turkey, eggs, beans) or as dietary supplements in the form of tablets.

Route of Administration: Oral

In Vitro Use Guide

Tryptophan hydroxylase activity was assayed in a low-speed supernatant fraction of cerebral cortex or midbrain from a single rat. The enzyme preparation contained 2 mM dithiothreitol and had been subjected to gel filtration to remove small molecules. The assay was carried out in the presence of 200 uM L-tryptophan and 50 gM DL-6-methyl-5,6,7,8-tetrahydropterin.