Related Searches: Tryptophan, 5-hydroxy-, tryptophan, 2-Hydroxy-5-nitropyridine, 2-Hydroxy-5-bromopyridine, Benzaldehyde,2-hydroxy-5-nitro-, View all

Tryptophan, 5-hydroxy-(CAS No. 56-69-9)

Tryptophan, 5-hydroxy- C11H12N2O3 (cas 56-69-9) Molecular Structure

56-69-9 Structure

Identification and Related Records

【Name】
Tryptophan, 5-hydroxy-
【CAS Registry number】
56-69-9
【Synonyms】
DL-5-HTP
DL-5-Hydroxytryptophan
DL-Hydroxytryptophan
NSC 92523
【EINECS(EC#)】
200-284-8
【Molecular Formula】
C11H12N2O3 (Products with the same molecular formula)
【Molecular Weight】
220.25
【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)
【Canonical SMILES】
C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N
【MOL File】
56-69-9.mol

Chemical and Physical Properties

【Appearance】
White Solid
【Density】
1.484
【Melting Point】
298-300°C
【Boiling Point】
520.6 °C at 760 mmHg
【Flash Point】
268.7 °C
【Solubilities】
Very soluble
【Color/Form】
Minute rods or needles from ethanol
【Stability】
No data.
【Storage temp】
2-8°C
【Spectral properties】
Max absorption (water at pH 6.0): 278 nm
IR: 2:1092G (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
NMR: 8:70B (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
【Computed Properties】
Molecular Weight:220.22458 [g/mol]
Molecular Formula:C11H12N2O3
XLogP3:-1.2
H-Bond Donor:4
H-Bond Acceptor:4
Rotatable Bond Count:3
Tautomer Count:9
Exact Mass:220.084792
MonoIsotopic Mass:220.084792
Topological Polar Surface Area:99.3
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
Feature 3D Acceptor Count:2
Feature 3D Donor Count:3
Feature 3D Anion Count:1
Feature 3D Cation Count:2
Feature 3D Ring Count:2
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:25

Safety and Handling

【Safety Statements 】
24/25-22
【Safety】
Poison by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
【PackingGroup 】
III
【Transport】
2811
【Specification】

Off-White to Pale Beige Solid
usageEng:A metabolite of Tryptophan
Safety Statements:24/25-22
24/25:Avoid contact with skin and eyes
22:Do not breathe dust
【Octanol/Water Partition Coefficient】
log Kow = -1.70 (est)
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

MANNICH CONDENSATION OF 5-BENZYLOXYINDOLE; CATALYTIC HYDROGENOLYSIS OF 5-BENZYLOXYTRYPTOPHAN; ENZYMATIC HYDROXYLATION OF TRYPTOPHAN
U.S. Production

(1979) NOT PRODUCED COMMERCIALLY IN US
【Usage】

Medication.

Biomedical Effects and Toxicity

【Pharmacological Action】
- A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake.
【Therapeutic Uses】
5-HTP has shown some usefulness in some conditions characterized, in part, by serotonin deficits, principally depression. It has also been shown to be useful in some with obesity, insomnia, fibromyalgia and chronic tension headache.
It has been long known that brain serotonin systems contribute to the modulation of food intake and satiety. An increase of intrasynaptic serotonin tends to reduce food consumption. Thus, one might consider that individuals taking 5-HTP might experience increase satiety and weight loss over a period of time. There are few studies on the effects of 5-HTP on obesity and they suggest an anorectic effect of 5-HTP.
There is some evidence that 5-HTP ... can improve postural equilibrium, dysarthria in patients with various inherited and acquired cerebellar ataxias, and particularly in those with lesions located precisely in the anterior lobe vermis. Improvements in coordination have been reported in patients with Friedreich"s ataxia; however, the effect is only partial and not clinically major.
Exptl Ther: Rats of the Dahl salt-sensitive (DS) and Dahl salt-resistant (DR) strains were placed on a 4% NaCl diet and blood pressures were monitored. Chronic subcutaneous infusion L-5-hydroxytryptophan (L-5-HTP, 12.6 mg/day) by osmotic minipumps significantly decreased the elevated systolic blood pressure of DS rats on a 4% NaCl diet. Blood pressures of DR rats were unaffected by treatment with L-5-HTP. Cardiac hypertrophy was associated with Dahl salt-induced hypertension. However, treatment with L-5-HTP failed to reduce the weight of the heart significantly. These results suggest that chronic administration of L-5-HTP was effective in reducing the elevated blood pressure in the DS model. The specific mechanisms by which L-5-HTP reduces the elevated blood pressure in DS rats is not clear and remains for further study. [Baron A et al; Pharmacology 42 (1): 15-22 (1991)]
【Biomedical Effects and Toxicity】
The immediate precursor in the serotonin synthetic route, 5-hydroxytryptophan (5-HTP), labeled with 11C in the beta position, has become available for studies using positron emission tomography (PET) to examine serotonin formation in human brain. Normalized uptake and intracerebral utilization of tracer amounts of (beta-11C)5-HTP were studied twice in six healthy male volunteers, three of them before and after pharmacological pretreatments ... Pretreatments with benserazide, p-chlorophenylalanine (PCPA), and unlabeled 5-HTP all significantly increased uptake of (beta-11C)5-HTP. The utilization rates in both striatal and frontal cortex were higher than those in the surrounding brain, indicating that PET studies using (beta-11C)5-HTP as a ligand quantitate selective processes in the utilization of 5-HTP. [Reibring L et al; Psychiatry Res 45(4): 215-25 (1992)] PubMed Abstract
The efficiency of absorption of 5HTP, as well as its decarboxylation product serotonin, is approximately 47% to 84%. Absorption of 5-HTP occurs by an active transport process. 5-HTP is transported by the portal circulation to the liver where approximately 25% of an administered dose is metabolized ... . 5-HTP that is not metabolized in the liver is transported by the general circulation to the various tissues of the body, including the brain. 5-HTP readily crosses the blood-brain barrier, and is converted to serotonin in brain cells.

Supplier Location

Top Suppliers

Diamond member Nanjing Bangnuo Biotechnology Co., Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-1732-7098554
Diamond member Hubei XinRunde Chemical Co., Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-188-74586545
Diamond member Hangzhou Dayangchem Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-571-88938639
Diamond member Wuhan Fortuna Chemical Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:0086-27-59207850
Diamond member FORT ST BIOLOGICAL TECHNOLOGY LIMITED
Country:ChinaChina
Business Type:Trading Company
Telephone:86-311-13292230735
Diamond member Jinlan Pharm-Drugs Technology Co., Limited
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-571-85829152
Diamond member AOPHARM
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-311-66600578
Diamond member Hangzhou J&H Chemical Co., Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-571-87396430
Shaanxi Yi An Biological Technology Co.,Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-29-88967065
Chengdu Herbpurify CO.,LTD
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-28-85249238

Quick Search

Cas    Name

Related products

L-Tryptophan,5-hydroxy-

Tryptophan,5-hydroxy-, L- (8CI);(S)-5-Hydroxytryptophan;5-Hydroxy-L-tryptophan;5-Hydroxyl-L-tryptophan;5-Hydroxytryptophan;Cincofarm;L-5-HTP;L-5-Hydro...

D-Tryptophan,5-hydroxy-

Tryptophan,5-hydroxy-, D- (8CI); 5-Hydroxy-D-tryptophan; D-5-HTP; D-5-Hydroxytryptophan

5-Hydroxy L-Tryptophan

5-Hydroxy L-Tryptophan-d4 (Major)

BOC-5-HYDROXY-L-TRYPTOPHAN

BOC-TRP(5-OH)-OH;BOC-5-HYDROXY-L-TRYPTOPHAN;BOC-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID;BOC-L-5-HYDROXYTRYPTOPHAN

Tryptophan, 5-hydroxy-alpha-methyl-

AC1O56U4;(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)-2-methylpropanoic acid

FMOC-5-HYDROXY-L-TRYPTOPHAN

FMOC-5-HYDROXY-L-TRYPTOPHAN

FMOC-5-HYDROXY-DL-TRYPTOPHAN

FMOC-5-HYDROXY-DL-TRYPTOPHAN

FMoc-5-Hydroxy-D-tryptophan

FMoc-5-Hydroxy-D-tryptophan

Boc-5-hydroxy-D-tryptophan

Boc-5-hydroxy-D-tryptophan

BOC-5-HYDROXY-DL-TRYPTOPHAN

BOC-5-HYDROXY-DL-TRYPTOPHAN

L-Tryptophan, a-(fluoromethyl)-5-hydroxy- (9CI)

alpha-(fluoromethyl)-5-hydroxytryptophan