5-Hydroxytryptophan
- Iupac Name：2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
- CAS No.: 56-69-9
- Molecular Weight：220.22458
- Modify Date.: 2023-02-01 20:09
- Introduction: 5-Hydroxytryptophan, a tryptophan metabolite, is a direct 5-hydroxytryptamine (5-HT) precursor and an L-aromatic amino acid decarboxylase substrate. [1][2][3].
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1. Names and Identifiers
- 1.1 Name
- 5-Hydroxytryptophan
- 1.2 Synonyms
(±)-5-hydroxytryptophan 2-Chloro-3-methylamine-5-trifluoromethylpyridine hydrochloride 5-HTP (Griffonia Seeds P.E.) 5-Hydroxy Tryptophan 5-HYDROXY-DL-TRYPTOPHAN 5-HYDROXY-TRYPTOPHAN 5-Hydroxytryptophan DL-form 5-Hydroxytryptophan(5-HTP) DL-2-Amino-3-(5-hydroxyindolyl)propionic acid, DL-5-HTP DL-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID DL-5-HTP DL-5-HYDROXYTRYPTOPHAN EINECS 200-284-8 HYDROXYTRYPTOPHAN MFCD00005651 Tryptophan, 5-hydroxy- Tryptophan, 5-hydroxy-, DL-
- 1.3 CAS No.
- 56-69-9
- 1.4 CID
- 144
- 1.5 EINECS(EC#)
- 200-284-8
- 1.6 Molecular Formula
- C11H12N2O3 (isomer)
- 1.7 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)
- 1.8 InChIkey
- LDCYZAJDBXYCGN-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N
- 1.10 Isomers Smiles
- C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N
2. Properties
- 2.1 Density
- 1.484
- 2.1 Melting point
- 298-300℃
- 2.1 Boiling point
- 520.6°C at 760 mmHg
- 2.1 Refractive index
- 1.737
- 2.1 Flash Point
- 268.7°C
- 2.1 Precise Quality
- 220.084793
- 2.1 PSA
- 99.34000
- 2.1 logP
- 1.52820
- 2.1 Solubility
- Soluble in water (4 mg/ml at 25°C), methanol.
- 2.2 Appearance
- Not Available
- 2.3 Storage
- 2-8°C
- 2.4 Chemical Properties
- Off-White to Pale Beige Solid
- 2.5 Color/Form
- White powder
- 2.6 pKa
- 2.22±0.10(Predicted)
- 2.7 Water Solubility
- Solubilities: 2.5 g/100 mL in 50% boiling alcohol; 5.5 g/100 mL in water at 100 deg C
In water, 1X10+4 mg/L at 5 deg C
- 2.8 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)
- 2.9 Stability
- AQ SOLN ARE STABLE @ LOW PH /DL-FORM/
- 2.10 StorageTemp
- Keep in dark place,Sealed in dry,Room Temperature
3. Use and Manufacturing
- 3.1 Usage
- A metabolite of Tryptophan
4. Safety and Handling
- 4.1 Risk Statements
- 25-65-36/37/38-20/21/22-20/21
- 4.1 Safety Statements
- S24/25
- 4.1 Packing Group
- III
- 4.1 Octanol/Water Partition Coefficient
- log Kow = -1.70 (est)
- 4.2 DisposalMethods
- 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.
- 4.3 RIDADR
- 2811
- 4.3 WGK Germany
- 3
- 4.3 RTECS
- YN7100000
- 4.3 Toxicity
- Organic Compound; Amine; Drug; Food Toxin; Metabolite; Nutraceutical; Animal Toxin; Natural Compound; Antidepressive Agent, Second-Generation
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
Acute toxicity - Inhalation, Category 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed H332 Harmful if inhaled |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
56-69-9Total: 4 Synthesis Route
8. Other Information
- 8.0 Chemical Properties
- Off-White to Pale Beige Solid, slightly salty in taste, soluble in methanol, ethanol, DMSO and other organic solvents, derived from African Ghana seeds.
- 8.1 Preparation
- The synthesis of 5-hydroxytryptophan (5-HTP) by the condensation of 5-benzyloxygramine with diethyl formaminomalonate, followed by saponification, decarboxylation, and hydrogenolysis was described in 1951 and 1954 and was an application of gramine synthesis, developed by Snyder and Smith ten years before. A few years later, another application of gramine synthesis was reported. In the same year, Frangatos and Chubb reported an application of the convenient tryptophan synthesis developed ten years before by eliminating the difficult and tedious preparation of 5-benzyloxyindole. The p-benzyloxyphenylhydrazone of γ,γ-dicarbethoxy-γ-acetamido-butyraldehyde (I) was prepared and cyclized, without isolation, to form ethyl β-(5-benzyloxyindol-3-)-αcarbethoxy-α-acetamidopropioilate (II). Saponification and partial decarboxylation of II, followed by hydrolysis of the acetamido group, gave 5-benzyloxytryptophan (III). 5-HTP was obtained by hydrogenolysis of III (Figure 1). However, this synthetic method suffers from the difficulty involved in the regioselective hydroxylation of tryptophan.
synthesis of 5-hydroxytryptophan (5-HTP)
- 8.2 Definition
- ChEBI: 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.
- 8.3 Biosynthesis
- 5-Hydroxytryptophan, an intermediate molecule in the serotonin biosynthesis pathway, is formed by the addition of a hydroxyl (OH) group to the fifth carbon of the indole ring of tryptophan. It is used as an antiepileptic and antidepressant.
- 8.4 Usage
- It is an immediate precursor that is used to assess central serotonergic function. It was used for the treatment of insomnia.
- 8.5 Merck
- 14,4847
- 8.6 BRN
- 88199
- 8.7 Description
- 5-Hydroxytryptophan (5-HTP) is an aromatic amino acid naturally produced by the body from the essential amino acid L-tryptophan (LT). Produced commercially by extraction from the seeds of the African plant, Griffonia simplicifolia, 5-HTP has been used clinically for over 30 years. The clinical efficacy of 5-HTP is due to its ability to increase production of serotonin in the brain.
- 8.8 Chemical Properties
- Off-White to Pale Beige Solid
- 8.9 Originator
- Levotonine,Panmedica,France,1973
- 8.10 Uses
- A metabolite of Tryptophan. 5-Hydroxytryptophan (5-HTP) is a direct 5-hydroxytryptamine (5-HT) precursor used to assess central serotonergic function.
- 8.11 Uses
- 5-Hydroxytryptophan (5-HTP) is an intermediate in the natural synthesis of the essential amino acid, tryptophan, to serotonin. Clinical studies suggest that 5-HTP supports healthy serotonin levels. In the body, 5-HTP converts to serotonin with the enzymatic removal of a carboxyl group (COOH). Serotonin is an important neurotransmitter involved in the regulation of endocrine and brain activity responsible for emotion, appetite and sleep/wake cycles.?
- 8.12 Application
- 5-hydroxytryptophan is a dietary supplement made from the seeds of the African plant Griffonia simplicifolia.
5-hydroxytryptophan has been used in alternative medicine as a possibly effective aid in treating depression or fibromyalgia.
Other uses not proven with research have included insomnia, alcohol withdrawal, headaches, premenstrual syndrome, binge-eating related to obesity, attention deficit disorder, and muscle spasms in the mouth.
5-hydroxytryptophan is often sold as an herbal supplement. There are no regulated manufacturing standards in place for many herbal compounds and some marketed supplements have been found to be contaminated with toxic metals or other drugs. Herbal/health supplements should be purchased from a reliable source to minimize the risk of contamination.
- 8.13 Manufacturing Process
- Preparation of 5-Hydroxytryptophan: 0.4 gram palladium chloride and 1.7 grams acid-washed charcoal were suspended in 157 ml water and hydrogenated at room temperature and atmospheric pressure until no further hydrogen uptake occurred. A suspension of 14.2 grams 5- benzyloxytryptophan in 175 ml ethyl alcohol was added and the mixture hydrogenated under similar conditions. A hydrogen uptake slightly in excess of theory was obtained. The suspension was warmed for a few minutes on the steam bath and filtered hot. The filter-cake was washed with hot water (3 x 20 ml) and the filtrate evaporated to 20 ml under reduced pressure in a nitrogen atmosphere.
The resultant mass of colorless crystals was triturated with 250 ml ice-cold ethyl alcohol under hydrogen, filtered, and washed with cold ethyl alcohol (2 x 15 ml). The 5-hydroxytryptophan (6.9 grams, 69%) had MP (sealed evacuated tube) 288°C, with softening, finally melting at 249° to 247°C (decomposition). Concentration of the liquors under reduced pressure in a nitrogen atmosphere, and trituration as before, gave a second crop (0.9 gram, 9%). The combined crops (7.8 grams) were dissolved in 120 ml hot water, charcoal added, and the mixture filtered hot. The filtrate was concentrated in a nitrogen atmosphere under reduced pressure and ethyl alcohol added. The 5-hydroxytryptophan then crystallized as colorless microneedles (6.5 grams,65%), had MP (sealed evacuated tube) 290°C, with slight softening, finally melting at 295° to 297°C (decomposition).
- 8.14 Therapeutic Function
- Antidepressant, Antiepileptic
- 8.15 Biochem/physiol Actions
- Immediate precursor of serotonin; L-aromatic amino acid decarboxylase substrate.
- 8.16 Source
- 5-HTP is derived from the Griffonia simplicifolia plant. Hypo-allergenic plant fiber is derived from pine cellulose.
- 8.17 Mode of action
- 5-Hydroxytryptophan acts primarily by increasing levels of serotonin within the central nervous system. Other neurotransmitters and CNS chemicals, such as melatonin, dopamine, norepinephrine, and beta-endorphin have also been shown to increase following oral administration of 5-HTP. This ability to increase not only serotonin levels in the brain, but also dopamine and norepinephrine, allows 5-HTP to produce some significant and unique effects on brain chemistry and on serotonin-related conditions which other substances, including LT, cannot duplicate.?
9. Computational chemical data
- Molecular Weight: 220.22458g/mol
- Molecular Formula: C11H12N2O3
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 220.08479225
- Monoisotopic Mass: 220.08479225
- Complexity: 272
- Rotatable Bond Count: 3
- Hydrogen Bond Donor Count: 4
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 99.3
- Heavy Atom Count: 16
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 1
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBzMAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgB8AAAHgAQCAAADCzBngQ8zvLJkgCoAzT3TACCgCAxIiAI2aG+bJgKJvLCkZOEcAhk0BHI2Ae42fKOgEABAAACAAAAgAIAAAQAAAAAAAAAAA==
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