56-69-9 Usage
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.
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.
Originator
Levotonine,Panmedica,France,1973
Uses
Different sources of media describe the Uses of 56-69-9 differently. You can refer to the following data:
1. A metabolite of Tryptophan. 5-Hydroxytryptophan (5-HTP) is a direct 5-hydroxytryptamine (5-HT) precursor used to assess central serotonergic function.
2. 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.
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)
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.
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.
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).
Therapeutic Function
Antidepressant, Antiepileptic
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.
Biochem/physiol Actions
Immediate precursor of serotonin; L-aromatic amino acid decarboxylase substrate.
Source
5-HTP is derived from the Griffonia simplicifolia plant. Hypo-allergenic plant fiber is derived from pine cellulose.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 56-69-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 56-69:
(4*5)+(3*6)+(2*6)+(1*9)=59
59 % 10 = 9
So 56-69-9 is a valid CAS Registry Number.
InChI:InChI=1/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)/t9-/m0/s1
56-69-9Relevant articles and documents
Syntheses of Substituted L- and D-Tryptophans
Irie, Kunihiko,Ishida, Akihiko,Nakamura, Tohru,Oh-ishi, Tokuro
, p. 2126 - 2139 (2007/10/02)
Several 5-substituted nb-methoxycarbonyl-L- and -D-tryptophan derivatives were synthesized from proline by a new route involving electrochemical oxidation, as well as by the known procedures.Removal of the Nb-methoxycarbonyl group was accomplished by treatment with Me3SiI in refluxing chloroform, then alkaline hydrolysis of the methyl esters afforded 5-substituted L- and D-tryptophans with high optical purities.Keywords - L-tryptophan 5-substituted; D-tryptophan 5-substituted; anodic oxidation; N-methoxycarbonyl group deprotection; Fischer indole synthesis; iodotrimethylsilane
5-HYDROXYTRYPTOPHAN AND SOLUBLE PIGMENT FORMATION IN CLAVICEPS SP. PRL 1980
Cho, Sung-Hwan,Anderson, John A.
, p. 1975 - 1976 (2007/10/02)
5-Hydroxytryptophan (156 mg/l) was identified in 15-day-old cultures of Claviceps sp.PRL 1980. DL-Tryptophan and 5-hydroxytryptophan were incorporated into the brown pigment in cultures of the same fungus, 6percent and 24percent, respectively.Key Word Index - Claviceps sp.PRL 1980; Clavicipitaceae; ergot; 5-hydroxytryptophan; pigment; biosynthesis.
Preparation of 5 hydroxytryptophan by microbiologic hydroxylation of L tryptophan
Daum,Kieslich
, p. 167 - 168 (2007/10/04)
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