(2S)-2-amino-3-(5-hydroxyindol-3-yl)propanoic acid

• ChemBase ID: 2668
• Molecular Formular: C11H12N2O3
• Molecular Mass: 220.22458
• Monoisotopic Mass: 220.08479225
• SMILES: N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cc1c[nH]c2c1cc(O)cc2)N
• 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)/t9-/m0/s1
• InChIKey: LDCYZAJDBXYCGN-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(5-hydroxyindol-3-yl)propanoic acid; (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: hydroxytryptophan; tryptophan, 5-hydroxy-, DL-; 5-hydroxytryptophan; 5-hydroxy-L-tryptophan; (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
• Synonyms: 5-Hydroxytryptophan; (S)-5-Hydroxytryptophan; 5-Hydroxyl-L-tryptophan; 5-Hydroxytryptophan; Cincofarm; Levothym; Levotinine; Oxitriptan; Oxyfan; Pretonine; Quietim; Serotonyl; Telesol; Tript-Oh; Triptene; 5-Hydroxy L-Tryptophan; 5-Hydroxy-L-Tryptophan; L-2-Amino-3-(5-hydroxyindolyl)propionic acid; 5-Hydroxy-L-tryptophan; L-5-HTP; L-5-Hydroxytryptophan; L-2-Amino-3-[3-(5-hydroxyindole)]propionic acid; 5-HTP; L-5-Hydroxytryptophan hydrate; Oxitriptan; 5-羟基-L-色氨酸; L-5-羟基色氨酸水合物

Database IDs

• CAS Number: 56-69-9; 4350-09-8
• EC Number: 224-411-1
• MDL Number: MFCD00064341
• Beilstein Number: 88200
• Merck Index: 144847
• PubChem SID: 24278131; 160966117; 24846778; 24880254
• PubChem CID: 144; 439280
• CHEBI ID: 17780
• ATC CODE: N06AX01
• CHEMBL: 350221
• Chemspider ID: 388413
• KEGG ID: D07339
• MeSH Name: 5-Hydroxytryptophan
• Unique Ingredient Identifier: C1LJO185Q9
• Wikipedia Title: 5-Hydroxytryptophan

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.152664
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -1.3896201
• LogD (pH = 7.4): -1.3962954
• Log P: -1.3896985
• Molar Refractivity: 58.1837 cm^3
• Polarizability: 23.689636 Å^3
• Polar Surface Area: 99.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.56
• LOG S: -1.78
• Solubility (Water): 3.63e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid; powder
• Melting Point: ~275 °C (dec.); 222-224°C (dec.); 258°C dec.; 270 °C (dec.)(lit.); 270°C (dec.); 298 - 300°C
• Boiling Point: 520.6°C
• Density: 0.902 g/mL at 25 °C(lit.); 1.484 g/mL
• Refractive Index: n20/D 1.4850(lit.)
• Optical Rotation: [α]20/D -33±2°, c = 1% in H2O; [α]22/D -30°, c = 1 in H2O; -33 (c=1 in water)

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• Storage Warning: IRRITANT
• RTECS: YN7110000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22; 22-36/37/38; R:22-36/37/38
• Safety Statements: 26; 36; S:25-26-36/37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335; H302
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338; P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR4(3360), HTR5A(3361), HTR5B(645694), HTR6(3362), HTR7(3363)
• Mechanism of Action: Precusor of 5-hydroxytryptamine

Product Information

• Purity: ≥99.0% (calc. based on dry substance, NT); 95+%; 98%; 99%
• Ignition Residue: ≤0.05%
• Biological Source: Metab. of Chromobacterium violaceum, constit. of the seeds of Griffonia simplicifolia. Occurs in large amts. in Panaeolus sphinctrinus and other Panaeolus spp.
• Loss on Drying: ≤2% loss on drying
• Application(s): Antidepressant; Psychostimulant
• Empirical Formula (Hill Notation): C11H12N2O3

DETAILS

MP Biomedicals - 05224995

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02100751

Purity: 99%
Crystalline
Precursor of serotonin

DrugBank - DB02959

• Drug Groups: experimental
• Description: 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN), is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitters serotonin and melatonin from tryptophan. 5-HTP is sold over-the-counter in the United Kingdom, United States and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid, and is also marketed in many European countries for the indication of major depression under trade names like Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. Several double-blind placebo-controlled clinical trials have demonstrated the effectiveness of 5-HTP in the treatment of depression, though a lack of high quality studies has been noted. More and larger studies are needed to determine if 5-HTP is truly effective in treating depression.
• Indication: For use as an antidepressant, appetite suppressant, and sleep aid.
• Pharmacology: The psychoactive action of 5-HTP is derived from its effect on the production of serotonin in central nervous system tissue. More specifically, 5-HTP increases the production of serotonin.
• Affected Organisms: Humans and other mammals
• Biotransformation: 5-Hydroxytryptophan is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme aromatic-L-amino-acid decarboxylase with the help of vitamin B6. This reaction occurs both in nervous tissue and in the liver.
• References: Turner EH, Blackwell AD: 5-Hydroxytryptophan plus SSRIs for interferon-induced depression: synergistic mechanisms for normalizing synaptic serotonin. Med Hypotheses. 2005;65(1):138-44. [Pubmed] ; Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. [Pubmed] ; Rahman MK, Nagatsu T, Sakurai T, Hori S, Abe M, Matsuda M: Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats. Jpn J Pharmacol. 1982 Oct;32(5):803-11. [Pubmed] ; Nakatani Y, Sato-Suzuki I, Tsujino N, Nakasato A, Seki Y, Fumoto M, Arita H: Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat. Eur J Neurosci. 2008 May;27(9):2466-72. [Pubmed] ; Bouchard S, Roberge AG: Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat. Can J Biochem. 1979 Jul;57(7):1014-8. [Pubmed] ; Amamoto T, Sarai K: On the tryptophan-serotonin metabolism in manic-depressive disorders. Changes in plasma 5-HT and 5-HIAA levels and urinary 5-HIAA excretion following oral loading of L-5HTP in patients with depression. Hiroshima J Med Sci. 1976 Sep;25(2-3):135-40. [Pubmed] ; Magnussen I, Jensen TS, Rand JH, Van Woert MH: Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man. Acta Pharmacol Toxicol (Copenh). 1981 Sep;49(3):184-9. [Pubmed] ; Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. [Pubmed] ; Sternberg EM, Van Woert MH, Young SN, Magnussen I, Baker H, Gauthier S, Osterland CK: Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa. N Engl J Med. 1980 Oct 2;303(14):782-7. [Pubmed] ; Caruso I, Sarzi Puttini P, Cazzola M, Azzolini V: Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome. J Int Med Res. 1990 May-Jun;18(3):201-9. [Pubmed] ; Trouillas P, Serratrice G, Laplane D, Rascol A, Augustin P, Barroche G, Clanet M, Degos CF, Desnuelle C, Dumas R, et al.: Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study. Arch Neurol. 1995 May;52(5):456-60. [Pubmed] ; Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. [Pubmed] ; De Benedittis G, Massei R: Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo. J Neurosurg Sci. 1985 Jul-Sep;29(3):239-48. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - H9772

Biochem/physiol Actions
Immediate precursor of serotonin; L-aromatic amino acid decarboxylase substrate.
Caution
Light sensitive
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H9772.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 107751

Packaging
1 g in glass bottle

Sigma Aldrich - 56570

Other Notes
Substrate of choice for the assay of aromatic L-amino acid decarboxylase1

Toronto Research Chemicals - H975710

5-Hydroxy-L-Tryptophan is a hydroxylated metabolite of L-Tryptophan (T947210).

REFERENCES

• Turner EH, Blackwell AD: 5-Hydroxytryptophan plus SSRIs for interferon-induced depression: synergistic mechanisms for normalizing synaptic serotonin. Med Hypotheses. 2005;65(1):138-44. Pubmed
• Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. Pubmed
• Rahman MK, Nagatsu T, Sakurai T, Hori S, Abe M, Matsuda M: Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats. Jpn J Pharmacol. 1982 Oct;32(5):803-11. Pubmed
• Nakatani Y, Sato-Suzuki I, Tsujino N, Nakasato A, Seki Y, Fumoto M, Arita H: Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat. Eur J Neurosci. 2008 May;27(9):2466-72. Pubmed
• Bouchard S, Roberge AG: Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat. Can J Biochem. 1979 Jul;57(7):1014-8. Pubmed
• Amamoto T, Sarai K: On the tryptophan-serotonin metabolism in manic-depressive disorders. Changes in plasma 5-HT and 5-HIAA levels and urinary 5-HIAA excretion following oral loading of L-5HTP in patients with depression. Hiroshima J Med Sci. 1976 Sep;25(2-3):135-40. Pubmed
• Magnussen I, Jensen TS, Rand JH, Van Woert MH: Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man. Acta Pharmacol Toxicol (Copenh). 1981 Sep;49(3):184-9. Pubmed
• Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. Pubmed
• Sternberg EM, Van Woert MH, Young SN, Magnussen I, Baker H, Gauthier S, Osterland CK: Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa. N Engl J Med. 1980 Oct 2;303(14):782-7. Pubmed
• Caruso I, Sarzi Puttini P, Cazzola M, Azzolini V: Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome. J Int Med Res. 1990 May-Jun;18(3):201-9. Pubmed
• Trouillas P, Serratrice G, Laplane D, Rascol A, Augustin P, Barroche G, Clanet M, Degos CF, Desnuelle C, Dumas R, et al.: Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study. Arch Neurol. 1995 May;52(5):456-60. Pubmed
• Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. Pubmed
• De Benedittis G, Massei R: Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo. J Neurosurg Sci. 1985 Jul-Sep;29(3):239-48. Pubmed
• Gartside, S., et al.: Eur. J. Pharmacol., 179, 103 (1990)
• Gijsman, H., et al.: J. Clin. Psychopharmacol., 22, 183 (1990)
• ; Schruers, K., et al.: Psychiatry Res., 113, 237 (1990)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 146B, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 673C; 673D, (ir)
• Witkop, B. et al., J.A.C.S., 1954, 76, 5579, (synth)
• Morris, A.J. et al., J.O.C., 1957, 22, 306, (resoln, abs config)
• Biochem. Prep., 1962, 9, 92, (synth)
• Tyler, V.E. et al., J. Pharm. Sci., 1964, 53, 462, (isol)
• Bell, E.A. et al., Nature (London), 1966, 210, 529, (isol)
• Wakahara, A. et al., Bull. Chem. Soc. Jpn., 1973, 46, 2475, (cryst struct)
• Frahn, J.L. et al., Aust. J. Chem., 1974, 27, 1367, (synth, deriv)
• Iriuchijima, S. et al., Agric. Biol. Chem., 1978, 42, 843, (synth, deriv)
• Francis, P. et al., Biomed. Mass Spectrom., 1980, 7, 294, (ms, deriv)
• Van Praag, H.M., Neuropharmacology, 1983, 22, 433, (rev)
• Irie, K. et al., Chem. Pharm. Bull., 1984, 32, 2126, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HOA575; HOA600; HON800; HOO000; HOO100
• For routes to 2-bromo-5-hydroxytryptophan derivatives, see: Synthesis, 28 (1996).