5-Hydroxy-L-tryptophan
5-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid l-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic l-amino acid decarboxylase (EC 4.1.1.28, AADC1 also known as dopa decarboxylase), an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumliation of 5-Hydroxy-L-tryptophan in cerebrospinal fluid occurs in Aromatic l-amino acid decarboxylase deficiency (OMIM 608643 ), accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinsons patients with severe postural instability and gait disorders. Confirmation of the diagnosis AADC deficiency is then required by enzyme activity measurement or genetic analysis. The amount of endogenous 5-Hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase (EC 1.14.16.4), indoleamine 2,3-dioxygenase (EC 1.13.11.52), and tryptophan 2,3-dioxygenase. (EC 1.13.11.11, TDO). 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to depression, the therapeutic administration of 5-Hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system (CNS) synthesis of serotonin. Supplementation with 5-Hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties. (PMID: 9295177 , 17240182 , 16023217 ).
Structure for HMDB00472 (5-Hydroxy-L-tryptophan)
C11H12N2O3
220.2246
220.08479226
2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
DL-5-hydroxytryptophan
4350-09-8
LDCYZAJDBXYCGN-UHFFFAOYSA-N
This compound belongs to the class of chemical entities known as serotonins. These are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.
Chemical entities
Organic compounds
Organoheterocyclic compounds
Indoles and derivatives
Serotonins
Aromatic heteropolycyclic compounds
Detected and Quantified
Not Available
Solid
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0090000000-823f10e31a9f15588233View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-053r-0900000000-d763102ca4968c158d29View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-053r-0900000000-500716cec2e9f8383df7View in MoNA
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0udi-0090000000-44c37ec15a5546b1c353View in MoNA
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-03di-0910000000-5e6f9e21dd30ec8c20f3View in MoNA
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001i-0900000000-b656dc85b8aff47fea96View in MoNA
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001i-3900000000-94c7412dbb7cb04c9f32View in MoNA
LC-MS/MS Spectrum – , positivesplash10-0w29-0790000000-233a5164a2a4514e5bb9View in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
None
None
DB02959
Not Available
Not Available
Not Available
FDB006231
C00001371
141
C01017
5-HYDROXY-TRYPTOPHAN
36630
5-HTP
HMDB00472
HMDB00472
Not Available
144
Not Available
28171
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- Magnussen I, Van Woert MH: Human pharmacokinetics of long term 5-hydroxytryptophan combined with decarboxylase inhibitors. Eur J Clin Pharmacol. 1982;23(1):81-6. [PubMed:6182005 ]
- Li Kam Wa TC, Freestone S, Samson RR, Johnson NR, Lee MR: A comparison of the renal and neuroendocrine effects of two 5-hydroxytryptamine renal prodrugs in normal man. Clin Sci (Lond). 1993 Nov;85(5):607-14. [PubMed:8287650 ]
- Li Kam Wa TC, Freestone S, Samson RR, Johnston NR, Lee MR: Renal metabolism and effects of the glutamyl derivatives of L-dopa and 5-hydroxytryptophan in man. Clin Sci (Lond). 1996 Aug;91(2):177-85. [PubMed:8795441 ]
- Iacono RP, Kuniyoshi SM, Ahlman JR, Zimmerman GJ, Maeda G, Pearlstein RD: Concentrations of indoleamine metabolic intermediates in the ventricular cerebrospinal fluid of advanced Parkinsons patients with severe postural instability and gait disorders. J Neural Transm (Vienna). 1997;104(4-5):451-9. [PubMed:9295177 ]
- Verbeek MM, Geurtz PB, Willemsen MA, Wevers RA: Aromatic L-amino acid decarboxylase enzyme activity in deficient patients and heterozygotes. Mol Genet Metab. 2007 Apr;90(4):363-9. Epub 2007 Jan 19. [PubMed:17240182 ]
- Turner EH, Loftis JM, Blackwell AD: Serotonin a la carte: supplementation with the serotonin precursor 5-hydroxytryptophan. Pharmacol Ther. 2006 Mar;109(3):325-38. Epub 2005 Jul 14. [PubMed:16023217 ]
- 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:39668 ]
- 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:1088369 ]
- 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:2193835 ]
- 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:3913752 ]
- 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:6175178 ]
- 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:6983619 ]
- 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:6997735 ]
- 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 Friedreichs ataxia. Results of a double-blind drug-placebo cooperative study. Arch Neurol. 1995 May;52(5):456-60. [PubMed:7733839 ]
- Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. [PubMed:9727088 ]
- Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. [PubMed:11869656 ]
- 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:15893130 ]
- 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. doi: 10.1111/j.1460-9568.2008.06201.x. [PubMed:18445233 ]
Enzymes
- General function:
- Involved in carboxy-lyase activity
- Specific function:
- Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
- Gene Name:
- DDC
- Uniprot ID:
- P20711
- Molecular weight:
- 53893.755
- General function:
- Involved in heme binding
- Specific function:
- Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
- Gene Name:
- IDO1
- Uniprot ID:
- P14902
- Molecular weight:
- 45325.89
- General function:
- Involved in amino acid binding
- Specific function:
- Not Available
- Gene Name:
- TPH1
- Uniprot ID:
- P17752
- Molecular weight:
- 50984.725
- General function:
- Involved in amino acid binding
- Specific function:
- Not Available
- Gene Name:
- TPH2
- Uniprot ID:
- Q8IWU9
- Molecular weight:
- 56056.295
- General function:
- Involved in heme binding
- Specific function:
- Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
- Gene Name:
- IDO2
- Uniprot ID:
- Q6ZQW0
- Molecular weight:
- 47074.745