Synonym
Oxitriptan, 5 Hydroxytryptophan, 5-hydroxy-L-tryptophan, 5-HTP, Oxytryptophan
IUPAC/Chemical Name
(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
InChi Key
LDCYZAJDBXYCGN-VIFPVBQESA-N
InChi Code
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
SMILES Code
O=C(O)[C@@H](N)CC1=CNC2=C1C=C(O)C=C2
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
L-5-Hydroxytryptophan (L-5-HTP), a naturally occurring amino acid and a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid, is the immediate precursor of the neurotransmitter serotonin and a reserpine antagonist.
In vitro activity:
L-5-HTP suppressed IFN-γ-induced PD-L1 expression in tumor cells transcriptionally, and this effect was directly due to itself. Mechanistically, L-5-HTP inhibited IFN-γ-induced expression of RTK ligands and thus suppressed phosphorylation-mediated activation of RTK receptors and the downstream MEK/ERK/c-JUN signaling cascade, leading to decreased PD-L1 induction.
Reference: J Immunother Cancer. 2022 Jun;10(6):e003957. https://pubmed.ncbi.nlm.nih.gov/35728870/
In vivo activity:
Finally, systemic administration of 5-hydroxytryptophan, the product of tryptophan hydroxylase activity, allowed frontal cortical serotonin response to stress in hyperphenylalaninaemic mice. Collectively, these results demonstrate that hyperphenylalaninaemia interferes with the ability of the mature prefrontal cortex to respond to psychological challenges, point to serotonin synthesis as the target of phenylalanine interference, and support the use of 5-hydroxytryptophan in lifelong treatment of hyperphenylalaninaemic subjects.
Reference: Int J Neuropsychopharmacol. 2009 Sep;12(8):1067-79. https://pubmed.ncbi.nlm.nih.gov/19664307/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
28.3 |
128.28 |
| Water |
2.0 |
9.08 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
220.22
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Huang J, Wang X, Li B, Shen S, Wang R, Tao H, Hu J, Yu J, Jiang H, Chen K, Luo C, Dang Y, Zhang Y. L-5-hydroxytryptophan promotes antitumor immunity by inhibiting PD-L1 inducible expression. J Immunother Cancer. 2022 Jun;10(6):e003957. doi: 10.1136/jitc-2021-003957. PMID: 35728870; PMCID: PMC9214382.
2. Choi Y, Huh E, Lee S, Kim JH, Park MG, Seo SY, Kim SY, Oh MS. 5-Hydroxytryptophan Reduces Levodopa-Induced Dyskinesia via Regulating AKT/mTOR/S6K and CREB/ΔFosB Signals in a Mouse Model of Parkinson's Disease. Biomol Ther (Seoul). 2023 Mar 15. doi: 10.4062/biomolther.2022.141. Epub ahead of print. PMID: 36918741.
3. Pascucci T, Andolina D, Mela IL, Conversi D, Latagliata C, Ventura R, Puglisi-Allegra S, Cabib S. 5-Hydroxytryptophan rescues serotonin response to stress in prefrontal cortex of hyperphenylalaninaemic mice. Int J Neuropsychopharmacol. 2009 Sep;12(8):1067-79. doi: 10.1017/S1461145709990381. Epub 2009 Aug 10. PMID: 19664307.
In vitro protocol:
1. Huang J, Wang X, Li B, Shen S, Wang R, Tao H, Hu J, Yu J, Jiang H, Chen K, Luo C, Dang Y, Zhang Y. L-5-hydroxytryptophan promotes antitumor immunity by inhibiting PD-L1 inducible expression. J Immunother Cancer. 2022 Jun;10(6):e003957. doi: 10.1136/jitc-2021-003957. PMID: 35728870; PMCID: PMC9214382.
In vivo protocol:
1. Choi Y, Huh E, Lee S, Kim JH, Park MG, Seo SY, Kim SY, Oh MS. 5-Hydroxytryptophan Reduces Levodopa-Induced Dyskinesia via Regulating AKT/mTOR/S6K and CREB/ΔFosB Signals in a Mouse Model of Parkinson's Disease. Biomol Ther (Seoul). 2023 Mar 15. doi: 10.4062/biomolther.2022.141. Epub ahead of print. PMID: 36918741.
2. Pascucci T, Andolina D, Mela IL, Conversi D, Latagliata C, Ventura R, Puglisi-Allegra S, Cabib S. 5-Hydroxytryptophan rescues serotonin response to stress in prefrontal cortex of hyperphenylalaninaemic mice. Int J Neuropsychopharmacol. 2009 Sep;12(8):1067-79. doi: 10.1017/S1461145709990381. Epub 2009 Aug 10. PMID: 19664307.
1: Shaw K, Turner J, Del Mar C. Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. Review. PubMed PMID: 11869656.
2: Lampert A, Joly P, Thomine E, Ortoli JC, Lauret P. [Scleroderma-like syndrome with bullous morphea during treatment with 5-hydroxytryptophan, carbidopa and flunitrazepam]. Ann Dermatol Venereol. 1992;119(3):209-11. Review. French. PubMed PMID: 1605525.
3: Simic MG, al-Sheikhly M, Jovanovic SV. Inhibition of free radical processes by antioxidants--tryptophan and 5-hydroxytryptophan. Bibl Nutr Dieta. 1989;(43):288-96. Review. PubMed PMID: 2658964.
4: Meltzer HY. Serotonergic function in the affective disorders: the effect of antidepressants and lithium on the 5-hydroxytryptophan-induced increase in serum cortisol. Ann N Y Acad Sci. 1984;430:115-37. Review. PubMed PMID: 6378031.
5: 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. Review. PubMed PMID: 16023217.
6: Corrêa F, Farah CS. Using 5-hydroxytryptophan as a probe to follow protein-protein interactions and protein folding transitions. Protein Pept Lett. 2005 Apr;12(3):241-4. Review. PubMed PMID: 15777272.
7: Shaw K, Turner J, Del Mar C. Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2001;(3):CD003198. Review. Update in: Cochrane Database Syst Rev. 2002;(1):CD003198. PubMed PMID: 11687048.
8: Birdsall TC. 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. Review. PubMed PMID: 9727088.
9: Milovanovic L, Kapetanovic V. Polarographic and potentiometric investigation of Co(II) complexes with 5-hydroxytryptophan. J Pharm Belg. 1993 Mar-Apr;48(2):85-91. Review. PubMed PMID: 8492290.
10: van Praag HM, Kahn RS. L-5-hydroxytryptophan in depression and anxiety. Schweiz Rundsch Med Prax. 1988 Aug 23;77(34A):40-6. Review. PubMed PMID: 3055148.
11: Uldry PA, Regli F. [Indications for L-5-hydroxytryptophan in neurology]. Rev Med Suisse Romande. 1987 Sep;107(9):703-7. Review. French. PubMed PMID: 2962265.
12: Byerley WF, Judd LL, Reimherr FW, Grosser BI. 5-Hydroxytryptophan: a review of its antidepressant efficacy and adverse effects. J Clin Psychopharmacol. 1987 Jun;7(3):127-37. Review. PubMed PMID: 3298325.
