Oxitriptan | CAS#4350-09-8

Oxitriptan
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318400

CAS#: 4350-09-8

Description: Oxitriptan 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. It is used as an antiepileptic and antidepressant.

Chemical Structure

Oxitriptan

CAS# 4350-09-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318400
Name: Oxitriptan
CAS#: 4350-09-8
Chemical Formula: C11H12N2O3
Exact Mass: 220.08
Molecular Weight: 220.225
Elemental Analysis: C, 59.99; H, 5.49; N, 12.72; O, 21.80

Price and Availability

Size	Price	Availability	Quantity
100g	USD -1
200g	USD -1
10mg	USD 220
25mg	USD 250
50mg	USD 280
100mg	USD 300
200mg	USD 350
500mg	USD 450
1g	USD 550
2g	USD 650
5g	USD 850
10g	USD 1050
20g	USD 1250
50g	USD 1450
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Appearance: Solid powder

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

More Info:

Product Data:

Product Data

Instruction:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	28.3	128.28
	Water	2.0	9.08

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.

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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.

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