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MedKoo Cat#: 540213 | Name: Hydroxytryptophol
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Description:

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

Hydroxytryptophol is a serotonin/melatonin analog found in various plant and food soruces and Trypanosoma brucei. It is used as a biomarker for recent alcohol consumption and causes sleeping sickness. It also inhibits oxidation of LDL.

Chemical Structure

Hydroxytryptophol
Hydroxytryptophol
CAS#154-02-9

Theoretical Analysis

MedKoo Cat#: 540213

Name: Hydroxytryptophol

CAS#: 154-02-9

Chemical Formula: C10H11NO2

Exact Mass: 177.0790

Molecular Weight: 177.20

Elemental Analysis: C, 67.78; H, 6.26; N, 7.90; O, 18.06

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
25mg USD 450.00 2 Weeks
100mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
5-Hydroxy-1H-indole-3-ethanol; 5-Hydroxyindole-3-ethanol; 5-Hydroxytryptophol
IUPAC/Chemical Name
3-(2-hydroxyethyl)-1H-indol-5-ol
InChi Key
KQROHCSYOGBQGJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2
SMILES Code
OCCC1=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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 177.20 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.

Recalculate based on batch purity %
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
1: Bergqvist PB, Some M, Apelqvist G, Helander A, Bengtsson F. Elevated brain 5-hydroxytryptophol levels in experimental portal-systemic encephalopathy. Pharmacol Toxicol. 1997 Apr;80(4):187-90. PubMed PMID: 9140138. 2: Dierkes J, Wolfersdorf M, Borucki K, Weinmann W, Wiesbeck G, Beck O, Borg S, Wurst FM. Determination of glucuronidated 5-hydroxytryptophol (GTOL), a marker of recent alcohol intake, by ELISA technique. Clin Biochem. 2007 Jan;40(1-2):128-31. Epub 2006 Oct 20. PubMed PMID: 17112495. 3: Krishnaswamy S, Hao Q, Von Moltke LL, Greenblatt DJ, Court MH. Evaluation of 5-hydroxytryptophol and other endogenous serotonin (5-hydroxytryptamine) analogs as substrates for UDP-glucuronosyltransferase 1A6. Drug Metab Dispos. 2004 Aug;32(8):862-9. PubMed PMID: 15258112. 4: Beck O, Eriksson CJ, Kiianmaa K, Lundman A. 5-Hydroxyindoleacetic acid and 5-hydroxytryptophol levels in rat brain: effects of ethanol, pyrazole, cyanamide and disulfiram treatment. Drug Alcohol Depend. 1986 Feb;16(4):303-8. PubMed PMID: 2421991. 5: Beck O, Borg S, Eriksson L, Lundman A. 5-hydroxytryptophol in the cerebrospinal fluid and urine of alcoholics and healthy subjects. Naunyn Schmiedebergs Arch Pharmacol. 1982 Dec;321(4):293-7. PubMed PMID: 7167204. 6: Spies CD, Herpell J, Beck O, Müller C, Pragst F, Borg S, Helander A. The urinary ratio of 5-hydroxytryptophol to 5-hydroxyindole-3-acetic acid in surgical patients with chronic alcohol misuse. Alcohol. 1999 Jan;17(1):19-27. PubMed PMID: 9895033. 7: Stephanson N, Dahl H, Helander A, Beck O. Determination of urinary 5-hydroxytryptophol glucuronide by liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Feb 25;816(1-2):107-12. PubMed PMID: 15664340. 8: Beck O, Borg S, Edman G, Fyrö B, Oxenstierna G, Sedvall G. 5-hydroxytryptophol in human cerebrospinal fluid: conjugation, concentration gradient, relationship to 5-hydroxyindoleacetic acid, and influence of hereditary factors. J Neurochem. 1984 Jul;43(1):58-61. PubMed PMID: 6202846. 9: Helander A, Beck O, Borg S. The use of 5-hydroxytryptophol as an alcohol intake marker. Alcohol Alcohol Suppl. 1994;2:497-502. Review. PubMed PMID: 8974374. 10: Yoshimoto K, Komura S, Kawamura K. Occurrence in vivo of 5-hydroxytryptophol in the brain of rats treated with ethanol. Alcohol Alcohol. 1992 Mar;27(2):131-6. PubMed PMID: 1524603. 11: Voltaire A, Beck O, Borg S. Urinary 5-hydroxytryptophol: a possible marker of recent alcohol consumption. Alcohol Clin Exp Res. 1992 Apr;16(2):281-5. PubMed PMID: 1375446. 12: Cheng FC, Dryhurst G. Electrochemical oxidation of 5-hydroxytryptophol. I: Studies in acid solution. J Pharm Sci. 1990 Mar;79(3):266-72. PubMed PMID: 2338638. 13: Beck O, Lundman A, Jonsson G. 5-Hydroxytryptophol and 5-hydroxyindoleacetic acid levels in rat brain: effects of various drugs affecting serotonergic transmitter mechanisms. J Neural Transm. 1987;69(3-4):287-98. PubMed PMID: 2442302. 14: Helander A, Beck O, Jones AW. Laboratory testing for recent alcohol consumption: comparison of ethanol, methanol, and 5-hydroxytryptophol. Clin Chem. 1996 Apr;42(4):618-24. PubMed PMID: 8605681. 15: Helander A, Wikström T, Löwenmo C, Jacobsson G, Beck O. Urinary excretion of 5-hydroxyindole-3-acetic acid and 5-hydroxytryptophol after oral loading with serotonin. Life Sci. 1992;50(17):1207-13. PubMed PMID: 1373788. 16: Helander A, Beck O, Jones AW. Distinguishing ingested ethanol from microbial formation by analysis of urinary 5-hydroxytryptophol and 5-hydroxyindoleacetic acid. J Forensic Sci. 1995 Jan;40(1):95-8. PubMed PMID: 7533206. 17: Beck O, Stephanson N, Böttcher M, Dahmen N, Fehr C, Helander A. Biomarkers to disclose recent intake of alcohol: potential of 5-hydroxytryptophol glucuronide testing using new direct UPLC-tandem MS and ELISA methods. Alcohol Alcohol. 2007 Jul-Aug;42(4):321-5. Epub 2007 May 28. PubMed PMID: 17533162. 18: Beck O, Borg S, Jonsson G, Lundman A, Valverius P. Measurement of 5-hydroxytryptophol and 5-hydroxyindoleacetic acid in human and rat brain and plasma. J Neural Transm. 1984;59(1):57-67. PubMed PMID: 6201590. 19: Hagan RL, Helander A. Urinary 5-hydroxytryptophol following acute ethanol consumption: clinical evaluation and potential aviation applications. Aviat Space Environ Med. 1997 Jan;68(1):30-4. PubMed PMID: 9006879. 20: Stephanson N, Helander A, Beck O. Alcohol biomarker analysis: simultaneous determination of 5-hydroxytryptophol glucuronide and 5-hydroxyindoleacetic acid by direct injection of urine using ultra-performance liquid chromatography-tandem mass spectrometry. J Mass Spectrom. 2007 Jul;42(7):940-9. PubMed PMID: 17565712.

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