Hydroxytryptophol | CAS#154-02-9 | serotonin/melatonin analog

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

MedKoo CAT#: 540213

CAS#: 154-02-9

Description: 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

CAS# 154-02-9

Instruction

Theoretical Analysis

MedKoo Cat#: 540213
Name: Hydroxytryptophol
CAS#: 154-02-9
Chemical Formula: C10H11NO2
Exact Mass: 177.08
Molecular Weight: 177.200
Elemental Analysis: C, 67.78; H, 6.26; N, 7.90; O, 18.06

Price and Availability

Size	Price	Availability
10mg	USD 250	2 Weeks
25mg	USD 450	2 Weeks
100mg	USD 950	2 Weeks
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: 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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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:
In vitro protocol:
In vivo protocol:

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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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