Art. -Nr.: HY-113440

5-Methoxytryptophol

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5-Methoxytryptophol is a 5-methoxyindole alcohol structurally homologous to Melatonin (HY-B0075). It is secreted by the mammalian pineal gland and exhibits an inverse circadian rhythm. 5-Methoxytryptophol regulates bone metabolism by activating the ERK1/2 pathway. It reduces the levels of pro-inflammatory cytokines TNF-α and IL-1β, as well as proteolytic enzymes MMP-1 and MMP-2, in serum and dental pulp tissues, thereby ameliorating acute pulpitis. 5-Methoxytryptophol induces rapid sleep in mice, while high doses cause respiratory depression and death. 5-Methoxytryptophol. 5-Methoxytryptophol can be used in studies related to acute pulpitis, hypnosis, and bone metabolism.

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Reinheit: 99.95%
CAS. Nr.: 712-09-4
Formel: C₁₁H₁₃NO₂
Molecular Weight:191.23

Speicherung:

Pure form -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

5-Methoxytryptophol Chemical Structure

CAS. Nr.: 712-09-4

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- In Vitro
- In Vivo
Chemical Information
Publications (1)
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

Human Endogenous Metabolite

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In Vitro

5-Methoxytryptophol (0.001-2.5 mM; 24 h) slightly reduces the metabolic activity of MC3T3-E1 preosteoblasts^[2].
5-Methoxytryptophol (0.001-2.5 mM; 48 h) exhibits cytotoxicity against MC3T3-E1 preosteoblasts at concentrations of 1 mM and 2.5 mM, while doses of 0.001 mM and 0.01 mM exert protective effects^[2].
5-Methoxytryptophol (0.001-2.5 mM; 14 days) reduces the total RNA content of MC3T3-E1 preosteoblasts at the concentration of 2.5 mM^[2].
5-Methoxytryptophol (0.001-1 mM; 14 days) reduces Rankl mRNA expression in MC3T3-E1 preosteoblasts in a dose-dependent manner (with a stronger inhibitory effect at low doses than melatonin), and decreases Opg mRNA expression at concentrations of 0.1 and 1 mM^[2].
5-Methoxytryptophol (0.1 mM; 14 days) significantly promotes osteocalcin secretion by MC3T3-E1 preosteoblasts^[2].
5-Methoxytryptophol (0.1 mM; 14 days) enhances the mineralization of MC3T3-E1 preosteoblasts^[2].
5-Methoxytryptophol (0.1 mM; 5 days) inhibits the formation of multinucleated TRAP-positive osteoclasts in RANKL-stimulated RAW264.7 preosteoclasts^[2].
5-Methoxytryptophol (0.1 mM; 5 days) reduces the mRNA expression of Mmp-9 and CtsK in RANKL-stimulated RAW264.7 preosteoclasts, without altering the mRNA level of Trap^[2].
5-Methoxytryptophol (0.1 mM; 5 days) inhibits the bone resorption activity of RANKL-stimulated RAW264.7 preosteoclasts on dentin slices^[2].
5-Methoxytryptophol (0.1 mM; 2 h) activates the ERK1/2 pathway in MC3T3-E1 osteoprogenitor cells and RAW264.7 preosteoclasts (by upregulating the expression of phosphorylated ERK1/2), and this activation is inhibited by pretreatment with the melatonin receptor antagonist luzindole (HY-101254)^[2].
5-Methoxytryptophol (0.01-10 mM; 50 min) inhibits lipid peroxidation in rat liver microsomal membranes, with an IC₅₀ of 0.7 mM. Concentrations of 0.01-3 mM dose-dependently maintain membrane fluidity against oxidative stress, while the 10 mM concentration, although capable of inhibiting lipid peroxidation, fails to prevent membrane rigidification^[4].
5-Methoxytryptophol (0.01-10 mM; 30 min) reduces the membrane fluidity of rat liver microsomal membranes at concentrations of 0.3-10 mM, and does not alter the level of lipid peroxidation in the absence of oxidative stress^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[2]

Cell Line:

MC3T3-E1 preosteoblastic cells
Concentration:

0.001 mM, 0.01 mM, 0.1 mM, 1 mM, 2.5 mM
Incubation Time:

24 h
Result:

Slightly reduced metabolic activity of MC3T3-E1 cells compared to vehicle control.
Showed a dose-response effect.

Cell Cytotoxicity Assay^[2]

Cell Line:

MC3T3-E1 preosteoblastic cells
Concentration:

0.001 mM, 0.01 mM, 0.1 mM, 1 mM, 2.5 mM
Incubation Time:

48 h
Result:

Produced significantly higher LDH release at 2.5 mM and 1 mM compared to control, indicating cytotoxicity.
Showed lower LDH release at 2.5 mM than 2.5 mM melatonin.
Reduced cell death by ≤5% at 0.001 mM and 0.01 mM doses, showing a protective effect.

Real Time qPCR^[2]

Cell Line:

MC3T3-E1 preosteoblastic cells
Concentration:

0.001 mM, 0.01 mM, 0.1 mM, 1 mM
Incubation Time:

14 days
Result:

Significantly decreased Rankl mRNA expression at all tested doses compared to control, with a dose-response effect where higher doses caused greater inhibition.
Decreased Rankl expression more than equivalent doses of melatonin at 0.001-0.1 mM doses.
Significantly decreased Opg mRNA expression at 0.1 mM and 1 mM compared to control.

Real Time qPCR^[2]

Cell Line:

RAW264.7 preosteoclastic cells
Concentration:

0.1 mM (with 4 ng/mL RANKL co-treatment)
Incubation Time:

5 days
Result:

Did not significantly change Trap mRNA levels compared to RANKL-only control.
Significantly decreased mRNA levels of functional osteoclast markers Mmp-9 and CtsK.

Immunofluorescence^[2]

Cell Line:

MC3T3-E1 preosteoblastic cells, RAW264.7 preosteoclastic cells
Concentration:

0.1 mM (with 0.1 mM luzindole pre-treatment for 2 h)
Incubation Time:

2 h
Result:

Increased phospho-ERK1/2 expression in both MC3T3-E1 and RAW264.7 cells to a greater degree than melatonin and vehicle control.
Pre-treatment with luzindole significantly reduced phospho-ERK1/2 expression induced by 5-MTX.

In Vivo

5-Methoxytryptophol (5 mg/kg; i.p.; single dose) significantly reduces proinflammatory cytokine and matrix metalloproteinase levels in serum and pulp tissue, and improves histopathological outcomes in a rat model of lipopolysaccharide-induced acute pulpitis^[1].
5-Methoxytryptophol (200-700 mg/kg; i.p.; single dose) induces rapid-onset sleep in healthy CD-1 mice, with mean sleep duration ranging from 5.2 min at 300 mg/kg to 43.9 min at 600 mg/kg, and an acute LD₅₀ of about 750 mg/kg^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Wistar albino rats (male and female, 200-250 g, lipopolysaccharide-induced acute pulpitis)^[1]
Dosage:

5 mg/kg
Administration:

i.p.; single dose
Result:

Reduced serum and pulp tissue levels of TNF-α, IL-1β, MMP-1, and MMP-2 significantly compared to the untreated acute pulpitis group.
Showed considerable histopathological improvement compared to the untreated acute pulpitis group: 50% of samples had inflammatory reaction restricted to the 60-67.5 degree region of the pulp cavity (score 4), 12.5% had inflammatory infiltrate intensity scores of 2 (20-40 cells), 50% had scores of 3 (40-60 cells), 37.5% had scores of 4 (over 60 cells), 100% had persistent inflammatory edema, 87.5% had pulp necrosis restricted to 20-30% of the 45-105 degree area (score 3), and 12.5% had over 30% necrosis (score 4).

Animal Model:

CD-1 (4-6 weeks old, 16-30 grams)^[3]
Dosage:

200 mg/kg; 300 mg/kg; 400 mg/kg; 500 mg/kg; 600 mg/kg; 700 mg/kg
Administration:

i.p.
Result:

Showed 0 out of 6 mice slept, with 0 min sleep onset and duration at 200 mg/kg.
Induced sleep in 5 out of 6 mice, with a mean sleep onset of 2.0 min and mean sleep duration of 5.2 min at 300 mg/kg.
Induced sleep in 4 out of 6 mice, with a mean sleep onset of 1.8 min and mean sleep duration of 13.8 min at 400 mg/kg.
Induced sleep in 5 out of 6 mice, with a mean sleep onset of 1.3 min and mean sleep duration of 16.3 min at 500 mg/kg.
Induced sleep in 5 out of 6 mice, with a mean sleep onset of 1.3 min and mean sleep duration of 43.9 min at 600 mg/kg.
Induced sleep in 4 out of 6 mice (2 mice died during observation), with a mean sleep onset of 1.2 min and mean sleep duration of 38.5 min at 700 mg/kg.
Exhibited an acute LD50 of about 750 mg/kg.

Chemical Information

CAS. Nr. 712-09-4
Appearance Viscous Liquid
Molecular Weight 191.23
Formel C₁₁H₁₃NO₂
Color Colorless to light yellow
SMILES

OCCC1=CNC2=C1C=C(OC)C=C2
Structure Classification
- Alkaloids
- Indole Alkaloids
Initial Source
- Endogenous metabolite
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Pure form	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Publications (1)

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STAR Protoc

Protocol for the quantification of melatonin and AFMK in cerebrospinal fluid by LC-MS/MS. [Abstract]

2025 Oct 23;6(4):104145. PMID: 41134672

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 100 mg/mL (522.93 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

5.2293 mL

26.1465 mL

52.2930 mL

5 mM

1.0459 mL

5.2293 mL

10.4586 mL

10 mM

0.5229 mL

2.6147 mL

5.2293 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.5 mg/mL (13.07 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 2.5 mg/mL (13.07 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (285 KB)
SDS (393 KB)
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- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
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- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Kermeoğlu F, et al. Anti-Inflammatory Effects of Melatonin and 5-Methoxytryptophol on Lipopolysaccharide-Induced Acute Pulpitis in Rats. Biomed Res Int. 2021;2021:8884041. Published 2021 Feb 12. [Content Brief]

[2]. Satué M, et al. A new role for 5‐methoxytryptophol on bone cells function in vitro. Journal of Cellular Biochemistry. 2015 Apr;116(4):551-8.

[3]. Feldstein A, Chang FH, Kucharski JM. Tryptophol, 5-hydroxytryptophol and 5-methoxytryptophol induced sleep in mice. Life Sciences. 1970 Mar 15;9(6):323-9.
[Content Brief]

[4]. García JJ, et al. 5-methoxytryptophol preserves hepatic microsomal membrane fluidity during oxidative stress. J Cell Biochem. 2000;76(4):651-657. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	5.2293 mL	26.1465 mL	52.2931 mL	130.7326 mL
	5 mM	1.0459 mL	5.2293 mL	10.4586 mL	26.1465 mL
	10 mM	0.5229 mL	2.6147 mL	5.2293 mL	13.0733 mL
	15 mM	0.3486 mL	1.7431 mL	3.4862 mL	8.7155 mL
	20 mM	0.2615 mL	1.3073 mL	2.6147 mL	6.5366 mL
	25 mM	0.2092 mL	1.0459 mL	2.0917 mL	5.2293 mL
	30 mM	0.1743 mL	0.8716 mL	1.7431 mL	4.3578 mL
	40 mM	0.1307 mL	0.6537 mL	1.3073 mL	3.2683 mL
	50 mM	0.1046 mL	0.5229 mL	1.0459 mL	2.6147 mL
	60 mM	0.0872 mL	0.4358 mL	0.8716 mL	2.1789 mL
	80 mM	0.0654 mL	0.3268 mL	0.6537 mL	1.6342 mL
	100 mM	0.0523 mL	0.2615 mL	0.5229 mL	1.3073 mL

5-Methoxytryptophol

1 Cited Publications

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5-Methoxytryptophol

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Publications Citing Use of MedChemExpress (MCE) 5-Methoxytryptophol

Alle Melatonin Receptor Isoform-spezifische Produkte anzeigen

Alle ERK Isoform-spezifische Produkte anzeigen

Alle TNF Receptor Isoform-spezifische Produkte anzeigen

Alle Interleukin Related Isoform-spezifische Produkte anzeigen

Alle MMP Isoform-spezifische Produkte anzeigen

Alle Endogenous Metabolite Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Publications (1)

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

5-Methoxytryptophol Related Classifications

HY-113440 Related Classifications