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3-Hydroxymethyl-β-carboline

3-Hydroxymethyl-β-carboline is a Benzodiazepine antagonist with a K_i value of ~1470 nM. 3-Hydroxymethyl-β-carboline reverses Flurazepam-induced sleep, cerebrovascular and cerebral metabolic inhibition, and also partially reverses Flurazepam-induced decreases in blood pressure and heart rate. 3-Hydroxymethyl-β-carboline disrupts the anticonvulsant and anxiolytic effects of Diazepam in male mice. 3-Hydroxymethyl-β-carboline has no effect on sodium-dependent high-affinity choline uptake in rat cortical or hippocampal synaptosomes.

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CAS No.: 65474-79-5
Formula: C₁₂H₁₀N₂O
Molecular Weight:198.22

Storage:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (275 KB)

3-Hydroxymethyl-β-carboline Chemical Structure

CAS No.: 65474-79-5

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Biological Activity
- Description
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Purity & Documentation
References
Calculators
Help & FAQs
Bioz

Biological Activity

Description

Cellular Effect

Cell Line	Type	Value	Description	References
A498	IC₅₀	>100 μM Compound: 9b	Cytotoxicity against human A498 cells incubated for 48 hrs by MTT assay Cytotoxicity against human A498 cells incubated for 48 hrs by MTT assay	[PMID: 26235951]
COLO 205	IC₅₀	>100 μM Compound: 9b	Cytotoxicity against human COLO205 cells incubated for 48 hrs by MTT assay Cytotoxicity against human COLO205 cells incubated for 48 hrs by MTT assay	[PMID: 26235951]
Detroit 551	IC₅₀	>100 μM Compound: 9b	Cytotoxicity against human Detroit 551 cells incubated for 48 hrs by MTT assay Cytotoxicity against human Detroit 551 cells incubated for 48 hrs by MTT assay	[PMID: 26235951]
Hep 3B2	IC₅₀	>100 μM Compound: 9b	Cytotoxicity against human Hep3B cells incubated for 48 hrs by MTT assay Cytotoxicity against human Hep3B cells incubated for 48 hrs by MTT assay	[PMID: 26235951]
HL-60	IC₅₀	>100 μM Compound: 9b	Cytotoxicity against human HL60 cells incubated for 48 hrs by MTT assay Cytotoxicity against human HL60 cells incubated for 48 hrs by MTT assay	[PMID: 26235951]
MCF-10A	IC₅₀	>40 μM Compound: 22a	Cytotoxicity against human MCF-10A cells assessed as inhibition of cell proliferation measured after 72 hrs by CCK-8 assay Cytotoxicity against human MCF-10A cells assessed as inhibition of cell proliferation measured after 72 hrs by CCK-8 assay	[PMID: 34365102]
MCF7	IC₅₀	>20 μM Compound: 22a	Antiproliferative activity against human MCF7 cells assessed as inhibition of cell proliferation measured after 72 hrs by CCK-8 assay Antiproliferative activity against human MCF7 cells assessed as inhibition of cell proliferation measured after 72 hrs by CCK-8 assay	[PMID: 34365102]
MDA-MB-231	IC₅₀	>20 μM Compound: 22a	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition of cell proliferation measured after 72 hrs by CCK-8 assay Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition of cell proliferation measured after 72 hrs by CCK-8 assay	[PMID: 34365102]
NCI-H460	IC₅₀	>100 μM Compound: 9b	Cytotoxicity against human H460 cells incubated for 48 hrs by MTT assay Cytotoxicity against human H460 cells incubated for 48 hrs by MTT assay	[PMID: 26235951]
SK-OV-3	IC₅₀	>100 μM Compound: 9b	Cytotoxicity against human SKOV3 cells incubated for 48 hrs by MTT assay Cytotoxicity against human SKOV3 cells incubated for 48 hrs by MTT assay	[PMID: 26235951]

In Vitro

3-Hydroxymethyl-β-carboline inhibits [³H]-diazepam binding to benzodiazepine receptors in vitro with a K_i of ~1470 nM^[2].

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

In Vivo

3-Hydroxymethyl-β-carboline (5-25 mg/kg; intravenous injection; single administration) acts as an active antagonist against Flurazepam-induced cerebrovascular and cerebral metabolic inhibition in rats. At a dose of 5 mg/kg, it reverses the aforementioned effects of 5 mg/kg Flurazepam; whereas administration of 25 mg/kg of this compound alone stimulates cortical and subcortical cerebral blood flow (CBF) as well as cortical cerebral metabolic rate of oxygen (CMRO₂)^[1].
3-Hydroxymethyl-β-carboline (2-100 mg/kg; i.p.; single administration) acts as a benzodiazepine antagonist, which significantly reduces the anticonvulsant protective effect of Diazepam on Mus musculus (reduced to 10% at 25 mg/kg) and the exploratory behavior induced by anxiolysis (reduced to 32.5 shuttles at 25 mg/kg), while high doses decrease spontaneous locomotor activity^[2].
Single administration of 3-Hydroxymethyl-β-carboline (20 mg/kg) has no effect on sodium-dependent high-affinity choline uptake in cortical or hippocampal synaptosomes of rats, and does not induce obvious behavioral changes^[3].

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

Animal Model:

Sprague-Dawley (male, 7 months old, anesthetized with 70% N₂O/30% O₂)^[1]
Dosage:

5 mg/kg (reversal of 5 mg/kg flurazepam); 25 mg/kg (reversal of 5 and 50 mg/kg flurazepam, standalone stimulation)
Administration:

i.v.; single dose; administered 5 minutes after flurazepam or vehicle
Result:

Showed no significant increase in cortical or subcortical CBF or cortical CMRO₂ compared to control when given alone at 5 mg/kg.
Reversed flurazepam (5 mg/kg)-induced decreases in right cortical CBF from 79 to 96 mL/100g per min, left cortical CBF from 80 to 93 mL/100g per min, right subcortical CBF from 60 to 72 mL/100g per min, left subcortical CBF from 63 to 74 mL/100g per min, and cortical CMRO₂ from 5.43 to 7.12 mL O₂/100g per min at 5 mg/kg.
Had little effect on flurazepam (50 mg/kg)-induced decreases in CBF and CMRO₂ at 5 mg/kg.
Produced a significant increase in cortical and subcortical CBF and cortical CMRO₂ compared to control when given alone at 25 mg/kg.
Reversed flurazepam (5 mg/kg)-induced decreases in CBF and CMRO₂ at 25 mg/kg.
Reversed flurazepam (50 mg/kg)-induced decreases in CBF and CMRO₂ at 25 mg/kg.
Failed to effectively reverse flurazepam-induced decreases in blood pressure and heart rate at both doses.

Chemical Information

CAS No. 65474-79-5
Molecular Weight 198.22
Formula C₁₂H₁₀N₂O
SMILES

C1=CC=C2C(=C1)C3=C(C=NC(=C3)CO)N2
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (275 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)

References

[1]. Hoffman WE, et al. Cerebrovascular and cerebral metabolic effects of flurazepam and a benzodiazepine antagonist, 3-hydroxymethyl-beta-carboline. Eur J Pharmacol. 1984 Nov 27;106(3):585-91. [Content Brief]

[2]. Skolinick P, et al. 3-hydroxymethyl-beta-carboline antagonizes some pharmacologic actions of diazepam. Eur J Pharmacol. 1981 Feb 19;69(4):525-7. [Content Brief]

[3]. Miller JA, et al. The regulation of high-affinity choline uptake in vitro in rat cortical and hippocampal synaptosomes by beta-carbolines administered in vivo. Neurosci Lett. 1990 Jul 13;114(3):351-5. [Content Brief]

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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.

Keywords

100 mg

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