3-Hydroxymethyl-β-carboline

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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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3-Hydroxymethyl-β-carboline Chemical Structure

CAS No. : 65474-79-5

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Biological Activity
Purity & Documentation
References
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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.

Molecular Weight

198.22

Formula

C₁₂H₁₀N₂O

CAS No.

65474-79-5

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

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]