BOLDINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H21NO4.ClH
Molecular Weight	363.835
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@]12CC3=CC(O)=C(OC)C=C3C4=C1C(CCN2C)=CC(O)=C4OC

InChI

InChIKey=MUGNKMCHLPQCMV-ZOWNYOTGSA-N

InChI=1S/C19H21NO4.ClH/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18;/h7-9,13,21-22H,4-6H2,1-3H3;1H/t13-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C19H21NO4
Molecular Weight	327.3743
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29157166 | https://www.ncbi.nlm.nih.gov/pubmed/29136766 | https://www.ncbi.nlm.nih.gov/pubmed/28826044 | https://www.ncbi.nlm.nih.gov/pubmed/25746354 | https://www.ncbi.nlm.nih.gov/pubmed/28719960

Boldine, an aporphine alkaloid, found abundantly in the leaves/bark of boldo (Peumus boldus Molina) widely consumed in the folk medicine of some regions. Boldine possesses various pharmacological properties including, anticancer activity. It exhibits a significant improvement of learning and memory through inhibition of brain acetylcholinesterase activity and alleviation of brain oxidative stress, which was shown on animal models. Boldine is a potentially useful agent for the treatment of leishmaniosis. In addition, it suppresses osteoclastogenesis, improves bone destruction and may be a potential therapeutic agent for rheumatoid arthritis. Besides, was shown, that boldine inhibits telomerase in cells treated with sub-cytotoxic concentrations. Telomerase inhibition occurs via down-regulation of human telomerase reverse transcriptase (hTERT), the catalytic subunit of the enzyme.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 207 Target ID: P22303\|\|\|Q53F46 Gene ID: 43.0 Gene Symbol: ACHE Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29136766	Inhibitor 8297
Telomerase reverse transcriptase 10 Target ID: O14746 Gene ID: 7015.0 Gene Symbol: TERT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25746354	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Leishmaniasis 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28719960	Primary	Basic research	Unknown Approved Use Unknown
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28826044	Primary	Preclinical	Unknown Approved Use Unknown
Mammary carcinoma 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27611982	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Halogenated boldine derivatives with enhanced monoamine receptor selectivity.	2000 Apr	10785418
Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity.	2002 Feb 22	11890906
Photostability and photoprotection factor of boldine and glaucine.	2005 Jul 1	15963438
Sensitive quantification of apomorphine in human plasma using a LC-ESI-MS-MS method.	2006 Jun	16778727
Direct identification of phenolic constituents in Boldo Folium (Peumus boldus Mol.) infusions by high-performance liquid chromatography with diode array detection and electrospray ionization tandem mass spectrometry.	2010 Jan 22	20022332

Sample Use Guides

In Vivo Use Guide

in mice: boldine (1.5, 3 and 6mg/kg, po) for 7 successive days exhibited significant improvement of learning and memory of young and aged mice anticonvulsant effects in mice: boldine (once in a day for 8 days, ip.) in mice: repeated i. p. injections of 30, 60, or 90 mg boldine/kg slowed tumor growth

Route of Administration: Other

In Vitro Use Guide

It was shown that boldine is a potentially useful agent for the treatment of leishmaniasis. The in vitro system consisted of murine macrophage infection with amastigotes of L. amazonensis treated with different concentrations from 50 to 600 μg/ml of boldine for 24 hr. Intracellular parasite destruction was assessed by morphological examination and boldine cytotoxicity to macrophages was tested by the MTT viability assay. When cells were treated with 100 μg/ml of boldine the reduction of parasite infection was 81% compared with untreated cultures cells.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:40:14 GMT 2023` Edited by `admin` on `Sat Dec 16 09:40:14 GMT 2023`
Record UNII	G6R77KSG8R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BOLDINE HYDROCHLORIDE

Common Name

English

6A.ALPHA.-APORPHINE-2,9-DIOL, 1,10-DIMETHOXY-, HYDROCHLORIDE

Systematic Name

English

4H-DIBENZO(DE,G)QUINOLINE-2,9-DIOL, 5,6,6A,7-TETRAHYDRO-1,10-DIMETHOXY-6-METHYL-, HYDROCHLORIDE, (6AS)-

Systematic Name

English

4H-DIBENZO(DE,G)QUINOLINE-2,9-DIOL, 5,6,6A,7-TETRAHYDRO-1,10-DIMETHOXY-6-METHYL-, HYDROCHLORIDE, (S)-

Systematic Name

English

BOLDINE HYDROCHLORIDE, (+)-

Common Name

English

4H-DIBENZO(DE,G)QUINOLINE-2,9-DIOL, 5,6,6A,7-TETRAHYDRO-1,10-DIMETHOXY-6-METHYL-, HYDROCHLORIDE (1:1), (6AS)-

Systematic Name

English

5,6,6A,7-TETRAHYDRO-2,9-DIHYDROXY-1,10-DIMETHOXY-6-METHYL-4H-DIBENZO(DE,G)QUINOLINIUM CHLORIDE

Common Name

English

Code System Code Type Description

PUBCHEM

45045237