CLORGILINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H15Cl2NO.ClH
Molecular Weight	308.631
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CN(CCCOC1=C(Cl)C=C(Cl)C=C1)CC#C

InChI

InChIKey=BBAZDLONIUABKI-UHFFFAOYSA-N

InChI=1S/C13H15Cl2NO.ClH/c1-3-7-16(2)8-4-9-17-13-6-5-11(14)10-12(13)15;/h1,5-6,10H,4,7-9H2,2H3;1H

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB04017 | https://www.ncbi.nlm.nih.gov/pubmed/9564606 | https://www.ncbi.nlm.nih.gov/pubmed/24040395 | https://www.ncbi.nlm.nih.gov/pubmed/6342562 | https://www.ncbi.nlm.nih.gov/pubmed/20060423 | https://www.ncbi.nlm.nih.gov/pubmed/12652347

Clorgiline is a monoamine oxidase (MAO) inhibitor. Specifically, it is an irreversible and selective inhibitor of MAO-A. Clorgiline was under investigation for antidepressant and anxiolytic potential but has never been marketed, likely due to efficacy concerns. It continues to see routine use as a molecular probe in biomedical research examining a number of neurological disease and cancer models. In addition to inhibiting the MAO-A receptor, it has also been found to bind to the sigma1 receptor, and with high affinity to the I2 imidazoline receptor.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Amine oxidase [flavin-containing] A 14 Target ID: P21397 Gene ID: 4128.0 Gene Symbol: MAOA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9564606	Inhibitor 8297	1.4 nM [IC50]
Sigma non-opioid intracellular receptor 1 26 Target ID: Q99720\|\|\|Q7Z653 Gene ID: 10280.0 Gene Symbol: SIGMAR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20060423	Binding Agent 1064
Nischarin 7 Target ID: Q9Y2I1\|\|\|Q9UFW3 Gene ID: 11188.0 Gene Symbol: NISCH Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12652347	Binding Agent 1064
Monoamine oxidase A 49 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9564606 \| https://www.medchemexpress.com/Clorgiline-hydrochloride.html	Inhibitor 8297	1.4 nM [IC50]
Sigma non-opioid intracellular receptor 1 26 Target ID: Q99720\|\|\|Q7Z653 Gene ID: 10280.0 Gene Symbol: SIGMAR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20060423	Binding Agent 1064
Nischarin 7 Target ID: Q9Y2I1\|\|\|Q9UFW3 Gene ID: 11188.0 Gene Symbol: NISCH Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12652347	Binding Agent 1064

Conditions

Condition	Modality	Highest Phase	Product
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9564606	Primary	Not Provided 504	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24040395 https://www.ncbi.nlm.nih.gov/pubmed/25152370	Primary	Basic research	Unknown Approved Use Unknown
Obsessive-compulsive disorder 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6342562	Primary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Treatment with clorgyline and pargyline differentially decreases clonidine-induced hypotension and bradycardia.	1984 Sep	6493360
Pharmacological characteristics of tremor, rigidity and hypokinesia induced by reserpine in rat.	1987 Sep	3670563
Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (clorgyline) or MAO-B (selegiline and pargyline).	1998	9564606
The monoamine oxidase A inhibitor clorgyline is a broad-spectrum inhibitor of fungal ABC and MFS transporter efflux pump activities which reverses the azole resistance of Candida albicans and Candida glabrata clinical isolates.	2012 Mar	22203607
A novel selective LSD1/KDM1A inhibitor epigenetically blocks herpes simplex virus lytic replication and reactivation from latency.	2013 Feb 5	23386436
Acute effects of resveratrol to enhance cocaine-induced dopamine neurotransmission in the striatum.	2013 May 10	23499958
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453

Patents

Sample Use Guides

In Vivo Use Guide

Patients suffering depression were administered 30 mg/day of Clorgyline for three or more weeks. However, this regime produced negligible changes in trace amine excretion including, phenylethylamine, para-tyramine, and meta-tyramine.

Route of Administration: Unknown

In Vitro Use Guide

T24, HCT116, and HL60 cells were incubated overnight and treated with 1 micro-, 0.3 µM or 0.1 µM of 5-Aza-CdR, respectively for 24 hours. After removal of 5-Aza-CdR, cells were treated with 10 µM clorgyline every day for 21 days. Multiple doses of clorgyline were tested: 1 µM, 10 µM, and 100 µM. Clorgyline was found to impair cell growth in a dose-dependent manner and the optimal dose was identified as 10 microM.

Name

Type

Language

CLORGILINE HYDROCHLORIDE

Common Name

English

N-(3-(2,4-DICHLOROPHENOXY)PROPYL)-N-METHYL-2-PROPYNYLAMINE HYDROCHLORIDE

Systematic Name

English

2-PROPYN-1-AMINE, N-(3-(2,4-DICHLOROPHENOXY)PROPYL)-N-METHYL-, HYDROCHLORIDE (1:1)

Systematic Name

English

CLORGYLINE HYDROCHLORIDE

Common Name

English

NSC-759306

Code

English

Code System Code Type Description

ECHA (EC/EINECS)

241-760-5