CLORGILINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H15Cl2NO
Molecular Weight	272.17
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=BTFHLQRNAMSNLC-UHFFFAOYSA-N

InChI=1S/C13H15Cl2NO/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

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
Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening.	2011	22028826
Synthesis, biological evaluation, and molecular modeling of donepezil and N-[(5-(benzyloxy)-1-methyl-1H-indol-2-yl)methyl]-N-methylprop-2-yn-1-amine hybrids as new multipotent cholinesterase/monoamine oxidase inhibitors for the treatment of Alzheimer's disease.	2011 Dec 22	22023459
Synthesis of three novel fluorine-18 labeled analogues of L-deprenyl for positron emission tomography (PET) studies of monoamine oxidase B (MAO-B).	2011 Oct 27	21923198
Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors.	2011 Oct 27	21923181
A novel selective LSD1/KDM1A inhibitor epigenetically blocks herpes simplex virus lytic replication and reactivation from latency.	2013 Feb 5	23386436

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

Official Name

English

CLORGYLINE

Common Name

English

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

Systematic Name

English

M&B-9302

Code

English

M&B 9302

Code

English

clorgiline [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667