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
Possible development of the serotonin syndrome in man.	1982 Jul	7091416
Selective and nonselective monoamine oxidase inhibitors: behavioral disturbances during their administration to depressed patients.	1982 May	7092487
Brain monoamine oxidase in suckling rabbits treated with organophosphorus compound. I. Acute intoxication.	1984 Mar-Apr	6443171
Treatment with clorgyline and pargyline differentially decreases clonidine-induced hypotension and bradycardia.	1984 Sep	6493360
Inhibition of monoamine oxidase activity by phenylpropanolamine, an anorectic agent.	1986 Feb	3961266
Pharmacological characteristics of tremor, rigidity and hypokinesia induced by reserpine in rat.	1987 Sep	3670563
Dissociation of norepinephrine turnover from alpha-2 responses after clorgiline.	1988 Jan	2826065
Evaluation of the effects of inhibition of monoamine oxidase and senescence on methamphetamine-induced neuronal damage.	1991	1905457
Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (clorgyline) or MAO-B (selegiline and pargyline).	1998	9564606
Effects of elevated serotonin levels on patterns of GAP-43 expression during barrel development in rat somatosensory cortex.	2002 Dec 15	12480131
Monoamine oxidase A rather than monoamine oxidase B inhibition increases nicotine reinforcement in rats.	2006 Dec	17229101
Anti-oncogenic and pro-differentiation effects of clorgyline, a monoamine oxidase A inhibitor, on high grade prostate cancer cells.	2009 Aug 20	19691856
Homoisoflavonoids: natural scaffolds with potent and selective monoamine oxidase-B inhibition properties.	2011 Apr 14	21405131
Chromone, a privileged scaffold for the development of monoamine oxidase inhibitors.	2011 Jul 28	21696156
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
Evaluation of metabolism dependent inhibition of CYP2B6 mediated bupropion hydroxylation in human liver microsomes by monoamine oxidase inhibitors and prediction of potential as perpetrators of drug interaction.	2015 Mar 25	25656918

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