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
SMILES
CN(CCCOC1=CC=C(Cl)C=C1Cl)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
| Molecular Formula | C13H15Cl2NO |
| Molecular Weight | 272.17 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 | Condition | Potency |
|---|---|---|---|
Target ID: P21397 Gene ID: 4128.0 Gene Symbol: MAOA Target Organism: Homo sapiens (Human) |
1.4 nM [IC50] | ||
Target ID: Q99720|||Q7Z653 Gene ID: 10280.0 Gene Symbol: SIGMAR1 Target Organism: Homo sapiens (Human) |
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Target ID: Q9Y2I1|||Q9UFW3 Gene ID: 11188.0 Gene Symbol: NISCH Target Organism: Homo sapiens (Human) |
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| 1.4 nM [IC50] | |||
Target ID: Q99720|||Q7Z653 Gene ID: 10280.0 Gene Symbol: SIGMAR1 Target Organism: Homo sapiens (Human) |
|||
Target ID: Q9Y2I1|||Q9UFW3 Gene ID: 11188.0 Gene Symbol: NISCH Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 2015-03-25 |
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| Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015-01-05 |
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| Piperine potentiates the antidepressant-like effect of trans-resveratrol: involvement of monoaminergic system. | 2013-12 |
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| Acute effects of resveratrol to enhance cocaine-induced dopamine neurotransmission in the striatum. | 2013-05-10 |
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| A novel selective LSD1/KDM1A inhibitor epigenetically blocks herpes simplex virus lytic replication and reactivation from latency. | 2013-02-05 |
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| 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. | 2012-03 |
|
| 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. | 2011-12-22 |
|
| Synthesis of three novel fluorine-18 labeled analogues of L-deprenyl for positron emission tomography (PET) studies of monoamine oxidase B (MAO-B). | 2011-10-27 |
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| Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors. | 2011-10-27 |
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| Chromone, a privileged scaffold for the development of monoamine oxidase inhibitors. | 2011-07-28 |
|
| Homoisoflavonoids: natural scaffolds with potent and selective monoamine oxidase-B inhibition properties. | 2011-04-14 |
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| Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening. | 2011 |
|
| Anti-oncogenic and pro-differentiation effects of clorgyline, a monoamine oxidase A inhibitor, on high grade prostate cancer cells. | 2009-08-20 |
|
| Monoamine oxidase A rather than monoamine oxidase B inhibition increases nicotine reinforcement in rats. | 2006-12 |
|
| The antioxidant anethole dithiolethione inhibits monoamine oxidase-B but not monoamine oxidase A activity in extracts of cultured astrocytes. | 2006-05 |
|
| Differential substrate specificity of monoamine oxidase in the rat heart and renal cortex. | 2003-07-11 |
|
| Effects of elevated serotonin levels on patterns of GAP-43 expression during barrel development in rat somatosensory cortex. | 2002-12-15 |
|
| Inhibition of MAO-A fails to alter cocaine-induced increases in extracellular dopamine and norepinephrine in rat nucleus accumbens. | 2001-03-05 |
|
| Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (clorgyline) or MAO-B (selegiline and pargyline). | 1998 |
|
| Evaluation of the effects of inhibition of monoamine oxidase and senescence on methamphetamine-induced neuronal damage. | 1991 |
|
| Dissociation of norepinephrine turnover from alpha-2 responses after clorgiline. | 1988-01 |
|
| Pharmacological characteristics of tremor, rigidity and hypokinesia induced by reserpine in rat. | 1987-09 |
|
| Inhibition of monoamine oxidase activity by phenylpropanolamine, an anorectic agent. | 1986-02 |
|
| Treatment with clorgyline and pargyline differentially decreases clonidine-induced hypotension and bradycardia. | 1984-09 |
|
| Brain monoamine oxidase in suckling rabbits treated with organophosphorus compound. I. Acute intoxication. | 1984-03-01 |
|
| Possible development of the serotonin syndrome in man. | 1982-07 |
|
| Selective and nonselective monoamine oxidase inhibitors: behavioral disturbances during their administration to depressed patients. | 1982-05 |
Sample Use Guides
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
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.
| Substance Class |
Chemical
Created
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admin
on
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Mon Mar 31 18:24:29 GMT 2025
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| Record UNII |
LYJ16FZU9Q
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Validated (UNII)
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C667
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CLORGILINE
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| Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
BINDING
IC50
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
IC50
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![Amine oxidase [flavin-containing] A (Rat)](https://drugs.ncats.io/assets/ginas/images/protein.svg "Amine oxidase [flavin-containing] A (Rat)")
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ACTIVE MOIETY |
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