Clorgyline, formerly known as Clorgiline, M&B 9302 or MB9302, is a potent, irreversible and selective inhibitor of monoamine oxidase (MAO), it is structurally related to pargyline which is described as an antidepressant. Specifically, it is an irreversible (covalent) and selective inhibitor of monoamine oxidase A (MAO-A). Clorgiline was never marketed, but it has found use in scientific research. In addition to its actions as an MAOI, clorgiline has been found to bind with high affinity to the σ1 receptor (Ki = 3.2 nM) and with very high affinity to the I2 imidazoline receptor (an allosteric site on the monoamine oxidase enzyme) (Ki = 40 pM).

Physicochemical Properties

Molecular Formula	C13H16CL3NO
Molecular Weight	272.1703
Exact Mass	307.029
CAS #	17780-75-5
Related CAS #	17780-72-2;17780-75-5 (HCl);
PubChem CID	4380
Appearance	White to off-white solid powder
Boiling Point	361.3ºC at 760mmHg
Flash Point	172.3ºC
Vapour Pressure	2.1E-05mmHg at 25°C
LogP	4.129
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	6
Heavy Atom Count	17
Complexity	263
Defined Atom Stereocenter Count	0
InChi Key	BTFHLQRNAMSNLC-UHFFFAOYSA-N
InChi Code	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
Chemical Name	N-(3-(2,4-dichlorophenoxy)propyl)-N-methylprop-2-yn-1-amine hydrochloride
Synonyms	M&B 9302 MB 9302 MB-9302 MB9302Clorgyline HCl Clorgyline hydrochloride Clorgiline
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[1]. Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (clorgyline) or MAO-B (selegiline and pargyline). Journal of neural transmission. Supplementum 52: 39-48. [2]. Monoamine oxidase A rather than monoamine oxidase B inhibition increases nicotine reinforcement in rats. Eur J Neurosci. 2006 Dec;24(12):3532-40. [3]. Conjugated dopamine in superfusates of slices of rat striatum. J Neurochem. 1982 Nov;39(5):1333-9.

Additional Infomation

Clorgyline is an aromatic ether that is the 2,4-dichlorophenyl ether of 3-aminopropan-1-ol in which the nitrogen is substituted by a methyl group and a prop-1-yn-3-yl group. A monoamine oxidase inhibitor, it was formerly used as an antidepressant. It has a role as an EC 1.4.3.4 (monoamine oxidase) inhibitor and an antidepressant. It is a tertiary amino compound, a terminal acetylenic compound, an aromatic ether and a dichlorobenzene. An antidepressive agent and monoamine oxidase inhibitor related to PARGYLINE. An antidepressive agent and monoamine oxidase inhibitor related to PARGYLINE.

Solubility Data

Solubility (In Vitro)

DMSO : ≥ 100 mg/mL (~324.01 mM) H2O : ~100 mg/mL (~324.01 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.10 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.10 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.10 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.6742 mL	18.3709 mL	36.7417 mL
	5 mM	0.7348 mL	3.6742 mL	7.3483 mL
	10 mM	0.3674 mL	1.8371 mL	3.6742 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.