PARGYLINE HYDROCHLORIDE Chemical Properties

Melting point:

160-163 °C(lit.)

storage temp. 

-20°C

solubility 

≥33.55 mg/mL in EtOH; ≥51.6 mg/mL in H2O; ≥7.55 mg/mL in DMSO

form 

A crystalline solid

color 

Crystals from EtOH/Et2O

Merck 

13,7110

BRN 

3699487

InChIKey

BCXCABRDBBWWGY-UHFFFAOYSA-N

CAS DataBase Reference

306-07-0

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

22-24/25

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

DP6650000

F 

10

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

2921199990

Toxicity

LD50 orl-rat: 250 mg/kg 27ZQAG -,401,72

MSDS

• Language:English Provider:SigmaAldrich

PARGYLINE HYDROCHLORIDE Usage And Synthesis

Originator

Eutonyl, Abbott , US ,1963

Uses

Pargyline hydrochloride has been used:

• as a histone demethylase inhibitor to treat monocytes to investigate whether various inhibitors affect training
• to maximize uptake into dopaminergic neurons (DA) neurons in experimental rats,
• to study its effect on discolouration of medullary tissues of sclerotia of S. sclerotiorum

Uses

Antihypertensor;Monoamine oxidase inhibitor

Manufacturing Process

A mixture of 23.8 grams (0.2 mol) of propargyl bromide, 24.2 grams (0.2 mol) of N-methylbenzylamine and 400 ml of anhydrous ethanol in the presence of 42.4 grams (0.4 mol) of anhydrous sodium carbonate was heated at the boiling temperature and under reflux for a period of 17 hours.
The sodium carbonate was then removed by filtration and the alcohol was removed by distillation under reduced pressure. The residue was treated with 300 ml of dry ether and the resulting solution was filtered to remove sodium bromide.
The filtrate was dried and fractionally distilled under reduced pressure to obtain the desired N-methyl-N-propargylbenzylamine which boiled at 96°97°C at 11 mm pressure.
Analysis calculated for C11H13N: C = 82.97%; H = 8.23%; N = 8.80%. Found: C = 82.71%; H = 8.51%; N = 8.93%.
The hydrochloride salt of this amine was prepared by dissolving the amine in ether and adding ethereal hydrogen chloride to the ether solution. The solid hydrochloride salt which precipitated was recrystallized from an ethanol-ether mixture and was found to melt at 154° - 155°C.

brand name

Eutonyl (Abbott).

Therapeutic Function

Antihypertensive

Biological Activity

pargyline, an irreversible and non-selective inhibitor of mao, is used to treat moderate hypertension and cancer cells. there are two isoforms of mao, mao-a and mao-b. mao-a preferentially deaminates melatonin, serotonin, norepinephrine and epinephrine. mao-b catalyzes the oxidative deamination and inactivation of certain catecholamines within the presynaptic nerve terminals.

Biochem/physiol Actions

Pargyline hydrochloride acts as a histone demethylase inhibitor. It has antihypertensive action.

Safety Profile

Poison by ingestion,intraperitoneal, and intravenous routes. Human systemiceffects by ingestion: effects on fluid intake, psychologicaleffects. Experimental reproductive effects. When heatedto decomposition it emits very toxic fumes of HCl andNOx.

in vitro

pargyline reduced the proliferation of human prostate carcinoma (lncap-ln3) cells in a time- and dose-dependent fashion. in addition, compared to the control, pargyline remarkably triggered cell cycle arrest at the g1 phase. pargyline elicited an increase in the cell death rate via promoting apoptosis, suggesting that pargyline was a powerful candidate drug for the treatment of human prostate cancer [1].

in vivo

male rats were injected intraperitoneally pargyline at a dose of 75 mg/kg for 80 min. pargyline significantly increased the concentration of extracellular dopamine in the striatum and simultaneously, significantly reduced the concentration of extracellular mao-derived metabolite 3,4-dihydroxyphenylacetic acid to undetectable levels [2].

IC 50

11.52 nm: inhibits monoamine oxidase (mao) type a (mao-a).

References

[1]. chai, y. effects of the monoamine oxidase inhibitors pargyline and tranylcypromine on cellular proliferation in human prostate cancer cells. oncology reports. 2013.
[2]. desvignes, c., bert, l., vinet, l., denoroy, l., renaud, b., & lambás-seas, l. evidence that the neuronal nitric oxide synthase inhibitor 7-nitroindazole inhibits monoamine oxidase in the rat: in vivo effects on extracellular striatal dopamine and 3,4-dihydroxyphenylacetic acid. neuroscience letters. 1999; 261(3):175-178.

PARGYLINE HYDROCHLORIDE(306-07-0)Related Product Information

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