306-07-0

Basic information

• Product Name: PARGYLINE HYDROCHLORIDE
• Synonyms: N-METHYL-N-PROPARGYLBENZYLAMINE HYDROCHLORIDE;N-METHYL-N-(2-PROPYNY)BENZYLAMINE HYDROCHLORIDE;N-METHYL-N-2-PROPYNYLBENZYLAMINE HYDROCHLORIDE;PARGYLINE HYDROCHLORIDE;benzylmethylpropynylaminehydrochloride;n-benzyl-n-methyl-2-propynylaminehydrochloride;n-benzyl-n-methyl-2-propynylaminhydrochloride;n-methyl-n-2-propynyl-benzylaminhydrochloride
• CAS NO: 306-07-0
• Molecular Formula: C₁₁H₁₃N*ClH
• Molecular Weight: 195.69
• EINECS: 206-175-1
• Mol File: 306-07-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 160-163 °C(lit.)
• Boiling Point: 228.4 ºC at 760 mmHg
• Flash Point: 83.9 ºC
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.0736mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: ≥33.55 mg/mL in EtOH; ≥51.6 mg/mL in H2O; ≥7.55 mg/mL in DMSO
• Merck: 13,7110
• BRN: 3699487
• CAS DataBase Reference: PARGYLINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PARGYLINE HYDROCHLORIDE(306-07-0)
• EPA Substance Registry System: PARGYLINE HYDROCHLORIDE(306-07-0)

Safety Data

• Hazard Codes: Xn
• 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
• Hazardous Substances Data: 306-07-0(Hazardous Substances Data)

Usage

Description

Pargyline hydrochloride, a derivative of phenylethylamine, is a potent and selective monoamine oxidase inhibitor (MAOI). It is a white crystalline powder that is soluble in water and has been widely used in the pharmaceutical industry due to its ability to inhibit the enzyme monoamine oxidase, which is involved in the metabolism of various neurotransmitters and hormones.

Uses

Used in Pharmaceutical Industry:
Pargyline hydrochloride is used as an antihypertensive agent for the treatment of high blood pressure. It works by inhibiting the enzyme monoamine oxidase, which helps to increase the levels of certain neurotransmitters, such as dopamine and norepinephrine, leading to a reduction in blood pressure.
Used in Research Applications:
Pargyline hydrochloride is used as a histone demethylase inhibitor to treat monocytes in experimental studies. This application aims to investigate whether various inhibitors affect the training to maximize uptake into dopaminergic (DA) neurons in experimental rats.
Used in Agricultural Research:
Pargyline hydrochloride has been used to study its effect on the discolouration of medullary tissues of sclerotia of Sclerotinia sclerotiorum, a plant pathogen that causes significant damage to various crops.
Brand Name:
Pargyline hydrochloride is marketed under the brand name Eutonyl by Abbott Laboratories.

Originator

Eutonyl, Abbott , US ,1963

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.

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.

InChI:InChI=1/C11H13N.ClH/c1-3-9-12(2)10-11-7-5-4-6-8-11;/h1,4-8H,9-10H2,2H3;1H