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PERHEXILINE MALEATE SALT

Product Name
PERHEXILINE MALEATE SALT
CAS No.
6724-53-4
Chemical Name
PERHEXILINE MALEATE SALT
Synonyms
Pexid;WSM-3978;WSM 3978G;perhexilinemaleate;perhexilene maleate;rac Perhexiline Maleate;PERHEXILINE MALEATE SALT;PERHEXILINE MALEATE SALT USP/EP/BP;2-(2,2-dicyclohexylethyl)piperidinemaleate;2-(2,2-dicyclohexylethyl)-piperidinmaleate(1:1)
CBNumber
CB1464993
Molecular Formula
C23H39NO4
Formula Weight
393.56
MOL File
6724-53-4.mol
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PERHEXILINE MALEATE SALT Property

Melting point:
181-183°C
storage temp. 
2-8°C
solubility 
DMSO: ≥5mg/mL
form 
powder
color 
white to tan
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Safety

WGK Germany 
2
RTECS 
TM7068000
Toxicity
LD50 in rats, mice (g/kg): >7, 4.37 orally (Causa, Perri)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0120
Product name
Perhexiline maleate salt
Purity
≥98% (HPLC)
Packaging
10mg
Price
$163
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0120
Product name
Perhexiline maleate salt
Purity
≥98% (HPLC)
Packaging
50mg
Price
$658
Updated
2024/03/01
Cayman Chemical
Product number
16982
Product name
Perhexiline (maleate)
Purity
≥95%
Packaging
1mg
Price
$36
Updated
2024/03/01
Cayman Chemical
Product number
16982
Product name
Perhexiline (maleate)
Purity
≥95%
Packaging
5mg
Price
$62
Updated
2024/03/01
Cayman Chemical
Product number
16982
Product name
Perhexiline (maleate)
Purity
≥95%
Packaging
10mg
Price
$105
Updated
2024/03/01
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PERHEXILINE MALEATE SALT Chemical Properties,Usage,Production

Description

Perhexiline is a carnitine palmitoyltransferase 1 (CPT1) and CPT2 inhibitor that was originally developed as an anti-anginal drug in the 1970s. It inhibits rat heart and liver CPT1 (IC50 = 77 and 148 μM, respectively) and rat heart CPT2 (IC50 = 79 μM). Inhibition of CPT reduces uptake of long-chain fatty acids into the mitochondria, thereby shifting cellular metabolism from β-oxidation to glycolysis. Perhexilin inhibits mTORC1 signaling at 10 μM and induces autophagy ~7-fold at a concentration of 10 μM in MCF-7 cells.

Chemical Properties

White Solid

Originator

Pexid, Merrell-Tourade ,France ,1973

Uses

Perhexiline maleate salt has been used to block fatty acid oxidation. It has also been used as 5′?adenosine?monophosphate-activated?protein kinase?(AMPK)?activator and in worm lifespan assay.

Uses

H1 antihistamine

Uses

PERHEXILINE MALEATE SALT is a Vasodilator, used in treatments for angina.

Manufacturing Process

1,1-Dicyclohexyl-2-(2'-pyridyl)ethanol hydrochloride (5 grams) was dehydrated by heating with 25 ml of concentrated hydrochloric acid at steam bath temperature for 10 minutes. 70 ml of water were added to the reaction mixture to give the crystalline hydrochloride salt. The product, 1,1dicyclohexyl-2-(2'-pyridyl)ethylene hydrochloride, was recrystallized from methanol-ethyl acetate to yield a white solid melting at 150°-151.5°C.
1,1-Dicyclohexyl-2-(2'-pyridyl)ethylene hydrochloride (15 grams) in 150 ml of ethanol was hydrogenated in the presence of platinum oxide at about 60 pounds per square inch of hydrogen pressure. The product, 1,1-dicyclohexyl2-(2'-piperidyl)ethane hydrochloride, crystallized from a mixture of methanol and methyl ethyl ketone as a white solid melting at 243° to 245.5°C.
The hydrochloride salt was neutralized with 10% sodium hydroxide solution and the free base so produced was dissolved in ether. The ether solution was dried over anhydrous magnesium sulfate. Addition of an excess of maleic acid in methanol to the solution yielded the acid maleate salt which melted at 188.5°-191°C.
The starting material was obtained by reacting ethyl formate with cyclohexylmagnesium bromide to give dicyclohexylcarbinol. That is oxidized to dicyclohexylketone and then reacted with α-picoline.

brand name

Pexid (Marion Merrell Dow).

Therapeutic Function

Coronary vasodilator

General Description

Perhexiline maleate regulates?coronary vasodilatation and blocks exercise-induced tachycardia. It is used to treat angina pectoris and variant angina. Perhexiline maleate functions as a cardiac metabolic agent. It is associated with peripheral neuropathy, high intracranial pressure with?papilledema?and proximal myopathy.

Biochem/physiol Actions

Perhexiline maleate is an anti-anginal metabolic modulator. It inhibits the mitochondrial enzyme carnitine palmitoyltransferase CPT-1 and to a lesser extent CPT-2. This causes a shift in myocardial substrate utilisation from long chain fatty acids to carbohydrates, resulting in increased glucose and lactate utilization and increased ATP production for the same O2 consumption as before and consequently increases myocardial efficiency. Perhexiline maleate was also recently found to inhibit the activity of mTORC1.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion.Human systemic effects by ingestion: muscle weakness, paresthesia, and hepatitis. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

in vitro

perhexiline maleate concentration-dependently and competitively inhibited cpt1 in rat cardiac and hepatic mitochondria, with an ic50 value of 77 and 148 μm, respectively. it was indicated that perhexiline maleate displayed a greater sensitivity of the cardiac than the hepatic enzyme when exhibiting inhibition effect [1]. perhexiline maleate produced concentration-dependent inhibition of cpt2 activity with an ic50 value of 79 μm [2]. in human breast cancer mcf-7 cells, perhexiline maleate blocked mtorc1 signaling at 10 μm and elicited autophagy ~7-fold at a concentration of 10 μm [3].

in vivo

adult mice of swiss nmri strain were orally administrated with perhexiline maleate at a dosage of 100 mg/kg body weight/day for 10 weeks. perhexiline maleate triggered changes in nerve, including a few cytoplasmic inclusions in schwann and perineurial cells of mice treated with perhexiline maleate. after 11 weeks of administration of the drug, and up to 18 weeks, small abnormal zones were displayed on several muscle fibers, which were formed by tubular aggregates [4].

storage

Store at +4°C

References

[1]. kennedy, j., unger, s., & horowitz, j. inhibition of carnitine palmitoyltransferase-1 in rat heart and liver by perhexiline and amiodarone. biochemical pharmacology. 1996; 52(2): 273-280.
[2]. kennedy, j., kiosoglous, a., murphy, g., pelle, m., & horowitz, j. effect of perhexiline and oxfenicine on myocardial function and metabolism during low-flow ischemia/reperfusion in the isolated rat heart. journal of cardiovascular pharmacology. 2000; 36(6): 794-801.
[3]. balgi, a., fonseca, b., donohue, e., tsang, t., lajoie, p., & proud, c. et al. screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mtorc1 signaling. plos one. 2009; 4(9): e7124.
[4]. fardeau, m., tomé, f., & simon, p. muscle and nerve changes induced by perhexiline maleate in man and mice. muscle & nerve. 1979; 2(1): 24-36.

PERHEXILINE MALEATE SALT Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from PERHEXILINE MALEATE SALT manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Perhexiline Maleate Salt 6724-53-4
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
500 MT
Release date
2020-05-11

6724-53-4, PERHEXILINE MALEATE SALTRelated Search:


  • 2-(2,2-dicyclohexylethyl)piperidinemaleate
  • 2-(2,2-dicyclohexylethyl)-piperidinmaleate(1:1)
  • perhexilinemaleate
  • perhexilene maleate
  • Pexid
  • WSM-3978
  • rac Perhexiline Maleate
  • 2-(2,2-dicyclohexylethyl)piperidinium hydrogen maleate
  • 2-[2,2-DICYCLOHEXYLETHYL]PIPERIDINE MALEATE SALT
  • 2-(2,2-dicyclohexylethyl)-piperidine, 2Z-butenedioate
  • PERHEXILINE MALEATE SALT
  • WSM 3978G
  • PERHEXILINE MALEATE SALT USP/EP/BP
  • Perhexiline maleate,inhibit,Perhexiline,Mitochondrial Metabolism,Inhibitor
  • 6724-53-4
  • C23H39NO4
  • C19H35NC4H4O4
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