Nalmefene Chemical Properties

Melting point:

182-185?C

Boiling point:

507.9±50.0 °C(Predicted)

Density 

1.38±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)

pka

pKa 7.63(H2O) (Uncertain)

form 

Solid

color 

White to Off-White

CAS DataBase Reference

55096-26-9

NIST Chemistry Reference

Nalmefene(55096-26-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazardous Substances Data

55096-26-9(Hazardous Substances Data)

MSDS

• Language:English Provider:Nalmefene
• Language:English Provider:SigmaAldrich

Nalmefene Usage And Synthesis

Description

Nalmefene is a 6-methylene analogue of naltrexone. It is a pure opioid receptor antagonist and has a high affinity for the κ-opioid receptor. Nalmefene has a long duration of action and is used in oral and parenteral formulations.

Chemical Properties

Off-White Solid

Originator

Nalmefene,Mallinckrodt Inc.

Uses

A structural analog of Naltrexone (N285780) with opiate antagonist activity used in pharmaceutical treatment of alcoholism. Other pharmacological applications of this compound aim to reduce food cravings, drug abuse and pulmonary disease in affected individuals. Used as an opioid-induced tranquilizer on large animals in the veterinary industry. Narcotic antagonist.

Uses

A structural labelled analog of Naltrexone (N285780) with opiate antagonist activity used in pharmaceutical treatment of alcoholism. Other pharmacological applications of this compound aim to reduce f ood cravings, drug abuse and pulmonary disease in affected individuals. Used as an opioid-induced tranquilizer on large animals in the veterinary industry. Narcotic antagonist.

Uses

opioid antagonists therapeutic for alcohol dependence

Definition

ChEBI: Nalmefene is a morphinane alkaloid.

Manufacturing Process

A dry, 2-liter, 3-neck, round bottom flask fitted with two stoppers and a magnetic stirring bar was charged with potassium t-butoxide (61.1 g, 0.545 mol) and methyltriphenylphosphonium bromide (194.4 g, 0.544 mol). Freshly distilled tetrahydrofuran (450 ml) was introduced at 20°C. The resultant thick, bright yellow dispersion was stirred at 20°C for 0.5 h and further dry tetrahydrofuran (100 ml) was added. A solution of dry naltrexone (30 g, 0.088 mol) in dry tetrahydrofuran (200 ml) was then added dropwise over 40 min. Then the reaction mixture was stirred for a further 1.25 h, then cooled to 10°C, and quenched with 20% aqueous ammonium chloride solution (75 ml) followed by water (100 ml). The organic layer was separated and the aqueous layer extracted with four 100 ml portions of chloroform. Solvent was evaporated from the tetrahydrofuran layer and the combined chloroform extracts, the residues combined and brought to pH 2 by addition of 2 N hydrochloric acid. The resultant precipitate was filtered, washed with chloroform and suspended in a mixture of chloroform (500 ml) and water (250 ml). Ammonium hydroxide was added to attain a pH of 8 and the aqueous layer separated. The organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent removed in vacuo. The resultant solid was dissolved in ethyl acetate (1400 ml), the solution filtered through a silica pad and the solvent evaporated. The product was recrystallized from chloroform and washed with hexane to yield pure 6-desoxy-6-methylenenaltrexone (also called nalmefene) as a white solid. Yield: 27.0 g, 88%.

Therapeutic Function

Antagonist to narcotics

Biological Functions

Nalmefene (Revex) is a long-acting injectable pure opioid antagonist recently introduced in the United States. It binds all opioid receptors and reverses the effects of opioid agonists at those receptors.The onset of action is 2 minutes after IV administration. Hepatic metabolism is slow and occurs via glucuronide conjugation to inactive metabolites. Its half-life of 11 hours is about 5 times that of naloxone. Indications include use in postoperative settings to reverse respiratory depression and in opioid overdose. Due to the long duration of action of nalmefene, however, naloxone may be preferred for treatment of overdose because it produces a shorter duration of withdrawal effects.

General Description

Nalmefene (Revex) is a pure opioid antagonist that is the6-methylene analog of naltrexone. It is available as a solutionfor IV, IM, or subcutaneous (SC) administration toreverse the effects of opioids after general anesthesia andin the treatment of overdose. It is longer acting than naloxonebut otherwise has a similar pharmacodynamic andmetabolic (3-glucuronidation) profile. Nalmefene hashigher oral bioavailability (approximately 40%) thannaloxone or naltrexone and is currently being investigatedas an oral treatment for pathological gambling and alcoholabuse.

Biochem/physiol Actions

Nonselective opioid receptor antagonist.

Synthesis

Nalmefene is synthesized by a Wittig reaction of naltrexone with triphenylmethylphosphonium bromide in DMSO under basic catalysis of NaH.

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