15284-15-8

Usage

Uses

Used in Pharmaceutical Industry:
S(+)-METHADONE HYDROCHLORIDE is used as an active pharmaceutical ingredient for the treatment of opioid dependence. It is particularly effective in managing withdrawal symptoms and reducing cravings associated with opioid addiction, thus playing a crucial role in the rehabilitation process for patients suffering from opioid use disorder.

Safety Profile

Poison by intravenous and intraperitoneal routes. Human systemic effects by ingestion: euphoria, somnolence (general depressed activity), and analgesia. Caution: Abuse leads to habituation or addction. When heated to decomposition it emits toxic fumes of Cland NOx. See also METHADONE HYDROCHLORIDE.

InChI:InChI=1/C21H27NO.ClH/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19;/h6-15,17H,5,16H2,1-4H3;1H/t17-;/m0./s1

Upstream product

• 86-29-3 Diphenylacetonitrile 
• 40916-65-2 (S)-2-(dimethylamino)-1-propanol 
• 76-99-3 Methadone 
• 5653-80-5 (S)-methadone 
• 1095-90-5 methadone hydrochloride 
• 7576-08-1 (S)-(+)-2,2-diphenyl-4-dimethylaminopentanenitrile 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 14019-10-4 (3S,6S)-Methadol 
• 43033-72-3 levomethadyl acetate hydrochloride 

Relevant academic research and scientific papers

SYNTHESIS OF LEVOMETHADONE HYDROCHLORIDE OR DEXTROMETHADONE HYDROCHLORIDE AND METHODS FOR USE THEREOF

Highly efficient methods for synthesis of levomethadone hydrochloride or dextromethadone hydrochloride are provided starting from D-alanine, or L-alanine, respectively, with retention of configuration. Methods for treating a subject are provided comprising administering a composition comprising an effective amount of levomethadone hydrochloride having not more than 10 ppm dextromethadone.

Non-Racemic Mixtures of Various Ratios of D- and L-methadone and Methods of Treating Pain Using the Same

Non-racemic mixtures of D- and L-methadone containing a ratio ranging from about 2.5:1 to about 3.5:1 by weight of D-methadone to L-methadone, such as for example about 2.9:1 to about 3.1:1 by weight of D-methadone to L-methadone, or about 3:1 by weight of D-methadone to L-methadone, have been found to exhibit surprising and unexpected beneficial results in the treatment of neuropathic pain. Additionally, non-racemic mixtures of D- and L-methadone containing a ratio ranging from about 2.5:1 to about 3.5:1 by weight of D-methadone to L-methadone, about 2.9:1 to about 3.1:1 by weight of D-methadone to L-methadone, or for example about 3:1 by weight of D-methadone to L-methadone, in combination with other non-methadone opioids have been found to exhibit surprising and unexpected beneficial results in the treatment of mixed pain.

Methadone chiral isolate as an improved pharmaceutical

Methadone is a frequently employed agent for the treatment of drug addiction and the treatment of pain. Methadone prolongs the cardiac action potential, which on the surface electrocardiogram is represented by QT prolongation. This QT prolongation is known to increase the risk for the development of cardiac arrhythmias, especially the form of ventricular tachycardia known as Torsade de Pointes. For this reason, the FDA has inserted a “black box” warning for potential life threatening arrhythmias. The invention described in this application is the surprising finding that the R-isomer of methadone causes less inhibition of the potassium channel, IKr and thus would have less of a chance of causing life threatening arrhythmias. What is claimed is a method of chirally separating methadone with one isomer having less QT prolongation and more analgesic action that would make a superior pharmacologic agent than the racemate R,S methadone.

Synthesis of optically active methadones, LAAM and bufuralol by lipase-catalysed acylations

(R)- and (S)-Methadones and levo-α-acetylmethadol (LAAM) have been synthesised starting from lipase-catalysed acylation of dimethylaminopropan-2-ol. An approach to the synthesis of (R)-bufuralol is also presented.