Methadone hydrochloride Chemical Properties

Melting point:

232-2340C

Density 

1.0103 (rough estimate)

refractive index 

1.5790 (estimate)

Flash point:

11 °C

storage temp. 

2-8°C

solubility 

Soluble in water, freely soluble in ethanol (96 per cent)

form 

powder

color 

white to off-white

Water Solubility 

120 mg/mL

Stability:

Stable. Incompatible with strong oxidizing agents.

CAS DataBase Reference

1095-90-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,F

Risk Statements 

25-39/23/24/25-23/24/25-11

Safety Statements 

45-36/37-16

RIDADR 

UN 2811

WGK Germany 

3

RTECS 

MJ6300000

HS Code 

2922310000

Toxicity

LD50 orally in rats: 95 mg/kg (Finnegan)

Methadone hydrochloride Usage And Synthesis

Description

(±)-Methadone (hydrochloride) (Item No. ISO00145) is an analytical reference material categorized as an opioid. (±)-Methadone has analgesic activity. Formulations containing (±)-methadone have been used in the treatment of opioid addiction. (±)-Methadone is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications.

Chemical Properties

White Solid

Originator

Dolophine ,Lilly,US,1947

Uses

Controlled substance (opiate). Methadone hydrochloride is used in treatment of opioid dependence.

Definition

A synthetic narcotic.

Manufacturing Process

Diphenylacetonitrile is condensed with 2-chloro-1-dimethylaminopropane to give 4-(dimethylamino)-2,2-diphenyl valeronitrile. It is then reacted with ethyl magnesium bromide and then hydrolyzed using HCl to give methadone hydrochloride.

brand name

Dolophine Hydrochloride (Roxane); Dolophine Hydrochloride (Xanodyne); Methadose (Mallinckrodt); Westadone (Sandoz).

Therapeutic Function

Narcotic analgesic

Hazard

Toxic. Addictive narcotic. Use restricted.

Clinical Use

Treatment of opioid drug addiction
Analgesic for moderate to severe pain

Drug interactions

Metabolised in the liver to the Potentially hazardous interactions with other drugs Analgesics: possible opioid withdrawal with buprenorphine and pentazocine. Antibacterials: metabolism increased by rifampicin; increased risk of ventricular arrhythmias with delamanid and telithromycin. Antidepressants: concentration possibly increased by fluoxetine, fluvoxamine, paroxetine and sertraline; possible CNS excitation or depression with MAOIs and moclobemide - avoid; possibly increased sedative effects with tricyclics; concentration possibly reduced by St John's wort. Antiepileptics: concentration reduced by carbamazepine, phenobarbital and phenytoin. Antifungals: concentration increased by fluconazole, ketoconazole, voriconazole and possibly itraconazole - may need to reduce methadone dose with voriconazole, avoid with ketoconazole. Antihistamines: increased sedative effects with sedating antihistamines.
Antimalarials: increased risk of ventricular arrhythmias with piperaquine with artenimol - avoid.
Antipsychotics: enhanced hypotensive and sedative effects; increased risk of ventricular arrhythmias with antipsychotics that prolong the QT interval - avoid with amisulpride.
Antivirals: methadone possibly increases
concentration of zidovudine; concentration reduced by efavirenz, fosamprenavir and ritonavir; concentration possibly reduced by abacavir, nevirapine and rilpivirine; concentration possibly affected by boceprevir; concentration of didanosine possibly reduced; increased risk of ventricular arrhythmias with saquinavir and telaprevir - avoid with saquinavir and use with caution with telaprevir.
Atomoxetine: increased risk of ventricular arrhythmias.
Cytotoxics: possible increased risk of ventricular arrhythmias with bosutinib, ceritinib, panobinostat and vandetanib.
Dopaminergics: avoid with selegiline.
Nalmefene: avoid concomitant use.
Sodium oxybate: enhanced effect of sodium oxybate - avoid

Metabolism

Metabolised in the liver to the major metabolite 2-ethylidine-1,5-dimethyl-3,3-diphenylpyrrolidine and the minor metabolite 2-ethyl-3,3-diphenyl-5- methylpyrrolidine, both of them inactive. Two other metabolites have also been identified. These metabolites are excreted in the faeces and urine with unchanged methadone

Purification Methods

The salt crystallises from EtOH, or EtOH/Et2O.

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