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M0267 Sigma

(±)-Methadone hydrochloride

powder, ≥98% (TLC)

Synonym: 6-Dimethylamino-4,4-diphenylheptan-3-one hydrochloride

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents, Calcium Channel Modulators,
assay   ≥98% (TLC)
form   powder
drug control   USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
color   white to off-white
solubility   H2O: >50 mg/mL, clear, colorless to yellow
originator   Novartis

Description

Biochem/physiol Actions

μ opioid receptor agonist that desensitizes both the μ opioid receptor and the δ opioid receptor on chronic exposure; narcotic analgesic, characterized by a gradual onset of action and prolonged, milder withdrawal; may also block L-type calcium channels independently of its effects on opioid receptors.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Price and Availability

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<SC>DL</SC>-Methadone-d<SUB>3</SUB> solution

98 atom % D, 1 mg/mL in methanol, drug standard

European Pharmacopoeia (EP)

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
25
Safety Statements (Europe) 
45
RIDADR 
UN 2811 6.1 / PGII
WGK Germany 
3
RTECS 
MJ6300000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Late Steps Of Ribosome Assembly In E. Coli Are Sensitive To A Severe Heat Stress But Are Assisted By The HSP70 Chaperone Machine. René, O., and Alix, J.H. Nucleic Acids Res. 39, 1855-67, (2011)

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Mu opioid receptor phosphorylation desensitization and ligand efficacy. Yu, Y. J. Biol. Chem. 272, 28869, (1997)

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Differential opioid agonist regulation of the mouse mu opioid receptor. Blake, A.D., et al. J. Biol. Chem. 272, 782-790, (1997)

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Methadone-induced desensitization of the delta-opioid receptor is mediated by uncoupling of receptor from G protein. Liu, J.G., et al. Eur. J. Pharmacol. 374, 301-308, (1999)

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The difference between methadone and morphine in regulation of delta-opioid receptors underlies the antagonistic effect of methadone on morphine-mediated cellular actions. Liu, J.G., et al. Eur. J. Pharmacol. 373, 233-239, (1999)

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Morphine and methadone have different effects on calcium channel currents in neuroblastoma cells. Yang, J.C., et al. Brain Res. 870, 199-203, (2000)

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Determinants of increased opioid-related mortality in the United States and Canada, 1990-2013: a systematic review. King NB, Fraser V, Boikos C, et al. Am. J. Public Health 104(8), e32-42, (2014)

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Factors associated with mortality of HIV-positive clients receiving methadone maintenance treatment in China. Liu E, Rou K, McGoogan JM, et al. J. Infect. Dis. 208(3), 442-53, (2013)

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Drug-induced long QT in adult psychiatric inpatients: the 5-year cross-sectional ECG Screening Outcome in Psychiatry study. Girardin FR, Gex-Fabry M, Berney P, et al. Am. J. Psychiatry 170(12), 1468-76, (2013)

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Pharmacogenetics of opiates in clinical practice: the visible tip of the iceberg. Hajj A, Khabbaz L, Laplanche JL, et al. Pharmacogenomics 14(5), 575-85, (2013)

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Buprenorphine: a new player in neonatal withdrawal syndrome. Nanda S, Brant R, Regier M, et al. W. V. Med. J. 111(1), 16-21, (2015)

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Methadone and prescription drug overdose. Hendrikson H and Hansen M NCSL Legisbrief 22(45), 1-2, (2014)

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Reversal of opioid overdose syndrome in morphine-dependent rats using buprenorphine. Zamani N, Hassanian-Moghaddam H, Bayat AH, et al. Toxicol. Lett. 232(3), 590-4, (2015)

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Association of opioid agonist therapy with lower incidence of hepatitis C virus infection in young adult injection drug users. Tsui JI, Evans JL, Lum PJ, et al. JAMA Intern. Med. 174(12), 1974-81, (2014)

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[Treatment of chronic hepatitis C in drug users: ethic, successful and useful]. Remy AJ, Wenger H, and Bouchkira H Presse Med. 43(12 Pt 1), 1314-6, (2014)

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Risk reduction with buprenorphine-naloxone and methadone: patient's choice. Newman RG J. Acquir. Immune Defic. Syndr. 67(5), e142, (2014)

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Cyclosporine-inhibitable cerebral drug transport does not influence clinical methadone pharmacodynamics. Meissner K, Blood J, Francis AM, et al. Anesthesiology 121(6), 1281-91, (2014)

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Methadone is a local anaesthetic-like inhibitor of neuronal Na+ channels and blocks excitability of mouse peripheral nerves. Stoetzer C, Kistner K, Stüber T, et al. Br. J. Anaesth. 114(1), 110-20, (2015)

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Opioid substitution treatment in New Zealand: a 40 year perspective. Deering D, Sellman JD, and Adamson S N. Z. Med. J. 127(1397), 57-66, (2014)

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What is your gut feeling about opioid rotation? Didwaniya N, Reddy A, Gottumukkala RS, et al. J. Clin. Oncol. 33(3), e11-2, (2015)

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Stroop task among patients with obsessive-compulsive disorder (OCD) and pathological gambling (PG) in methadone maintenance treatment (MMT). Peles E, Weinstein A, Sason A, et al. CNS Spectr. 19(6), 509-18, (2014)

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Patterns of care and side effects for patients prescribed methadone for treatment of chronic pain. Macey TA, Weimer MB, Grimaldi EM, et al. J. Opioid Manag. 9(5), 325-33, (2013)

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HIV prevalence and related risk behaviours among female sex workers in Iran: results of the national biobehavioural survey, 2010. Sajadi L, Mirzazadeh A, Navadeh S, et al. Sex. Transm. Infect. 89 Suppl 3, iii37-40, (2013)

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The lethal burden of drug overdose. Lancet 382(9895), 833, (2013)

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HIV prevalence and related risk behaviours among prisoners in Iran: results of the national biobehavioural survey, 2009. Navadeh S, Mirzazadeh A, Gouya MM, et al. Sex. Transm. Infect. 89 Suppl 3, iii33-6, (2013)

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[Rapid opiate detoxification under anesthesia (RODA)]. Dubols N, Hallet C, Luppens D, et al. Rev. Med. Liege. 68(5-6), 298-302, (2013)

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[Postmortem detection of accidental methadone intoxication in a 10-year-old girl]. Thierauf A, Vogt S, Pollak S, et al. Arch. Kriminol. 231(5-6), 175-82, (2013)

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Consumer attitudes about opioid addiction treatment: a focus group study in New York City. Sohler NL, Weiss L, Egan JE, et al. J. Opioid Manag. 9(2), 111-9, (2013)

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Hypoglycemia during rapid methadone dose escalation. Moryl N, Pope J, and Obbens E J. Opioid Manag. 9(1), 29-34, (2013)

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[Methadone. Reducing the transmission of HIV]. Sabourin G Perspect. Infirm. 10(3), 56, (2013)

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[Supervised injection. Under the watchful eye of nurses]. Gagné L Perspect. Infirm. 10(2), 17-20, (2013)

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Problem based review: The patient taking methadone. Arora A and Williams K Acute Med. 12(1), 51-4, (2013)

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Enhanced antinociceptive efficacy of epidural compared with i.v. methadone in a rat model of thermal nociception. Haroutiunian S, Kagan L, Yifrach-Damari I, et al. Br. J. Anaesth. 112(1), 150-8, (2014)

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A randomized trial of a hepatitis care coordination model in methadone maintenance treatment. Masson CL, Delucchi KL, McKnight C, et al. Am. J. Public Health 103(10), e81-8, (2013)

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Computer-assisted delivery of cognitive-behavioral therapy: efficacy and durability of CBT4CBT among cocaine-dependent individuals maintained on methadone. Carroll KM, Kiluk BD, Nich C, et al. Am. J. Psychiatry 171(4), 436-44, (2014)

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Trends in reporting methadone-associated cardiac arrhythmia, 1997-2011: an analysis of registry data. Kao D, Bucher Bartelson B, Khatri V, et al. Ann. Intern. Med. 158(10), 735-40, (2013)

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Visual outcome in infants born to drug-misusing mothers prescribed methadone in pregnancy. McGlone L, Hamilton R, McCulloch DL, et al. Br. J. Ophthalmol. 98(2), 238-45, (2014)

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Clinical care for opioid-using pregnant and postpartum women: the role of obstetric providers. Jones HE, Deppen K, Hudak ML, et al. Am. J. Obstet. Gynecol. 210(4), 302-10, (2014)

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Screening and confirmation of 62 drugs of abuse and metabolites in urine by ultra-high-performance liquid chromatography-quadrupole time-of-flight mass spectrometry. Tsai IL, Weng TI, Tseng YJ, et al. J. Anal. Toxicol. 37(9), 642-51, (2013)

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Methadone toxicity: comparing tablet and syrup formulations during a decade in an academic poison center of Iran. Shadnia S, Rahimi M, Hassanian-Moghaddam H, et al. Clin. Toxicol. (Phila.) 51(8), 777-82, (2013)

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QTc interval screening in an opioid treatment program. Katz DF, Sun J, Khatri V, et al. Am. J. Cardiol. 112(7), 1013-8, (2013)

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In utero drug and alcohol exposure in infants born to mothers prescribed maintenance methadone. McGlone L, Mactier H, Hassan H, et al. Arch. Dis. Child Fetal Neonatal Ed. 98(6), F542-4, (2013)

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Continuing methadone for pain in palliative care. Hawley P, Liebscher R, and Wilford J Pain Res. Manag. 18(2), 83-6, (2013)

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Electrocatalytic oxidation and selective determination of an opioid analgesic methadone in the presence of acetaminophen at a glassy carbon electrode modified with functionalized multi-walled carbon nanotubes: application for human urine, saliva and pharmaceutical samples analysis. Amiri-Aref M, Raoof JB, and Ojani R Colloids Surf. B Biointerfaces 109, 287-93, (2013)

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The effectiveness comparison of Jitai tablets versus methadone in community-based drug treatment: a 1-year follow-up study. Hao SQ, Zhao M, Zhang RW, et al. Addict. Behav. 38(10), 2596-600, (2013)

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Diversion of benzodiazepines through healthcare sources. Ibañez GE, Levi-Minzi MA, Rigg KK, et al. J. Psychoactive Drugs 45(1), 48-56, (2013)

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Behavioral effects of perinatal opioid exposure. Fodor A, Tímár J, and Zelena D Life Sci. 104(1-2), 1-8, (2014)

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The obstetrical and neonatal impact of maternal opioid detoxification in pregnancy. Stewart RD, Nelson DB, Adhikari EH, et al. Am. J. Obstet. Gynecol. 209(3), 267.e1-5, (2013)

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Methadone maintenance treatment experience in Macao--prospective follow-up for initial 4.5 years. Adelson M, Wilson HW, Celeste VY, et al. J. Psychoactive Drugs 45(4), 313-21, (2013)

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Pain relief and opioid requirements in the first 24 hours after surgery in patients taking buprenorphine and methadone opioid substitution therapy. Macintyre PE, Russell RA, Usher KA, et al. Anaesth. Intensive Care 41(2), 222-30, (2013)

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Mechanism of autoinduction of methadone N-demethylation in human hepatocytes. Campbell SD, Crafford A, Williamson BL, et al. Anesth. Analg. 117(1), 52-60, (2013)

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Daily temporal patterns of heroin and cocaine use and craving: relationship with business hours regardless of actual employment status. Phillips KA, Epstein DH, and Preston KL Addict. Behav. 38(10), 2485-91, (2013)

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Opioid overdose mortality in Kansas, 2001-2011: toxicologic evaluation of intent. Okic M, Cnossen L, Crifasi JA, et al. J. Anal. Toxicol. 37(9), 629-35, (2013)

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Disaccharides in urine samples as markers of intravenous abuse of methadone and buprenorphine. Jungen H, Andresen-Streichert H, Müller A, et al. J. Anal. Toxicol. 37(9), 652-8, (2013)

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New formulation of methadone for opioid dependence in France: acceptability and diversion/misuse liability. Eiden C, Léglise Y, Bertomeu L, et al. Therapie. 68(2), 107-11, (2013)

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The effects of gabapentin on methadone based addiction treatment: a randomized controlled trial. Moghadam MS and Alavinia M Pak. J. Pharm. Sci. 26(5), 985-9, (2013)

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[Levamethadone as substitution treatment of opioid-dependent patients]. Mueller EA and Kirch W Dtsch. Med. Wochenschr. 138(40), 2052-6, (2013)

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Methadone as an additional opioid for a cancer patient with severe neuropathic and bone pain not responsive to other opioids and adjuvant analgesics. Leppert W and Kowalski G J. Palliat. Care 29(2), 119-21, (2013)

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A comparative study of beneficial effects of Olanzapine and sodium valproate on aggressive behavior of patients who are on methadone maintenance therapy: a randomized triple blind clinical trial. Zarghami M, Sheikhmoonesi F, Ala S, et al. Eur. Rev. Med. Pharmacol. Sci. 17(8), 1073-81, (2013)

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Review on the demographic and social impact of methadone-medication therapy on Malaysian patients. Manan MM, Ali SM, Khan MA, et al. Pak. J. Pharm. Sci. 26(4), 841-6, (2013)

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Quality of life in patients on methadone maintenance treatment: a three-month assessment. Lashkaripour K, Bakhshani NM, and Sadjadi SA J. Pak. Med. Assoc. 62(10), 1003-7, (2012)

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[Opiate substitution treatment's cycles in a five-year followed-up cohort in ambulatory practice]. Dupouy J, Bez J, Barsony J, et al. Therapie. 68(3), 155-61, (2013)

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Russia's ban on methadone for drug users in Crimea will worsen the HIV/AIDS epidemic and risk public health. Kazatchkine M BMJ 348, g3118, (2014)

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Computerization of the therapeutic task of working through. Freedman R Am. J. Psychiatry 171(4), 388-90, (2014)

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Confronting the stigma of opioid use disorder--and its treatment. Olsen Y and Sharfstein JM JAMA 311(14), 1393-4, (2014)

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Access to treatment for opioid dependence in rural America: challenges and future directions. Sigmon SC JAMA Psychiatry 71(4), 359-60, (2014)

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Take-home naloxone kits preventing overdose deaths. Eggertson L CMAJ 186(1), 17, (2014)

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The obstetric and neonatal impact of maternal opioid detoxification in pregnancy. Terplan M Am. J. Obstet. Gynecol. 210(4), 375-6, (2014)

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Reply: To PMID 23727040. Stewart RD, Dashe JS, and Sheffield JS Am. J. Obstet. Gynecol. 210(4), 376, (2014)

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Syncope: a tale of two triggers. Katz DF, Varosy PD, and Masoudi FA JAMA Intern. Med. 173(16), 1543-4, (2013)

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Methadone and torsade de pointes: how can we better understand the association? Hasnain M, Vieweg WV, Breden Crouse EL, et al. Am. J. Med. 126(9), 757-8, (2013)

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Advice on methadone and oral health: dental public health in action. Jones CM and Isherwood G Community Dent. Health 30(2), 68-70, (2013)

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Efforts to reduce overdose deaths. Sherman SG, Han J, Welsh C, et al. Am. J. Public Health 103(8), e1-2, (2013)

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Schwartz et al. respond. Schwartz RP, Gryczynski J, O'Grady KE, et al. Am. J. Public Health 103(8), e2-3, (2013)

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[Evolution of patients treated with methadone in general practice]. Poloméni P, Pachabezian V, Pequart C, et al. Presse Med. 42(12), 1660-2, (2013)

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HIV prevention, treatment, and care for people who inject drugs. Larney S, Zaller ND, and Rich JD J. Infect. Dis. 208(3), 370-2, (2013)

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