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M0267

Sigma-Aldrich

(±)-Methadone hydrochloride

powder, ≥98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C21H27NO · HCl
CAS Number:
1095-90-5
Molecular Weight:
345.91
EC Number:
214-140-7
MDL number:
MFCD00058014
UNSPSC Code:
12352200
PubChem Substance ID:
24896546
NACRES:
NA.77

assay

≥98%

form

powder

drug control

USDEA Schedule II; Home Office Schedule 2; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; estupefaciente (Spain); Decreto Lei 15/93: Tabela IA (Portugal)

color

white to off-white

solubility

H2O: 50 mg/mL, clear, colorless to yellow

originator

Novartis

SMILES string

Cl.CCC(=O)C(CC(C)N(C)C)(c1ccccc1)c2ccccc2

InChI

1S/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

InChI key

FJQXCDYVZAHXNS-UHFFFAOYSA-N

Gene Information

human ... OPRM1(4988)

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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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300,H336

Hazard Classifications

Acute Tox. 2 Oral - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A D Blake et al.
The Journal of biological chemistry, 272(2), 782-790 (1997-01-10)
Mu opioid receptors mediate the analgesia induced by morphine. Prolonged use of morphine causes tolerance development and dependence. To investigate the molecular basis of tolerance and dependence, the cloned mouse mu opioid receptor with an amino-terminal epitope tag was stably
Olivier René et al.
Nucleic acids research, 39(5), 1855-1867 (2010-11-10)
The late stages of 30S and 50S ribosomal subunits biogenesis have been studied in a wild-type (wt) strain of Escherichia coli (MC4100) subjected to a severe heat stress (45-46°C). The 32S and 45S ribosomal particles (precursors to 50S subunits) and
Y Yu et al.
The Journal of biological chemistry, 272(46), 28869-28874 (1997-11-20)
Mu opioid receptors are subject to phosphorylation and desensitization through actions of at least two distinct biochemical pathways: agonist-dependent mu receptor phosphorylation and desensitization induced by a biochemically distinct second pathway dependent on protein kinase C activation (1). To better
S Haroutiunian et al.
British journal of anaesthesia, 112(1), 150-158 (2013-07-12)
The properties of methadone suggest a potential advantage for epidural over i.v. administration for pain relief, but little supportive evidence exists. To investigate the pharmacokinetic and the pharmacodynamic properties of epidural and i.v. methadone, four doses of methadone (0.1, 0.25
David Kao et al.
Annals of internal medicine, 158(10), 735-740 (2013-05-22)
Long-acting opioids are a leading cause of accidental death in the United States, and methadone is associated with greater mortality rates. Whether this increase is related to the proarrhythmic properties of methadone is unclear. To describe methadone-associated arrhythmia events reported
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