(6S)-6-(dimethylamino)-4,4-diphenylheptan-3-one hydrochloride

• ChemBase ID: 131540
• Molecular Formular: C21H28ClNO
• Molecular Mass: 345.90612
• Monoisotopic Mass: 345.1859422
• SMILES: CCC(=O)C(C[C@H](C)N(C)C)(c1ccccc1)c1ccccc1.Cl
• Canonical SMILES: CCC(=O)C(c1ccccc1)(c1ccccc1)C[C@@H](N(C)C)C.Cl
• InChI: 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/t17-;/m0./s1
• InChIKey: FJQXCDYVZAHXNS-LMOVPXPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S)-6-(dimethylamino)-4,4-diphenylheptan-3-one hydrochloride
• IUPAC Traditional name: (+/-)-methadone hydrochloride
• Synonyms: S(+)-Methadone hydrochloride; (6R)-6-(Dimethylamino)-4,4-diphenyl-3-heptanone Hydrochloride; L-6-(Dimethylamino)-4,4-diphenyl-3-heptanone Hydrochloride; (-)-Methadone Hydrochloride; Levomethadone Hydrochloride; Levothyl Hydrochloride; Polamivet Hydrochloride; (R)-Methadone Hydrochloride; (6S)-6-(Dimethylamino)-4,4-diphenyl-3-heptanone Hydrochloride; Dextromethadone Hydrochloride; D-6-(Dimethylamino)-4,4-diphenyl-3-heptanone Hydrochloride; (+)-Methadone Hydrochloride; (S)-Methadone Hydrochloride

Database IDs

• CAS Number: 5653-80-5(freebase); 5967-73-7; 15284-15-8
• MDL Number: MFCD00151717
• PubChem SID: 162225818
• PubChem CID: 20055402

CALCULATED PROPERTIES

• Acid pKa: 18.780819
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.7526444
• LogD (pH = 7.4): 3.2887921
• Log P: 5.0071716
• Molar Refractivity: 97.2689 cm^3
• Polarizability: 38.16956 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; H2O: soluble; Methanol; Water
• Apperance: N/AOff-White to Pale Beige Solid; white; White Solid
• Melting Point: 220-227°C; 239-242°C (dec.)

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: MJ6000000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38-42/43
• Safety Statements: 22-26-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

DETAILS

Sigma Aldrich - M150

Other Notes
Enantiomer of methadone that is either inactive or a weak agonist at opioid receptors; NMDA antagonist that blocks the development of morphine tolerance.

Toronto Research Chemicals - M225880

A component of pharmaceuticals used in the treatment of opioid dependence.

Toronto Research Chemicals - M225885

A component of pharmaceuticals used in the treatment of opioid dependence.

REFERENCES

• Shiran, M., et al.: Brit. J. Clin. Pharmacol., 67, 29 (2008)
• Esteban, J., et al.: Drug Metab. Lett., 2, 269 (2008)
• Tolson, A., et al.: Drug Metab. Disposition, 37, 1887 (2008)
• Deeb, T., et al.: Mol. Pharmacol., 75, 908 (2008)
• Shiran, M., et al.: Brit. J. Clin. Pharmacol., 67, 29 (2008)
• Esteban, J., et al.: Drug Metab. Lett., 2, 269 (2008)
• Tolson, A., et al.: Drug Metab. Disposition, 37, 1887 (2008)
• Deeb, T., et al.: Mol. Pharmacol., 75, 908 (2008)