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

• ChemBase ID: 131219
• Molecular Formular: C21H28ClNO
• Molecular Mass: 345.90612
• Monoisotopic Mass: 345.1859422
• SMILES: CCC(=O)C(CC(C)N(C)C)(c1ccccc1)c1ccccc1.Cl
• Canonical SMILES: CCC(=O)C(c1ccccc1)(c1ccccc1)CC(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
• InChIKey: FJQXCDYVZAHXNS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(dimethylamino)-4,4-diphenylheptan-3-one hydrochloride
• IUPAC Traditional name: methadone hydrochloride
• Synonyms: 6-Dimethylamino-4,4-diphenylheptan-3-one hydrochloride; (±)-Methadone hydrochloride; 6-(Dimethylamino)-4,4-diphenyl-3-heptanone Hydrochloride; (+/-)-Methadone Hydrochloride; AN 148; Adanon; Depridol; Diaminon Hydrochloride; Methadose; Miadone; Moheptan; rac Methadone Hydrochloride

Database IDs

• CAS Number: 1095-90-5
• EC Number: 214-140-7
• MDL Number: MFCD00058014
• PubChem SID: 162225497; 24896546
• PubChem CID: 14184

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: >50 mg/mL, clear, colorless to yellow; Methanol; Water
• Apperance: White Solid; white to off-white powder
• Melting Point: 232-234°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: MJ6300000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - M0267

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.

Toronto Research Chemicals - M225865

Controlled substance (opiate). Used in treatment of opioid dependence.

REFERENCES

• Bishara, R.H., et al.: Anal. Profiles Drug Subs., 3, 365 (1974)
• Senay, E.C., et al.: Int. J. Addict., 20, 803 (1974)
• Inturrisi, C.E., et al.: Clin. Pharmacol. Ther., 41, 392 (1974)
• Sees, K.L., et al.: J. Am. Med. Assoc., 283, 1303 (1974)