3-(3-ethyl-1-methylazepan-3-yl)phenol hydrochloride

• ChemBase ID: 154801
• Molecular Formular: C15H24ClNO
• Molecular Mass: 269.81016
• Monoisotopic Mass: 269.15464207
• SMILES: CCC1(CCCCN(C1)C)c1cccc(c1)O.Cl
• Canonical SMILES: CCC1(CCCCN(C1)C)c1cccc(c1)O.Cl
• InChI: InChI=1S/C15H23NO.ClH/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13;/h6-8,11,17H,3-5,9-10,12H2,1-2H3;1H
• InChIKey: MPJUSISYVXABBH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3-ethyl-1-methylazepan-3-yl)phenol hydrochloride
• IUPAC Traditional name: meptazinol hydrochloride
• Synonyms: 3-(3-ethylhexahydro-1-methyl-1H-azepin-3-yl)-phenol hydrochloride; IL-22811 hydrochloride; WY-22811 hydrochloride; Meptazinol hydrochloride; 3-(3-Ethylhexahydro-1-methyl-1H-azepin-3-yl)phenol; 1-Methyl-3-ethyl-3-(m-hydroxy-phenyl)hexahydro-1H-azepine; Meptazinol Hydrochloride; Meptazinol HCl

Database IDs

• CAS Number: 59263-76-2
• EC Number: 261-683-0
• MDL Number: MFCD00941476
• PubChem SID: 162248939
• PubChem CID: 65483

CALCULATED PROPERTIES

• Acid pKa: 10.227932
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.16047607
• LogD (pH = 7.4): 1.5519505
• Log P: 3.0681393
• Molar Refractivity: 72.2777 cm^3
• Polarizability: 28.251764 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: >10 mg/mL; Methanol; Water
• Apperance: white to off-white powder; White to Off-WHite Solid
• Melting Point: 250-252°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: SL4250000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: HCl
• Empirical Formula (Hill Notation): C15H23NO· HCl

DETAILS

Sigma Aldrich - M2824

Biochem/physiol Actions
Meptazinol entered the human pharmaceutical market as a racemic mixture in the 1980s for use as an analgesic. Its pharmacology is not completely understood; however, its analgesic properties are mostly due to its partial agonism at the mu1 opioid receptor. Due to its partial agonism, Meptazinol antagonizes morphine dependence in vivo. Its advantage over other opiates is its reduced capacity to cause addition and respiratory depression, also due to its intrinsic activity as a partial agonist. Meptazinol has been found to have additional activity as an acetylcholinesterase (AChE) inhibitor, particularly in its (-) enantiomeric form, which may partially explain its analgesic properties. AChE inhibitors are used to treat Alzheimer′s disease, providing additional interest in this compound.

Toronto Research Chemicals - M225080

Mixed opioid agonist-antagonist. Analgesic (narcotic).

REFERENCES

• Davies, G., et al.: Eur. J. Clin. Pharmacol., 23, 535 (1982)
• Johnson, Holmes, B., et al.: Drugs, 30, 285 (1982)
• R.E., et al.: Clin. Pharmacol. Ther., 41, 426 (1982)