1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one

• ChemBase ID: 130337
• Molecular Formular: C15H21NO2
• Molecular Mass: 247.33274
• Monoisotopic Mass: 247.15722892
• SMILES: O=C(C1(c2cccc(O)c2)CCN(C)CC1)CC
• Canonical SMILES: CCC(=O)C1(CCN(CC1)C)c1cccc(c1)O
• InChI: InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3
• InChIKey: ALFGKMXHOUSVAD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one
• IUPAC Traditional name: ketobemidone
• Synonyms: Ketobemidone; Cliradoe; Cymidoe; Ketogae; Ketorax; Ketobemidone; 1-[4-(3-Hydroxyphenyl)-1-methyl-4-piperidinyl]-1-propanone; 1-[4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone; 4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl Ethyl Ketone; A 21 Lundbeck; Cetobemidone; Ciba 7115; Cliradone; K 4710; NSC 117863

Database IDs

• CAS Number: 469-79-4
• PubChem SID: 162224616
• PubChem CID: 10101
• ATC CODE: N02AB01
• CHEMBL: 47072
• Chemspider ID: 9697
• KEGG ID: D08100
• Unique Ingredient Identifier: PQS1L514CF
• Wikipedia Title: Ketobemidone

CALCULATED PROPERTIES

• Acid pKa: 9.440829
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.12300116
• LogD (pH = 7.4): 1.8908951
• Log P: 2.4890444
• Molar Refractivity: 73.1249 cm^3
• Polarizability: 28.375544 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral, rectal, intravenous
• Bioavailability: 34% (oral), 44% (rectal)
• Legal Status: Schedule I (US)

DETAILS

Toronto Research Chemicals - K175000

An opioid analgesic. Used as a substitute to morphine for postoperative pain in children.

REFERENCES

• Lundeberg, S. et al.: Acta Anaesthesiol. Scand., 54, 435 (2010)
• Christensen, T. et al.: Neurosci. Res. Comm., 26, 77 (2010)