diphenyl(piperidin-4-yl)methanol

• ChemBase ID: 76871
• Molecular Formular: C18H21NO
• Molecular Mass: 267.36544
• Monoisotopic Mass: 267.1623143
• SMILES: N1CCC(C(c2ccccc2)(c2ccccc2)O)CC1
• Canonical SMILES: OC(c1ccccc1)(c1ccccc1)C1CCNCC1
• InChI: InChI=1S/C18H21NO/c20-18(15-7-3-1-4-8-15,16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-10,17,19-20H,11-14H2
• InChIKey: ZMISODWVFHHWNR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenyl(piperidin-4-yl)methanol
• IUPAC Traditional name: diphenyl(piperidin-4-yl)methanol; azacyclonol
• Synonyms: diphenyl(piperidin-4-yl)methanol; α,α-Diphenyl-4-piperidinemethanol; 4-(Diphenylhydroxymethyl)piperidine; 4-(Hydroxydiphenylmethyl)piperidine; Ataractan; Calmeran; Diphenyl-4-piperidylmethanol; Frenoton; MDL 4829; MER 17; Psychosan; γ-Pipradol; α-(4-Piperidyl)benzhydrol; Alpha-4-Piperidylbenzhydrol; Gamma-Pipradrol; Azacyclonol; MER-17, MDL-4,829; Azacyclonol; Diphenyl(piperidin-4-yl)methanol; Azacyclonol; alpha-(Piperidin-4-yl)benzhydrol; 4-[Hydroxy(diphenyl)methyl]piperidine

Database IDs

• CAS Number: 115-46-8
• MDL Number: MFCD00066980
• PubChem SID: 162041773
• PubChem CID: 15723
• CHEMBL: 127508
• Chemspider ID: 14952
• Unique Ingredient Identifier: 2MMR990PEM
• Wikipedia Title: Azacyclonol

CALCULATED PROPERTIES

• Acid pKa: 13.21939
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.3413978
• LogD (pH = 7.4): 0.33140144
• Log P: 2.8795443
• Molar Refractivity: 82.2217 cm^3
• Polarizability: 32.43273 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: Irritant

Pharmacology Properties

• Target: Others
• Admin Routes: Oral
• Legal Status: Rx-only
• Mechanism of Action: Antagonist to mescaline and LSD

Product Information

• Purity: 97%
• Salt Data: Free Base
• Application(s): Psychosedative; Tranquilliser

DETAILS

Toronto Research Chemicals - P481995

α-(4-Piperidyl)benzhydrol is a key intermediate in the synthesis of Fexofenadine (F322490).

REFERENCES

• Berthon, B., et al.: Biochem. Pharmcol., 47, 789 (1994)
• Di Giacomo, B., et al.: Farmco, 54, 600 (1994)
• Leues, R., et al.: Pharmacol. Ther., 66, 413 (1994)
• Brown, B.A. et al., J. Pharmacol. Exp. Ther., 1956, 118, 153, (pharmacol)
• U.K. Pat., 1958, 801 712; CA, 53, 7204, (synth)
• U.S. Pat., 1959, 2 898 339; CA, 54, 581, (derivs)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 566
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PIY750