Compound: Azacyclonol
SMILES: OC(c1ccccc1)(c2ccccc2)C3CCNCC3
InChIKey: ZMISODWVFHHWNR-UHFFFAOYSA-N
Synonyms: Azacyclonol, 115-46-8, diphenyl(piperidin-4-yl)methanol, gamma-Pipradol, Azaciclonolo, Azacyclonolum, azaciclonol, 2MMR990PEM, DTXSID2045280, DTXCID0025280, RefChem:115914, 204-092-5, alpha,alpha-diphenyl-4-piperidinomethanol, alpha-(4-Piperidyl)benzhydrol, Diphenyl(4-piperidinyl)methanol, 4-Piperidinemethanol, alpha,alpha-diphenyl-, alpha,alpha-Diphenyl-4-piperidinemethanol, Ataractan, Calmeran, Psychosan, Diphenyl-piperidin-4-yl-methanol, Frenoton, Diphenyl-4-piperidylmethanol, MER 17, MFCD00066980, a-(4-Piperidyl)benzhydrol, MLS000558844, CHEMBL127508, NCGC00016366-01, CAS-115-46-8, SMR000149160, Diphenyl(piperidin-4-yl)methanol (Azacyclonol), 4-Piperidinemethanol, .alpha.,.alpha.-diphenyl-, diphenyl-4-piperidylmethan-1-ol, Azaciclonolo [DCIT], Azacyklonol, Azacyclonol [INN:BAN], Azacyclonolum [INN-Latin], Fexofenadine EP Impurity E, EINECS 204-092-5, UNII-2MMR990PEM, BRN 0230221, diphenyl(4-piperidyl)methanol, Azacyclonol;, Ataractan;, Calmeran;, Frenoton;, Gamma-Pipradrol;, .gamma.-Pipradol, Prestwick_84, 4-(Diphenylhydroxymethyl)piperidine, AZACYCLONOL [MI], Maybridge3_001033, Opera_ID_1183, Prestwick0_000093, Prestwick1_000093, Prestwick2_000093, Prestwick3_000093, AZACYCLONOL [INN], TERFENADINE_met007, EC 204-092-5, |A-(4-Piperidyl)benzhydrol, Alpha-4-Piperidylbenzhydrol;, Azacyclonol (MDL 4829), Oprea1_114075, Oprea1_848733, AZACYCLONOL [WHO-DD], BSPBio_000046, diphenyl 4-piperidyl carbinol, MLS001201777, SCHEMBL241817, SPBio_001985, BPBio1_000052, orb1310727, SCHEMBL4425169, CHEBI:93706, .alpha.-(4-Piperidyl)benzhydrol, Diphenyl(4-piperidinyl)methanol #, GLXC-08087, HMS1433O21, HMS1568C08, HMS2095C08, HMS2230G14, HMS3652K11, HMS3712C08, HMS3885E13, 4-(hydroxydiphenylmethyl)piperidine, HY-B0530, 4-(diphenylhydroxymethyl) piperidine, Tox21_110399, AC2248, BBL010986, BDBM50017724, CCG-51239, EBC-03796, s3196, SBB003057, STK802108, 4-[Hydroxy(diphenyl)methyl]piperidine, AKOS000121583, Tox21_110399_1, 4-(hydroxy-diphenyl-methyl)-piperidine, AC-2127, 4-Piperidinemethanol, |A,|A-diphenyl-, IDI1_012420, NCGC00016366-02, NCGC00016366-04, NCGC00179677-01, AS-13114, FA160305, SY036924, alpha, alpha-diphenyl-4-piperidinemethanol, alpha,alpha -diphenyl-4-piperidinemethanol, alpha,alpha -diphenyl-4-piperidine-methanol, DB-041270, NS00003707, P1369, ST50275420, SW196396-3, TERFENADINE IMPURITY I [EP IMPURITY], .alpha.,.alpha.-Diphenyl-4-piperidinemethanol, EN300-17628, SR-01000640550, Q4832014, SR-01000640550-1, SR-01000640550-4, BRD-K97061094-001-03-2, BRD-K97061094-001-20-6, BRD-K97061094-001-21-4, Fexofenadine EP Impurity E; Terfenadine EP Impurity I, Z56969317, FEXOFENADINE HYDROCHLORIDE IMPURITY E [EP IMPURITY], |A inverted exclamation mark,|A inverted exclamation mark-Diphenyl-4-piperidinemethanol, Diphenyl(piperidin-4-yl)methanol (Azacyclonol; Pipradrol 4-Isomer) 1.0 mg/ml in Methanol
Theoretical properties:
molecular_formula: C18H21NO
molecular_weight: 267.4 g/mol
exact_mass: 267.162314293 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 20
topological_polar_surface_area: 32.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: >40.1 [ug/mL] (The mean of the results at pH 7.4)
Descriptions:
pubchem: Diphenyl(4-piperidinyl)methanol is a diarylmethane.
chembl: AZACYCLONOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Azacyclonol (trade names Ataractan, Calmeran, Frenoton, Frenquel, Psychosan), also known as γ-pipradrol, is a drug which is an ataractive, i.e., an agent which diminishes hallucinations in psychotic individuals. It has also been called a tranquilizer and antipsychotic, though these definitions are not accurate as it does not actually possess such properties. Despite being a positional isomer of pipradrol, it is not a psychostimulant, and instead has mild depressant effects.
The drug was introduced in Europe in the mid-1950s for the treatment of schizophrenia likely because it was found to attenuate the subjective psychedelic effects of LSD and mescaline in humans. However, due to poor and mixed clinical effectiveness, it never gained widespread acceptance and was eventually discontinued.
Azacyclonol is also known as diphenylmethanolpiperidine and is the parent structure of the antihistamines fexofenadine and terfenadine. Terfenadine produces azacyclonol as a major active metabolite.
It is made by the organometallic addition of 4-bromopyridine to benzophenone, followed by catalytic hydrogenation of the pyridine heteroaromatic ring system to the corresponding piperidine.