Azacyclonol

Title: Azacyclonol
CAS Registry Number: 115-46-8
CAS Name: a,a-Diphenyl-4-piperidinemethanol
Additional Names: a-(4-piperidyl)benzhydrol; diphenyl (g-pyridyl)carbinol; gamma-pipradrol
Manufacturers' Codes: MER-17
Molecular Formula: C18H21NO
Molecular Weight: 267.37
Percent Composition: C 80.86%, H 7.92%, N 5.24%, O 5.98%
Literature References: Prepd by hydrogenation of a,a-diphenyl-4-pyridinemethanol: Schumann et al., US 2804422 (1957 to Merrell).
Properties: Crystals, mp 160-161°.
Melting point: mp 160-161°
Derivative Type: Hydrochloride
CAS Registry Number: 1798-50-1
Trademarks: Frenquel (Cassenne); Frenoton (Draco)
Molecular Formula: C18H21NO.HCl
Molecular Weight: 303.83
Percent Composition: C 71.16%, H 7.30%, N 4.61%, O 5.27%, Cl 11.67%
Properties: Crystals from butanone, mp 283-285°. Slightly bitter taste. Moderately sol in water.
Melting point: mp 283-285°
Therap-Cat: Anxiolytic.
Status: This monograph has been retired and is no longer subject to revision or update.
Azafenidin Azafrin Azamethonium Bromide Azanidazole Azaperone

Azacyclonol
Azacyclonol.png
Systematic (IUPAC) name
Diphenyl(piperidin-4-yl)methanol
Clinical data
Legal status Prescription only
Routes Oral
Identifiers
CAS number 115-46-8 N
1798-50-1 (HCl)
ATC code None
PubChem CID 15723
ChemSpider 14952 YesY
UNII 2MMR990PEM YesY
ChEMBL CHEMBL127508 YesY
Synonyms MER-17, MDL-4,829
Chemical data
Formula C18H21NO 
Mol. mass 267.37 g/mol
 N (what is this?)  (verify)

Azacyclonol (trade names Ataractan, Calmeran, Frenoton, Frenquel, Psychosan), also known as γ-pipradol, is a drug which is a so-called ataractive, or agent which diminishes hallucinations in psychotic individuals.[1][2] 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.[1][3]

The drug was introduced in Europe in the mid-1950s for the treatment of schizophrenia likely on account of the fact that it was found to attenuate the subjective psychedelic effects of LSD and mescaline in humans.[1][4] However, due to poor and mixed clinical effectiveness[4] it never gained widespread acceptance and was eventually discontinued.

The antihistamine agent terfenadine produces azacyclonol as an active major metabolite.[5]