U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H21NO
Molecular Weight 267.3654
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZACYCLONOL

SMILES

OC(C1CCNCC1)(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=ZMISODWVFHHWNR-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Azacyclonol (aka gamma-pipradrol) is an ataractive agent; a compound which diminished hallucinations in psychotic individuals. It is sometimes referred to as a tranquilizer or antipsychotic, though it does not actually possess these properties. It was used in Europe during the 1950's for treatment of schizophrenia; likely to reduce the psychedelic effects of LSD and mescaline. However, it had mixed clinical effectiveness and did not gain widespread adoption and was eventually discontinued. Azacyclonol was sold under several trade names: Ataractan, Calmeran, Frenoton, Frenquel and Psychosan.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Frenquel

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
400 mg 1 times / day multiple, oral
Studied dose
Dose: 400 mg, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg, 1 times / day
Sources:
unhealthy
n = 18
Health Status: unhealthy
Condition: schizophrenia
Population Size: 18
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Azacyclonol (frenquel) hydrochloride in the treatment of chronic schizophrenia; a double-blind, controlled study.
1957 Sep 28
Intravenous use of azacyclonol.
1958 May
Azacyclonol in chronic schizophrenia.
1959 Sep 1
[Azacyclonol (Frenquel). Uses and results].
1960 Oct
THE HYPOGLYCAEMIC EFFECT OF AZACYCLONOL AND ITS MECHANISM.
1963 Oct 1
Interplay between CYP3A-mediated metabolism and polarized efflux of terfenadine and its metabolites in intestinal epithelial Caco-2 (TC7) cell monolayers.
1999 May
The effect of rifampin administration on the disposition of fexofenadine.
2001 Mar
Hepatobiliary disposition of a drug/metabolite pair: Comprehensive pharmacokinetic modeling in sandwich-cultured rat hepatocytes.
2006 Aug
The effect of short- and long-term administration of verapamil on the disposition of cytochrome P450 3A and P-glycoprotein substrates.
2006 Mar
Patents

Sample Use Guides

Chronic Schizophrenics were treated for four weeks with daily oral doses of 20 mg Frenquel to control the hallucinogenic effects of LSD. Twenty-one of thirty-eight patients showed definite improvements, while seven more showed doubtful-improvement. Frenquel was also used in oral doses of up to 400 mg daily.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
AZACYCLONOL
INN   MI   WHO-DD  
INN  
Official Name English
TERFENADINE IMPURITY I [EP IMPURITY]
Common Name English
Azacyclonol [WHO-DD]
Common Name English
FEXOFENADINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]
Common Name English
AZACYCLONOL [MI]
Common Name English
azacyclonol [INN]
Common Name English
DIPHENYL(PIPERIDIN-4-YL)METHANOL
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
Code System Code Type Description
FDA UNII
2MMR990PEM
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
MERCK INDEX
m575
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
3680
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
SMS_ID
100000086907
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
CAS
115-46-8
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
INN
655
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID2045280
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
EVMPD
SUB05628MIG
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
PUBCHEM
15723
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
MESH
C100095
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
WIKIPEDIA
AZACYCLONOL
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-092-5
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL127508
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY
NCI_THESAURUS
C76502
Created by admin on Fri Dec 15 15:08:17 GMT 2023 , Edited by admin on Fri Dec 15 15:08:17 GMT 2023
PRIMARY