AZACYCLONOL

US Previously Marketed

First approved in 1955

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 Search

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

Molecular Formula	C18H21NO
Molecular Weight	267.3654
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13368052 | https://www.ncbi.nlm.nih.gov/pubmed/13383414

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.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hallucinations 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13383414	Primary		Not Provided 504	Frenquel Approved Use Unknown

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/13383414	unhealthy n = 18 Health Status: unhealthy Condition: schizophrenia Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/13383414	Sources: https://pubmed.ncbi.nlm.nih.gov/13383414

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY20975	https://www.001chemical.com/chem/115-46-8
3B Scientific (Wuhan) Corp	3B3-004428	http://www.3bsc.com/index/pro_info.php?id=26318
AA Blocks	AA000FGV	https://www.aablocks.com/goods/Goods/detail?id=AA000FGV
AEchem Scientific Corp., USA	AE026013	http://www.aechemsc.com/info_products/AE026013.php
AHH Chemical co.,ltd	MT-11379	http://www.ahhchemical.com/product/MT-11379.html
AK Scientific, Inc. (AKSCI)	H361	http://www.aksci.com/item_detail.php?cat=H361
Aaron Chemicals	AR000G8N	http://www.aaronchem.com/115-46-8
AbMole Bioscience	M2413	http://www.abmole.com/products/azacyclonol.html
Accela ChemBio Inc	SY036924	http://www.accelachem.com/cn/search.html?keyword=SY036924&attname=GoodsCode
Aceschem	ACS012081	https://www.aceschem.com/catalog/115-46-8.html
Achemica	ACMC-2099qa	http://www.achemica.com/prodinfo/?id=120083
Achemo Scientific Limited	AC-15357	http://www.achemo.com/search/?Keyword=115-46-8
Achemtek	0104-014641	http://www.achemtek.com/115-46-8
Acros Organics	AC232520050	https://www.fishersci.com/shop/products/diphenyl-4-piperidinomethanol-98-acros-organics/AC232520050
Acros Organics	AC232520250	https://www.fishersci.com/shop/products/diphenyl-4-piperidinomethanol-98-acros-organics/AC232520250
Adooq BioScience	A11806	https://www.adooq.com/azacyclonol.html
Alfa Aesar	H61281	https://www.alfa.com/en/catalog/H61281/
Allbio Pharm Co., Ltd	AD11606	http://www.allbiopharm.com/product/n/AD11606
Ambinter	Amb1546046	http://www.ambinter.com/reference/1546046
Anward	ANW-16880	http://www.anward.com/pro_result/21092
ApexBio Technology	B1891	http://www.apexbt.com/azacyclonol.html
Aurum Pharmatech LLC	M-1450	http://www.Aurumpharmatech.com/Product/ProductDetails/M_1450
BioCrick	BCC4761	http://www.biocrick.com/Azacyclonol-BCC4761.html
BioSynth	J-003293	https://www.biosynth.com/en/products/all-products/products/J-003293.html
BioSynth	J-523943	https://www.biosynth.com/en/products/all-products/products/J-523943.html
Boerchem	BC208224	http://www.boerchem.com/?product_41475.html
Capot Chemical	23824	http://www.capotchem.com/en/23824.htm
Capot Chemical	PubChem23824	http://www.capotchem.com/en/23824.htm
Chem Scene	CS-2754	http://www.chemscene.com/115-46-8.html
ChemMol	30104167	http://www.chemmol.com/chemmol/30104167.html
ChemMol	44003171	http://www.chemmol.com/chemmol/44003171.html
ChemMol	49408166	http://www.chemmol.com/chemmol/49408166.html
Chemenu	CM110610	http://www.chemenu.com/products/CM110610
Chemspace	CSSB00016989146	https://chem-space.com/CSSB00016989146
Clearsynth	CS-O-14190	http://www.clearsynth.com/en/CSO14190.html
Clearsynth	CS-O-00907	https://www.clearsynth.com/en/CSO00907.html
DC Chemicals	DC37488	http://www.dcchemicals.com//product_show-Azacyclonol.html
Debye Scientific	DB-041270	http://www.debyesci.com/cas_115-46-8.html
Finetech	FT-0622512	http://www.finetechnology-ind.com/prod/detail/pub/115-46-8.html
Glentham Life Sciences	GE0221	http://www.glentham.com/products/product/GE0221/
Hairui	HR145256	http://www.hairuichem.com/en/product/115-46-8.html
Hefei Hirisun Pharmatech Co., Ltd	HR012083	http://www.hirisunpharm.com/115-46-8.html
LGC Standards	LGCAMP0055.02-01	https://www.lgcstandards.com/US/en/p/LGCAMP0055.02-01
LGC Standards	LGCFOR0055.02	https://www.lgcstandards.com/US/en/p/LGCFOR0055.02
LGC Standards	MM0055.02	https://www.lgcstandards.com/US/en/p/MM0055.02
Lab Network	LN00225302	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00225302
MedChem Express	HY-B0530	https://www.medchemexpress.com/Azacyclonol.html
Molcore	MC20975	https://www.molcore.com/product/115-46-8
MuseChem	A000182	https://www.musechem.com/product/A000182.html
Oakwood	57908	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=47227&ExtHyperLink=1
Sigma-Aldrich	PH009693_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/ph009693
Smolecule	S519985	http://www.smolecule.com/products/s519985
TCI (Tokyo Chemical Industry)	P1369	http://www.tcichemicals.com/eshop/en/us/commodity/P1369/index.html
THE BioTek	bt-260381	https://www.thebiotek.com/product/inhibitors/bt-260381
VladaChem	VL264407-100G	https://www.vladachem.com/product.php?products=115-46-8
Yuhao Chemical	CJ2758	http://www.chemyuhao.com/115-46-8.html
abcr GmbH	AB141159	http://www.abcr.com/shop/en/AB141159
eNovation Chemicals	D518987	http://www.enovationchem.com/productDetails.asp?productID=D518987
eNovation Chemicals	D619633	https://www.enovationchem.com/ProductDetails.asp?ProductID=D619633
iChemical	EBD33008	http://www.ichemical.com/chemicals/cas-115-46-8
mcule	MCULE-3573622912	https://mcule.com/MCULE-3573622912/

PubMed

Title	Date	PubMed
Azacyclonol (frenquel) hydrochloride in the treatment of chronic schizophrenia; a double-blind, controlled study.	1957 Sep 28	13462791
Intravenous use of azacyclonol.	1958 May	13541823
Azacyclonol in chronic schizophrenia.	1959 Sep 1	13800347
[Azacyclonol (Frenquel). Uses and results].	1960 Oct	13713843
THE HYPOGLYCAEMIC EFFECT OF AZACYCLONOL AND ITS MECHANISM.	1963 Oct 1	14067559
The effect of rifampin administration on the disposition of fexofenadine.	2001 Mar	11240975
Hepatobiliary disposition of a drug/metabolite pair: Comprehensive pharmacokinetic modeling in sandwich-cultured rat hepatocytes.	2006 Aug	16690724
The effect of short- and long-term administration of verapamil on the disposition of cytochrome P450 3A and P-glycoprotein substrates.	2006 Mar	16513446

Patents

Sample Use Guides

In Vivo Use Guide

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:08:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:08:17 GMT 2023`
Record UNII	2MMR990PEM
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AZACYCLONOL

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