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Details

Stereochemistry MIXED
Molecular Formula C20H23NO2
Molecular Weight 309.4021
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOXADROL

SMILES

C1OC(OC1C2CCCCN2)(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=HGKAMARNFGKMLC-UHFFFAOYSA-N
InChI=1S/C20H23NO2/c1-3-9-16(10-4-1)20(17-11-5-2-6-12-17)22-15-19(23-20)18-13-7-8-14-21-18/h1-6,9-12,18-19,21H,7-8,13-15H2

HIDE SMILES / InChI

Molecular Formula C20H23NO2
Molecular Weight 309.4021
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Dioxadrol is the antidepressant agent. It was synthesized in 1966 and pharmacologically evaluated as a local anesthetic and general anesthetic drug. It was shown that dexoxadrol binds with high affinity toward NMDA receptor. Dioxadrol exists in four isomeric forms. alpha-(+)-Dioxadrol (dexoxadrol) showed phencyclidine (PCP)-like activity in rhesus monkeys trained to discriminate subcutaneous administration of ketamine, but neither alpha-(-)-dioxadrol (levoxadrol) nor beta-(+/-)-dioxadrol showed such activity. During clinical evaluation, it became obvious that non-tolerable side effects (retrograde amnesia, psychotomimetic effects) are associated with the application of dexoxadrol. These observations have led to termination of clinical development.

Approval Year

PubMed

PubMed

TitleDatePubMed
The effect of the dioxolanes on amino acid induced excitation in the mammalian spinal cord.
1984 Jul 30
Local anesthetic properties of opioids and phencyclidines: interaction with the voltage-dependent, batrachotoxin binding site in sodium channels.
1985 Feb
Effects of phencyclidine, SKF 10,047 and related psychotomimetic agents on N-methyl-D-aspartate receptor mediated synaptic responses in rat hippocampal slices.
1987 Jul
Enantiomeric and diastereomeric dioxadrols: behavioral, biochemical and chemical determination of the configuration necessary for phencyclidine-like properties.
1987 Oct
Structure-affinity relationship studies of non-competitive NMDA receptor antagonists derived from dexoxadrol and etoxadrol.
2005 Dec 15
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:48:56 GMT 2023
Edited
by admin
on Fri Dec 15 18:48:56 GMT 2023
Record UNII
4D70V7R51N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIOXADROL
INN   MI  
INN  
Official Name English
dioxadrol [INN]
Common Name English
DIOXADROL [MI]
Common Name English
2-(2,2-DIPHENYL-1,3-DIOXOLAN-4-YL)PIPERIDINE
Systematic Name English
PIPERIDINE, 2-(2,2-DIPHENYL-1,3-DIOXOLAN-4-YL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
66270
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
EVMPD
SUB07200MIG
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
DRUG CENTRAL
3158
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
NCI_THESAURUS
C166752
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
SMS_ID
100000082873
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
MERCK INDEX
m4597
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY Merck Index
CAS
6495-46-1
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
MESH
C005840
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID10863446
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
FDA UNII
4D70V7R51N
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
INN
1505
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL26479
Created by admin on Fri Dec 15 18:48:56 GMT 2023 , Edited by admin on Fri Dec 15 18:48:56 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY