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
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
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
Title | Date | PubMed |
---|---|---|
The effect of the dioxolanes on amino acid induced excitation in the mammalian spinal cord. | 1984 Jul 30 |
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Local anesthetic properties of opioids and phencyclidines: interaction with the voltage-dependent, batrachotoxin binding site in sodium channels. | 1985 Feb |
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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 |
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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
Edited
Fri Dec 15 18:48:56 GMT 2023
by
admin
on
Fri Dec 15 18:48:56 GMT 2023
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Record UNII |
4D70V7R51N
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Record Status |
Validated (UNII)
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Record Version |
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66270
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SUB07200MIG
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3158
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C166752
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100000082873
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m4597
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6495-46-1
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C005840
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DTXSID10863446
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4D70V7R51N
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1505
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CHEMBL26479
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Related Record | Type | Details | ||
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ACTIVE MOIETY |