Compounds > etoxadrol
Page last updated: 2024-12-06

etoxadrol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

etoxadrol: was heading 1975-94 (see under PIPERIDINES 1975-90); use PIPERIDINES to search ETOXADROL 1975-90; dissociative anesthetic with some cardiovascular effects [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID14208380
CHEMBL ID305904
CHEBI ID135073
SCHEMBL ID1066638
MeSH IDM0225293

Synonyms (28)

Synonym
etoxadrol
nsc-288020
CHEBI:135073
CHEMBL305904
siq2uwr01k ,
etoxadrol [inn]
piperidine, 2-(2-ethyl-2-phenyl-1,3-dioxolan-4-yl)-
etoxadrolum
unii-siq2uwr01k
nsc 288020
etoxadrolum [inn-latin]
(2s)-2-((2s,4s))-2-(2-ethyl-2-phenyl-1,3-dioxolan-4-yl)piperidine
piperidine, 2-(2-ethyl-2-phenyl-1,3-dioxolan-4-yl)
etoxadrol [mi]
(+)-2-(2-ethyl-2-phenyl-1,3-dioxolan-4-yl)piperidine
SCHEMBL1066638
bdbm50130938
(2s)-2-[(2s,4s)-2-ethyl-2-phenyl-1,3-dioxolan-4-yl]piperidine
DTXSID10912322
Q5404857
RO44G6QT80 ,
piperidine, 2-(2-ethyl-2-phenyl-1,3-dioxolan-4-yl)-, (2.alpha.,4.beta.(r*))-(+/-)-
30163-01-0
etoxadrol, (+/-)-
piperidine, 2-(2-ethyl-2-phenyl-1,3-dioxolan-4-yl)-, (2alpha,4beta(r*))-(+/-)-
unii-ro44g6qt80
CS-0027193
HY-107040
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
ketalAn acetal of formula R2C(OR)2 (R =/= H) derived from a ketone by replacement of the oxo group by two hydrocarbyloxy groups. The class name 'ketals', once abandoned by IUPAC, has been reinstated as a subclass of acetals.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor ionotropic, NMDA 1Homo sapiens (human)Ki0.02200.00120.48246.0000AID1255983
Glutamate receptor ionotropic, NMDA 2AHomo sapiens (human)Ki0.02200.00120.62056.0000AID1255983
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (45)

Processvia Protein(s)Taxonomy
cellular response to amyloid-betaGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
monoatomic cation transportGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
brain developmentGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
visual learningGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
positive regulation of calcium ion transport into cytosolGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
propylene metabolic processGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
calcium-mediated signalingGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
ionotropic glutamate receptor signaling pathwayGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
regulation of membrane potentialGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
response to ethanolGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
regulation of synaptic plasticityGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
regulation of neuronal synaptic plasticityGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
protein heterotetramerizationGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergicGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
calcium ion homeostasisGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
excitatory postsynaptic potentialGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
calcium ion transmembrane import into cytosolGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
monoatomic cation transmembrane transportGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
excitatory chemical synaptic transmissionGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
positive regulation of reactive oxygen species biosynthetic processGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
regulation of monoatomic cation transmembrane transportGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
response to glycineGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
positive regulation of excitatory postsynaptic potentialGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
chemical synaptic transmissionGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
cellular response to amyloid-betaGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
startle responseGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
response to amphetamineGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
glutamate receptor signaling pathwayGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
chemical synaptic transmissionGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
brain developmentGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
learning or memoryGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
memoryGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
visual learningGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
response to xenobiotic stimulusGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
response to woundingGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
sensory perception of painGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
calcium-mediated signalingGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
neurogenesisGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
protein catabolic processGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
sleepGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
directional locomotionGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
ionotropic glutamate receptor signaling pathwayGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
negative regulation of protein catabolic processGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
dopamine metabolic processGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
serotonin metabolic processGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
positive regulation of apoptotic processGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
response to ethanolGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
regulation of synaptic plasticityGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
regulation of neuronal synaptic plasticityGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
activation of cysteine-type endopeptidase activityGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
calcium ion transmembrane import into cytosolGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
monoatomic cation transmembrane transportGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
excitatory chemical synaptic transmissionGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
protein localization to postsynaptic membraneGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
regulation of monoatomic cation transmembrane transportGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
positive regulation of excitatory postsynaptic potentialGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
synaptic transmission, glutamatergicGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
excitatory postsynaptic potentialGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
long-term synaptic potentiationGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
NMDA glutamate receptor activityGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
calcium channel activityGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
amyloid-beta bindingGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
NMDA glutamate receptor activityGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
calcium ion bindingGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
protein bindingGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
calmodulin bindingGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
glycine bindingGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
glutamate bindingGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
glutamate-gated calcium ion channel activityGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
protein-containing complex bindingGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
signaling receptor activityGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
ligand-gated monoatomic ion channel activityGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
amyloid-beta bindingGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
NMDA glutamate receptor activityGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
protein bindingGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
zinc ion bindingGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
glutamate-gated calcium ion channel activityGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potentialGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (20)

Processvia Protein(s)Taxonomy
cytoplasmGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
plasma membraneGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
synaptic vesicleGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
cell surfaceGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
postsynaptic densityGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
NMDA selective glutamate receptor complexGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
dendriteGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
neuron projectionGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
synaptic cleftGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
terminal boutonGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
dendritic spineGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
synapseGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
postsynaptic membraneGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
excitatory synapseGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
synaptic membraneGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
synapseGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
plasma membraneGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
neuron projectionGlutamate receptor ionotropic, NMDA 1Homo sapiens (human)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
plasma membraneGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
synaptic vesicleGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
cell surfaceGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
postsynaptic densityGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
NMDA selective glutamate receptor complexGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
cytoplasmic vesicle membraneGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
presynaptic membraneGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
dendritic spineGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
postsynaptic membraneGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
synaptic membraneGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
glutamatergic synapseGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
plasma membraneGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
postsynaptic density membraneGlutamate receptor ionotropic, NMDA 2AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1255978Displacement of [3H]MK801 from NMDA receptor PCP binding site in guinea pig brain cortex membranes incubated for 120 mins by scintillation counting method2015Journal of medicinal chemistry, Nov-12, Volume: 58, Issue:21
Novel Potent N-Methyl-d-aspartate (NMDA) Receptor Antagonists or σ1 Receptor Ligands Based on Properly Substituted 1,4-Dioxane Ring.
AID600271Displacement of [3H]-(+)-MK801 from NMDA receptor PCP binding site in pig cortex membrane after 90 mins by liquid scintillation counting2011European journal of medicinal chemistry, Jun, Volume: 46, Issue:6
Synthesis of 4-(aminoalkyl) substituted 1,3-dioxanes as potent NMDA and σ receptor antagonists.
AID599549Displacement of [3H]TCP from NMDA receptor PCP binding site in rat brain2011European journal of medicinal chemistry, Jun, Volume: 46, Issue:6
Synthesis of 4-(aminoalkyl) substituted 1,3-dioxanes as potent NMDA and σ receptor antagonists.
AID156972Displacement of [3H]TCP from PCP receptor in tissue preparation of whole rat brain minus cerebellum.1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Analogues of the dioxolanes dexoxadrol and etoxadrol as potential phencyclidine-like agents. Synthesis and structure-activity relationships.
AID1255983Binding affinity to NMDA receptor (unknown origin)2015Journal of medicinal chemistry, Nov-12, Volume: 58, Issue:21
Novel Potent N-Methyl-d-aspartate (NMDA) Receptor Antagonists or σ1 Receptor Ligands Based on Properly Substituted 1,4-Dioxane Ring.
AID145233Displacement of [3H]TCP from tissue homogenate preparation of whole rat brain minus cerebellum1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis, absolute configuration, and molecular modeling study of etoxadrol, a potent phencyclidine-like agonist.
AID144840Evaluated for their affinity at the PCP site for displacement of [3H]TCP in rat brain homogenates1993Journal of medicinal chemistry, Mar-19, Volume: 36, Issue:6
Synthesis and pharmacological evaluation of hexahydrofluorenamines as noncompetitive antagonists at the N-methyl-D-aspartate receptor.
AID599550Displacement of [3H]-(+)-MK801 from NMDA receptor PCP binding site2011European journal of medicinal chemistry, Jun, Volume: 46, Issue:6
Synthesis of 4-(aminoalkyl) substituted 1,3-dioxanes as potent NMDA and σ receptor antagonists.
AID176305Behavioral potency by which rat discriminate phencyclidine from saline in a 2 lever drug discrimination procedure1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis, absolute configuration, and molecular modeling study of etoxadrol, a potent phencyclidine-like agonist.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (14.29)18.7374
1990's2 (28.57)18.2507
2000's2 (28.57)29.6817
2010's2 (28.57)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phencyclidine
Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.		7.9340benzenes;
piperidines		anaesthetic;
neurotoxin;
NMDA receptor antagonist;
psychotropic drug
1,3-ditolylguanidine
1,3-ditolylguanidine: structure given in first source; a selective ligand for the sigma binding sites in the brain		2.4920toluenes
dioxadrol
dioxadrol: See also records for d- and l-forms which are referred to as dexoxadrol and levoxadrol, respectfully		3.5320diarylmethane
dizocilpine
[no description available]		1.9810secondary amino compound;
tetracyclic antidepressant		anaesthetic;
anticonvulsant;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist
esketamine
esketamine : The S- (more active) enantiomer of ketamine.		2.1110ketamineanalgesic;
intravenous anaesthetic;
NMDA receptor antagonist
dexoxadrol
[no description available]		7.9240
piperidines
Piperidines: A family of hexahydropyridines.		3.5320
ConditionIndicatedRelationship StrengthStudiesTrials
Absence Seizure
[description not available]		01.9810
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		01.9810
Ache
[description not available]		02.1110
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		02.1110