Page last updated: 2024-12-06

metazocine

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

Description

metazocine: more than 13 isomers available; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3037886
CHEMBL ID257661
MeSH IDM0136530
PubMed CID443404
CHEBI ID6799
SCHEMBL ID1649365
MeSH IDM0136530

Synonyms (35)

Synonym
methobenzmorphan
CHEMBL257661
ids-nm-001
bdbm50367062
C11789 ,
metazocine
3734-52-9
metazocine, trans-(-)-
2,6-methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-3,6,11-trimethyl-, (2alpha,6alpha,11s)-
(-)-9-epi-metazocine
unii-e8l57a7w0w
metazocine (2r,6r,11s)-form [mi]
metazocine, cis-(-)-
2,6-methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-3,6,11-trimethyl-, (2alpha,6alpha,11r)-
metazocine (2r,6r,11r)-form [mi]
43f5bf98qo ,
metazocine, (-)-
(-)-metazocine
cis-(-)-metazocine
21286-60-2
unii-43f5bf98qo
alpha-(-)-metazocine
.alpha.-(-)-metazocine
2,6-methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-3,6,11-trimethyl-, (2.alpha.,6.alpha.,11r)-
e8l57a7w0w ,
21286-57-7
trans-(-)-metazocine
nih-8178
SCHEMBL1649365
CHEBI:6799
surecn1649365
DTXSID20872483
bdbm224014
Q27890225
(1r,9r,13r)-1,10,13-trimethyl-10-azatricyclo[7.3.1.0?,?]trideca-2,4,6-trien-4-ol

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzazocine
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLS proteinHomo sapiens (human)Potency25.11890.35487.935539.8107AID624170
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorHomo sapiens (human)Ki0.00380.00000.419710.0000AID410718
Delta-type opioid receptorHomo sapiens (human)Ki0.14000.00000.59789.9300AID410719
Kappa-type opioid receptorHomo sapiens (human)Ki0.00990.00000.362410.0000AID410720
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorHomo sapiens (human)EC50 (µMol)0.04000.00000.32639.4000AID410728
Kappa-type opioid receptorHomo sapiens (human)EC50 (µMol)0.12000.00000.22448.9900AID410731
Mas-related G-protein coupled receptor member X2Homo sapiens (human)EC50 (µMol)17.00000.14003.73818.9000AID1802708; AID1802709
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (56)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMu-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
sensory perceptionMu-type opioid receptorHomo sapiens (human)
negative regulation of cell population proliferationMu-type opioid receptorHomo sapiens (human)
sensory perception of painMu-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
behavioral response to ethanolMu-type opioid receptorHomo sapiens (human)
positive regulation of neurogenesisMu-type opioid receptorHomo sapiens (human)
negative regulation of Wnt protein secretionMu-type opioid receptorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeMu-type opioid receptorHomo sapiens (human)
calcium ion transmembrane transportMu-type opioid receptorHomo sapiens (human)
cellular response to morphineMu-type opioid receptorHomo sapiens (human)
regulation of cellular response to stressMu-type opioid receptorHomo sapiens (human)
regulation of NMDA receptor activityMu-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayMu-type opioid receptorHomo sapiens (human)
immune responseDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerDelta-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
adult locomotory behaviorDelta-type opioid receptorHomo sapiens (human)
negative regulation of gene expressionDelta-type opioid receptorHomo sapiens (human)
negative regulation of protein-containing complex assemblyDelta-type opioid receptorHomo sapiens (human)
positive regulation of CREB transcription factor activityDelta-type opioid receptorHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationDelta-type opioid receptorHomo sapiens (human)
response to nicotineDelta-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
eating behaviorDelta-type opioid receptorHomo sapiens (human)
regulation of mitochondrial membrane potentialDelta-type opioid receptorHomo sapiens (human)
regulation of calcium ion transportDelta-type opioid receptorHomo sapiens (human)
cellular response to growth factor stimulusDelta-type opioid receptorHomo sapiens (human)
cellular response to hypoxiaDelta-type opioid receptorHomo sapiens (human)
cellular response to toxic substanceDelta-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayDelta-type opioid receptorHomo sapiens (human)
immune responseKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
chemical synaptic transmissionKappa-type opioid receptorHomo sapiens (human)
sensory perceptionKappa-type opioid receptorHomo sapiens (human)
locomotory behaviorKappa-type opioid receptorHomo sapiens (human)
sensory perception of painKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
response to insulinKappa-type opioid receptorHomo sapiens (human)
positive regulation of dopamine secretionKappa-type opioid receptorHomo sapiens (human)
negative regulation of luteinizing hormone secretionKappa-type opioid receptorHomo sapiens (human)
response to nicotineKappa-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
maternal behaviorKappa-type opioid receptorHomo sapiens (human)
eating behaviorKappa-type opioid receptorHomo sapiens (human)
response to estrogenKappa-type opioid receptorHomo sapiens (human)
estrous cycleKappa-type opioid receptorHomo sapiens (human)
response to ethanolKappa-type opioid receptorHomo sapiens (human)
regulation of saliva secretionKappa-type opioid receptorHomo sapiens (human)
behavioral response to cocaineKappa-type opioid receptorHomo sapiens (human)
sensory perception of temperature stimulusKappa-type opioid receptorHomo sapiens (human)
defense response to virusKappa-type opioid receptorHomo sapiens (human)
cellular response to lipopolysaccharideKappa-type opioid receptorHomo sapiens (human)
cellular response to glucose stimulusKappa-type opioid receptorHomo sapiens (human)
positive regulation of p38MAPK cascadeKappa-type opioid receptorHomo sapiens (human)
positive regulation of potassium ion transmembrane transportKappa-type opioid receptorHomo sapiens (human)
response to acrylamideKappa-type opioid receptorHomo sapiens (human)
positive regulation of eating behaviorKappa-type opioid receptorHomo sapiens (human)
conditioned place preferenceKappa-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayKappa-type opioid receptorHomo sapiens (human)
sensory perception of painMas-related G-protein coupled receptor member X2Homo sapiens (human)
sleepMas-related G-protein coupled receptor member X2Homo sapiens (human)
positive regulation of cytokinesisMas-related G-protein coupled receptor member X2Homo sapiens (human)
mast cell degranulationMas-related G-protein coupled receptor member X2Homo sapiens (human)
mast cell activationMas-related G-protein coupled receptor member X2Homo sapiens (human)
G protein-coupled receptor signaling pathwayMas-related G-protein coupled receptor member X2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
G-protein alpha-subunit bindingMu-type opioid receptorHomo sapiens (human)
G protein-coupled receptor activityMu-type opioid receptorHomo sapiens (human)
beta-endorphin receptor activityMu-type opioid receptorHomo sapiens (human)
voltage-gated calcium channel activityMu-type opioid receptorHomo sapiens (human)
protein bindingMu-type opioid receptorHomo sapiens (human)
morphine receptor activityMu-type opioid receptorHomo sapiens (human)
G-protein beta-subunit bindingMu-type opioid receptorHomo sapiens (human)
neuropeptide bindingMu-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor activityDelta-type opioid receptorHomo sapiens (human)
protein bindingDelta-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingDelta-type opioid receptorHomo sapiens (human)
G protein-coupled enkephalin receptor activityDelta-type opioid receptorHomo sapiens (human)
neuropeptide bindingDelta-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor activityKappa-type opioid receptorHomo sapiens (human)
protein bindingKappa-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingKappa-type opioid receptorHomo sapiens (human)
dynorphin receptor activityKappa-type opioid receptorHomo sapiens (human)
neuropeptide bindingKappa-type opioid receptorHomo sapiens (human)
G protein-coupled receptor activityMas-related G-protein coupled receptor member X2Homo sapiens (human)
neuropeptide bindingMas-related G-protein coupled receptor member X2Homo sapiens (human)
mast cell secretagogue receptor activityMas-related G-protein coupled receptor member X2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (23)

Processvia Protein(s)Taxonomy
endosomeMu-type opioid receptorHomo sapiens (human)
endoplasmic reticulumMu-type opioid receptorHomo sapiens (human)
Golgi apparatusMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
axonMu-type opioid receptorHomo sapiens (human)
dendriteMu-type opioid receptorHomo sapiens (human)
perikaryonMu-type opioid receptorHomo sapiens (human)
synapseMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
neuron projectionMu-type opioid receptorHomo sapiens (human)
plasma membraneDelta-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneDelta-type opioid receptorHomo sapiens (human)
dendrite membraneDelta-type opioid receptorHomo sapiens (human)
presynaptic membraneDelta-type opioid receptorHomo sapiens (human)
axon terminusDelta-type opioid receptorHomo sapiens (human)
spine apparatusDelta-type opioid receptorHomo sapiens (human)
postsynaptic density membraneDelta-type opioid receptorHomo sapiens (human)
neuronal dense core vesicleDelta-type opioid receptorHomo sapiens (human)
plasma membraneDelta-type opioid receptorHomo sapiens (human)
neuron projectionDelta-type opioid receptorHomo sapiens (human)
nucleoplasmKappa-type opioid receptorHomo sapiens (human)
mitochondrionKappa-type opioid receptorHomo sapiens (human)
cytosolKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
membraneKappa-type opioid receptorHomo sapiens (human)
sarcoplasmic reticulumKappa-type opioid receptorHomo sapiens (human)
T-tubuleKappa-type opioid receptorHomo sapiens (human)
dendriteKappa-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneKappa-type opioid receptorHomo sapiens (human)
presynaptic membraneKappa-type opioid receptorHomo sapiens (human)
perikaryonKappa-type opioid receptorHomo sapiens (human)
axon terminusKappa-type opioid receptorHomo sapiens (human)
postsynaptic membraneKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
neuron projectionKappa-type opioid receptorHomo sapiens (human)
membraneMas-related G-protein coupled receptor member X2Homo sapiens (human)
plasma membraneMas-related G-protein coupled receptor member X2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID320416Antinociceptive activity in sc dosed mouse assessed as inhibition of morphin response by tail flick assay2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans.
AID79038Mu opioid receptor agonist activity as inhibition of electrically stimulated mysenteric plexus in guinea pig ileum1982Journal of medicinal chemistry, Dec, Volume: 25, Issue:12
Synthesis and biological evaluation of a metazocine-containing enkephalinamide. Evidence for nonidentical roles of the tyramine moiety in opiates and opioid peptides.
AID410733Activity at human cloned kappa opioid receptor expressed in CHO cells assessed as inhibition of U50488-induced [35S]GTPgammaS binding2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID151914Binding constant for the antagonist state was measured for its ability to displace [3H]naloxone from opioid mu 1 receptor buffered homogenate of rat brain membranes1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
Structure-activity relationships for drugs binding to the agonist and antagonist states of the primary morphine receptor.
AID320414Antinociceptive activity in sc dosed mouse by phenylquinone antiwrithing assay2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans.
AID410731Activity at human cloned kappa opioid receptor expressed in CHO cells by [35S]GTPgammaS binding assay2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID204636Binding affinity measured on Sigma receptor type 1 from guinea pig brain membranes using [3H]pentazocine as radioligand.1995Journal of medicinal chemistry, Jul-21, Volume: 38, Issue:15
Synthesis and sigma binding properties of 2'-substituted 5,9 alpha-dimethyl-6,7-benzomorphans.
AID320413Antinociceptive activity in sc dosed mouse by hot plate method2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans.
AID1145722Narcotic agonist activity in sc dosed albino mouse assessed as protection against acetylcholine-induced writhing administered 20 mins prior to acetylcholine challenge measured for 2 mins1977Journal of medicinal chemistry, May, Volume: 20, Issue:5
Synthesis and narcotic agonist-antagonist evaluation of some 2,6-methano-3-benzazocine-11 propanols. Analogues of the ring C bridged oripavine-7-mehtanols.
AID410732Activity at human cloned kappa opioid receptor expressed in CHO cells by [35S]GTPgammaS binding assay relative to basal GTPgammaS binding2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID410719Displacement of [3H]Naltrindole form human delta opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID111978Percent analgesic activity in mice after subcutaneous administration; 20-30%1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Novel nonnarcotic analgesics with an improved therapeutic ratio. Structure-activity relationships of 8-(methylthio)- and 8-(acylthio)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines.
AID410722Ratio of Ki for human delta opioid receptor to Ki for human kappa opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID410721Ratio of Ki for human mu opioid receptor to Ki for human kappa opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID410730Activity at human cloned mu opioid receptor expressed in CHO cells assessed as inhibition of DAMGO-induced [35S]GTPgammaS binding2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID410718Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID151584Binding constant for the agonist state was measured for its ability to displace [3H]naloxone from opioid mu 1 receptor buffered homogenate of rat brain membranes1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
Structure-activity relationships for drugs binding to the agonist and antagonist states of the primary morphine receptor.
AID320415Antinociceptive activity in sc dosed mouse by tail flick method2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans.
AID410720Displacement of [3H]U69593 form human kappa opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID410729Activity at human cloned mu opioid receptor expressed in CHO cells by [35S]GTPgammaS binding assay relative to basal GTPgammaS binding2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID23717Partition coefficient (logP)1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
Structure-activity relationships for drugs binding to the agonist and antagonist states of the primary morphine receptor.
AID410728Activity at human cloned mu opioid receptor expressed in CHO cells by [35S]GTPgammaS binding assay2009Bioorganic & medicinal chemistry letters, Jan-01, Volume: 19, Issue:1
Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.
AID79216Mu opioid receptor agonist activity was determined by inhibition of electrically stimulated myenteric plexus in guinea pig ileum, value determined relative to morphine1982Journal of medicinal chemistry, Dec, Volume: 25, Issue:12
Synthesis and biological evaluation of a metazocine-containing enkephalinamide. Evidence for nonidentical roles of the tyramine moiety in opiates and opioid peptides.
AID1145724Narcotic antagonist activity in rat assessed as inhibition of phenazocine-induced response at 80 mg/kg, sc1977Journal of medicinal chemistry, May, Volume: 20, Issue:5
Synthesis and narcotic agonist-antagonist evaluation of some 2,6-methano-3-benzazocine-11 propanols. Analogues of the ring C bridged oripavine-7-mehtanols.
AID1802709PRESTO-Tango Assay from Article 10.1038/nchembio.2334: \\In silico design of novel probes for the atypical opioid receptor MRGPRX2.\\2017Nature chemical biology, 05, Volume: 13, Issue:5
In silico design of novel probes for the atypical opioid receptor MRGPRX2.
AID1802708Intracellular Calcium Mobilization Assay from Article 10.1038/nchembio.2334: \\In silico design of novel probes for the atypical opioid receptor MRGPRX2.\\2017Nature chemical biology, 05, Volume: 13, Issue:5
In silico design of novel probes for the atypical opioid receptor MRGPRX2.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (38.89)18.7374
1990's6 (33.33)18.2507
2000's4 (22.22)29.6817
2010's1 (5.56)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%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]