Page last updated: 2024-11-13

(1R,3S)-3-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid methyl ester

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

(1R,3S)-3-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid methyl ester is a complex organic molecule with the following key features:

* **Structure:** It contains a bicyclic ring system, an iodine atom, a methyl group, and a carboxylic acid methyl ester. The specific stereochemistry of the molecule is denoted by the prefixes (1R,3S). This means that the molecule has specific 3-dimensional arrangements of its substituents.
* **Chemical Properties:** The iodine atom makes this molecule amenable to various chemical reactions, particularly those involving coupling or substitution reactions. The carboxylic acid methyl ester group can be easily hydrolyzed to form a free carboxylic acid, which is a useful functional group for further modifications.
* **Biological Activity:** The bicyclic ring system and the specific stereochemistry of the molecule make it a potential candidate for interactions with biological targets. It is possible that this molecule exhibits pharmacological activity.

**Importance for Research:**

This molecule is likely being investigated in research for several reasons:

* **Drug Discovery:** The complex structure and potential for biological activity make it a good candidate for drug discovery efforts. Researchers might be investigating its potential to bind to specific receptors or enzymes involved in various biological processes.
* **Synthetic Chemistry:** The molecule can be used as a starting point for the development of new synthetic methods and strategies. The iodine atom and the carboxylic acid methyl ester group provide opportunities for selective chemical modifications.
* **Material Science:** The molecule's unique structure and chemical properties might make it suitable for the development of new materials with specific properties, such as optical or electronic properties.

**Without specific context on the research project, it is impossible to definitively state why this particular molecule is important.** However, the features described above suggest that it is being investigated in areas related to drug discovery, synthetic chemistry, and potentially materials science.

Cross-References

ID SourceID
PubMed CID44295709
CHEMBL ID300226
CHEBI ID125381
SCHEMBL ID14173836

Synonyms (9)

Synonym
CHEBI:125381
CHEMBL300226 ,
3-(4-iodo-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester
bdbm50005576
(3s,8r)-3-(4-iodo-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester
BRD-A25037258-001-01-7
SCHEMBL14173836
Q27215801
(1r,3s)-3-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid methyl ester
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
azabicycloalkane
[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 (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium-dependent dopamine transporterRattus norvegicus (Norway rat)IC50 (µMol)0.00120.00070.97749.7000AID64866; AID64872; AID65021; AID65033
Sodium-dependent serotonin transporterHomo sapiens (human)IC50 (µMol)0.00300.00010.86458.7096AID203943; AID204062
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)IC50 (µMol)0.00420.00030.81978.4900AID204374; AID204376
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)Ki0.00040.00000.705610.0000AID204852
Sodium-dependent dopamine transporter Homo sapiens (human)IC50 (µMol)0.00120.00071.841946.0000AID64206; AID64343
Sigma non-opioid intracellular receptor 1Homo sapiens (human)IC50 (µMol)0.00250.00030.70285.3660AID203943
TransporterRattus norvegicus (Norway rat)IC50 (µMol)0.03600.00081.95628.8000AID145714; AID147737
TransporterRattus norvegicus (Norway rat)Ki0.02160.00010.866710.0000AID147749
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (57)

Processvia Protein(s)Taxonomy
monoamine transportSodium-dependent serotonin transporterHomo sapiens (human)
response to hypoxiaSodium-dependent serotonin transporterHomo sapiens (human)
neurotransmitter transportSodium-dependent serotonin transporterHomo sapiens (human)
response to nutrientSodium-dependent serotonin transporterHomo sapiens (human)
memorySodium-dependent serotonin transporterHomo sapiens (human)
circadian rhythmSodium-dependent serotonin transporterHomo sapiens (human)
response to xenobiotic stimulusSodium-dependent serotonin transporterHomo sapiens (human)
response to toxic substanceSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of gene expressionSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of serotonin secretionSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of cerebellar granule cell precursor proliferationSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of synaptic transmission, dopaminergicSodium-dependent serotonin transporterHomo sapiens (human)
response to estradiolSodium-dependent serotonin transporterHomo sapiens (human)
social behaviorSodium-dependent serotonin transporterHomo sapiens (human)
vasoconstrictionSodium-dependent serotonin transporterHomo sapiens (human)
sperm ejaculationSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of neuron differentiationSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of cell cycleSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of organ growthSodium-dependent serotonin transporterHomo sapiens (human)
behavioral response to cocaineSodium-dependent serotonin transporterHomo sapiens (human)
enteric nervous system developmentSodium-dependent serotonin transporterHomo sapiens (human)
brain morphogenesisSodium-dependent serotonin transporterHomo sapiens (human)
serotonin uptakeSodium-dependent serotonin transporterHomo sapiens (human)
membrane depolarizationSodium-dependent serotonin transporterHomo sapiens (human)
platelet aggregationSodium-dependent serotonin transporterHomo sapiens (human)
cellular response to retinoic acidSodium-dependent serotonin transporterHomo sapiens (human)
cellular response to cGMPSodium-dependent serotonin transporterHomo sapiens (human)
regulation of thalamus sizeSodium-dependent serotonin transporterHomo sapiens (human)
conditioned place preferenceSodium-dependent serotonin transporterHomo sapiens (human)
sodium ion transmembrane transportSodium-dependent serotonin transporterHomo sapiens (human)
amino acid transportSodium-dependent serotonin transporterHomo sapiens (human)
monoamine transportSodium-dependent dopamine transporter Homo sapiens (human)
neurotransmitter transportSodium-dependent dopamine transporter Homo sapiens (human)
lactationSodium-dependent dopamine transporter Homo sapiens (human)
sensory perception of smellSodium-dependent dopamine transporter Homo sapiens (human)
locomotory behaviorSodium-dependent dopamine transporter Homo sapiens (human)
response to xenobiotic stimulusSodium-dependent dopamine transporter Homo sapiens (human)
response to iron ionSodium-dependent dopamine transporter Homo sapiens (human)
dopamine transportSodium-dependent dopamine transporter Homo sapiens (human)
adenohypophysis developmentSodium-dependent dopamine transporter Homo sapiens (human)
response to nicotineSodium-dependent dopamine transporter Homo sapiens (human)
positive regulation of multicellular organism growthSodium-dependent dopamine transporter Homo sapiens (human)
regulation of dopamine metabolic processSodium-dependent dopamine transporter Homo sapiens (human)
response to cocaineSodium-dependent dopamine transporter Homo sapiens (human)
dopamine biosynthetic processSodium-dependent dopamine transporter Homo sapiens (human)
dopamine catabolic processSodium-dependent dopamine transporter Homo sapiens (human)
response to ethanolSodium-dependent dopamine transporter Homo sapiens (human)
cognitionSodium-dependent dopamine transporter Homo sapiens (human)
dopamine uptake involved in synaptic transmissionSodium-dependent dopamine transporter Homo sapiens (human)
response to cAMPSodium-dependent dopamine transporter Homo sapiens (human)
norepinephrine uptakeSodium-dependent dopamine transporter Homo sapiens (human)
prepulse inhibitionSodium-dependent dopamine transporter Homo sapiens (human)
dopamine uptakeSodium-dependent dopamine transporter Homo sapiens (human)
hyaloid vascular plexus regressionSodium-dependent dopamine transporter Homo sapiens (human)
amino acid transportSodium-dependent dopamine transporter Homo sapiens (human)
norepinephrine transportSodium-dependent dopamine transporter Homo sapiens (human)
sodium ion transmembrane transportSodium-dependent dopamine transporter Homo sapiens (human)
lipid transportSigma non-opioid intracellular receptor 1Homo sapiens (human)
nervous system developmentSigma non-opioid intracellular receptor 1Homo sapiens (human)
G protein-coupled opioid receptor signaling pathwaySigma non-opioid intracellular receptor 1Homo sapiens (human)
regulation of neuron apoptotic processSigma non-opioid intracellular receptor 1Homo sapiens (human)
protein homotrimerizationSigma non-opioid intracellular receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (25)

Processvia Protein(s)Taxonomy
integrin bindingSodium-dependent serotonin transporterHomo sapiens (human)
monoatomic cation channel activitySodium-dependent serotonin transporterHomo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent serotonin transporterHomo sapiens (human)
serotonin:sodium:chloride symporter activitySodium-dependent serotonin transporterHomo sapiens (human)
protein bindingSodium-dependent serotonin transporterHomo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent serotonin transporterHomo sapiens (human)
antiporter activitySodium-dependent serotonin transporterHomo sapiens (human)
syntaxin-1 bindingSodium-dependent serotonin transporterHomo sapiens (human)
cocaine bindingSodium-dependent serotonin transporterHomo sapiens (human)
sodium ion bindingSodium-dependent serotonin transporterHomo sapiens (human)
identical protein bindingSodium-dependent serotonin transporterHomo sapiens (human)
nitric-oxide synthase bindingSodium-dependent serotonin transporterHomo sapiens (human)
actin filament bindingSodium-dependent serotonin transporterHomo sapiens (human)
serotonin bindingSodium-dependent serotonin transporterHomo sapiens (human)
protease bindingSodium-dependent dopamine transporter Homo sapiens (human)
signaling receptor bindingSodium-dependent dopamine transporter Homo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent dopamine transporter Homo sapiens (human)
dopamine:sodium symporter activitySodium-dependent dopamine transporter Homo sapiens (human)
protein bindingSodium-dependent dopamine transporter Homo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent dopamine transporter Homo sapiens (human)
dopamine bindingSodium-dependent dopamine transporter Homo sapiens (human)
amine bindingSodium-dependent dopamine transporter Homo sapiens (human)
protein-containing complex bindingSodium-dependent dopamine transporter Homo sapiens (human)
metal ion bindingSodium-dependent dopamine transporter Homo sapiens (human)
protein phosphatase 2A bindingSodium-dependent dopamine transporter Homo sapiens (human)
heterocyclic compound bindingSodium-dependent dopamine transporter Homo sapiens (human)
norepinephrine:sodium symporter activitySodium-dependent dopamine transporter Homo sapiens (human)
G protein-coupled opioid receptor activitySigma non-opioid intracellular receptor 1Homo sapiens (human)
protein bindingSigma non-opioid intracellular receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (31)

Processvia Protein(s)Taxonomy
plasma membraneSodium-dependent serotonin transporterHomo sapiens (human)
focal adhesionSodium-dependent serotonin transporterHomo sapiens (human)
endosome membraneSodium-dependent serotonin transporterHomo sapiens (human)
endomembrane systemSodium-dependent serotonin transporterHomo sapiens (human)
presynaptic membraneSodium-dependent serotonin transporterHomo sapiens (human)
membrane raftSodium-dependent serotonin transporterHomo sapiens (human)
synapseSodium-dependent serotonin transporterHomo sapiens (human)
postsynaptic membraneSodium-dependent serotonin transporterHomo sapiens (human)
serotonergic synapseSodium-dependent serotonin transporterHomo sapiens (human)
synapseSodium-dependent serotonin transporterHomo sapiens (human)
plasma membraneSodium-dependent serotonin transporterHomo sapiens (human)
neuron projectionSodium-dependent serotonin transporterHomo sapiens (human)
cytoplasmSodium-dependent dopamine transporter Homo sapiens (human)
plasma membraneSodium-dependent dopamine transporter Homo sapiens (human)
cell surfaceSodium-dependent dopamine transporter Homo sapiens (human)
membraneSodium-dependent dopamine transporter Homo sapiens (human)
axonSodium-dependent dopamine transporter Homo sapiens (human)
neuron projectionSodium-dependent dopamine transporter Homo sapiens (human)
neuronal cell bodySodium-dependent dopamine transporter Homo sapiens (human)
axon terminusSodium-dependent dopamine transporter Homo sapiens (human)
membrane raftSodium-dependent dopamine transporter Homo sapiens (human)
postsynaptic membraneSodium-dependent dopamine transporter Homo sapiens (human)
dopaminergic synapseSodium-dependent dopamine transporter Homo sapiens (human)
flotillin complexSodium-dependent dopamine transporter Homo sapiens (human)
axonSodium-dependent dopamine transporter Homo sapiens (human)
presynaptic membraneSodium-dependent dopamine transporter Homo sapiens (human)
plasma membraneSodium-dependent dopamine transporter Homo sapiens (human)
neuronal cell body membraneSodium-dependent dopamine transporter Homo sapiens (human)
nuclear envelopeSigma non-opioid intracellular receptor 1Homo sapiens (human)
nuclear inner membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
nuclear outer membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
endoplasmic reticulumSigma non-opioid intracellular receptor 1Homo sapiens (human)
endoplasmic reticulum membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
lipid dropletSigma non-opioid intracellular receptor 1Homo sapiens (human)
cytosolSigma non-opioid intracellular receptor 1Homo sapiens (human)
postsynaptic densitySigma non-opioid intracellular receptor 1Homo sapiens (human)
membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
growth coneSigma non-opioid intracellular receptor 1Homo sapiens (human)
cytoplasmic vesicleSigma non-opioid intracellular receptor 1Homo sapiens (human)
anchoring junctionSigma non-opioid intracellular receptor 1Homo sapiens (human)
postsynaptic density membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
endoplasmic reticulumSigma non-opioid intracellular receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID145714Inhibition of [3H]nisoxetine binding to norepinephrine (NE) transporter1994Journal of medicinal chemistry, Apr-15, Volume: 37, Issue:8
Secondary amine analogues of 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid esters and N-norcocaine exhibit enhanced affinity for serotonin and norepinephrine transporters.
AID203943Binding affinity of [3H]citalopram for serotonin transporter in monkey1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
The discovery of an unusually selective and novel cocaine analog: difluoropine. Synthesis and inhibition of binding at cocaine recognition sites.
AID232749Selectivity index as ratio of IC50 for 5-HT and DA transporters1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
The discovery of an unusually selective and novel cocaine analog: difluoropine. Synthesis and inhibition of binding at cocaine recognition sites.
AID65033Concentration required to inhibit 50% of radioligand binding ([3H]WIN-35428) to the dopamine (DA) transporter in rat1994Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18
Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3 beta-(3'-substituted phenyl)-, 3 beta-(4'-substituted phenyl)-, and 3 beta-(3',4'-disubstituted phenyl)tropane-2 beta-carboxylic acid methyl esters.
AID204374Inhibition of [3H]paroxetine binding at serotonin transporter was determined2003Journal of medicinal chemistry, May-08, Volume: 46, Issue:10
2002 Medicinal Chemistry Division Award address: monoamine transporters and opioid receptors. Targets for addiction therapy.
AID64206Displacement of [3H]WIN-35428 from monkey dopamine transporter1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
The discovery of an unusually selective and novel cocaine analog: difluoropine. Synthesis and inhibition of binding at cocaine recognition sites.
AID64343Compounds binding ability to dopamine transporter was evaluated by displacing [3H]beta-CFT in baboon brain1993Journal of medicinal chemistry, Jun-25, Volume: 36, Issue:13
Enantioselectivity of cocaine recognition sites: binding of (1S)- and (1R)-2 beta-carbomethoxy-3 beta-(4-iodophenyl)tropane (beta-CIT) to monoamine transporters.
AID227870Tested for its ability to displace [125I]- (1R)-beta-CIT with rat striatal membranes1993Journal of medicinal chemistry, Jun-25, Volume: 36, Issue:13
Enantioselectivity of cocaine recognition sites: binding of (1S)- and (1R)-2 beta-carbomethoxy-3 beta-(4-iodophenyl)tropane (beta-CIT) to monoamine transporters.
AID147749Affinity for norepinephrine transporter determined by [3H]nisoxetine displacement.2003Journal of medicinal chemistry, May-08, Volume: 46, Issue:10
2002 Medicinal Chemistry Division Award address: monoamine transporters and opioid receptors. Targets for addiction therapy.
AID64866Inhibition of [3H]WIN-35428 binding at dopamine transporter was determined2003Journal of medicinal chemistry, May-08, Volume: 46, Issue:10
2002 Medicinal Chemistry Division Award address: monoamine transporters and opioid receptors. Targets for addiction therapy.
AID204376Inhibition of [3H]paroxetine binding to 5-hydroxytryptamine (5-HT) transporter1994Journal of medicinal chemistry, Apr-15, Volume: 37, Issue:8
Secondary amine analogues of 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid esters and N-norcocaine exhibit enhanced affinity for serotonin and norepinephrine transporters.
AID65021Potency for the inhibition of [3H]WIN-35428 binding to the dopamine transporter1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter.
AID220018Tested for its ability to displace [125I]- (1R)-beta-CIT with rat cortical membranes1993Journal of medicinal chemistry, Jun-25, Volume: 36, Issue:13
Enantioselectivity of cocaine recognition sites: binding of (1S)- and (1R)-2 beta-carbomethoxy-3 beta-(4-iodophenyl)tropane (beta-CIT) to monoamine transporters.
AID64872Inhibition of [3H]WIN-35428 binding to dopamine (DA) transporter1994Journal of medicinal chemistry, Apr-15, Volume: 37, Issue:8
Secondary amine analogues of 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid esters and N-norcocaine exhibit enhanced affinity for serotonin and norepinephrine transporters.
AID229546Relative affinity for norepinephrine and dopamine transporters1994Journal of medicinal chemistry, Apr-15, Volume: 37, Issue:8
Secondary amine analogues of 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid esters and N-norcocaine exhibit enhanced affinity for serotonin and norepinephrine transporters.
AID204852Inhibition of [3H]paroxetine binding at serotonin transporter was determined2003Journal of medicinal chemistry, May-08, Volume: 46, Issue:10
2002 Medicinal Chemistry Division Award address: monoamine transporters and opioid receptors. Targets for addiction therapy.
AID229540Relative affinity for serotonin and dopamine transporters1994Journal of medicinal chemistry, Apr-15, Volume: 37, Issue:8
Secondary amine analogues of 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid esters and N-norcocaine exhibit enhanced affinity for serotonin and norepinephrine transporters.
AID64845Affinity against cocaine binding site of dopamine transporter in rat striatum using [3H]2b as radioligand.1991Journal of medicinal chemistry, Sep, Volume: 34, Issue:9
Synthesis, ligand binding, QSAR, and CoMFA study of 3 beta-(p-substituted phenyl)tropane-2 beta-carboxylic acid methyl esters.
AID204062Compounds binding ability to serotonin transporter was evaluated by displacing [3H]paroxetine in baboon brain1993Journal of medicinal chemistry, Jun-25, Volume: 36, Issue:13
Enantioselectivity of cocaine recognition sites: binding of (1S)- and (1R)-2 beta-carbomethoxy-3 beta-(4-iodophenyl)tropane (beta-CIT) to monoamine transporters.
AID147737Inhibition of [3H]nisoxetine binding at norepinephrine transporter2003Journal of medicinal chemistry, May-08, Volume: 46, Issue:10
2002 Medicinal Chemistry Division Award address: monoamine transporters and opioid receptors. Targets for addiction therapy.
[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-19900 (0.00)18.7374
1990's6 (85.71)18.2507
2000's1 (14.29)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.10

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.10 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.18 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.10)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (28.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (71.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]