Page last updated: 2024-11-07

(3h)2-carbomethoxy-3-(4-fluorophenyl)tropane

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Description

(1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester: RN given refers to (1R-(exo,exo))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID105056
CHEMBL ID1944829
SCHEMBL ID1573076
MeSH IDM0075941

Synonyms (53)

Synonym
win-35428
[3h]win 35,428
methyl (1r,2s,3s,5s)-3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
bdbm22397
win 35428
(1r-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester
8-azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(4-fluorophenyl)-8-methyl-, methyl ester, (1r,2s,3s,5s)-
2-cmft
2-cft
(3h)2-carbomethoxy-3-(4-fluorophenyl)tropane
beta-cft
2-carbomethoxy-3-(4-fluorophenyl)tropane
50370-56-4
win 35,428
CFT ,
PDSP2_001576
8-azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(4-fluorophenyl)-8-methyl-, methyl ester, (1r,2s,3s,5s)-
(1r-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester
2beta-carbomethoxy-3beta-(4-fluorophenyl)tropane
AKOS016008694
8zt6kj947t ,
unii-8zt6kj947t
CHEMBL1944829
[3h]-win35428
gtpl4606
2beta-carboxymethy-3beta-(4-fluorophenyl)tropane
[3h]win35428
gtpl4605
win35428
[3h]-2beta-carboxymethy-3beta-(4-fluorophenyl)tropane
[3h]-beta-cft
2beta-carbomethoxy-3beta(4'-fluorophenyl)tropane
QUSLQENMLDRCTO-YJNKXOJESA-N
methyl (1r,5s)-3beta-(p-fluorophenyl)tropane-2beta-carboxylate
(1r,2s,3s)-2-carbomethoxy-3-(4-fluorophenyl)tropane
(1r, 2s, 3s)-2-carbomethoxy-3-(4-fluorophenyl)tropane
SCHEMBL1573076
42L ,
(1r,2s,3s,5s)-methyl 3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
(1r,2s,3s,5s)-3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester
2.beta.-carbomethoxy-3.beta.-(4'-fluorophenyl)tropane
(-)-win 35,428
.beta.-cft
methyl (1r,2s,3s,5s)-3-(4-fluorophenyl)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylate
BCP18674
win 35428; win-35428; (c)micro-cft; (c)microcft;beta-cft
rel-(1r,2s,3s,5s)-methyl 3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
357924-75-5
Q7950808
8-azabicyclo[3.2.1]octane-2-carboxylic acid,3-(4-fluorophenyl)-8-methyl-, methyl ester, (1r,2s,3s,5s)-
beta-cftau
2-beta-carbomethoxy-3-beta-(4-fluorophenyl)tropane
rel-(1r,2s,3s,5s)-methyl3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"In mice, the recreational drug (+/-)3,4-methylenedioxymethamphetamine [MDMA ("ecstasy")] produces a selective toxic effect on brain dopamine (DA) neurons."( Identification and characterization of metallothionein-1 and -2 gene expression in the context of (+/-)3,4-methylenedioxymethamphetamine-induced toxicity to brain dopaminergic neurons.
Becker, KG; Cheadle, C; Donovan, DM; McCann, UD; Mechan, AO; Ricaurte, GA; Tong, L; Xie, T; Yuan, J, 2004
)
0.32

Pharmacokinetics

ExcerptReferenceRelevance
" The period of escalating doses (EDs) is likely associated with development of tolerance to aspects of METH's pharmacologic and toxic effects but the relative contributions of pharmacokinetic and pharmacodynamic factors have not been well defined."( Escalating dose pretreatment induces pharmacodynamic and not pharmacokinetic tolerance to a subsequent high-dose methamphetamine binge.
Cho, AK; Kuczenski, R; Lacan, G; Melega, WP; O'Neil, ML; Segal, DS, 2006
)
0.33

Compound-Compound Interactions

ExcerptReferenceRelevance
"The effects of the dopamine transporter (DAT) inhibitors cocaine and GBR12909 on DAT and dopamine D(2) receptors were evaluated in the brains under awake and isoflurane-anesthetized monkeys using high-resolution positron emission tomography (PET) in combination with microdialysis."( Isoflurane anesthesia enhances the inhibitory effects of cocaine and GBR12909 on dopamine transporter: PET studies in combination with microdialysis in the monkey brain.
Harada, N; Kakiuchi, T; Nakanishi, S; Nishiyama, S; Ohba, H; Sato, K; Tsukada, H, 1999
)
0.3
"The effects of ketamine, a noncompetitive antagonist of NMDA receptors, on the striatal dopaminergic system were evaluated multiparametrically in the monkey brain using high-resolution positron emission tomography (PET) in combination with microdialysis."( Ketamine decreased striatal [(11)C]raclopride binding with no alterations in static dopamine concentrations in the striatal extracellular fluid in the monkey brain: multiparametric PET studies combined with microdialysis analysis.
Fukumoto, D; Harada, N; Kakiuchi, T; Nishiyama, S; Ohba, H; Sato, K; Tsukada, H, 2000
)
0.31

Dosage Studied

ExcerptRelevanceReference
" PCPA pretreatment shifted the cocaine dose-response curve to the right and blocked the ability of zacopride to reverse cocaine-induced activity."( 5-HT3 receptor antagonists block cocaine-induced locomotion via a PCPA-sensitive mechanism.
Hitzemann, R; Svingos, AL, 1992
)
0.28
" Based on the present and previous results, it appears that the regulation of the DAT is fairly plastic, and is highly sensitive to cocaine dosing regimes and withdrawal intervals."( Cocaine use increases [3H]WIN 35428 binding sites in human striatum.
Carroll, FI; Clark, TB; Duncan, GE; Kirkman, JA; Little, KY, 1993
)
0.29
" Parallel line analysis indicated that the slopes of the ascending portion of the RTI-121 and RTI-130 dose-response curves differed from that of cocaine, suggesting the involvement of mechanisms different from that of cocaine."( Highly potent cocaine analogs cause long-lasting increases in locomotor activity.
Boja, JW; Carroll, FI; Fleckenstein, AE; Kopajtic, TA; Kuhar, MJ, 1996
)
0.29
"1 for protocols 1 and 2, respectively) in stimulating the 5-HTP-induced HTR and produced a bell-shaped dose-response curve."( The stimulatory and inhibitory components of cocaine's actions on the 5-HTP-induced 5-HT2A receptor response.
Darmani, NA; Reeves, SL, 1996
)
0.29
") was administered 30 min prior to a neurotoxic MeAmp dosage for this species (2 x 2 mg/kg, 4 h apart); control subjects received MeAmp."( Dizocilpine and reduced body temperature do not prevent methamphetamine-induced neurotoxicity in the vervet monkey: [11C]WIN 35,428 - positron emission tomography studies.
Harvey, DC; Huang, SC; Lacan, G; Melega, WP; Phelps, ME, 1998
)
0.3
", 24 hours apart; a neurotoxic dosage for this species)."( Long-term methamphetamine-induced decreases of [(11)C]WIN 35,428 binding in striatum are reduced by GDNF: PET studies in the vervet monkey.
Desalles, AA; Lacan, G; Melega, WP; Phelps, ME, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium-dependent dopamine transporter Homo sapiens (human)Ki0.02420.00021.11158.0280AID1653639; AID644411
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium-dependent serotonin transporterHomo sapiens (human)Activity0.16000.08970.12480.1600AID652925
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (52)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (24)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1653639Displacement of [3H]WIN 35428 from human DAT transiently expressed in COS7 cells
AID652925Binding affinity to SERT2012Bioorganic & medicinal chemistry, Apr-15, Volume: 20, Issue:8
Synthesis and structure-activity relationship studies of 3-biaryl-8-oxabicyclo[3.2.1]octane-2-carboxylic acid methyl esters.
AID644411Displacement of [3H]WIN35428 from human cloned DAT receptor expressed in human HEK293 cells2012Bioorganic & medicinal chemistry, Feb-15, Volume: 20, Issue:4
QSAR study and synthesis of new phenyltropanes as ligands of the dopamine transporter (DAT).
AID652924Binding affinity to rhesus monkey DAT2012Bioorganic & medicinal chemistry, Apr-15, Volume: 20, Issue:8
Synthesis and structure-activity relationship studies of 3-biaryl-8-oxabicyclo[3.2.1]octane-2-carboxylic acid methyl esters.
AID1653649Displacement of [3H]WIN 35428 from human DAT Y156F mutant transiently expressed in COS7 cells
AID1653651Selectivity ratio of Ki for displacement of [3H]WIN35428 from human DAT Y156F mutant transiently expressed in COS7 cells to Ki for displacement of [3H]WIN35428 from human DAT transiently expressed in COS7 cells
AID1346963Human DAT (Monoamine transporter subfamily)1994Molecular pharmacology, Jan, Volume: 45, Issue:1
Pharmacological heterogeneity of the cloned and native human dopamine transporter: disassociation of [3H]WIN 35,428 and [3H]GBR 12,935 binding.
AID1346963Human DAT (Monoamine transporter subfamily)
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (392)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (2.04)18.7374
1990's184 (46.94)18.2507
2000's158 (40.31)29.6817
2010's39 (9.95)24.3611
2020's3 (0.77)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.14

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 Index10.14 (24.57)
Research Supply Index6.00 (2.92)
Research Growth Index6.13 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.14)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (1.26%)5.53%
Reviews1 (0.25%)6.00%
Case Studies3 (0.76%)4.05%
Observational0 (0.00%)0.25%
Other388 (97.73%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]