Page last updated: 2024-11-12

methyl 4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate

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

Description

methyl 4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate: a dopamine transporter ligand; structure in first source; do not confuse with CPCA cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10015831
CHEMBL ID46413
SCHEMBL ID527574
MeSH IDM0440331
PubMed CID10333222
CHEMBL ID296019
SCHEMBL ID1086468
MeSH IDM0440331

Synonyms (34)

Synonym
bdbm50090493
CHEMBL46413 ,
A814717
205805-13-6
methyl 4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate
AKOS015966727
SCHEMBL527574
racemic methyl 4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate
GDFVYUDIAQQDTA-UHFFFAOYSA-N
DTXSID10434256
FT-0742380
(+,-)-cis-methyl-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate
4-(4-chlorophenyl)-1-methyl-3-piperidinecarboxylic acid methyl ester
PDSP1_001293
(3r,4s)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylic acid methyl ester
TL8002108 ,
PDSP2_001277
CHEMBL296019 ,
(3r,4s)-4-(4-chloro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester
bdbm50099288
4-(4-chloro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester
(+)-cpca
263769-22-8
3alpha-carbomethoxy-4beta-(4-chlorophenyl)-n-methylpiperidine
(+)-methyl 4beta-(4-chlorophenyl)-1-methylpiperidine-3alpha-carboxylate
nocaine
SCHEMBL1086468
DTXSID80180975
(3r,4s)-4-(4-chloro-phenyl)-1-methylpiperidine-3-carboxylic acid(ome)
mfcd09835335
Q4540627
methyl (3r,4s)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate
3-piperidinecarboxylic acid, 4-(4-chlorophenyl)-1-methyl-, methyl ester, (3r,4s)-
(3r,4s)-methyl 4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Both compounds maintained responding with sigmoidal or biphasic dose-response functions (0."( Reinforcing strength of a novel dopamine transporter ligand: pharmacodynamic and pharmacokinetic mechanisms.
Kozikowski, A; Ordway, GA; Paul, IA; Petukhov, P; Ranaldi, R; Wang, Z; Woolverton, WL, 2002
)
0.31
" Hence, the successful development of future TRIs for depression will demand strong translational evidence, an optimal dosing regimen, and better tolerability."( Triple Reuptake Inhibitors as Potential Therapeutics for Depression and Other Disorders: Design Paradigm and Developmental Challenges.
Subbaiah, MAM, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium-dependent dopamine transporterRattus norvegicus (Norway rat)Ki0.24420.00030.37088.1600AID239595; AID65501
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)Ki8.49000.00000.705610.0000AID239641
TransporterRattus norvegicus (Norway rat)Ki0.25200.00010.866710.0000AID239623
Sodium-dependent dopamine transporterRattus norvegicus (Norway rat)IC50 (µMol)0.16240.00070.97749.7000AID1388153; AID64678
Sodium-dependent dopamine transporterRattus norvegicus (Norway rat)Ki0.26050.00030.37088.1600AID65183; AID65354; AID65355
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)IC50 (µMol)8.49000.00030.81978.4900AID1388151
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)Ki8.49000.00000.705610.0000AID204525; AID204712
TransporterRattus norvegicus (Norway rat)IC50 (µMol)0.25200.00081.95628.8000AID1388152
TransporterRattus norvegicus (Norway rat)Ki0.25200.00010.866710.0000AID145393; AID147746
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (40)

Assay IDTitleYearJournalArticle
AID65502Inhibition of [3H]DA binding to dopamine transporter of rat brain synaptosomes2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and biological evaluation of 1-azabicyclo-[3.2.1]octanes: new dopamine transporter inhibitors.
AID239641Inhibition of high affinity uptake by the serotonin transporter (5-HT) from rat synaptosomal nerve endings by using [3H]5-HT as radioligand2004Journal of medicinal chemistry, Nov-18, Volume: 47, Issue:24
Piperidine-based nocaine/modafinil hybrid ligands as highly potent monoamine transporter inhibitors: efficient drug discovery by rational lead hybridization.
AID145884Inhibition of [3H]NE binding to norepinephrine transporter of rat brain synaptosomes2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and biological evaluation of 1-azabicyclo-[3.2.1]octanes: new dopamine transporter inhibitors.
AID204857Inhibition of [3H]-5-HT binding to serotonin transporter of rat brain synaptosomes2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and biological evaluation of 1-azabicyclo-[3.2.1]octanes: new dopamine transporter inhibitors.
AID239623Inhibition of high affinity uptake by the norepinephrine transporter from rat synaptosomal nerve endings by using [3H]NE as radioligand2004Journal of medicinal chemistry, Nov-18, Volume: 47, Issue:24
Piperidine-based nocaine/modafinil hybrid ligands as highly potent monoamine transporter inhibitors: efficient drug discovery by rational lead hybridization.
AID230942Relative affinity for serotonin and dopamine transporters2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and biological evaluation of 1-azabicyclo-[3.2.1]octanes: new dopamine transporter inhibitors.
AID65501Inhibition of [3H]- Mazindol binding to dopamine transporter of rat striatal membrane.2000Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15
Synthesis and biological evaluation of 1-azabicyclo-[3.2.1]octanes: new dopamine transporter inhibitors.
AID239595Inhibition of high affinity uptake by the dopamine transporter from rat synaptosomal nerve endings by using [3H]DA as radioligand2004Journal of medicinal chemistry, Nov-18, Volume: 47, Issue:24
Piperidine-based nocaine/modafinil hybrid ligands as highly potent monoamine transporter inhibitors: efficient drug discovery by rational lead hybridization.
AID493017Wombat Data for BeliefDocking1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
Chemistry and pharmacology of the piperidine-based analogues of cocaine. Identification of potent DAT inhibitors lacking the tropane skeleton.
AID493017Wombat Data for BeliefDocking2002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
SAR studies of piperidine-based analogues of cocaine. 4. Effect of N-modification and ester replacement.
AID64678Ability to displace [3H]WIN-35428 binding to dopamine transporter from rat striatal membranes1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
Chemistry and pharmacology of the piperidine-based analogues of cocaine. Identification of potent DAT inhibitors lacking the tropane skeleton.
AID145393Inhibition of high affinity uptake of [3H]NE by norepinephrine transporter in nerve endings obtained from rat brain.2002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
SAR studies of piperidine-based analogues of cocaine. 4. Effect of N-modification and ester replacement.
AID65354Inhibition of high affinity uptake of [3H]DA using rat nerve endings obtained from brain regions enriched in DAT.2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Sar studies of piperidine-based analogues of cocaine. Part 3: oxadiazoles.
AID204526Ability to inhibit high affinity uptake of [3H]-5-HT at Serotonin transporter (SERT) using rat midbrain2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis, molecular modeling, and biological studies of novel piperidine-based analogues of cocaine: evidence of unfavorable interactions proximal to the 3alpha-position of the piperidine ring.
AID232405Ratio of Ki at norepinephrine transporter and Ki at dopamine transporter.2002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
SAR studies of piperidine-based analogues of cocaine. 4. Effect of N-modification and ester replacement.
AID1388151Inhibition of rat brain SERT assessed as reduction of [3H]5-HT re-uptake preincubated for 30 mins followed by [3H]5-HT addition measured after 5 mins by scintillation counting2018Journal of medicinal chemistry, 03-22, Volume: 61, Issue:6
Triple Reuptake Inhibitors as Potential Therapeutics for Depression and Other Disorders: Design Paradigm and Developmental Challenges.
AID226487Hill coefficient was determined1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
Chemistry and pharmacology of the piperidine-based analogues of cocaine. Identification of potent DAT inhibitors lacking the tropane skeleton.
AID230708Ratio of affinity for Norepinephrine transporter to that of Serotonin transporter2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis, molecular modeling, and biological studies of novel piperidine-based analogues of cocaine: evidence of unfavorable interactions proximal to the 3alpha-position of the piperidine ring.
AID232403Ratio of Ki at 5-HT transporter and Ki at dopamine transporter.2002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
SAR studies of piperidine-based analogues of cocaine. 4. Effect of N-modification and ester replacement.
AID232406Ratio of Ki at norepinephrine transporter and Ki at 5-HT transporter.2002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
SAR studies of piperidine-based analogues of cocaine. 4. Effect of N-modification and ester replacement.
AID145729Ability to inhibit high affinity uptake of norepinephrine transporter into the nerve endings of rat synaptosomes using [3H]NE radioligand2001Journal of medicinal chemistry, May-10, Volume: 44, Issue:10
Pharmacological and behavioral analysis of the effects of some bivalent ligand-based monoamine reuptake inhibitors.
AID230710Ratio of affinity for Norepinephrine transporter to that of dopamine transporter2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis, molecular modeling, and biological studies of novel piperidine-based analogues of cocaine: evidence of unfavorable interactions proximal to the 3alpha-position of the piperidine ring.
AID204525Inhibition of high affinity uptake of [3H]5-HT by serotonin transporter in nerve endings obtained from rat brain.2002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
SAR studies of piperidine-based analogues of cocaine. 4. Effect of N-modification and ester replacement.
AID65183Inhibition of high affinity uptake of [3H]-DA by dopamine transporter in nerve endings obtained from rat brain.2002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
SAR studies of piperidine-based analogues of cocaine. 4. Effect of N-modification and ester replacement.
AID65178Displacement of [3H]mazindol binding to dopamine transporter (DAT) in rat synaptosomes2001Journal of medicinal chemistry, May-10, Volume: 44, Issue:10
Pharmacological and behavioral analysis of the effects of some bivalent ligand-based monoamine reuptake inhibitors.
AID64997Inhibition of high-affinity uptake of [3H]dopamine at dopamine transporter into rat striatal nerve endings (synaptosomes)1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
Chemistry and pharmacology of the piperidine-based analogues of cocaine. Identification of potent DAT inhibitors lacking the tropane skeleton.
AID1388152Inhibition of rat brain NET assessed as reduction of [3H]-NE re-uptake preincubated for 30 mins followed by [3H]-NE addition measured after 5 mins by scintillation counting2018Journal of medicinal chemistry, 03-22, Volume: 61, Issue:6
Triple Reuptake Inhibitors as Potential Therapeutics for Depression and Other Disorders: Design Paradigm and Developmental Challenges.
AID230871Ratio of affinity for serotonin transporter to that of dopamine transporter2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis, molecular modeling, and biological studies of novel piperidine-based analogues of cocaine: evidence of unfavorable interactions proximal to the 3alpha-position of the piperidine ring.
AID65184Ability to inhibit high affinity uptake of [3H]DA at Dopamine transporter (DAT) using rat brain striatum2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis, molecular modeling, and biological studies of novel piperidine-based analogues of cocaine: evidence of unfavorable interactions proximal to the 3alpha-position of the piperidine ring.
AID204524Inhibition of high affinity serotonin uptake into rat synaptosomes using [3H]5-HT2001Journal of medicinal chemistry, May-10, Volume: 44, Issue:10
Pharmacological and behavioral analysis of the effects of some bivalent ligand-based monoamine reuptake inhibitors.
AID234941Selectivity in uptake of NE to that of DA2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Sar studies of piperidine-based analogues of cocaine. Part 3: oxadiazoles.
AID1388153Inhibition of rat brain DAT assessed as reduction of [3H]-DA re-uptake preincubated for 30 mins followed by [3H]-DA addition measured after 5 mins by scintillation counting2018Journal of medicinal chemistry, 03-22, Volume: 61, Issue:6
Triple Reuptake Inhibitors as Potential Therapeutics for Depression and Other Disorders: Design Paradigm and Developmental Challenges.
AID15715Calculated partition coefficient (clogP)2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis, molecular modeling, and biological studies of novel piperidine-based analogues of cocaine: evidence of unfavorable interactions proximal to the 3alpha-position of the piperidine ring.
AID65824Inhibition of high affinity DA uptake into rat synaptosomes using [3H]DA2001Journal of medicinal chemistry, May-10, Volume: 44, Issue:10
Pharmacological and behavioral analysis of the effects of some bivalent ligand-based monoamine reuptake inhibitors.
AID234939Selectivity in uptake of 5-HT to that of DA2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Sar studies of piperidine-based analogues of cocaine. Part 3: oxadiazoles.
AID147746Displacement of [3H]NE from Norepinephrine transporter of rat brain2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Sar studies of piperidine-based analogues of cocaine. Part 3: oxadiazoles.
AID65355Displacement of [3H]WIN-35248 from dopamine transporter (DAT) of rat striatal membrane2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Sar studies of piperidine-based analogues of cocaine. Part 3: oxadiazoles.
AID145861Ability to inhibit high affinity uptake of [3H]NE at Norepinephrine transporter (NET) using rat brain parietal/occipital cortex2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis, molecular modeling, and biological studies of novel piperidine-based analogues of cocaine: evidence of unfavorable interactions proximal to the 3alpha-position of the piperidine ring.
AID234940Selectivity in uptake of NE to that of 5-HT2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Sar studies of piperidine-based analogues of cocaine. Part 3: oxadiazoles.
AID204712Displacement of [3H]5-HT from serotonin transporter of rat brain2001Bioorganic & medicinal chemistry letters, Aug-20, Volume: 11, Issue:16
Sar studies of piperidine-based analogues of cocaine. Part 3: oxadiazoles.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (8.33)18.7374
1990's1 (8.33)18.2507
2000's9 (75.00)29.6817
2010's1 (8.33)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: 12.56

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 Index12.56 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.76 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]