Page last updated: 2024-12-08

dexmethylphenidate

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

Description

dexmethylphenidate : A methyl phenyl(piperidin-2-yl)acetate in which both stereocentres have R configuration. It is the active enantiomer in the racemic drug methylphenidate. [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]

Cross-References

ID SourceID
PubMed CID154101
CHEMBL ID827
CHEBI ID51860
SCHEMBL ID34326

Synonyms (48)

Synonym
PDSP1_000871
PDSP2_000889
PDSP1_000903
PDSP2_000857
dexmethylphenidatum
(+)-threo-methylphenidate
d-threo-methylphenidate
40431-64-9
methyl (r)-phenyl[(r)-piperidin-2-yl]acetate
dexmetilfenidato
methyl (2r)-phenyl[(2r)-piperidin-2-yl]acetate
dexmethylphenidate
CHEBI:51860 ,
CHEMBL827 ,
methylphenidate d-threo-form
d-tmp
DB06701
methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate
dexmethylphenidate (inn)
D07806
bdbm50062915
unii-m32rh9mfgp
dex methylphenidate
2-piperidineacetic acid, alpha-phenyl-, methyl ester, (alphar,2r)-
threo-(+)-methylphenidate
dexmethylphenidate [inn]
m32rh9mfgp ,
methyl d-phenidate
d-mph
40572-71-2
methyl (2r)-phenyl((2r)-piperidin-2-yl)acetate
2-piperidineacetic acid, .alpha.-phenyl-, methyl ester, (.alpha.r,2r)-
methylphenidate d-threo-form [mi]
dexmethylphenidate [who-dd]
dexmethylphenidate [vandf]
gtpl7554
attenade
dex-methylphenidate
DUGOZIWVEXMGBE-CHWSQXEVSA-N
d-threo methylphenidate
d-methylphenidate
SCHEMBL34326
DTXSID70893769 ,
2-piperidineacetic acid, .alpha.-phenyl-, methyl ester, (.alpha.s,2s)-
Q1207210
n06ba11
methyl (r)-phenyl((r)-piperidin-2-yl)acetate
dtxcid301323804

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" 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]

Roles (1)

RoleDescription
adrenergic agentAny agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.
[role 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]

Drug Classes (1)

ClassDescription
methyl phenyl(piperidin-2-yl)acetateA amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group.
[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)0.03580.00070.97749.7000AID65012; AID65013
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)IC50 (µMol)224.00000.00030.81978.4900AID204389
Sodium-dependent dopamine transporter Homo sapiens (human)IC50 (µMol)0.15600.00071.841946.0000AID550044
Sodium-dependent dopamine transporter Homo sapiens (human)Ki0.02050.00021.11158.0280AID550043; AID673691
Sigma non-opioid intracellular receptor 1Homo sapiens (human)IC50 (µMol)224.00000.00030.70285.3660AID204389
TransporterRattus norvegicus (Norway rat)IC50 (µMol)0.98900.00081.95628.8000AID145722
[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)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (47)

Processvia Protein(s)Taxonomy
cholesterol biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
response to toxic substanceLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol effluxLiver carboxylesterase 1Homo sapiens (human)
negative regulation of cholesterol storageLiver carboxylesterase 1Homo sapiens (human)
epithelial cell differentiationLiver carboxylesterase 1Homo sapiens (human)
cholesterol homeostasisLiver carboxylesterase 1Homo sapiens (human)
reverse cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
medium-chain fatty acid metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cellular response to cholesterolLiver carboxylesterase 1Homo sapiens (human)
cellular response to low-density lipoprotein particle stimulusLiver carboxylesterase 1Homo sapiens (human)
cholesterol ester hydrolysis involved in cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid secretionLiver carboxylesterase 1Homo sapiens (human)
lipid catabolic processLiver carboxylesterase 1Homo 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 (18)

Processvia Protein(s)Taxonomy
sterol esterase activityLiver carboxylesterase 1Homo sapiens (human)
methylumbelliferyl-acetate deacetylase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylesterase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylic ester hydrolase activityLiver carboxylesterase 1Homo 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 (27)

Processvia Protein(s)Taxonomy
cytoplasmLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulum lumenLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
cytosolLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo 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 (22)

Assay IDTitleYearJournalArticle
AID195888Ability to inhibit the uptake of norepinephrine [3H]-NE in to rat brain synaptosomes1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
Asymmetric synthesis and pharmacology of methylphenidate and its para-substituted derivatives.
AID550044Inhibition of [3H]dopamine uptake at human DAT expressed in mouse N2A cells2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling.
AID64208Inhibition of [3H]WIN-35428 Binding to the Dopamine Transporter in Rhesus (Macaca mulatta) orCynomolgus Monkey (Macaca fascicularis) Caudate-Putamen2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Synthesis and evaluation of dopamine and serotonin transporter inhibition by oxacyclic and carbacyclic analogues of methylphenidate.
AID515950Displacement of [3H]WIN 35428 from Sprague-Dawley rat striatal tissue after 2 hrs by liquid scintillation counting2010Bioorganic & medicinal chemistry, Oct-15, Volume: 18, Issue:20
Quantitative structure-activity relationship studies of threo-methylphenidate analogs.
AID204389Selectivity for the Serotonin transporter using [3H]paroxetine binding assay1999Journal of medicinal chemistry, Nov-18, Volume: 42, Issue:23
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes.
AID65012Inhibitory potency against [3H]DA uptake using [3H]WIN-35428 (WIN-) binding assay1999Journal of medicinal chemistry, Nov-18, Volume: 42, Issue:23
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes.
AID456232Activity at human recombinant CES1 expressed in baculovirus-infected Spodoptera frugiperda Sf21 cells assessed as substrate hydrolysis by fluorescence assay2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
In silico prediction of human carboxylesterase-1 (hCES1) metabolism combining docking analyses and MD simulations.
AID673691Displacement of [3H]WIN-35,428 from human DAT expressed in mouse N2A cells after 15 mins by liquid scintillation counting2012ACS medicinal chemistry letters, May-10, Volume: 3, Issue:5
Evolution of a Compact Photoprobe for the Dopamine Transporter Based on (±)-threo-Methylphenidate.
AID229297Ratio of IC50 of NE (norepinephrine transporter) to IC50 of DA (dopamine transporter)1999Journal of medicinal chemistry, Nov-18, Volume: 42, Issue:23
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes.
AID195887Ability to inhibit the uptake of dopamine [3H]DA in to rat brain synaptosomes1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
Asymmetric synthesis and pharmacology of methylphenidate and its para-substituted derivatives.
AID1474166Liver toxicity in human assessed as induction of drug-induced liver injury by measuring severity class index2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID1388097In vivo receptor occupancy at DAT in iv dosed human measured up to 15 mins by PET analysis2018Journal 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.
AID226226Eudisimic ratio for NE is the ratio of the IC50 values l-isomer and d-isomer1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
Asymmetric synthesis and pharmacology of methylphenidate and its para-substituted derivatives.
AID550043Displacement of [3H]WIN-35428 from human DAT stably expressed in mouse N2A cells by scintillation countnig2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling.
AID229276Ratio of IC50 of 5-HT (serotonin transporter)to IC50 of DA (dopamine transporter)1999Journal of medicinal chemistry, Nov-18, Volume: 42, Issue:23
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes.
AID65013Inhibitory potency against dopamine (DA) transporter using [3H]WIN-35428 (WIN-) binding assay.1999Journal of medicinal chemistry, Nov-18, Volume: 42, Issue:23
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes.
AID145722Selectivity for the norepinephrine transporter using [3H]nisoxetine binding assay1999Journal of medicinal chemistry, Nov-18, Volume: 42, Issue:23
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes.
AID226225Eudisimic ratio for DA uptake is the ratio of the IC50 values l-isomer and d-isomer1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
Asymmetric synthesis and pharmacology of methylphenidate and its para-substituted derivatives.
AID1474167Liver toxicity in human assessed as induction of drug-induced liver injury by measuring verified drug-induced liver injury concern status2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID1388096Half life in human brain2018Journal 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.
AID1346963Human DAT (Monoamine transporter subfamily)2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling.
AID1346944Rat NET (Monoamine transporter subfamily)2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: restricted rotation analogues of methylphenidate.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (20.00)18.2507
2000's2 (20.00)29.6817
2010's6 (60.00)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: 99.24

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index99.24 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index172.90 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (99.24)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]