Page last updated: 2024-12-09

(R)-ketamine

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

Description

There is no known or widely recognized compound specifically referred to as (R)-ketamine. Ketamine, itself, is a chiral molecule, meaning it exists in two mirror-image forms:

* **(S)-ketamine:** This is the primary enantiomer found in commercially available ketamine. It's the form responsible for most of the drug's effects, including anesthetic and dissociative properties.
* **(R)-ketamine:** This is the less dominant enantiomer. While it also has anesthetic properties, its effects are significantly weaker compared to (S)-ketamine.

**Why (R)-ketamine is important for research:**

Although less potent, (R)-ketamine is being researched for its potential therapeutic benefits, particularly in:

* **Treating Depression:** Some studies suggest that (R)-ketamine may have antidepressant effects with fewer side effects than (S)-ketamine. This is because it interacts with different brain receptors and pathways.
* **Reducing Chronic Pain:** Early research suggests that (R)-ketamine might be effective in managing chronic pain, potentially with fewer hallucinogenic side effects than (S)-ketamine.
* **Improving Cognitive Function:** Studies are exploring the potential of (R)-ketamine to enhance cognitive function, potentially by boosting neuroplasticity (the brain's ability to adapt and grow).

**Key Points to Note:**

* **Research is still ongoing:** Understanding the full therapeutic potential of (R)-ketamine is still in its early stages. More research is needed to confirm its efficacy and safety.
* **Dosage and administration:** The proper dosage and administration methods for (R)-ketamine are yet to be fully established and may differ from (S)-ketamine.
* **Potential risks:** (R)-ketamine can still have side effects, including disorientation, hallucinations, and addiction potential.

**Overall, (R)-ketamine is an area of active research with promising potential for treating various conditions. However, it's crucial to remember that it's still a relatively new area of study with ongoing research needed to determine its true benefits and risks.**

(R)-ketamine : The R- (less active) enantiomer of ketamine. [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 CID644025
CHEMBL ID467505
CHEBI ID580604
SCHEMBL ID16104

Synonyms (36)

Synonym
(r)-(+)-ketamine
cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2r)-
d-ketamine
(r)-ketamine
33643-49-1
cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (r)-
(+)-ketamine
cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2r)- (9ci)
cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (+)- (8ci)
(2r)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
(2r)-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone
(2r)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone
CHEBI:580604 ,
CHEMBL467505
NCGC00185909-01
dtxsid2048747 ,
tox21_113205
dtxcid9028673
cas-33643-49-1
rke ,
SCHEMBL16104
(2r)-2-(2-chlorophenyl)-2-methylaminocyclohexan-1-one
(s) ketamine
gtpl9153
J238.629A ,
esketamine hydrochloride impurity d [ep impurity]
arketamine
pcn-101
ketamine, (r)-
Y2RI13H7VW ,
unii-y2ri13h7vw
hr-071603
ketamine, r-
cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (+)-
arketamine [who-dd]
Q20707684

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
intravenous anaestheticnull
analgesicAn agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
NMDA receptor antagonistAny substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
[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
ketamineA member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino 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 (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
estrogen nuclear receptor alphaHomo sapiens (human)Potency15.31140.000229.305416,493.5996AID743069; AID743075
[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)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Ki1.98500.00030.86666.6900AID1692782; AID1692783
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)Ki1.98500.00030.68056.6900AID1692782; AID1692783
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)Ki1.98500.00030.70716.6900AID1692782; AID1692783
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)Ki1.98500.00030.81966.6900AID1692782; AID1692783
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)Ki1.98500.00030.70726.6900AID1692782; AID1692783
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)Ki1.98500.00030.70726.6900AID1692782; AID1692783
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)Ki1.98500.00030.70726.6900AID1692782; AID1692783
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID353103Displacement of [3H]MK801 from NMDA receptor in rat brain neuronal membrane2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds.
AID353104Ratio of Ki for rat brain NMDA receptor in presence of 100 uM spermine to Ki for rat brain NMDA receptor in absence of spermine2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds.
AID1741562Displacement of [3H]MK801 from NMDA receptor (unknown origin) by radioligand binding assay2020European journal of medicinal chemistry, Oct-15, Volume: 204Open and rearranged norbornane derived polycyclic cage molecules as potential neuroprotective agents through attenuation of MPP
AID1247108Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 30 uM spermine to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 30 uM spermine2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.
AID1247113Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 20 mM NH4+ to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 20 mM NH4+2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.
AID1247110Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of H+ at pH 6.4 to 8.2 to IC50 for NMDA receptor in Wistar rat brain membranes in absence of H+ at pH 6.4 to 8.22015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.
AID1692776Cmax in mouse brain at 10 mg/kg, ip measured after 10 mins2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Repurposing of Drugs-The Ketamine Story.
AID1247109Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 10 to 50 mM Tris to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 10 to 50 mM Tris2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.
AID1247107Displacement of [3H]MK-801 from NMDA receptor in Wistar rat brain membranes by scintillation counting analysis2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.
AID1247112Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 50 mM K+ to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 50 mM K+2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.
AID1247111Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 3 to 50 mM Na+ to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 3 to 50 mM Na+2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.
AID1247114Ratio of IC50 for NMDA receptor in Wistar rat brain membranes in presence of 1.3 mM Mg2+ to IC50 for NMDA receptor in Wistar rat brain membranes in absence of 1.3 mM Mg2+2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.
AID1692782Displacement of [3H]-MK801 from NMDA receptor in rat brain homogenate2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Repurposing of Drugs-The Ketamine Story.
AID1692783Displacement of [3H]-MK801 from NMDA receptor in rat brain membranes2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Repurposing of Drugs-The Ketamine Story.
[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's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's2 (28.57)24.3611
2020's4 (57.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 52.79

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 Index52.79 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index5.21 (4.65)
Search Engine Demand Index76.77 (26.88)
Search Engine Supply Index1.99 (0.95)

This Compound (52.79)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]