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R ketamine

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(R)-Ketamine is a chemical compound used in research and scientific applications. It is the R-enantiomer of the drug ketamine. The core function of (R)-Ketamine is to serve as a research tool for studying the pharmacological and biochemical properties of this stereoisomer.

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Lab products found in correlation

S ketamine, by Merck Group (4 mentions) Benserazide hydrochloride, by Merck Group (2 mentions) L dopa, by Merck Group (2 mentions) Peg400, by Merck Group (2 mentions) Phencyclidine pcp, by Merck Group (2 mentions) Mk 801, by Merck Group (2 mentions) Desipramine, by Merck Group (2 mentions) Acetylacetone, by Merck Group (1 mentions) Esf af culture media, by Expression Systems (1 mentions) Trichoplusia ni tni cells, by Expression Systems (1 mentions) Spodoptera frugiperda sf9 cells, by Thermo Fisher Scientific (1 mentions) Bacpak baculovirus rapid titer kit, by Takara Bio (1 mentions) Formaldehyde, by Merck Group (1 mentions)

6 protocols using r ketamine

1

Ketamine and HNK Dose Responses

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(R,S)-ketamine (Sigma Aldrich, St. Louis, MO, United States) was administered at various doses (3 mg/kg, 10 mg/kg, 30 mg/kg, 100 mg/kg, i.p.). (S)-ketamine (Sigma Aldrich) and (R)-ketamine (Cayman Chemical, Ann Arbor, MI, United States) were administered at a dose of 15 mg/kg (i.p.); (2R,6R)-HNK (NCATS Chemical Genomics Center, Bethesda, MD, United States) was administered at a dose of 30 mg/kg (i.p.). 0.9% saline was used as the vehicle for all experiments, and administered through the same route as drug treatment.
Hare B.D., Pothula S., DiLeone R.J, & Duman R.S. (2020). Ketamine increases vmPFC activity: Effects of (R)- and (S)-stereoisomers and (2R,6R)- hydroxynorketamine metabolite. Neuropharmacology, 166, 107947.
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2

Pharmacological Modulation of Dopamine Signaling

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All systemic drugs were administered at a volume of 1 ml/kg via intraperitoneal (i.p.) injection. In Experiment 1, ketamine (20 mg/kg; VetOne), R-ketamine (10 mg/kg; Cayman Chemicals, Ann Arbor, MI), and L-DOPA (6 and 12 mg/kg; Sigma-Aldrich) combined with benserazide hydrochloride (14 mg/kg; Sigma-Aldrich) were formulated in the vehicle solution, 0.9% USP grade sterile saline (VetOne). Benserazide is a peripherally acting aromatic L-amino acid decarboxylase or DOPA decarboxylase inhibitor, which is unable to cross the blood–brain barrier, used to prevent conversion of L-DOPA to dopamine in the bloodstream. In Experiment 2, ketamine (20 mg/kg; VetOne) was formulated in the vehicle solution, 0.9% USP grade sterile saline (VetOne). In Experiment 3, ketamine (20 mg/kg; VetOne) and L-DOPA (6 mg/kg) combined with benserazide (14 mg/kg) were formulated in 0.9% USP grade sterile saline (VetOne). N-[2-[(2-oxoazepan-3-yl)carbamoyl]phenyl]-1-benzothiophene-2-carboxamide (ANA-12; 0.5 mg/kg; Tocris Bioscience, Minneapolis, MN) was dissolved in 5% DMSO, 55% polyethylene glycol 400 (PEG-400; Sigma-Aldrich), and 40% normal saline. ANA-12 is a tropomyosin receptor kinase B (TrkB)-receptor antagonist used to probe for involvement of the BDNF pathway (Cazorla et al., 2011 (link)).
Bartlett M.J., Flores A.J., Ye T., Smidt S.I., Dollish H.K., Stancati J.A., Farrell D.C., Parent K.L., Doyle K.P., Besselsen D.G., Heien M.L., Cowen S.L., Steece-Collier K., Sherman S.J, & Falk T. (2020). Preclinical evidence in support of repurposing sub-anesthetic ketamine as a treatment for L-DOPA-induced dyskinesia. Experimental neurology, 333, 113413.
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3

Synthesis and Characterization of Ketamine Analogues

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(R,S)-ketamine, (S)-ketamine, desipramine, MK-801, phencyclidine (PCP) (Sigma-Aldrich, St. Louis, MO, USA), (R)-ketamine (Cayman Chemicals, Ann Arbor, MI, USA) and NBQX (National Institute of Mental Health Chemical Synthesis and Drug Supply Program) were dissolved in 0.9% saline. (2S,6S)-HNK, (2R,6R)-HNK, and 6,6-dideuteroketamine hydrochloride were synthesised and characterised both internally at the National Center for Advancing Translational Sciences and at SRI International (Menlo Park, CA, USA) as described in Supplementary Information. Absolute and relative stereochemistry for (2S,6S)-HNK and (2R,6R)-HNK were confirmed by small molecule x-ray crystallography, as described in the Supplementary Information.
All drugs were dissolved in 0.9% saline, and administered intraperitoneally (i.p.) in a volume of 7.5 ml/kg of body mass by a male experimenter for the behavioural studies. Corticosterone (4-pregnen-11β, 21-diol-3, 20-dione 21-hemisuccinate; Steraloids, Newport, RI, USA) was dissolved in tap water. For the electrophysiology recordings, test drugs were diluted in artificial cerebrospinal fluid (ACSF).
Zanos P., Moaddel R., Morris P.J., Georgiou P., Fischell J., Elmer G.I., Alkondon M., Yuan P., Pribut H.J., Singh N.S., Dossou K.S., Fang Y., Huang X.P., Mayo C.L., Wainer I.W., Albuquerque E.X., Thompson S.M., Thomas C.J., Zarate CA J.r, & Gould T.D. (2016). NMDAR inhibition-independent antidepressant actions of ketamine metabolites. Nature, 533(7604), 481-486.
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4

Pharmacological Modulation of Dopamine Signaling

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All systemic drugs were administered at a volume of 1 ml/kg via intraperitoneal (i.p.) injection. In Experiment 1, ketamine (20 mg/kg; VetOne), R-ketamine (10 mg/kg; Cayman Chemicals, Ann Arbor, MI), and L-DOPA (6 and 12 mg/kg; Sigma-Aldrich) combined with benserazide hydrochloride (14 mg/kg; Sigma-Aldrich) were formulated in the vehicle solution, 0.9% USP grade sterile saline (VetOne). Benserazide is a peripherally acting aromatic L-amino acid decarboxylase or DOPA decarboxylase inhibitor, which is unable to cross the blood–brain barrier, used to prevent conversion of L-DOPA to dopamine in the bloodstream. In Experiment 2, ketamine (20 mg/kg; VetOne) was formulated in the vehicle solution, 0.9% USP grade sterile saline (VetOne). In Experiment 3, ketamine (20 mg/kg; VetOne) and L-DOPA (6 mg/kg) combined with benserazide (14 mg/kg) were formulated in 0.9% USP grade sterile saline (VetOne). N-[2-[(2-oxoazepan-3-yl)carbamoyl]phenyl]-1-benzothiophene-2-carboxamide (ANA-12; 0.5 mg/kg; Tocris Bioscience, Minneapolis, MN) was dissolved in 5% DMSO, 55% polyethylene glycol 400 (PEG-400; Sigma-Aldrich), and 40% normal saline. ANA-12 is a tropomyosin receptor kinase B (TrkB)-receptor antagonist used to probe for involvement of the BDNF pathway (Cazorla et al., 2011 (link)).
Bartlett M.J., Flores A.J., Ye T., Smidt S.I., Dollish H.K., Stancati J.A., Farrell D.C., Parent K.L., Doyle K.P., Besselsen D.G., Heien M.L., Cowen S.L., Steece-Collier K., Sherman S.J, & Falk T. (2020). Preclinical evidence in support of repurposing sub-anesthetic ketamine as a treatment for L-DOPA-induced dyskinesia. Experimental neurology, 333, 113413.
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5

Synthesis and Characterization of Ketamine Analogues

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(R,S)-ketamine, (S)-ketamine, desipramine, MK-801, phencyclidine (PCP) (Sigma-Aldrich, St. Louis, MO, USA), (R)-ketamine (Cayman Chemicals, Ann Arbor, MI, USA) and NBQX (National Institute of Mental Health Chemical Synthesis and Drug Supply Program) were dissolved in 0.9% saline. (2S,6S)-HNK, (2R,6R)-HNK, and 6,6-dideuteroketamine hydrochloride were synthesised and characterised both internally at the National Center for Advancing Translational Sciences and at SRI International (Menlo Park, CA, USA) as described in Supplementary Information. Absolute and relative stereochemistry for (2S,6S)-HNK and (2R,6R)-HNK were confirmed by small molecule x-ray crystallography, as described in the Supplementary Information.
All drugs were dissolved in 0.9% saline, and administered intraperitoneally (i.p.) in a volume of 7.5 ml/kg of body mass by a male experimenter for the behavioural studies. Corticosterone (4-pregnen-11β, 21-diol-3, 20-dione 21-hemisuccinate; Steraloids, Newport, RI, USA) was dissolved in tap water. For the electrophysiology recordings, test drugs were diluted in artificial cerebrospinal fluid (ACSF).
Zanos P., Moaddel R., Morris P.J., Georgiou P., Fischell J., Elmer G.I., Alkondon M., Yuan P., Pribut H.J., Singh N.S., Dossou K.S., Fang Y., Huang X.P., Mayo C.L., Wainer I.W., Albuquerque E.X., Thompson S.M., Thomas C.J., Zarate CA J.r, & Gould T.D. (2016). NMDAR inhibition-independent antidepressant actions of ketamine metabolites. Nature, 533(7604), 481-486.
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6

Ketamine Analogs Synthesis and Characterization

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Formaldehyde, acetylacetone and S-ketamine were purchased from Sigma-Aldrich (St Louis, MO). R-ketamine was purchased from Cayman Chemical (Ann Arbor, MI). Racemic RS-ketamine was from Spectrum Chemical Corp (New Brunswick, NJ). Norketamine (d0 and d4) were from Cerilliant (Round Rock, TX). Spodoptera frugiperda (Sf9) cells and Sf-900 III SFM culture media were purchased from ThermoFisher (Waltham, MA). Trichoplusia ni (Tni) cells, ESF AF culture media, and BestBac 2.0 Baculovirus Cotransfection Kits were from Expression Systems (Davis, CA). BacPAK Baculovirus Rapid Titer Kit was from Clontech (Mountain View, CA). Strata-X 33u (30 mg) solid-phase extraction plates were from Phenomenex (Torrance, CA). Other reagents were from SigmaAldrich. Ketamine analogs deschloroketamine (2-phenyl-2-(methylamino)cyclohexan-1-one), fluoroketamine (2-(2-fluorophenyl)-2-(methylamino)cyclohexan-1-one, and bromoketamine (2-(2-bromophenyl)-2-(methylamino)cyclohexan-1-one were synthesized using reported methods.
Wang P.F., Neiner A., Lane T.R., Zorn K.M., Ekins S, & Kharasch E.D. (2019). Halogen Substitution Influences Ketamine Metabolism by Cytochrome P450 2B6: In Vitro and Computational Approaches. Molecular pharmaceutics, 16(2), 898-906.
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