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Submit Review2R,6R-Hydroxynorketamine hydrochloride
Description: Enhances AMPA currents; decreases D-serine (a NMDA co-agonist); lacks ketamine-related side effects
Chemical Name: (2R,6R)-2-Amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride
Purity: ≥98% (HPLC)
Biological Activity for 2R,6R-Hydroxynorketamine hydrochloride
2R,6R-Hydroxynorketamine hydrochloride is a ketamine metabolite. It enhances AMPA receptor-mediated excitatory post-synaptic potentials in the CA1 region of hippocampal slices and decreases intracellular D-serine (a NMDA co-agonist) concentrations in PC-12 cells (IC50 = 0.68 nM). 2R,6R-Hydroxynorketamine upregulates KCNQ2 channels in mouse ventral hippocampal glutamatergic neurons in vitro and in vivo. Exerts antidepressant effects in mice. Lacks ketamine-related side effects.
2S,6S-Enantiomer and Racemate also available.
Licensing Information
Sold under license from the NIH, US patent 62/313,309
Technical Data for 2R,6R-Hydroxynorketamine hydrochloride
| M. Wt | 276.16 |
| Formula | C12H14ClNO2.HCl |
| Storage | Store at RT |
| Purity | ≥98% (HPLC) |
| CAS Number | 1430202-69-9 |
| PubChem ID | 121513910 |
| InChI Key | ZQJVHBJDLMIKJK-MHDYBILJSA-N |
| Smiles | ClC1=C([C@@]2(N)C([C@H](O)CCC2)=O)C=CC=C1.Cl |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for 2R,6R-Hydroxynorketamine hydrochloride
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 13.81 | 50 | |
| DMSO | 27.62 | 100 |
Preparing Stock Solutions for 2R,6R-Hydroxynorketamine hydrochloride
The following data is based on the product molecular weight 276.16. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 3.62 mL | 18.11 mL | 36.21 mL |
| 5 mM | 0.72 mL | 3.62 mL | 7.24 mL |
| 10 mM | 0.36 mL | 1.81 mL | 3.62 mL |
| 50 mM | 0.07 mL | 0.36 mL | 0.72 mL |
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Product Datasheets for 2R,6R-Hydroxynorketamine hydrochloride
References for 2R,6R-Hydroxynorketamine hydrochloride
References are publications that support the biological activity of the product.
Singh et al (2016) KA metabolites enantioselectively decrease intracellular D-serine concentrations in PC-12 cells. PLoS One 11 e0149499 PMID: 27096720
Zanos et al (2016) NMDAR inhibition-independent antidepressant actions of KA metabolites. Nature 533 481 PMID: 27144355
Lopez et al (2022) Ketamine exerts its sustained antidepressant effects via cell-type-specific regulation of Kcnq2. Neuron 110 2283 PMID: 35649415
If you know of a relevant reference for 2R,6R-Hydroxynorketamine hydrochloride, please let us know.
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Keywords: 2R,6R-Hydroxynorketamine hydrochloride, 2R,6R-Hydroxynorketamine hydrochloride supplier, Potent, AMPA, agonists, agonism, ketamine, metabolites, antidepressants, enantiomer, APJ, 2R,6R-HNK, depression, Receptors, Ketamine, and, Metabolites, 6094, Tocris Bioscience
10 Citations for 2R,6R-Hydroxynorketamine hydrochloride
Citations are publications that use Tocris products. Selected citations for 2R,6R-Hydroxynorketamine hydrochloride include:
Jian-Hua et al (2020) The Ventrolateral Periaqueductal Gray Contributes to Depressive-Like Behaviors in Recovery of Inflammatory Bowel Disease Rat Model. Front Neurosci 14 254 PMID: 32265648
Xiangmin et al (2020) Subanesthetic Ketamine Reactivates Adult Cortical Plasticity to Restore Vision from Amblyopia. Curr Biol 30 3591-3603.e8 PMID: 32822611
Eero et al (2019) Pharmacologically diverse antidepressants facilitate TRKB receptor activation by disrupting its interaction with the endocytic adaptor complex AP-2. J Biol Chem 294 18150-18161 PMID: 31631060
Ago et al (2019) (R)-Ketamine induces a greater increase in prefrontal 5-HT release than (S)-Ketamine and Ketamine Metabolites via an AMPA receptor-independent mechanism. Int J Neuropsychopharmacol 22 665 PMID: 31325908
Ye et al (2019) KA metabolite (2R,6R)-hydroxynorKA enhances aggression via periaqueductal gray glutamatergic transmission. Neuropharmacology 157 PMID: 31207251
Plinio C et al (2023) Ketamine and its metabolite 2R,6R-hydroxynorketamine promote ocular dominance plasticity and release tropomyosin-related kinase B from inhibitory control without reducing perineuronal nets enwrapping parvalbumin interneurons. Eur J Neurosci 57 940-950 PMID: 36740723
Eero et al (2023) TRKB interaction with PSD95 is associated with latency of fluoxetine and 2R,6R-hydroxynorketamine. Eur J Neurosci 57 1215-1224 PMID: 36876503
Tomasz et al (2023) Psychedelics promote plasticity by directly binding to BDNF receptor TrkB. Nat Neurosci 26 1032-1041 PMID: 37280397
Eero et al (2022) Antidepressant and Antipsychotic Drugs Reduce Viral Infection by SARS-CoV-2 and Fluoxetine Shows Antiviral Activity Against the Novel Variants in vitro. Front Pharmacol 12 755600 PMID: 35126106
Chou et al (2018) (2R,6R)-hydroxynorKA rescues chronic stress-induced depression-like behavior through its actions in the midbrain periaqueductal gray. Neuropharmacology 139 1 PMID: 29953886
Do you know of a great paper that uses 2R,6R-Hydroxynorketamine hydrochloride from Tocris? Please let us know.
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
Addiction Poster
The key feature of drug addiction is the inability to stop using a drug despite clear evidence of harm. This poster describes the brain circuits associated with addiction, and provides an overview of the main classes of addictive drugs and the neurotransmitter systems that they target.
Depression Poster
Major depressive disorder is characterized by depressed mood and a loss of interest and/or pleasure. Updated in 2015 this poster highlights presynaptic and postsynaptic targets for the potential treatment of major depressive disorder, as well as outlining the pharmacology of currently approved antidepressant drugs.