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K2753 Sigma

(±)-Ketamine hydrochloride

solid

Synonym: (±)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone hydrochloride

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
form   solid
drug control   USDEA Schedule III; stupéfiant; regulated under CDSA - not available from Sigma-Aldrich Canada
color   white
solubility   H2O: soluble200 mg/mL
originator   Pfizer
storage temp.   2-8°C

Description

Biochem/physiol Actions

Selective NMDA glutamate receptor antagonist; veterinary anesthetic.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Pfizer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
26
WGK Germany 
3
RTECS 
GW1400000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Discover Bioactive Small Molecules for Neuroscience

The nervous system, comprised of the brain and spinal cord (central nervous system, or CNS) and network of nerves that connects the CNS to the rest of the body (peripheral nervous system, or PNS) is ...
Keywords: Bioactive small molecules, Central Nervous System, Diseases, Metabolism, Neurodegenerative Diseases, Neuroscience, Neurotransmission, Neurotransmitters

Peer-Reviewed Papers

References

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Effects of ketamine, a noncompetitive NMDA antagonist, on the acquisition of the lever-press response in rats. Pallers, et al. Physiol. Behav. 57, 389, (1995)

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Intraplantar injection of dextrorphan, ketamine or memantine attenuates formalin-induced behaviors. Davidson, et al. Brain Res. 785, 136, (1998)

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Ketamine inhibits the tonic response to carbachol and histamine in the guinea pig trachea. Sato, et al. Eur. J. Anaesthesiol. 15, 486, (1998)

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New paradigms for treatment-resistant depression. Zarate C, Duman RS, Liu G, et al. Ann. N. Y. Acad. Sci. 1292(1), 21-31, (2013)

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The analgesic efficiency of combined pregabalin and ketamine for total hip arthroplasty: a randomised, double-blind, controlled study. Martinez V, Cymerman A, Ben Ammar S, et al. Anaesthesia 69(1), 46-52, (2014)

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Bilateral central pain sensitization in rats following a unilateral thalamic lesion may be treated with high doses of ketamine. Castel A, Hélie P, Beaudry F, et al. BMC Vet. Res. 9, 59, (2013)

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Imaging patients with psychosis and a mouse model establishes a spreading pattern of hippocampal dysfunction and implicates glutamate as a driver. Schobel SA, Chaudhury NH, Khan UA, et al. Neuron 78(1), 81-93, (2013)

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Ketamine hydrochloride. A second look. Med. Lett. Drugs Ther. 14(20), 75-6, (1972)

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The use of injectable alphaxalone as a single agent and in combination with ketamine, xylazine, and morphine in the Chilean rose tarantula, Grammostola rosea. Gjeltema J, Posner LP, and Stoskopf M J. Zoo Wildl. Med. 45(4), 792-801, (2014)

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Comparison of xylazine-ketamine and dexmedetomidine-ketamine anesthesia in captive Formosan serows (Capricornis swinhoei). Yu JF, Lien CY, and Wang LC J. Zoo Wildl. Med. 45(4), 787-91, (2014)

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Rave drug tested against depression. Reardon S Nature 517(7533), 130-1, (2015)

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Reasons to be cheerful. Nature 517(7533), 121, (2015)

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Reversal of non-suppression of cortisol levels in a patient with refractory depression receiving ketamine. Ostroff R and Kothari JS Am. J. Psychiatry 172(1), 95-6, (2015)

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[Ketamine alters socially-evoked activity in the amygdala]. Mihara T and Siegel SJ Nippon. Yakurigaku Zasshi. 144(6), 272-6, (2014)

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Biomedical Research. Researchers struggle to gauge risks of childhood anesthesia. Servick K Science 346(6214), 1161-2, (2014)

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The association between ketamine given for prehospital chemical restraint with intubation and hospital admission. Burnett AM, Peterson BK, Stellpflug SJ, et al. Am. J. Emerg. Med. 33(1), 76-9, (2015)

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Acute ketamine impairs mitochondrial function and promotes superoxide dismutase activity in the rat brain. Venâncio C, Félix L, Almeida V, et al. Anesth. Analg. 120(2), 320-8, (2015)

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Pharmacological modulation of spreading depolarizations. Sánchez-Porras R, Zheng Z, and Sakowitz OW Acta Neurochir. Suppl. 120, 153-7, (2015)

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[Instruments for spinal cord stimulation]. Yamamoto T, Fukaya C, and Yoshino A Masui. 63(7), 775-82, (2014)

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[Posttraumatic stress: the "k-hole", minute treatment for forgetting]. Haroche A Soins. Psychiatr. (293), 7, (2014)

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The ketamine effect on intracranial pressure in nontraumatic neurological illness. Zeiler FA, Teitelbaum J, West M, et al. J. Crit. Care 29(6), 1096-106, (2014)

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Dexmedetomidine and ketamine sedation for dental extraction in children with cyanotic heart disease. Hasan MS and Chan L J. Oral Maxillofac. Surg. 72(10), 1920.e1-4, (2014)

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Ketamine as an antidepresessant: a brief research history. Wanderer JP and Rathmell JP Anesthesiology 121(1), A29, (2014)

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A review of the use of ketamine in pain management. Tawfic QA J. Opioid Manag. 9(5), 379-88, (2013)

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In reply: Propofol and additives in studies evaluating inflammatory responses. Bertolizio G and Ingelmo P J. Pediatr. Hematol. Oncol. 37(1), 73-4, (2015)

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[Effect of electroacupuncture intervention at different time-points in a day on expression of c-fos and neuronal nitric oxide synthase in medial prefrontal cortex in ketamine addiction rats]. Wu F, Huang R, and Xiong KR Zhen Ci Yan Jiu 38(5), 386-92, (2013)

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Ketamine for acute-on-chronic pain. Vaid P Can. Nurse 109(8), 20-1, (2013)

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A review of FDA-approved treatment options in bipolar depression. McIntyre RS, Cha DS, Kim RD, et al. CNS Spectr. 18 Suppl 1, 4-20; quiz 21, (2013)

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Treatment of ketamine-associated cystitis with chondroitin sulphate. Smart C, Kabir M, and Pati J Br. J. Nurs. 22(18), S4, S6, S8-9, (2013)

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The promise and perils of ketamine research. Arnold C Lancet Neurol. 12(10), 940-1, (2013)

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[Ketamine for treatment of acute depression]. Hjerrild S, Bjerre J, Pedersen RH, et al. Ugeskr. Laeg. 175(37), 2090-3, (2013)

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[Ketamine for treatment of depression?]. Vinberg M Ugeskr. Laeg. 175(37), 2089, (2013)

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Effects of ketamine on major depressive disorder in a patient with posttraumatic stress disorder. Womble AL AANA J. 81(2), 118-9, (2013)

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Emergency management of dyspnea in dying patients. Shreves A and Pour T Emerg. Med. Pract. 15(5), 1-19; quiz 19-20, (2013)

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Ketamine infusion as a treatment for major depressive disorder: a new role for anesthesiologists? Dilley JD, Gentry WB, and Golden KJ Middle East J. Anesthesiol. 21(6), 871-3, (2012)

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Sedation of children--perspectives across hospital specialties. Sury M SAAD Dig. 29, 60-3, (2013)

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Intravenous ketamine and propofol in paediatric dental sedation: safe and effective? Wood M SAAD Dig. 29, 31-9, (2013)

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The use of intravenous midazolam and ketamine in paediatric dental sedation. Wood M SAAD Dig. 29, 18-30, (2013)

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General anaesthetics do not impair developmental expression of the KCC2 potassium-chloride cotransporter in neonatal rats during the brain growth spurt. Lacoh CM, Bodogan T, Kaila K, et al. Br. J. Anaesth. 110 Suppl 1, i10-8, (2013)

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The [18F]FDG μPET readout of a brain activation model to evaluate the metabotropic glutamate receptor 2 positive allosteric modulator JNJ-42153605. Wyckhuys T, Wyffels L, Langlois X, et al. J. Pharmacol. Exp. Ther. 350(2), 375-86, (2014)

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Antidepressant efficacy of ketamine in treatment-resistant major depression: a two-site randomized controlled trial. Murrough JW, Iosifescu DV, Chang LC, et al. Am. J. Psychiatry 170(10), 1134-42, (2013)

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Synaptic mechanisms underlying rapid antidepressant action of ketamine. Kavalali ET and Monteggia LM Am. J. Psychiatry 169(11), 1150-6, (2012)

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Disruption of frontal-parietal communication by ketamine, propofol, and sevoflurane. Lee U, Ku S, Noh G, et al. Anesthesiology 118(6), 1264-75, (2013)

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(R,S)-Ketamine metabolites (R,S)-norketamine and (2S,6S)-hydroxynorketamine increase the mammalian target of rapamycin function. Paul RK, Singh NS, Khadeer M, et al. Anesthesiology 121(1), 149-59, (2014)

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Topical and peripheral ketamine as an analgesic. Sawynok J Anesth. Analg. 119(1), 170-8, (2014)

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Acute suppression of spontaneous neurotransmission drives synaptic potentiation. Nosyreva E, Szabla K, Autry AE, et al. J. Neurosci. 33(16), 6990-7002, (2013)

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A phase III randomized, placebo-controlled study of topical amitriptyline and ketamine for chemotherapy-induced peripheral neuropathy (CIPN): a University of Rochester CCOP study of 462 cancer survivors. Gewandter JS, Mohile SG, Heckler CE, et al. Support Care Cancer 22(7), 1807-14, (2014)

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Nonhuman primate model of schizophrenia using a noninvasive EEG method. Gil-da-Costa R, Stoner GR, Fung R, et al. Proc. Natl. Acad. Sci. U. S. A. 110(38), 15425-30, (2013)

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Medial septal cholinergic neurons modulate isoflurane anesthesia. Tai SK, Ma J, and Leung LS Anesthesiology 120(2), 392-402, (2014)

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Developmental neurotoxicity of ketamine in pediatric clinical use. Dong C and Anand KJ Toxicol. Lett. 220(1), 53-60, (2013)

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Indistinguishable synaptic pharmacodynamics of the N-methyl-D-aspartate receptor channel blockers memantine and ketamine. Emnett CM, Eisenman LN, Taylor AM, et al. Mol. Pharmacol. 84(6), 935-47, (2013)

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NMR structures of the human α7 nAChR transmembrane domain and associated anesthetic binding sites. Bondarenko V, Mowrey DD, Tillman TS, et al. Biochim. Biophys. Acta 1838(5), 1389-95, (2014)

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Topically applied caffeine induces miosis in the ketamine/xylazine anesthetized rat. Kronschläger M, Yu Z, Talebizadeh N, et al. Exp. Eye Res. 127, 179-83, (2014)

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Club drugs: methylenedioxymethamphetamine, flunitrazepam, ketamine hydrochloride, and gamma-hydroxybutyrate. Smith KM, Larive LL, and Romanelli F Am. J. Health Syst. Pharm. 59(11), 1067-76, (2002)

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Increased apoptosis and suburothelial inflammation in patients with ketamine-related cystitis: a comparison with non-ulcerative interstitial cystitis and controls. Lee CL, Jiang YH, and Kuo HC BJU Int. 112(8), 1156-62, (2013)

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The role of mTOR in depression and antidepressant responses. Abelaira HM, Réus GZ, Neotti MV, et al. Life Sci. 101(1-2), 10-4, (2014)

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Hemodynamic consequences of ketamine vs etomidate for endotracheal intubation in the air medical setting. Price B, Arthur AO, Brunko M, et al. Am. J. Emerg. Med. 31(7), 1124-32, (2013)

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Pharmacological inhibition of p38 mitogen-activated protein kinases affects KC/CXCL1-induced intraluminal crawling, transendothelial migration, and chemotaxis of neutrophils in vivo. Xu N, Hossain M, and Liu L Mediators Inflamm. 2013, 290565, (2013)

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Traditional Chinese medicine diagnoses in persons with ketamine abuse. Tang W, Lam M, Leung W, et al. J. Tradit. Chin. Med. 33(2), 164-9, (2013)

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Propofol with ketamine following sedation with xylazine for routine induction of general anaesthesia in horses. Posner LP, Kasten JI, and Kata C Vet. Rec. 173(22), 550, (2013)

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Effective analgesia with low-dose ketamine and reduced dose hydromorphone in ED patients with severe pain. Ahern TL, Herring AA, Stone MB, et al. Am. J. Emerg. Med. 31(5), 847-51, (2013)

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Evaluation of medetomidine-ketamine and atipamezole for reversible anesthesia of free-ranging gray wolves (Canis lupus). Arnemo JM, Evans AL, Ahlqvist P, et al. J. Wildl. Dis. 49(2), 403-7, (2013)

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Topical amitriptyline combined with ketamine for the treatment of erythromelalgia: a retrospective study of 36 patients at Mayo Clinic. Poterucha TJ, Weiss WT, Warndahl RA, et al. Journal. of. Drugs in. Dermatology. 12(3), 308-10, (2013)

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Effects of isoflurane anesthesia on F-waves in the sciatic nerve of the adult rat. Nowicki M, Baum P, Kosacka J, et al. Muscle Nerve 50(2), 257-61, (2014)

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Cellular registration without behavioral recall of olfactory sensory input under general anesthesia. Samuelsson AR, Brandon NR, Tang P, et al. Anesthesiology 120(4), 890-905, (2014)

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Brief report: perioperative analgesic efficacy and plasma concentrations of S+ -ketamine in continuous epidural infusion during thoracic surgery. Feltracco P, Barbieri S, Rizzi S, et al. Anesth. Analg. 116(6), 1371-5, (2013)

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Ketamine-medetomidine regimen for chemical immobilisation of free-ranging chimpanzees (Pan troglodytes schweinfurthii) in Uganda. Hyeroba D, Apell P, Goldberg T, et al. Vet. Rec. 172(18), 475, (2013)

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Prior determination of baseline minimum alveolar concentration (MAC) of isoflurane does not influence the effect of ketamine on MAC in rabbits. Gianotti G, Valverde A, Sinclair M, et al. Can. J. Vet. Res. 76(4), 261-7, (2012)

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Relationship of ketamine's antidepressant and psychotomimetic effects in unipolar depression. Sos P, Klirova M, Novak T, et al. Neuro Endocrinol. Lett. 34(4), 287-93, (2013)

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Nasal inhalation of butorphanol in combination with ketamine quickly elevates the mechanical pain threshold in the model of chronic constriction injury to the sciatic nerve of rat. Chen F, Wang L, Chen S, et al. J. Surg. Res. 186(1), 292-6, (2014)

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A comparison of anaesthetic recoveries in cats following induction with either alfaxalone or ketamine and diazepam. Gieseg M, Hon H, Bridges J, et al. N. Z. Vet. J. 62(3), 103-9, (2014)

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Use of xylazine hydrochloride-ketamine hydrochloride for immobilization of Indian fox (Vulpes bengalensis) in field situations. Belsare AV and Vanak AT J. Zoo Wildl. Med. 44(3), 753-5, (2013)

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Comparison of two injectable immobilization combinations in Himalayan tahr (Hemitragus jemlahicus): medetomidine, ketamine, and atipamezole versus carfentanil, xylazine, naltrexone, and atipamezole. Rainwater KL, Valitutto MT, Kalk P, et al. J. Zoo Wildl. Med. 44(3), 596-604, (2013)

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Renal infarction secondary to ketamine abuse. Chen JL, Cha TL, Wu ST, et al. Am. J. Emerg. Med. 31(7), 1153.e3-5, (2013)

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Blockade of the human ether-a-go-go-related gene potassium channel by ketamine. Zhang P, Xing J, Luo A, et al. J. Pharm. Pharmacol. 65(9), 1321-8, (2013)

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Physiologic and serum biochemistry values in free-ranging Hoffmann's two-toed (Choloepus hoffmanni) and brown-throated three-toed (Bradypus variegatus) sloths immobilized using dexmedetomidine and ketamine. Kinney ME, Cole GA, Vaughan C, et al. J. Zoo Wildl. Med. 44(3), 570-80, (2013)

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Should ketamine be used as an induction agent in traumatic brain injury? McDermott P and Sebastian J Br. J. Hosp. Med. (Lond.) 74(9), 538, (2013)

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Ketamine is toxic to chondrocyte cell cultures. Ozturk AM, Ergun MA, Demir T, et al. Bone Joint J. 96-B(7), 989-94, (2014)

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Electroconvulsive therapy is a standard treatment; ketamine is not (yet). Kellner CH, Greenberg RM, Ahle GM, et al. Am. J. Psychiatry 171(7), 796, (2014)

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Ketamine metabolomics in the treatment of major depression. van Velzen M and Dahan A Anesthesiology 121(1), 4-5, (2014)

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Treatment of epidermolysis bullosa pruriginosa using systemic and topical agents. Mangold AR, Cole CM, DiCaudo DJ, et al. J. Am. Acad. Dermatol. 70(6), e136-7, (2014)

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Current drug development for antidepressants and ideas addressing downstream glutamate: the ketamine example. Potter WZ and Brady LS CNS Spectr. 19(2), 112-4, (2014)

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Trial watch: phase II boost for glutamate-targeted antidepressants. Flight MH Nat. Rev. Drug Discov. 12(12), 897, (2013)

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Re: The prevalence and natural history of urinary symptoms among recreational ketamine users. Wein AJ J. Urol. 190(5), 1816, (2013)

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Mechanism of action of dextromethorphan/quinidine:comparison with ketamine. Stahl SM CNS Spectr. 18(5), 225-7, (2013)

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Ketamine for treatment-resistant depression: ready or not for clinical use? Rush AJ Am. J. Psychiatry 170(10), 1079-81, (2013)

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Going beyond anesthesia in space exploration missions: emergency medicine and emergency medical care. Hinkelbein J and Spelten O Aviat. Space. Environ. Med. 84(7), 747, (2013)

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Current status of ketamine and related compounds for depression. Mathews DC and Zarate CA J. Clin. Psychiatry 74(5), 516-7, (2013)

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The study of consciousness comes of age. Sleigh JW Anesthesiology 118(6), 1245-6, (2013)

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Reply to K. Jackson et al and W. Leppert. Hardy J, Quinn S, Fazekas B, et al. J. Clin. Oncol. 31(10), 1375-6, (2013)

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In response. Grady MV, Mascha E, Sessler DI, et al. Anesth. Analg. 116(4), 950-1, (2013)

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Merck 14,5295

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