- Ketamine
- Arketamine (R-enantiomer)
- CI-581
- Esketamine (S-enantiomer)
Wallach, J; Kang, H; Colestock, T; Morris, H; Bortolotto, ZA; Collingridge, GL; Lodge, D; Halberstadt, AL; Brandt, SD; Adejare, A. Pharmacological investigations of the dissociative “Legal Highs” diphenidine, methoxphenidine and analogues. PLOS ONE, 17 Jun 2016, 11 (6), e0157021. 8.9 MB. https://doi.org/10.1371/journal.pone.0157021 #Ketamine GC,MS,NMR
Wallach, J; Kavanagh, PV; McLaughlin, G; Morris, N; Power, JD; Elliott, SP; Mercier, MS; Lodge, D; Morris, H; Dempster, NM; Brandt, SD. Preparation and characterization of the ‘research chemical’ diphenidine, its pyrrolidine analogue, and their 2,2-diphenylethyl isomers. Drug Test. Anal., 1 May 2015, 7 (5), 358-367. 632 kB. https://doi.org/10.1002/dta.1689
EMCDDA. Report on the risk assessment of ketamine, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, . 1.3 MB.
Morris, H; Wallach, J. From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 614-632. 942 kB. https://doi.org/10.1002/dta.1620 #Ketamine
Fenderson5555. Reactions in the synthesis of ketamine. , 1 Oct 2014. . Fenderson5555 1.4 MB. #Ketamine
Colestock, T; Wallach, J; Mansi, M; Filemban, N; Morris, H; Elliott, SP; Westphal, F; Brandt, SD; Adejare, A. Syntheses, analytical and pharmacological characterizations of the ‘legal high’ 4-[1-(3-methoxyphenyl)cyclohexyl]morpholine (3-MeO-PCMo) and analogues. Drug Test. Anal., 1 Feb 2018, 10 (2), 272-283. 1.3 MB. https://doi.org/10.1002/dta.2213
Shulgin, AT; MacLean, DE. Illicit synthesis of phencyclidine (PCP) and several of its analogs. Clin. Toxicol., 1 Jan 1976, 9 (4), 553–560. 352 kB. https://doi.org/10.3109/15563657608988157 #Ketamine Rhodium.
Sleigh, J; Harvey, M; Voss, L; Denny, B. Ketamine – More mechanisms of action than just NMDA blockade. Curr. Anaesth. Crit. Care, 1 Jun 2014, 4 (2–3), 76–81. 531 kB. https://doi.org/10.1016/j.tacc.2014.03.002
Morris, H; Wallach, J. Arylcyclohexylamines. Psymposium 2014, 27 Oct 2015. 39:47. Psymposia Big hug to W. Snow for providing the video. Unfortunately I just cannot seem to make it work. It may be a bug in my code. For now, the link points to YouTube.
EMCDDA. New drugs in Europe, 2011, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Apr 2012. 401 kB.
Roth, BL; Gibbons, S; Arunotayanun, W; Huang, X; Setola, V; Treble, R; Iversen, L. The ketamine analogue methoxetamine and 3- and 4-methoxy analogues of phencyclidine are high affinity and selective ligands for the glutamate NMDA receptor. PLoS ONE, 19 Mar 2013, 8 (3), e59334. 453 kB. https://doi.org/10.1371/journal.pone.0059334 #Ketamine
Hermle, L; Kraehenmann, R. Experimental psychosis research and schizophrenia—Similarities and dissimilarities in psychopathology. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 313-332. 446 kB. https://doi.org/10.1007/7854_2016_460
Lladó-Pelfort, L; Celada, P; Riga, MS; Troyano-Rodríguez,, E. Effect of hallucinogens on neuronal activity. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 75-105. 902 kB. https://doi.org/10.1007/7854_2017_473
Halpern, JH; Lerner, AG; Passie, T. A review of hallucinogen persisting perception disorder (HPPD) and an exploratory study of subjects claiming symptoms of HPPD. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 333-360. 579 kB. https://doi.org/10.1007/7854_2016_457
Montenarh, D; Hopf, M; Warth, S; Maurer, HH; Schmidt, P; Ewald, AH. A simple extraction and LC-MS/MS approach for the screening and identification of over 100 analytes in eight different matrices: Detection of 130 analytes in eight biosamples using only one LC-MS/MS method. Drug Test. Anal., 1 Mar 2015, 7 (3), 214-240. 593 kB. https://doi.org/10.1002/dta.1657
Wallach, JV. Structure activity relationship (SAR) studies of arylcycloalkylamines as N-methyl-D-aspartate receptor antagonists. Ph. D. Thesis, 19 Dec 2014. #2
Burns, L; Roxburgh, A; Bruno, R; Van Buskirk, J. Monitoring drug markets in the Internet age and the evolution of drug monitoring systems in Australia. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 840-845. 113 kB. https://doi.org/10.1002/dta.1613
Vidal Giné, C; Espinosa, IF; Vilamala, MV. New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon? Drug Test. Anal., 1 Jul 2014, 6 (7-8), 819-824. 113 kB. https://doi.org/10.1002/dta.1610
Wilkins, C; Sweetsur, P. The impact of the prohibition of benzylpiperazine (BZP) ‘legal highs’ on the prevalence of BZP, new legal highs and other drug use in New Zealand. Drug Alcohol Depend., 1 Jan 2013, 127 (1-3), 72-80. 521 kB. https://doi.org/10.1016/j.drugalcdep.2012.06.014
Shulgin, AT. Chemistry of psychotomimetics. In Handbook of Experimental Pharmacology. Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs; Hoffmeister, F; Stille, G, Eds., Springer-Verlag, Berlin, 1 Jan 1982; Vol. 55 (3), pp 3–29. 928 kB. https://doi.org/10.1007/978-3-642-67770-0_1 #17
Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., Wiley & Co., ; pp 1109–1137. 4.7 MB. #49
Shulgin, AT. Psychotomimetic agents. In Psychopharmacological Agents; Gordon, M, Ed., Academic Press, New York, ; Vol. 4, pp 59–146. 3.1 MB. #CV
Ahmadi, A; Khalili, M; Hajikhani, R; Hosseini, H; Afshin, N; Nahri-Niknafs, B. Synthesis and study the analgesic effects of new analogues of ketamine on female Wistar rats. Med. Chem., 29 Feb 2012, 8 (2), n/a. 132 kB. https://doi.org/10.2174/157340612800493683 #I
Ahmadi, A; Khalili, M; Mihandoust, F; Barghi, L. Synthesis and determination of acute and chronic pain activities of 1-[1-(3-methylphenyl) (tetralyl)]piperidine as a new derivative of phencyclidine via tail immersion and formalin tests. Arzneim. Forsch., 1 Jan 2010, 60 (01), 30–35. 251 kB. https://doi.org/10.1055/s-0031-1296245 #II
Wallach, J; Brandt, SD. Phencyclidine-based new psychoactive substances. In New Psychoactive Substances : Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 261-303. 515 kB. https://doi.org/10.1007/164_2018_124 #Ketamine
Zanos, P; Moaddel, R; Morris, PJ; Georgiou, P; Fischell, J; Elmer, GI; Gould, TD. NMDAR inhibition-independent antidepressant actions of ketamine metabolites. Nature, 1 May 2016, 533 (7604), 481–486. 6.4 MB. https://doi.org/10.1038/nature17998 #KET LC,MS,NMR,other
Wallach, J; Brandt, SD. 1,2-Diarylethylamine- and ketamine-based new psychoactive substances. In New Psychoactive Substances : Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 305-352. 593 kB. https://doi.org/10.1007/164_2018_148 #Ketamine
Johnson, MW; Griffiths, RR; Hendricks, PS; Henningfield, JE. The abuse potential of medical psilocybin according to the 8 factors of the Controlled Substances Act. Neuropharmacology, 1 Jun 2018, n/a. 2.5 MB. https://doi.org/10.1016/j.neuropharm.2018.05.012 #Ketamine
Baumeister, D; Barnes, G; Giaroli, G; Tracy, D. Classical hallucinogens as antidepressants? A review of pharmacodynamics and putative clinical roles. Ther. Adv. Psychopharmacol., 1 Aug 2014, 4 (4), 156–169. 1.1 MB. https://doi.org/10.1177/2045125314527985 #Ketamine
Chambers, SA; DeSousa, JM; Huseman, ED; Townsend, SD. The DARK side of total synthesis: Strategies and tactics in psychoactive drug production. ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2307–2330. 8.1 MB. https://doi.org/10.1021/acschemneuro.7b00528 #165
Tyler, MW; Yourish, HB; Ionescu, DF; Haggarty, SJ. Classics in Chemical Neuroscience: Ketamine. ACS Chem. Neurosci., 21 Jun 2017, 8 (6), 1122–1134. 1.3 MB. https://doi.org/10.1021/acschemneuro.7b00074 #1
Passie, T; Brandt, SD. Self-experiments with psychoactive substances: A historical perspective. In New Psychoactive Substances : Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 69-110. 563 kB. https://doi.org/10.1007/164_2018_177 #Ketamine
Jose, J; Gamage, SA; Harvey, MG; Voss, LJ; Sleigh, JW; Denny, WA. Structure–activity relationships for ketamine esters as short-acting anaesthetics. Bioorg. Med. Chem., 1 Sep 2013, 21 (17), 5098–5106. 701 kB. https://doi.org/10.1016/j.bmc.2013.06.047 #1 MS,NMR
Dimitrov, I; Denny, W; Jose, J. Syntheses of ketamine and related analogues: A mini review. Synthesis, 1 Nov 2018, 50 (21), 4201–4215. 793 kB. https://doi.org/10.1055/s-0037-1609935 #Ketamine
Bertron, JL; Seto, M; Lindsley, CW. DARK classics in chemical neuroscience: Phencyclidine (PCP). ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2459-2474. 9.9 MB. https://doi.org/10.1021/acschemneuro.8b00266 #7
Linders, J; Furlano, D; Mattson, M; Jacobson, A; Rice, K. Synthesis and preliminary biochemical evaluation of novel derivatives of PCP. Lett. Drug Des. Discov., 1 Feb 2010, 7 (2), 79–87. 1.3 MB. https://doi.org/10.2174/157018010790225813 #3 MS,NMR,other
Berger, ML; Schweifer, A; Rebernik, P; Hammerschmidt, F. NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds. Bioorg. Med. Chem., 1 May 2009, 17 (9), 3456–3462. 340 kB. https://doi.org/10.1016/j.bmc.2009.03.025 #1b NMR,IR,other
Olson, DE. Psychoplastogens: A promising class of plasticity-promoting neurotherapeutics. J. Exp. Neurosci., 1 Jan 2018, 12 117906951880050. 204 kB. https://doi.org/10.1177/1179069518800508 #Ketamine
Hägele, JS; Basrak, M; Schmid, MG. Enantioselective separation of novel psychoactive substances using a Lux® AMP 3 μm column and HPLC-UV. J. Pharm. Biomed. Anal., 5 Feb 2020, 179 112967. 3.6 MB. https://doi.org/10.1016/j.jpba.2019.112967 #E1 LC
Sherwood, AM; Claveau, R; Lancelotta, R; Kaylo, KW; Lenoch, K. Synthesis and characterization of 5-MeO-DMT succinate for clinical use. ACS Omega, 15 Dec 2020, 5 (49), 32067–32075. 3.2 MB. https://doi.org/10.1021/acsomega.0c05099 #5 MS,NMR
Kohtala, S. Ketamine—50 years in use: from anesthesia to rapid antidepressant effects and neurobiological mechanisms. Pharmacol. Rep, 20 Feb 2021, n/a. 9.1 MB. https://doi.org/10.1007/s43440-021-00232-4 #Ketamine
Takahashi, M; Suzuki, J; Nagashima, M; Seto, T; Yasuda, I. Analysis of anesthetics in uncontrolled drugs. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 65–68. 975 kB. #KET GC,LC,MS,NMR,IR,UV,TLC,other
Antonides, LH; Brignall, RM; Costello, A; Ellison, J; Firth, SE; Gilbert, N; Groom, BJ; Hudson, SJ; Hulme, MC; Marron, J; Pullen, ZA; Robertson, TBR; Schofield, CJ; Williamson, DC; Kemsley, EK; Sutcliffe, OB; Mewis, RE. Rapid identification of novel psychoactive and other controlled substances using low-field 1H NMR spectroscopy. ACS Omega, 30 Apr 2019, 4 (4), 7103–7112. 1.3 MB. https://doi.org/10.1021/acsomega.9b00302 #Ketamine NMR
Frison, G; Zamengo, L; Zancanaro, F; Tisato, F; Traldi, P. Characterization of the designer drug deschloroketamine (2-methylamino-2-phenylcyclohexanone) by gas chromatography/mass spectrometry, liquid chromatography/high-resolution mass spectrometry, multistage mass spectrometry, and nuclear magnetic resonance. Rapid Commun. Mass Spectrom., 15 Jan 2016, 30 (1), 151–160. 1.7 MB. https://doi.org/10.1002/rcm.7425 #Ketamine MS,NMR,other
Urban, BW; Bleckwenn, M. Concepts and correlations relevant to general anaesthesia. British Journal of Anaesthesia, 1 Jul 2002, 89 (1), 3–16. 684 kB. https://doi.org/10.1093/bja/aef164 #Ketamine
Angenoorth, TJF; Stankovic, S; Niello, M; Holy, M; Brandt, SD; Sitte, HH; Maier, J. Interaction profiles of central nervous system active drugs at human organic cation transporters 1–3 and human plasma membrane monoamine transporter. IJMS, 30 Nov 2021, 22 (23), 12995. 5.1 MB. https://doi.org/10.3390/ijms222312995 #Ketamine
Philp, M; Shimmon, R; Stojanovska, N; Tahtouh, M; Fu, S. Development and validation of a presumptive colour spot test method for the detection of piperazine analogues in seized illicit materials. Anal. Methods, 1 Jan 2013, 5 (20), 5402. 783 kB. https://doi.org/10.1039/c3ay40511g #Ketamine MS,NMR,IR,spot