- 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. #Ketamine
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 #11, 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., John Wiley & Sons, Inc., 1 Jan 1981; pp 1109–1137. 4.7 MB. #49
Shulgin, AT. Psychotomimetic agents. In Psychopharmacological Agents; Gordon, M, Ed., Academic Press, New York, 1 Jan 1976; 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), 246-251. 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 Nov 2018, 142, 143-166. 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 (2018). 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, 73 (2), 323-345. 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,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. Br. J. Anaesth., 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. Int. J. Mol. Sci., 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
Halberstadt, AL. Recent advances in the neuropsychopharmacology of serotonergic hallucinogens. Behav. Brain Res., 15 Jan 2015, 277, 99–120. 4.1 MB. https://doi.org/10.1016/j.bbr.2014.07.016 #Ketamine
Irie, T; Yanase, Y; Demizu, Y; Usami, M; Kikura-Hanajiri, R. Derivatives of methoxetamine and major methoxetamine metabolites potently block NMDA receptors. J. Pharmacol. Sci., 1 Dec 2022, 150 (4), 233–243. 2.9 MB. https://doi.org/10.1016/j.jphs.2022.09.005 #Ketamine
Krupitsky, EM; Burakov, AM; Romanov, TN; Grinenko, AY; Strassman, RJ. Ketamine-assisted psychotherapy (KPT) of heroin addiction: Immediate effects and six month follow-up. Heffter Rev., , 2, 88–101. 277 kB. #Ketamine
Ortiz, DMD; Kim, M; Lee, HJ; Botanas, CJ; Custodio, RJP; Sayson, LV; Campomayor, NB; Lee, C; Lee, YS; Cheong, JH; Kim, HJ. 4-F-PCP, a novel PCP analog ameliorates the depressive-like behavior of chronic social defeat stress mice via NMDA receptor antagonism. Biomol. Ther., 1 Mar 2023, 31 (2), 227–239. 5.7 MB. https://doi.org/10.4062/biomolther.2022.159 #Ketamine
Makino, Y; Kurobane, S; Miyasaka, K. Profiling of ecstasy tablets seized in Japan. Microgram J., 1 Jul 2003, 1 (3–4), 169–176. 614 kB.
Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB. MS
Sarwar, M. A new, highly specific color test for ketamine. Microgram J., 1 Jan 2006, 4 (1–4), 24–28. 93 kB. #Ketamine spot