DARK Classics in Chemical Neuroscience: Etonitazene and Related Benzimidazoles

Gulland J. M., 1925, Mem. Proc. Manchester Lit. Philos. Soc., 69, 79

10.1021/ja01124a538

10.1002/prac.19160940112

10.1055/s-0028-1120563

10.1002/jlac.19495610107

10.1111/j.1399-6576.1982.tb01765.x

10.1007/BF02161116

10.1007/BF02161117

10.1002/hlca.19600430323

10.1002/hlca.19600430412

10.1002/hlca.19600430634

10.1007/164_2018_160

European Monitoring Centre for Drugs and Drug Addiction, 2020, European Drug Report 2020: Trends and Developments

European Monitoring Centre for Drugs and Drug Addiction. European Database on New Drugs. https://ednd2.emcdda.europa.eu/ednd (accessed Feb 24, 2021).

United Nations Office on Drugs and Crime, 2021, World Drug Report 2020

United Nations Office on Drugs and Crime. growing complexity of the opioid crisis. Global SMART Update Vol. 24, UNODC, Vienna, 2020. https://www.unodc.org/documents/scientific/Global_SMART-2020-Vol_24_web.pdf (accessed Feb 24, 2021).

10.1021/acschemneuro.8b00150

10.1021/acschemneuro.8b00459

10.1021/acschemneuro.8b00546

10.1021/acschemneuro.0c00495

10.1021/acschemneuro.0c00262

10.1021/acschemneuro.8b00174

10.1021/acschemneuro.0c00441

10.1021/acschemneuro.0c00330

10.1021/jm00237a024

Grimmett M. R., 2002, Hetarenes and Related Ring Systems. Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms, Science of Synthesis, 12, 529

10.1111/j.2042-7158.1966.tb07782.x

StarDrop, version 6.6 software, Optibrium Ltd., Cambridge, U.K.

Molinspiration property engine version 2018.10. https://www.molinspiration.com/cgi-bin/properties (accessed Feb 24, 2021).

Hansch, C., Leo, A., and Hoekman, D. Exploring QSAR. Hydrophobic, electronic, and steric constants; American Chemical Society: Washington, DC, 1995; p 178.

10.1021/cn200100h

Grimmett M. R., 1997, Imidazole and Benzimidazole Synthesis

10.1080/00397911.2020.1841239

10.1002/cber.18720050295

10.1002/cber.187500801209

Hoffmann, K., Hunger, A., Kebrle, J., and Rossi, A. (1959) Verfahren zur Herstellung analgetisch wirksamer Benzimidazole. Bundesrepublik Deutschland Patentschrift DBP 1057123.

Hoffmann, K., Hunger, A., Kebrle, J., and Rossi, A. (1960) Benzimidazoles. U.S. Patent US2935514.

10.1002/jhet.5570040217

Sparatore F., 1968, Farmaco, Ed. Sci., 23, 344

Bucha M., 2018, Indian J. Heterocycl. Chem., 28, 321

10.1016/S0040-4039(97)01136-2

Hoffmann, K., Hunger, A., Kebrle, J., and Rossi, A. (1962) Verfahren zur Herstellung neuer Benzimidazole. Swiss Patent CH362080.

10.1093/jat/bkaa016

10.1055/s-2004-834926

Hoffmann, K., Hunger, A., Kebrle, J., and Rossi, A. (1961) Certain 1H[4,5-c]-imidazopyridines. U.S. Patent US2987518.

European Monitoring Centre for Drugs and Drug Addiction, 2020, Risk assessment report on the new psychoactive substance N,N-diethyl-2-[[4-(1-methylethoxy)phenyl]methyl]-5-nitro-1H-benzimidazole-1-ethanamine (isotonitazene) in accordance with Article 5c of Regulation (EC) No. 1920/2006 (as amended)

DrugsData.org. Test Details: Results #8739: Heroin 8739. 2020. https://drugsdata.org/view.php?id=8739 (accessed Feb 24, 2021).

World Health Organization. Critical Review Report: ISOTONITAZENE, 2020. https://www.who.int/docs/default-source/controlled-substances/43rd-ecdd/isonitazene-43rd-final-complete-a.pdf (accessed Feb 24, 2021).

Centre Sida Amitié. Alerte surdose. 2020. https://twitter.com/Sidaamitie/status/1221966482147610624 (accessed Mar 9, 2021).

Gonthier, V. Une toute nouvelle drogue inquiete les autorites. Le Journal du Quebec. 1 Février, 2020. https://journaldequebec.com/2020/02/01/une-toute-nouvelle-drogue-inquiete-les-autorites (accessed Feb 24, 2021).

Drug Enforcement Administration, U.S. Department of Justice. Schedules of Controlled Substances: Temporary Placement of Isotonitazene in Schedule I. 2020. https://www.regulations.gov/document/DEA-2020-0017-0003 (accessed Mar 8, 2021).

10.1007/s11419-020-00552-9

United Nations International Narcotic Control Board, 2019, Narcotic Drugs: Estimated World Requirements for 2019; Statistics for 2017, 10.18356/ba5179d3-en-fr-es

Sorokin V. I., 1999, J. Clandestine Lab. Invest. Chem. Assoc., 9, 20

10.1097/00000542-199505000-00018

Brittain R. T., 1973, Br. J. Pharmacol., 49, 158P

10.1111/j.1476-5381.1980.tb07041.x

10.1016/j.phrs.2010.02.011

Jacobson A. E., 1992, Problems of Drug Dependence, 1991, NIDA Research Monograph Series 119, 490

Aceto M. D., 1994, Problems of Drug Dependence, 1993, NIDA Research Monograph Series 140, 103

10.1007/BF01486702

Deneau, G. A., McCarthy, D. A., and Seevers, M. H. (1959) Addendum 1. Physical dependence liability studies in the monkey. Presented at the 20th Meeting, Washington, D.C., January 10–11, 1959, pp 1–13, Committee on Drug Addiction and Narcotics, National Academy of Sciences, National Research Council.

Aceto M. D., 1992, Problems of Drug Dependence, 1991, NIDA Research Monograph Series 119, 513

10.1007/BF00426626

10.1007/s00213-009-1480-0

Anonymous. Addictiveness of two benzimidazole derivatives. Preliminary report. US CIA MK Ultra, 1959. http://archive.org/details/DOC_0000151874 (accessed Feb 24, 2021).

Eddy N. B., 1959, Chem. Ind., 47, 1462

Fraser H. F., 1960, Minutes of the Twenty-First Meeting, 11–12 January, 1960, Committee on Drug Addiction and Narcotics, 35

Wikler A., 1960, Annual Progress Report

10.1007/s002130000620

10.1111/j.1476-5381.2011.01335.x

1961, World Health Organization Technical Report Series No. 211, 1

Federal Register 7351 Proclamation 3362. Determining certain drugs to be opiates. (Aug 5, 1960) https://www.loc.gov/item/fr025152 (accessed Feb 24, 2021).

10.1007/BF02142268

Butelman E. R., 1993, J. Pharmacol. Exp. Ther., 264, 145

10.1007/BF00348594

10.1111/j.1476-5381.1975.tb07373.x

10.1073/pnas.70.8.2243

10.1002/dta.2738

10.1016/0014-2999(75)90197-1

10.3109/15563650.2016.1157722

10.1016/0091-3057(77)90154-X

10.1016/0091-3057(82)90350-1

10.1146/annurev-med-062613-093100

10.1016/j.biopsych.2019.08.028

10.1016/j.biopsych.2019.10.020

10.3390/molecules25184257

10.3390/molecules25173870

10.1124/mol.119.119214

10.1126/science.367.6481.966

10.1016/0014-2999(83)90331-X

10.1002/syn.890210109

10.1016/0024-3205(93)90118-m

Emmerson P. J., 1994, J. Pharmacol. Exp. Ther., 271, 1630

10.1016/0024-3205(95)02204-V

Toll L., 1998, NIDA Research Monograph Series 178, 440

10.1021/acschemneuro.1c00064

10.1124/mol.112.082875

10.1016/j.tins.2020.03.011

10.1016/j.febslet.2015.07.025

10.1007/s002130050486

10.1002/jlcr.2580210802

10.1021/jm00378a008

Rothman R. B., 1985, Mol. Pharmacol., 27, 399

10.1016/0014-2999(87)90742-4

10.1002/cne.902550403

10.1016/0028-3908(88)90125-6

10.1016/S0196-9781(98)00046-1

10.1124/dmd.30.12.1364

10.31788/RJC.2018.1144087

Lecolier S., 1967, Chim. Ther., 2, 16

10.1002/hlca.19610440513

10.1248/yakushi1947.85.11_962

10.1248/yakushi1947.87.3_301

10.1248/yakushi1947.89.5_617

10.3181/00379727-116-29406

10.3906/kim-1612-76

10.2174/1570180815666181004103112

10.36468/pharmaceutical-sciences.642

10.1021/jm00310a045

10.1021/jm00317a016

Lénárd K., 1962, Acta Chim. Acad. Sci. Hung., 34, 439

10.1002/jps.2600551022

10.1021/ml200268w

10.1016/j.bmcl.2008.05.073

10.1039/C8MD00461G

10.1021/acs.jmedchem.7b01760

10.1016/j.cell.2018.11.040

10.1124/jpet.115.225326

10.1021/jm901672k

Janssen, P. A. J. (1965) Benzimidazolinyl piperidines. U.S. Patent US3196157.

Janssen Pharmaceutica. (1965) Derivaten van piperidyl-benzimidazolinone. Belgian Patent BE663433.

Janssen P. A. J., 1971, Arzneim.-Forsch., 21, 862

Janssen P. A. J., 1968, Drugs Affecting the Central Nervous System, 2, 25

10.1021/jm990517p

Li Q., 1984, Acta Pharm. Sin., 19, 124

10.1016/j.cell.2017.10.035

10.1021/acs.jmedchem.8b01136

10.1007/s00204-020-02855-7

National Forensic Laboratory Information System. New drug reports in NFLIS-Drug. December 2019 Snapsot. 2020. https://www.nflis.deadiversion.usdoj.gov/DeskTopModules/ReportDownloads/Reports/NFLIS_Snapshot_122019.pdf (accessed Feb 24, 2021).

Department of Justice., 2021, Fed. Regist., 86, 11862

10.1093/jat/bkaa094

European Monitoring Centre for Drugs and Drug Addiction. (January 22, 2021) EU Early Warning System Advisory. Fake oxycodone tablets containing brorphine—Slovenia, 2021. ID: EU-EWS-RCS-AD-2021-0001, EMCDDA.

10.1021/ja01176a532

Holliday E. R., 1949, J. Pharm. Pharmacol., 1, 734

10.1007/978-3-7091-7162-2_4

10.1007/s00044-015-1495-5

10.1016/j.ejmech.2016.12.010

10.2174/1389557519666191122125453

10.1002/prac.18990590117

Ramsh S. M., 2011, Stud. Hist. Biol., 3, 36

European Medicines Agency, Committee on Herbal Medicinal Products. Adaptogenic concept. 2008. https://www.ema.europa.eu/en/adaptogenic-concept (accessed Feb 24, 2021).

Bendazol. https://www.rlsnet.ru/mnn_index_id_42.htm (accessed Mar 13, 2021).

Feitelson B. N., 1958, J. Chem. Soc., 2426

United Nations. Single Convention on Narcotic Drugs, 1961, as amended by the Protocol amending the Single Convention on Narcotic Drugs, 1961. 1975. https://treaties.un.org/Pages/ViewDetails.aspx?src=TREATY&mtdsg_no=VI-18&chapter=6&clang=_en (accessed Feb 24, 2021).

The Hive. Etonitazene analogs? 2020. https://the-hive.archive.erowid.org/forum/showflat.pl?/Cat=&Number-376117 (accessed Dec 15, 2020).

Brandenberger H., 1974, Dtsch. Lebensmitt. Rundsch., 70, 31

Anonymous., 1987, BKA - Wöchentlicher Lagebericht, 87, 9

Sorokin V. I., 1999, Microgram, 32, 239

Anonymous., 2003, Microgram Bull., 36, 275

Reavy, P. Utah case of potent drug is U.S. first. Deseret News, Jun 3, 2003. https://www.deseretnews.com/2003/6/3/19726293/utah-case-of-potent-drug-is-u-s-first (accessed Mar 13, 2021).

Morris, H. Synthetic opioids: the most addictive drug in the world. Hamilton’s Pharmacopeia, 2009. https://www.vice.com/en_us/article/9bdymy/hamiltons-pharmacopeia-804-v16n4 (accessed Feb 24, 2021).

10.2166/wst.2002.0063

10.1016/j.atmosenv.2004.07.027

10.1002/jssc.201601313

10.1016/j.forsciint.2021.110686

10.1097/ADM.0000000000000775

Power, M. 40 Americans are dying every month from taking this new, legal opioid. 2020. https://www.vice.com/en/article/wxebjb/40-americans-are-dying-every-month-from-taking-this-new-legal-opioid (accessed Mar 13, 2021).

Logan, B. K., Krotulski, A. J., Papsun, D. M., and Kacinko, S. L. Isotonitazene: a novel benzimidazole μ-opioid agonist as the latest novel opioid. https://www.npsdiscovery.org/wp-content/uploads/2020/10/Logan_Isotonitazene-Presentation_SOFT-2020.pdf (accessed Feb 24, 2021).

Center for Forensic Science Research and Education. https://www.npsdiscovery.org/reports (accessed Mar 13, 2021).

Commission Delegate Directive (EU) 2020/1687. https://eur-lex.europa.eu/eli/dir_del/2020/1687/oj (accessed Feb 24, 2021).

DrugsData.org. Test Details: Results #9782. Feb 08 2021. https://drugsdata.org/view.php?id=9782 (accessed Mar 13, 2021).

Cayman Chemical. Product Information: Protonitazene. https://www.caymanchem.com/product/29381 (accessed Feb 24, 2021).

deStevens G., 1965, Analgetics, 405

10.1371/journal.pone.0197734

10.1021/jp202542g

Casy, A. F., and Parfitt, R. T. (1986) Opioid Analgesics: Chemistry and Receptors, pp 445–502, Plenum Press, New York.

10.3987/COM-94-S(B)70

10.1021/acsomega.9b02244

10.1124/mol.119.119339

Archer S., 1965, Progr. Drug Res., 8, 261