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⫸STICKY⫷ Useful neuroscience/pharmacology threads

ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Heterocyclic Communications vol. 4 iss. 2
3-CARBOMETHOXY FENTANYL: SYNTHESIS, PHARMACOLOGY AND CONFORMATIONAL ANALYSIS
DOI: 10.1515/HC.1998.4.2.171 a a
Μίćονίć, I.V.; Ivanovic, M. D.; Vućković, S.; Jovanović-Mićić, D.; Beleslin, D.; Dośen-Mićović, Lj.; Kiricojević, V. D.1998 JanuaryEnglish
PLoS ONE vol. 9 iss. 9 pp.e108250
An Efficient, Optimized Synthesis of Fentanyl and Related Analogs
DOI: 10.1371/journal.pone.0108250 a a
Valdez, Carlos A. ;Leif, Roald N. ;Mayer, Brian P. ;Lahmann, Martina (editor)Public Library of Science (PLoS)2014 September 18English
Journal of the Serbian Chemical Society vol. 69 iss. 11 pp.955—968
The synthesis and pharmacological evaluation of (±)-2, 3- seco-fentanyl analogues
DOI: 10.2298/jsc0411955i a a
Ivanovic, Milovan ;Micovic, I.V. ;Vuckovic, Sonja ;Prostran, Milica ;Todorovic, Zoran ;Ivanovic, Evica ;[...]National Library of Serbia2004English
Journal of Synthetic Organic Chemistry Japan vol. 78 iss. 9 pp.875—885
Synthesis of Drug Vaccine against Heroin Contaminated with Fentanyl and Their Biological Evaluation
DOI: 10.5059/yukigoseikyokaishi.78.875 a a
Natori, Yoshihiro ;Janda, Kim D.The Society of Synthetic Organic Chemistry, Japan2020 9月 01Japanese
ChemInform vol. 28 iss. 10 pp.no—no
ChemInform Abstract: The Synthesis of Lactam Analogues of Fentanyl (XVII).
DOI: 10.1002/chin.199710120 a a
I. V. MICOVIC; G. M. ROGLIC; M. D. IVANOVIC; L. DOSEN-MICOVIC; V. D. KIRICOJEVIC; J. B. POPOVIC2010 August 04
ChemInform vol. 31 iss. 47 pp.no—no
ChemInform Abstract: The Synthesis and Preliminary Pharmacological Evaluation of 4-Methyl Fentanyl.
DOI: 10.1002/chin.200047139 a a
Ivan V. Micovic; Milovan D. Ivanovic; Sonja M. Vuckovic; Milica S. Prostran; Ljiljana Dosen-Micovic; Vesna D. Kiricojevic2000 November 21
ChemInform vol. 33 iss. 20 pp.no—no
ChemInform Abstract: Long-Acting Fentanyl Analogues: Synthesis and Pharmacology of N-(1-Phenylpyrazolyl)-N-(1-phenylalkyl-4-piperidyl)propanamides.
DOI: 10.1002/chin.200220109 a a
Pilar Goya; et al. et al.2010 May 21
ChemInform vol. 36 iss. 49 pp.0—0
A Convenient One-Pot Synthesis of Fentanyl.
DOI: 10.1002/chin.200549130 a a
Pradeep Kumar Gupta; Kumaran Ganesan; Ambuja Pande; Ramesh Chandra Malhotra2005 December 06
Journal of Labelled Compounds vol. 23 iss. 3 pp.277—293
Synthesis and evaluation of fluorinated derivatives of fentanyl as candidates for opiate receptor studies using positron emission tomograpry
DOI: 10.1002/jlcr.2580230306 a a
Dah-Ren Hwang; Anthony L. Feliu; Alfred P. Wolf; Robert R. Macgregor; Joanna S. Fowler; Carroll D. Amett;[...]1986 MarsFrench;English
Journal of Labelled Compounds vol. 31 iss. 11 pp.945—950
Synthesis and analysis of the opioid analgesic [14C]-fentanyl
DOI: 10.1002/jlcr.2580311113 a a
Jerome R. Bagley; Jeffrey A. Wilhelm1992 NovembreFrench;English
Bioorganic & Medicinal Chemistry Letters vol. 16 iss. 18 pp.4946—4950
Synthesis and evaluation of 3-aminopropionyl substituted fentanyl analogues for opioid activity
DOI: 10.1016/j.bmcl.2006.06.040 a a
Ravil R. Petrov; Ruben S. Vardanyan; Yeon S. Lee; Shou-wu Ma; Peg Davis; Lucinda J. Begay; Josephine Y. Lai;[...]2006 SeptemberEnglish
Bioorganic & Medicinal Chemistry vol. 14 iss. 19 pp.6570—6580
Synthesis and pharmacological studies of new hybrid derivatives of fentanyl active at the μ-opioid receptor and I2–imidazoline binding sites
DOI: 10.1016/j.bmc.2006.06.007 a a
Christophe Dardonville; Cristina Fernandez-Fernandez; Sarah-Louise Gibbons; Gary J. Ryan; Nadine Jagerovic;[...]2006 OctoberEnglish
Bioorganic & Medicinal Chemistry Letters vol. 10 iss. 17 pp.2011—2014
The Synthesis and preliminary pharmacological evaluation of 4-Methyl fentanyl
DOI: 10.1016/s0960-894x(00)00394-2 a a
Ivan V. Mićović; Milovan D. Ivanović; Sonja M. Vuckovic; Milica Š. Prostran; Ljiljana Došen-Mićović; Vesna D. Kiricojević2000 SeptemberEnglish
Bioorganic & Medicinal Chemistry vol. 10 iss. 3 pp.817—827
Long-Acting Fentanyl Analogues: Synthesis and Pharmacology of N-(1-Phenylpyrazolyl)-N-(1-phenylalkyl-4-piperidyl)propanamides
DOI: 10.1016/s0968-0896(01)00345-5 a a
Nadine Jagerovic; Carolina Cano; José Elguero; Pilar Goya; Luis F Callado; J Javier Meana; Rocı́o Girón;[...]2002 MarchEnglish
Archives of Pharmacal Research vol. 21 iss. 1 pp.70—72
Total synthesis of fentanyl
DOI: 10.1007/bf03216756 a a
Young-Ger Suh; Kyung-Ho Cho; Dong-Yoon Shin1998 FebruaryEnglish
Helvetica Chimica Acta vol. 95 iss. 5 pp.818—824
Designing and Synthesis of Novel Amidated Fentanyl Analogs
DOI: 10.1002/hlca.201100392 a a
Yaghoub Haghighatnia; Saeed Balalaie; Hamid Reza Bijanzadeh2012 Kann 16German;English
Journal of Heterocyclic Chemistry vol. 27 iss. 2 pp.375—384
Synthesis and x-ray crystal structures of isonipecotinamide derivatives as reverse amide analogues of fentanyl
DOI: 10.1002/jhet.5570270251 a a
Ronald F. Borne; Catherine L. Gatchell; Cheryl L. Klein; John Harris; Portia Ellis1990 FebruaryEnglish
Journal of Heterocyclic Chemistry vol. 31 iss. 2 pp.313—318
Synthesis, structural, conformational and pharmacological study of new fentanyl derivatives of the camphidine system
DOI: 10.1002/jhet.5570310209 a a
B. Rico; E. Gálvez; M. L. Izquierdo; M. S. Arias; A. Orjales; A. Berisa; L. Labeaga1994 MarchEnglish
Acta Pharmacologica et Toxicologica vol. 57 iss. 1 pp.23—29
Effects of Anaesthetics on Protein Synthesis in Isolated Rat Hepatocytes: Inhibition by Diethyl Ether in Contrast to No Influence by Pentobarbital and Fentanyl
DOI: 10.1111/j.1600-0773.1985.tb00004.x a a
Bessesen, Atle ;Merland, Jørg2009 March 13
Journal of Medicinal Chemistry vol. 20 iss. 4 pp.600—602
Synthesis of some conformationally restricted analogs of fentanyl
DOI: 10.1021/jm00214a035 a a
Berger, Joel G.; Davidson, Fredric; Langford, Gordon E.1977 AprilEnglish
Life Sciences vol. 71 iss. 9 pp.1023—1034
Synthesis and opioid activity of new fentanyl analogs
DOI: 10.1016/s0024-3205(02)01798-8 a a
Rocı́o Girón; Raquel Abalo; Carlos Goicoechea; Ma Isabel Martı́n; Luis F Callado; Carolina Cano; Pilar Goya;[...]2002 JulyEnglish
Journal of the Chemical Society Perkin Transactions 2 iss. 4 pp.687—695
Synthesis, and structural, conformational and pharmacological studies of new fentanyl derivatives of the norgranatane system
DOI: 10.1039/p29920000687 a a
Fern�ndez, M. J.; Huertas, R. M.; G�lvez, E.; Orjales, A.; Berisa, A.; Labeaga, L.; Gago, F.; Fonseca, I.;[...]1992
Journal of Medicinal Chemistry vol. 27 iss. 10 pp.1271—1275
Conformationally restrained fentanyl analogs. 2. Synthesis and analgetic evaluation of perhydro-1,6-naphthyridin-2-ones
DOI: 10.1021/jm00376a007 a a
Borne, Ronald F.; Fifer, E. Kim; Waters, I. W.1984 OctoberEnglish
Journal of Medicinal Chemistry vol. 26 iss. 3 pp.348—352
Synthesis and evaluation of 1- and 2-substituted fentanyl analogs for opioid activity
DOI: 10.1021/jm00357a007 a a
Essawi, Mohamed Y. H.; Portoghese, Philip S.1983 MarchEnglish
Medicinal Chemistry Research vol. 22 iss. 8 pp.3888—3896
Synthesis and comparative bioefficacy ofN-(1-phenethyl-4-piperidinyl)propionanilide (fentanyl) and its 1-substituted analogs in Swiss albino mice
DOI: 10.1007/s00044-012-0390-6 a a
Gupta, Pradeep Kumar; Yadav, Shiv Kumar; Bhutia, Yangchen Doma; Singh, Poonam; Rao, Pooja; Gujar, Niranjan Laxman;[...]2012 December 15English
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Journal of Medicinal Chemistry vol. 24 iss. 1 pp.79—88
Synthesis and stereochemistry of 7-phenyl-2-propionanilidobenzo[a]quinolizidine derivatives. Structural probes of fentanyl analgesics
DOI: 10.1021/jm00133a017 a a
Maryanoff, Bruce E.; McComsey, David F.; Taylor, Russell J.; Gardocki, Joseph F.1981 JanuaryEnglish
Applied Mechanics and Materials vol. 217-219 pp.937—940
Design, Synthesis and Biological Evaluation of Novel Fentanyl Analogues as Agonist of μ-Opioid Receptor
DOI: 10.4028/www.scientific.net/AMM.217-219.937 a a
Liu, Ming; Hu, Wen Xiang2012 November
Interdisciplinary Toxicology vol. 7 iss. 2 pp.93—102
Synthesis and biological evaluation of some novel 1-substituted fentanyl analogs in Swiss albino mice
DOI: 10.2478/intox-2014-0013 a a
Yadav, Shiv Kumar; Maurya, Chandra Kant; Gupta, Pradeep Kumar; Jain, Ajai Kumar; Ganesan, Kumaran; Bhattacharya, Rahul2014 June 01English
Journal of the Chinese Chemical Society vol. 27 iss. 4 pp.147—149
A New Process for the Synthesis of Fentanyl
DOI: 10.1002/jccs.198000026 a a
Zee, Sheng-Hsu; Wang, Wan-Kung1980 DecemberEnglish
ChemInform vol. 23 iss. 33 pp.no—no
ChemInform Abstract: Synthesis, and Structural, Conformational and Pharmacological Studies of New Fentanyl Derivatives of the Norgranatane System.
DOI: 10.1002/chin.199233196 a a
FERNANDEZ, M. J. ;HUERTAS, R. M. ;GALVEZ, E. ;ORJALES, A. ;BERISA, A. ;LABEAGA, L. ;GAGO, F. ;FONSECA, I. ;[...]2010 August 21
ChemInform vol. 21 iss. 33
ChemInform Abstract: Synthesis and X-Ray Crystal Structures of Isonipecotinamide Derivatives as Reverse Amide Analogues of Fentanyl.
DOI: 10.1002/chin.199033181 a a
BORNE, R. F.; GATCHELL, C. L.; KLEIN, C. L.; HARRIS, J.; ELLIS, P.1990 August 14
RSC Advances vol. 7 iss. 32 pp.20015—20019
Synthesis and biological evaluation of fentanyl acrylic derivatives
DOI: 10.1039/C7RA01346A a a
Li, Shaohua; Cohen-Karni, Devora; Kovaliov, Marina; Tomycz, Nestor; Cheng, Boyle; Whiting, Donald; Averick, Saadyah2017English
Organic Preparations and Procedures International vol. 49 iss. 5 pp.467—470
An Operationally Simple Synthesis of Fentanyl Citrate
DOI: 10.1080/00304948.2017.1374129 a a
Walz, Andrew J.; Hsu, Fu-Lian2017 September 03English
Chemischer Informationsdienst vol. 9 iss. 28
ChemInform Abstract: SEARCH FOR A NEW METHOD FOR SYNTHESIS OF THE ANALGESIC AGENT ′FENTANYL′
DOI: 10.1002/chin.197828181 a a
JONCZYK, A.; JAWDOSIUK, M.; MAKOSZA, M.; CZYZEWSKI, J.1978 July 11
Chemischer Informationsdienst vol. 10 iss. 20
ChemInform Abstract: SYNTHESIS AND PHARMACOLOGICAL SCREENING OF PYRIDINE ANALOGS OF FENTANYL
DOI: 10.1002/chin.197920220 a a
GROSSMANN, S.; MOSER, U.; MUTSCHLER, E.1979 May 15
Chemischer Informationsdienst vol. 14 iss. 34
ChemInform Abstract: SYNTHESIS AND EVALUATION OF 1- AND 2-SUBSTITUTED FENTANYL ANALOGS FOR OPIOID ACTIVITY
DOI: 10.1002/chin.198334198 a a
ESSAWI, M. Y. H.; PORTOGHESE, P. S.1983 August 23
Chemischer Informationsdienst vol. 9 iss. 28
ChemInform Abstract: SYNTHESIS OF THE ANALGESIC FENTANYL ON AN INDUSTRIAL SCALE
DOI: 10.1002/chin.197828182 a a
JONCZYK, A.; JAWDOSIUK, M.; MAKOSZA, M.1978 July 11
ACS Chemical Neuroscience vol. 10 iss. 1 pp.201—208
Synthesis and biological evaluation of fentanyl analogues modified at phenyl groups with alkyls
DOI: 10.1021/acschemneuro.8b00363 a a
Qin, Yajuan; Ni, Luofan; Shi, Jiawei; Zhu, Zhiying; Shi, Saijian; Lam, Ai Leen; Magiera, Julia; Sekar, Sunderajhan;[...]2018 September 04English
Chemischer Informationsdienst vol. 7 iss. 13 pp.no—no
ChemInform Abstract: SYNTHESIS AND PHARMACOLOGICAL ACTIVITIES OF CYCLIC ANALOGS OF FENTANYL
DOI: 10.1002/chin.197613276 a a
KLEIN, W.; BACK, W.; MUTSCHLER, E.1976 March 30
Talanta vol. 203 pp.122—130
Attribution of fentanyl analogue synthesis routes by multivariate data analysis of orthogonal mass spectral data
DOI: 10.1016/j.talanta.2019.05.025 a a
Mörén, Lina; Qvarnström, Johanna; Engqvist, Magnus; Afshin-Sander, Robin; Wu, Xiongyu; Dahlén, Johan;[...]2019 OctoberEnglish
Forensic Chemistry vol. 17 pp.100203
Unique Bipiperidinyl Impurities Produced from the “One-Pot” Synthesis of Fentanyl
DOI: 10.1016/j.forc.2019.100203 a a
Casale, John F.; Hays, Patrick A.; Toske, Steven G.; Mallette, Jennifer R.2020 MarchEnglish
Chemischer Informationsdienst vol. 16 iss. 8
ChemInform Abstract: CONFORMATIONALLY RESTRAINED FENTANYL ANALOGS. 2. SYNTHESIS AND ANALGETIC EVALUATION OF PERHYDRO-1,6-NAPHTHYRIDIN-2-ONES
DOI: 10.1002/chin.198508200 a a
BORNE, R. F.; FIFER, E. K.; WATERS, I. W.1985 February 26
Chemischer Informationsdienst vol. 8 iss. 36 pp.no—no
ChemInform Abstract: SYNTHESIS OF SOME CONFORMATIONALLY RESTRICTED ANALOGS OF FENTANYL
DOI: 10.1002/chin.197736256 a a
BERGER, J. G.; DAVIDSON, F.; LANGFORD, G. E.1977 September 06
Chemischer Informationsdienst vol. 12 iss. 23
ChemInform Abstract: SYNTHESIS AND STEREOCHEMISTRY OF 7-PHENYL-2-PROPIONANILIDOBENZO(A)QUINOLIZIDINE DERIVATIVES. STRUCTURAL PROBES OF FENTANYL ANALGESICS
DOI: 10.1002/chin.198123258 a a
MARYANOFF, B. E.; MCCOMSEY, D. F.; TAYLOR, R. J. JUN.; GARDOCKI, J. F.1981 June 09
Journal of the Chemical Society Perkin Transactions 1 iss. 16 pp.2041—2050
The synthesis of lactam analogues of fentanyl
DOI: 10.1039/P19960002041 a a
Mi?ovi?, Ivan V.; Rogli?, Goran M.; Ivanovi?, M. D.; Do?en-Mi?ovi?, Ljiljana; Kiricojevi?, Vesna D.; Popovi?, Jelena B.

I will just leave these here and walk away....
 
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Psychopharmacology vol. 59 iss. 3 pp.225—229
Etonitazene as a reinforcer: Oral intake of etonitazene by rhesus monkeys
DOI: 10.1007/bf00426626 a a
Marilyn E. Carroll; Richard A. Meisch1978English
Psychopharmacology vol. 63 iss. 1 pp.97—98
Etonitazene as a reinforcer for rats: Increased etonitazene-reinforced behavior due to food deprivation
DOI: 10.1007/bf00426928 a a
R. A. Meisch; D. J. Kliner1979English
Pharmacology Biochemistry and Behavior vol. 50 iss. 4 pp.571—580
Oral self-administration of etonitazene in rhesus monkeys: Use of a fading procedure to establish etonitazene as a reinforcer
DOI: 10.1016/0091-3057(94)00343-2 a a
Richard A. Meisch1995 AprilEnglish
PsycEXTRA Dataset
The etonitazene-dependent rhesus monkey as a model to study narcotic agonist and antagonist activities.: (474002004-001)
DOI: 10.1037/e474002004-001 dataset l
Tang, Andrew H.American Psychological Association (APA)1982
Analytical Biochemistry vol. 106 iss. 2 pp.377—379
Quantitative determination of etonitazene
DOI: 10.1016/0003-2697(80)90536-9 a a
G. Gabor; H. Leader1980 AugustEnglish
Journal of Neuroscience Methods vol. 80 iss. 2 pp.149—154
Lever-press responding maintained by contingent intraperitoneal administration of etonitazene in Long Evans hooded rats
DOI: 10.1016/s0165-0270(97)00208-2 a a
J.A Ahlgren-Beckendorf; Robert B Stewart; Thomas H Gomez; Peter B Silverman; Richard A Meisch1998 AprilEnglish
Psychopharmacology vol. 5 iss. 1 pp.55—76
Factors regulating oral consumption of an opioid (etonitazene) by morphine-addicted rats
DOI: 10.1007/bf00405575 a a
Abraham Wikler; William R. Martin; Frank T. Pescor; Charles G. Eades1963English
Psychopharmacology vol. 64 iss. 1 pp.1—7
Concurrent etonitazene and water intake in rats: Role of taste, olfaction, and auditory stimuli
DOI: 10.1007/bf00427336 a a
Marilyn E. Caroll; Richard A. Meisch1979English
Psychopharmacology vol. 47 iss. 3 pp.273—279
Narcotic blockade, length of addiction and persistence of etonitazene consumption in rats
DOI: 10.1007/bf00427613 a a
R. E. Meyer; R. Marcus; G. Carnathan; J. Cochin1976English
Psychopharmacology vol. 82 iss. 3 pp.151—152
Effects of dose on increased etonitazene self-administration by rats due to food deprivation
DOI: 10.1007/bf00427762 a a
Marilyn E. Carroll; Irwin N. Boe1984English
Psychopharmacology vol. 111 iss. 4 pp.409—414
Oral etonitazene and cocaine consumption by AA, ANA and Wistar rats
DOI: 10.1007/bf02253529 a a
P. Hyyatiä; J. D. Sinclair1993 JulyEnglish
Psychopharmacology vol. 204 iss. 3 pp.489—498
Intravenous self-administration of etonitazene alone and combined with cocaine in rhesus monkeys: comparison with heroin and antagonism by naltrexone and naloxonazine
DOI: 10.1007/s00213-009-1480-0 a a
Cindy Achat-Mendes; Glenn R. Valdez; Donna M. Platt; James K. Rowlett; Roger D. Spealman2009 February 19English
Psychopharmacology vol. 153 iss. 1 pp.134—138
Reinforcing effects of contingently administered subcutaneous injections of etonitazene in rats
DOI: 10.1007/s002130000440 a a
Thomas H. Gomez; Richard A. Meisch2000 December 12English
Psychopharmacology vol. 154 iss. 2 pp.131—142
Differential tolerance to antinociceptive effects of µ opioids during repeated treatment with etonitazene, morphine, or buprenorphine in rats
DOI: 10.1007/s002130000620 a a
Ellen A. Walker; Alice M. Young2001 March 05English
Psychopharmacology vol. 135 iss. 1 pp.63—69
Effects of acute administration of ethanol and the μ-opiate agonist etonitazene on thyroid hormone metabolism in rat brain
DOI: 10.1007/s002130050486 a a
A. Baumgartner; G. Pinna; L. Hiedra; F. Bauer; J. Wolf; M. Eravci; H. Prengel; O. Brödel; G. Schmidt;[...]1998 January 08English
Cellular and Molecular Life Sciences vol. 23 iss. 1 pp.57—59
Effects of etonitazene upon respiratory neurons
DOI: 10.1007/bf02142268 a a
E. J. A. Carregal; Betriz Williams1967 January 01English
Pharmacology Biochemistry and Behavior vol. 4 iss. 2 pp.137—141
Schedule-induced oral self administration of etonitazene
DOI: 10.1016/0091-3057(76)90005-8 a a
D.E. McMillan; J.D. Leander1976 FebruaryEnglish
Pharmacology Biochemistry and Behavior vol. 6 iss. 2 pp.215—219
Antagonism of Etonitazene's effects in rats and pigeons
DOI: 10.1016/0091-3057(77)90076-4 a a
Linda A. Dykstra; Walker Wharton; D.E. McMillan1977 FebruaryEnglish
Pharmacology Biochemistry and Behavior vol. 7 iss. 3 pp.195—203
Establishment of etonitazene as a reinforcer for rats by use of schedule-induced drinking
DOI: 10.1016/0091-3057(77)90134-4 a a
Richard A. Meisch; Linda J. Stark1977 SeptemberEnglish
Pharmacology Biochemistry and Behavior vol. 6 iss. 1 pp.17—20
Differential motor effects of intraventricular infusion of morphine and etonitazene
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P. Shizgal; L.S. Sklar; Z.W. Brown; Z. Amit1977 JanuaryEnglish
Pharmacology Biochemistry and Behavior vol. 10 iss. 1 pp.155—159
Effects of food deprivation on etonitazene consumption in rats
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Marilyn E. Carroll; Richard A. Meisch1979 JanuaryEnglish
Pharmacology Biochemistry and Behavior vol. 14 iss. 6 pp.871—876
A precision drinking device for rats tested with water, etonitazene, and ethanol
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Patrick M. Beardsley; Richard A. Meisch1981 JuneEnglish
Pharmacology Biochemistry and Behavior vol. 42 iss. 4 pp.579—586
Etonitazene delivered orally serves as a reinforcer for Lewis but not Fischer 344 rats
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Tsutomu Suzuki; Frank R. George; Richard A. Meisch1992 AugustEnglish
Pharmacology Biochemistry and Behavior vol. 45 iss. 1 pp.251—253
Genetic factors in conditioned tolerance to the analgesic effects of etonitazene
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Gregory I. Elmer; Clyde B. Mathura; Steven R. Goldberg1993 MayEnglish
Pharmacology Biochemistry and Behavior vol. 79 iss. 2 pp.261—267
Direct relation between etonitazene dose and response rate: responding under a single FI per session
DOI: 10.1016/j.pbb.2004.07.005 a a
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Acta Crystallographica Section B Structural Crystallography & Crystal Chemistry (International Union of Crystallography) vol. 34 iss. 12 pp.3828—3829
2-[2-(4-Ethoxyphenyl)methyl-5-nitro-1H-benzimidazolyl]-N,N-diethylethanaminium chloride–acetic acid:etonitazene
DOI: 10.1107/s0567740878012376 a a
Humblet, C. ;Evrard, G. ;Durant, F.1978 December 01
Journal of Medicinal Chemistry vol. 18 iss. 3 pp.318—320
Etonitazene. Improved synthesis
DOI: 10.1021/jm00237a024 a a
Carroll, Frank I.; Coleman, Michael C.1975 MarchEnglish
European Journal of Pharmacology vol. 217 iss. 1 pp.37—41
Dose-dependent conditioned place preference produced by etonitazene and morphine
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Mariaelvina Sala; Daniela Braida; Paola Calcaterra; Maria Primula Leone; Enzo Gori1992 JuneEnglish
European Journal of Pharmacology vol. 271 iss. 2-3 pp.497—504
Relationship between morphine and etonitazene-induced working memory impairment and analgesia
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Daniela Braida; Enzo Gori; Mariaelvina Sala1994 DecemberEnglish
Neuroscience Letters vol. 275 iss. 2 pp.109—112
Effects of etonitazene consumption and abstinence on the signal transmission of μ-opioid receptors in brain membranes of rats
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Torsten May; Folkert Juilfs; Jochen Wolffgramm1999 NovemberEnglish
Life Sciences vol. 52 iss. 18 pp.PL199—PL203
Etonitazene: An opioid selective for the mu receptor types
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Marjorie S. Moolten; Jordan B. Fishman; Jin-Chung Chen; Kristin R. Carlson1993 JanuaryEnglish
Life Sciences vol. 54 iss. 21 pp.PL369—PL374
Etonitazene-induced antinociception in μ1 opioid receptor deficient CXBK mice: Evidence for a role for μ2 receptors in supraspinal antinociception
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Charlene D. Connelly; Rebecca P. Martinez; James J. Schupsky; Frank Porreca; Robert B. Raffa1994 JanuaryEnglish
Pharmacological Research vol. 22 pp.64
Inability of etonitazene and haloperidol to elicit conditioned taste aversion
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Braida, D.; Calcaterra, P.; Leone, M.P.; Comotti, F.A.; Gianola, S.; Sala, M.1990 SeptemberEnglish
Pharmacological Research vol. 25 pp.329—329
Comparison morphine and etonitazene in rat conditioned place preference (CPP) test
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BRAIDA, D; SALA, M; CALCATERRA, P; LEONE, M; GORI, E1992 MayEnglish
Drug and Alcohol Dependence vol. 14 iss. 2 pp.179—186
The influence of haloperidol and aminooxyacetic acid on etonitazene, alcohol, diazepam and barbital consumption
DOI: 10.1016/0376-8716(84)90043-7 a a
Fuchs, V.; Burbes, E.; Coper, H.1984 OctoberEnglish
Bulletin of the Psychonomic Society vol. 23 iss. 3 pp.241—244
Failure to block opiate effects of oral etonitazene with naltrexone during 24-h choice testing
DOI: 10.3758/BF03329838 a a
Lynch, Minda R.; Porter, Joseph H.1985 March
Behavioural Pharmacology vol. 3 iss. Supplement pp.65
A COMPARISON OF DIFFERING INTENSITIES OF STIMULUS CUES IN ETONITAZENE PLACE CONDITIONING IN C57BL/6J MICE
DOI: 10.1097/00008877-199204001-00202 a a
PIEPER, J O; ELMER, G I; SANCHEZ-SANTED, F; SCHINDLER, C W; GOLDBERG, S R1992 AprilEnglish
Heterocycles vol. 39 iss. 2 pp.751
X-Ray Crystal Structures of Potent Receptor Ligands: Etonitazene, cis-(+)-3-Methylfentanyl, Etorphine, Diprenorphine, and Buprenorphine
DOI: 10.3987/COM-94-S(B)70 a a
Pizzonero, Mathieu; L. Flippen-Anderson, Judith; George, Clifford; M. Bertha, Craing; C. Rice, Kenner1994English
Chemischer Informationsdienst vol. 6 iss. 27 pp.no—no
ChemInform Abstract: ETONITAZENE, AN IMPROVED SYNTHESIS
DOI: 10.1002/chin.197527243 a a
CARROLL, F. I.; COLEMAN, M. C.1975 July 08
The Japanese Journal of Pharmacology vol. 61 pp.300
studies on drug dependence (Rept. 227): Reinforcing properties of morphine and etonitazene by conditioned place preference in two inbred strains of rats.
DOI: 10.1016/s0021-5198(19)39628-3 a a

And leave that there....
 
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Helvetica Chimica Acta vol. 43 iss. 4 pp.1046—1056
Benzimidazol-Derivate und verwandte Heterocyclen. IV. Die Kondensation von o-Phenylendiamin mit α-Aryl- und γ-Aryl-acetessigester
DOI: 10.1002/hlca.19600430413 a a
A. Rossi; A. Hunger; J. Kebrle; K. Hoffmann1960German;English
Helvetica Chimica Acta vol. 43 iss. 5 pp.1298—1313
Benzimidazol-Derivate und verwandte Heterocyclen V. Die Kondensation von o-Phenylendiamin mit aliphatischen und alicyclischen β-Ketoestern
DOI: 10.1002/hlca.19600430515 a a
A. Rossi; A. Hunger; J. Kebrle; K. Hoffmann1960German;English
Helvetica Chimica Acta vol. 43 iss. 6 pp.1727—1733
Benzimidazol-Derivate und verwandte Heterocyclen VI. Synthese von Phenyl-[1-aminoalkyl-benzimidazolyl-(2)]-essigsäure-estern und -amiden
DOI: 10.1002/hlca.19600430634 a a
A. Hunger; J. Kebrle; A. Rossi; K. Hoffmann1960German;English
Helvetica Chimica Acta vol. 43 iss. 3 pp.800—809
Benzimidazol-Derivate und verwandte Heterocyclen. II. Synthese von 1-Aminoalkyl-2-benzyl-benzimidazolen
DOI: 10.1002/hlca.19600430323 a a
A. Hunger; J. Kebrle; A. Rossi; K. Hoffmann1960German;English
Helvetica Chimica Acta vol. 43 iss. 4 pp.1032—1046
Benzimidazol-Derivate und verwandte Heterocyclen III. Synthese von 1-Aminoalkyl-2-nenzyl-nitro-benzimidazolen
DOI: 10.1002/hlca.19600430412 a a
A. Hunger; J. Kebrle; A. Rossi; K. Hoffmann1960German;English
Helvetica Chimica Acta vol. 44 iss. 5 pp.1273—1282
Benzimidazol-Derivate und verwandte Heterocyclen VII. Synthese neuer 2-Amino-benzimidazole
DOI: 10.1002/hlca.19610440513 a a
A. Hunger; J. Kebrle; A. Rossi; K. Hoffmann

Ah - forgot to include the full CIBA papers including the derivatives that are more potent than the original compound.
 
Title: Synthese basisch substituierter, analgetisch wirksamer Benzimidazol-Derivate
Series: Cellular and Molecular Life Sciences 1957-oct vol. 13 iss. 10
Author(s): A. Hunger; J. Kebrle; A. Rossi; K. Hoffmann
Year: 1957

Above is the paper which has the chiral benzaldehyde that increases the potency of the nitazine class by a factor of 4.

I think it important to remember that animal models aren't always accurate. BDPC was originally listed as being >x10000 morphine but in man, it's x527. I have read the human trial of etonitazene (for the purposes of opiate detoxification) and orally, it was shown to be x60 morphine and so I suggest that example 5 (with the chiral carboxamide) is some x240 morphine.

Now I cannot speak for others, but I consider x240 M to be MORE than sufficient.

Of course nations will ban the whole scaffold... and THEN people will struggle to find a compound similar to fentanyl in potency and synthetic complexity.

It may NOT be x4 more potent in preventing abstinence syndrome because the carboxamide increases NOP affinity.
 
Last edited:

European Journal of Medicinal Chemistry
vol. 23 iss. 6 pp.511—515

Synthesis and pharmacological investigation of the 3-analogs of viminol
DOI: 10.1016/0223-5234(88)90093-1 a a
Marco de Amici; Carlo de Micheli; Fabio Platini; Davide Della Bella; Ida Caramazza1988 NovembreFrench;English
Pharmacological Research Communications vol. 8 iss. 2 pp.111—126
Absolute configuration and biological activity of viminol stereoisomers
DOI: 10.1016/0031-6989(76)90001-1 a a
D. Della Bella; G. Benelli; A. Sassi1976 April
Pharmacology Biochemistry and Behavior vol. 20 iss. 1 pp.59—62
The discriminative stimulus properties of the R2 isomer of viminol
DOI: 10.1016/0091-3057(84)90101-1 a a
Jennifer E. Shook; Mary Jeanne Kallman; William L. Dewey1984 JanuaryEnglish
Acta Crystallographica Section B Structural Crystallography & Crystal Chemistry (International Union of Crystallography) vol. 31 iss. 6 pp.1576—1581
The crystal and molecular structure of the analgesic [S(R,R)]-viminol; [αS(R,R)]-α-[(di-s-butylamino)methyl]-1-(2-chlorobenzyl)-1H-2-pyrrolemethanol p-hydroxybenzoate
DOI: 10.1107/s0567740875005717 a a
Silverton, J. V. ;Lloyd, H. A.1975 June 15
European Journal of Pharmacology vol. 23 iss. 2 pp.137—146
Some behavioral and EEG effects of a new analgesic agent (viminol) in comparison with morphine in rats
DOI: 10.1016/0014-2999(73)90049-6 a a
M. Babbini; M. Gaiardi; M. Bartoletti1973 AugustEnglish
Life Sciences vol. 17 iss. 1 pp.73—74
Viminol stereoisomers and lamina V interneurons activity: Preliminary results
DOI: 10.1016/0024-3205(75)90238-6 a a
Davide Della Bella; Giancarlo Benelli; Jean-Marie Besson1975 JulyEnglish
Journal of Substance Use vol. 12 iss. 4 pp.301—305
Dependence on Viminol
DOI: 10.1080/14659890701237124 a a
Turkiewicz, G.; Baltieri, D. A.2007 JanuaryEnglish
ChemInform vol. 20 iss. 19
ChemInform Abstract: Synthesis and Pharmacological Investigation of the 3-Analogues of Viminol.
DOI: 10.1002/chin.198919183 a a

Above are all the papers covering Viminol derivatives including Z4349 which is x318 M in potency
 


Without a shadow of a doubt, the papers in the above hotlinks provide most important data when it comes to the identification and optimization of selective, duel and non-selective opiate agonists as well as high-potency mu ligands.

Fig 1 of the first paper shows the relative spatial position and orientation (RPO) of the key moieties. You will notice that for mu agonists, the paper identifies:

1) 2x hydrogen bond acceptors (HBA)
2) positive ionizable point (PI)
3) ring aromatic group (RA)

This is a limitation as it doesn't identify the SECOND RA (ring aromatic), generally required to achieve very high potency. The second paper DOES identify this second ring.

If you employ the RPO and devise a sufficiently large and varied training set, you will discover that even the most bizarre high-potency ligands fid into these simple rules. However, their is a SIXTH binding site that appears to require pi-bonding and yet does not require a RA. Examples of this are allyl prodine & 14-cinnamyloxycodone although some early synthetic opioids such as alimadol and even the Bentley compounds may have stumbled upon this, The latter may seem an odd example but their are a number of compounds in the class in which the dihydro derivatives are significantly LESS potent.

With the above, it's now possible to state with >98% certainty that any compound with:

1) Biosteric minimum small enough to fid into mu receptor
2) Physical properties (RO5)
3) Ability to cross BBB

WILL be an active opioid.

NB the training-sets are listed from compounds with the highest affinity down to those with the lowest affinity.
 
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Journal of Organic Chemistry vol. 48 iss. 2 pp.227—238
Codeine analogs. Synthesis of 4a-aryldecahydroisoquinolines containing nitrogen ring functionality and of octahydro-1H-indeno[1,2,3-ef]isoquinolines. A total synthesis of codeine
DOI: 10.1021/jo00150a017 a a
Moos, Walter H.; Gless, Richard D.; Rapoport, Henry1983 JanuaryEnglish
Chemischer Informationsdienst vol. 14 iss. 23
ChemInform Abstract: CODEINE ANALOGS. SYNTHESIS OF 4A-ARYLDECAHYDROISOQUINOLINES CONTAINING NITROGEN RING FUNCTIONALITY AND OF OCTAHYDRO-1H-INDENO(1,2,3-EF)ISOQUINOLINES. A TOTAL SYNTHESIS OF CODEINE
DOI: 10.1002/chin.198323256 a a
MOOS, W. H.; GLESS, R. D.; RAPOPORT, H.1983 June 07
Tetrahedron vol. 44 iss. 5 pp.1567—1572
A new approach to the synthesis of morphinans and 4a-aryldecahydroisoquinolines
DOI: 10.1016/s0040-4020(01)85936-6 a a
C.W. Bird; K. Naidoo1988 JanvierFrench;English;German
Journal of Medicinal Chemistry vol. 31 iss. 3 pp.555—560
Synthesis and analgesic properties of N-substituted trans-4a-aryldecahydroisoquinolines
DOI: 10.1021/jm00398a011 a a
Zimmerman, Dennis M.; Cantrell, Buddy E.; Swartzendruber, John K.; Jones, Noel D.; Mendelsohn, Laura G.;[...]1988 MarchEnglish
Journal of Organic Chemistry vol. 51 iss. 4 pp.561—564
Effect of A-strain on a diastereoselective synthesis of 6-hydroxy-4a-aryldecahydroisoquinolines; revised structures of N-acyliminium ion-polyene cyclization products
DOI: 10.1021/jo00354a035 a a
Kano, Shinzo; Yokomatsu, Tsutomu; Nemoto, Hajime; Shibuya, Shiroshi1986 FebruaryEnglish
Journal of Organic Chemistry vol. 42 iss. 9 pp.1485—1495
Synthesis of 4a-aryldecahydroisoquinolines. Functionality in the carbocyclic ring
DOI: 10.1021/jo00429a001 a a
Weller, Dwight D.; Gless, Richard D.; Rapoport, Henry1977 AprilEnglish
ChemInform vol. 19 iss. 29
ChemInform Abstract: A New Approach to the Synthesis of Morphinans and 4a-Aryldecahydroisoquinolines.
DOI: 10.1002/chin.198829310 a a
BIRD, C. W.; NAIDOO, K.1988 July 19
Chemischer Informationsdienst vol. 17 iss. 34
ChemInform Abstract: Effect of A-Strain on a Diastereoselective Synthesis of 6-Hydroxy-4a-aryldecahydroisoquinolines. Revised Structures of N-Acyliminium Ion- Polyene Cyclization Products.
DOI: 10.1002/chin.198634231 a a
KANO, S.; YOKOMATSU, T.; NEMOTO, H.; SHIBUYA, S.1986 August 26
Chemischer Informationsdienst vol. 8 iss. 41 pp.no—no
ChemInform Abstract: SYNTHESIS OF 4A-ARYLDECAHYDROISOQUINOLINES. FUNCTIONALITY IN THE CARBOCYCLIC RING
DOI: 10.1002/chin.197741267 a a
WELLER, D. D.; GLESS, R. D.; RAPOPORT, H.

Above are hotlinks to an entirely overlooked class of potent mu agonists.
 
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Journal of the Chemical Society (Resumed) pp.52
11. Aminoalkyl tertiary carbinols and derived products. Part IV. Spasmolytics. Phenyl- and cyclohexylphenyl-carbinols
DOI: 10.1039/jr9510000052 a a
Adamson, D. W. ;Barrett, P. A. ;Wilkinson, S.1951
Journal of the Chemical Society (Resumed) vol. 0 iss. 0 pp.312—324
61. Aminoalkyl tertiary carbinols and derived products. Part VI. The stereochemistry of some 1-phenyl-1-2′-pyridylprop-1-enes, and of some 3-(tertiary amino)-1-phenyl-1-2′-pyridylprop-1-enes carrying additional substituents
DOI: 10.1039/JR9580000312 a a
Adamson, D. W. ;Barrett, P. A. ;Billinghurst, J. W. ;Jones, T. S. G.1958
Journal of the Chemical Society (Resumed) pp.1039
212. Aminoalkyl tertiary carbinols and derived products. Part III. 3-Tertiary-amino-1-aryl-1-(2-pyridyl)-propan-1-ols and -prop-1-enes
DOI: 10.1039/JR9500001039 a a
Adamson, D. W. ;Billinghurst, J. W.1950
Journal of the Chemical Society (Resumed) vol. 0 iss. 0 pp.885—890
180. Aminoalkyl tertiary carbinols and derived products. Part II. 3-Amino-1 : 1-di-2′-thienyl-alkan-1-ols and -alk-1-enes
DOI: 10.1039/JR9500000885 a a
Adamson, D. W.1950
Journal of the Chemical Society (Resumed) pp.2315
445. Aminoalkyl tertiary carbinols and derived products. Part V. Antihistamines. The stereochemistry of cis- and trans-3-phenyl-3-pyridylallylamines
DOI: 10.1039/JR9570002315 a a
Adamson, D. W. ;Barrett, P. A. ;Billinghurst, J. W. ;Jones, T. S. G.1957
Journal of the Chemical Society (Resumed) pp.325
62. Aminoalkyl tertiary carbinols and derived products. Part VII. A new synthesis of 1-arylpyrrocolines
DOI: 10.1039/JR9580000325 a a
Barrett, P. A.1958
Journal of the Chemical Society (Resumed) pp.338
63. Aminoalkyl tertiary carbinols and derived products. Part VIII. Some 1-alkyl- and 1 : 2-cycloalkano-pyrrocolines
DOI: 10.1039/JR9580000338 a a
Barrett, P. A. ;Chambers, K. A.1958
Journal of the Chemical Society (Resumed) pp.S144
S 32. Aminoalkyl tertiary carbinols and derived products. Part I. 3-Amino-1 : 1-diphenylpropan-1-ols
DOI: 10.1039/jr949000s144 a a
Adamson, D. W.1949

Above are hotlinks for the thiambutene class of opioids,
 
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Psychopharmacology vol. 57 iss. 1 pp.21—26
Narcotic cuing and analgesic activity of narcotic analgesics: Associative and dissociative characteristics
DOI: 10.1007/bf00426952 a a
Francis C. Colpaert; Carlos J. E. Niemegeers; Paul A. J. Janssen1978English
Cellular and Molecular Life Sciences vol. 12 iss. 8 pp.293—294
Mydriatic activity of analgesics in mice
DOI: 10.1007/bf02159614 a a
P. A. J. Janssen; A. Jageneau1956 AugustEnglish
Acta Anaesthesiologica Scandinavica vol. 26 iss. 3 pp.262—268
Potent, New Analgesics, Tailor-Made for Different Purposes
DOI: 10.1111/j.1399-6576.1982.tb01765.x a a
P. A. J. Janssen1982 JuneEnglish
Journal of Medicinal Chemistry vol. 17 iss. 10 pp.1047—1051
Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-[3-methyl-1-(2-phenylethyl)-4-piperidyl]-N-phenylpropanamide and N-[3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl]-N-phenylpropanamide
DOI: 10.1021/jm00256a003 a a
Van Bever, Willem F. M.; Niemegeers, Carlos J. E.; Janssen, Paul A. J.1974 OctoberEnglish
Journal of Pharmacy and Pharmacology vol. 10 iss. 1 pp.14—21
A NEW SERIES OF POTENT ANALGESICS: Dextro 2:2-diphenyl-3-methyl-4-morpholinobutyrylpyrrolidine and related basic amides: Part II :Comparative analgesic activity, acute toxicity and tolerance development in rats for R875, morphine, pethidine and methadone
DOI: 10.1111/j.2042-7158.1958.tb10268.x a a
Janssen, Paul A. J.; Jageneau, Anton H.1958 SeptemberEnglish
Journal of the American Chemical Society vol. 78 iss. 15 pp.3862—3862
A NEW SERIES OF POTENT ANALGESICS
DOI: 10.1021/ja01596a087 a a
Janssen, Paul A. J.; Janseen, J. C.1956 AugustEnglish
Medical Hypotheses vol. 40 iss. 1 pp.66—74
Analgesics abuse: Theoretical and practical considerations
DOI: 10.1016/0306-9877(93)90199-Z a a
Driesens, F; Awouters, F; Goossens, T; Janssen, P1993 JanuaryEnglish
Journal of Pharmacy and Pharmacology vol. 9 iss. 1 pp.381—400
A NEW SERIES OF POTENT ANALGESICS
DOI: 10.1111/j.2042-7158.1957.tb12290.x a a
P. A. J. Janssen; A. H. Jageneau1957 SeptemberEnglish
Chemischer Informationsdienst vol. 7 iss. 46 pp.no—no
ChemInform Abstract: SYNTHETIC ANALGESICS- N-(1-(2-ARYLETHYL)-4-SUBSTITUTED 4-PIPERIDINYL)-N-ARYLALKANAMIDES
DOI: 10.1002/chin.197646236 a a
VAN DAELE, P. G. H.; DE BRUYN, M. F. L.; BOEY, J. M.; SANCZUK, S.; AGTEN, J. T. M.; JANSSEN, P. A. J.1976 November 16
Chemischer Informationsdienst vol. 6 iss. 5 pp.no—no
ChemInform Abstract: SYNTHETIC ANALGESICS, SYNTHESIS AND PHARMACOLOGY OF THE DIASTEREOISOMERS OF N-(3-METHYL-1-(2-PHENYLETHYL)-4-PIPERIDYL)-N-PHENYLPROPANAMIDE AND N-(3-METHYL-1-(1-METHYL-2-PHENYLETHYL)-4-PIPERIDYL)-N-PHENYLPROPANAMIDE
DOI: 10.1002/chin.197505282 a a
VAN BEVER, W. F. M.; NIEMEGEERS, C. E. J.; JANSSEN, P. A. J.1975 February 04
Synthetic Analgesics. Diphenylpropylamines part I b lJanssen P.1960189English
Synthetic Analgesics Part I: Diphenylpropylamines b lPaul A. J. Janssen1960189English

Above are hotlinks for all the opioids discovered by Paul Janssen.
 
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Journal of Medicinal Chemistry vol. 24 iss. 3 pp.341—346
4-Aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. m-Hydroxyphenyl derivatives
DOI: 10.1021/jm00135a019 a a
Lednicer, Daniel; Von Voigtlander, Philip F.; Emmert, D. Edward1981 MarchEnglish
Journal of Medicinal Chemistry vol. 23 iss. 4 pp.424—430
4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring
DOI: 10.1021/jm00178a014 a a
Lednicer, Daniel; Von Voigtlander, Philip F.; Emmert, D. Edward1980 AprilEnglish
Journal of Medicinal Chemistry vol. 24 iss. 4 pp.404—408
4-Amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function
DOI: 10.1021/jm00136a010 a a
Lednicer, Daniel; VonVoigtlander, Philip F.; Emmert, D. Edward1981 AprilEnglish
Chemischer Informationsdienst vol. 12 iss. 34
ChemInform Abstract: 4-AMINO-4-ARYLCYCLOHEXANONES AND THEIR DERIVATIVES: A NOVEL CLASS OF ANALGESICS. PART 2. MODIFICATION OF THE CARBONYL FUNCTION
DOI: 10.1002/chin.198134185 a a
LEDNICER, D.; VON VOIGTLANDER, P. F.; EMMERT, D. E.1981 August 25
Chemischer Informationsdienst vol. 12 iss. 32
ChemInform Abstract: 4-ARYL-4-AMINOCYCLOHEXANONES AND THEIR DERIVATIVES, A NOVEL CLASS OF ANALGESICS. 3. M-HYDROXYPHENYL DERIVATIVES
DOI: 10.1002/chin.198132152 a a
LEDNICER, D.; VON VOIGTLANDER, P. F.; EMMERT, D. E.1981 August 11
Chemischer Informationsdienst vol. 11 iss. 34
ChemInform Abstract: 4-AMINO-4-ARYLCYCLOHEXANONES AND THEIR DERIVATIVES, A NOVEL CLASS OF ANALGESICS. 1. MODIFICATION OF THE ARYL RING
DOI: 10.1002/chin.198034168 a a
LEDNICER, D.; VON VOIGTLANDER, P. F.; EMMERT, D. E.1980 August 26

Above are hotlinks to all of the opioids discovered by Dr. Danial Lednicer
 
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Bioorganic & Medicinal Chemistry Letters vol. 3 iss. 12 pp.2641—2646
Phenalene analogs of the kappa opiate agonist, U-50,488
DOI: 10.1016/s0960-894x(01)80733-2 a a
Shikai Zhao; Jeremiah P. Freeman; Philip F. VonVoigtlander; Martin W. Smith; Jacob Szmuszkovicz1993 DecemberEnglish
Heterocycles vol. 52 iss. 1 pp.325
Phenanthridone Analogs of the Opiate Agonist U-47,700 in the trans-1,2-Diaminocyclohexane Benzamide Series
DOI: 10.3987/com-99-s27 a a
Szmuszkovicz, Jacob; Zhao, Shikai; J. Totleben, Michael; A. Mizsak, Stephen; P. Freeman, Jeremiah2000English

Above are the hotlinks to the opioids discovered by Dr. Jacob Szmuszkovicz, a chemist at Upjohn who worked with Dan and who Dan evidently didn't care for on a personal level - usually because Dan was the boss and Jacob hated being told what to do... even though Dan actually did all of the prototyping.
 

An absolute CLASSIC by Nathen B. Eddy who worked with Grewe, Besendorf & Pellmont.

An index paper for those studying QSAR of mu ligands.
 
ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Alcoholism: Clinical and Experimental Research vol. 29 iss. 8 pp.1390—1401
Selective GABAAα5 Benzodiazepine Inverse Agonist Antagonizes the Neurobehavioral Actions of Alcohol
DOI: 10.1097/01.alc.0000175073.94575.86 a a
Jason B. Cook; Katrina L. Foster; William J. A. Eiler II; Peter F. McKay; James Woods II; Scott C. Harvey;[...]2005 AugustEnglish
Journal of Vascular Surgery vol. 14 iss. 2 pp.147—151
Thrombomodulin activity on human saphenous vein grafts prepared for coronary artery bypass
DOI: 10.1067/mva.1991.28730 a a
Cook, James M.; Cook, Christine D.; Marlar, Richard; Solis, Maurice M.; Fink, Lou; Eidt, John F.1991 AugustEnglish
Phytochemistry vol. 12 iss. 6 pp.1467—1474
Further alkaloids of Alstonia muelleriana
DOI: 10.1016/0031-9422(73)80586-2 a a
David E. Burke; Gloria A. Cook; James M. Cook; Kathleen G. Haller; Harvey A. Lazar; Philip W. Le Quesne1973 JuneEnglish
Psychopharmacology vol. 187 iss. 3 pp.321—330
Enhanced sucrose pellet consumption induced by benzodiazepine-type drugs in squirrel monkeys: role of GABAAreceptor subtypes
DOI: 10.1007/s00213-006-0431-2 a a
Angela N. Duke; Donna M. Platt; James M. Cook; Shengming Huang; Wenyuan Yin; Bruce A. Mattingly; James K. Rowlett2006 June 17English
Psychopharmacology vol. 203 iss. 3 pp.539—546
Contribution of α1 subunit-containing γ-aminobutyric acidA(GABAA) receptors to motor-impairing effects of benzodiazepines in squirrel monkeys
DOI: 10.1007/s00213-008-1401-7 a a
Stephanie C. Licata; Donna M. Platt; James M. Cook; Michael L. Van Linn; James K. Rowlett2008 November 25English
Pharmacology Biochemistry and Behavior vol. 24 iss. 4 pp.963—965
Differential antagonism of diazepam-induced loss of the righting response
DOI: 10.1016/0091-3057(86)90443-0 a a
Jeffrey M. Witkin; James E. Barrett; James M. Cook; Paul Larscheid1986 AprilEnglish
European Journal of Pharmacology vol. 106 iss. 3 pp.585—591
Cerebrovascular and cerebral metabolic effects of clurazepam and a benzodiazepine antagonist, 3-hydroxymethyl-β-carboline
DOI: 10.1016/0014-2999(84)90062-1 a a
William E. Hoffman; James M. Feld; Paul Larscheid; James M. Cook; Ronald F. Albrecht; David J. Miletich1984 NovemberEnglish
Neuropharmacology vol. 58 iss. 2 pp.357—364
Discriminative stimulus effects of L-838,417 (7-tert-butyl-3-(2,5-difluoro-phenyl)-6-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine): Role of GABAA receptor subtypes
DOI: 10.1016/j.neuropharm.2009.10.004 a a
Stephanie C. Licata; Donna M. Platt; Daniela Rüedi-Bettschen; John R. Atack; Gerard R. Dawson; Michael L. Van Linn;[...]2010 FebruaryEnglish
Neuropharmacology vol. 59 iss. 7-8 pp.612—618
Anxiolytic-like effects of 8-acetylene imidazobenzodiazepines in a rhesus monkey conflict procedure
DOI: 10.1016/j.neuropharm.2010.08.011 a a
Bradford D. Fischer; Stephanie C. Licata; Rahul V. Edwankar; Zhi-Jian Wang; Shengming Huang; Xiaohui He;[...]2010 DecemberEnglish
Bioorganic & Medicinal Chemistry vol. 16 iss. 19 pp.8853—8862
A study of the structure–activity relationship of GABAA–benzodiazepine receptor bivalent ligands by conformational analysis with low temperature NMR and X-ray analysis
DOI: 10.1016/j.bmc.2008.08.072 a a
Dongmei Han; F. Holger Försterling; Xiaoyan Li; Jeffrey R. Deschamps; Damon Parrish; Hui Cao; Sundari Rallapalli;[...]2008 OctoberEnglish
Tetrahedron vol. 47 iss. 23 pp.3665—3710
General approach for the synthesis of polyquinenes via the Weiss reaction
DOI: 10.1016/s0040-4020(01)80896-6 a a
Ashok K. Gupta; Xiaoyong Fu; James P. Snydert; James M. Cook1991French;English;German
Tetrahedron Letters vol. 17 iss. 50 pp.4549—4552
Reactions of dicarbonyl compounds with dimethyl β-ketoglutarate V. Simple synthesis of tricyclo [6.3.0.01,5] Undecane-3, 7, 9-trione, a novel cyclopentanoid compound
DOI: 10.1016/s0040-4039(00)93928-5 a a
James Oehldrich; James M. Cook; Ulrich Weiss1976French;German;English
Psychopharmacology vol. 161 iss. 2 pp.180—188
Role of GABAA/benzodiazepine receptors containing α1and α5subunits in the discriminative stimulus effects of triazolam in squirrel monkeys
DOI: 10.1007/s00213-002-1037-y a a
Snjezana Lelas; James K. Rowlett; Roger D. Spealman; James M. Cook; Chunrong Ma; Xiaoyan Li; Wenyuan Yin2002 May 01English
Psychopharmacology vol. 165 iss. 3 pp.209—215
Discriminative stimulus effects of zolpidem in squirrel monkeys: role of GABAA/α1receptors
DOI: 10.1007/s00213-002-1275-z a a
James K. Rowlett; Roger D. Spealman; Snjezana Lelas; James M. Cook; Wenyuan Yin2003 JanuaryEnglish
Evolution vol. 63 iss. 4 pp.854—869
EXTREME HOST PLANT CONSERVATISM DURING AT LEAST 20 MILLION YEARS OF HOST PLANT PURSUIT BY OAK GALLWASPS
DOI: 10.1111/j.1558-5646.2008.00604.x a a
Graham N. Stone; Antonio Hernandez-Lopez; James A. Nicholls; Erica Di Pierro; Juli Pujade-Villar; George Melika;[...]2009 AprilEnglish
Bioorganic & Medicinal Chemistry vol. 21 iss. 1 pp.93—101
Search for α3β2/3γ2 subtype selective ligands that are stable on human liver microsomes
DOI: 10.1016/j.bmc.2012.10.057 a a
Ojas A. Namjoshi; Zhi-jian Wang; Sundari K. Rallapalli; Edward Merle Johnson Jr.; Yun-Teng Johnson; Hanna Ng;[...]2013 JanuaryEnglish
Evolution vol. 63 iss. 4 pp.854—869
Extreme Host Plant Conservatism during at Least 20 Million Years of Host Plant Pursuit by Oak Gallwasps
DOI: 10.2307/25483638 a a
Graham N. Stone, Antonio Hernandez-Lopez, James A. Nicholls, Erica di Pierro, Juli Pujade-Villar, George Melika and James M. Cook2009 AprilEnglish
Phytotherapy Research vol. 24 iss. 9 pp.1309—1316
Behavioural characterization of four endemic Stachys taxa
DOI: 10.1002/ptr.3106 a a
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Synthesis and structure–activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein
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Bioorganic & Medicinal Chemistry vol. 18 iss. 12 pp.4178—4186
A new class of potential anti-tuberculosis agents: Synthesis and preliminary evaluation of novel acrylic acid ethyl ester derivatives
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Bioorganic & Medicinal Chemistry Letters vol. 18 iss. 21 pp.5745—5749
New classes of Gram-positive selective antibacterials: Inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis
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Progress in Neuro-Psychopharmacology and Biological Psychiatry vol. 34 iss. 2 pp.376—386
Novel positive allosteric modulators of GABAA receptors: Do subtle differences in activity at α1 plus α5 versus α2 plus α3 subunits account for dissimilarities in behavioral effects in rats?
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ChemInform vol. 30 iss. 21 pp.no—no
ChemInform Abstract: Extension of the Tandem Pauson—Khand Reaction to [5.6.6.5]Tetracycles: A Unique Entry into cis-Fused Decalins.
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First Enantiospecific Total Synthesis of the Important Biogenetic Intermediates, (+)-Polyneuridine(Ia) and (+)-Polyneuridine Aldehyde(IIa), as well as 16-Epi-vellosimine (IIb) and Macusine A (Ib).
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Wenyuan Yin; Jun Ma; Felix M. Rivas; James M. Cook2007 May 22

Now of course we went a step further an carried a proper human study. Pyeyzolam (selective a5) and Zolpidem (selective a1) strongly suggest that all of the positive subjective effects of alcohol are mediated by the a5 subunit whereas the negative effects are mediated by the a1 subunit. Anyone familiar with Zoplidem will recognise that it does has so nasty psychological side-effects such as loss of executive control, retrograde amnesia, mood lability and so forth.

The few who have sampled pyeyzolam will recognize that huge difference in subjective effects. One can get roughly 2 bottles of wine drunk inside 30 minutes and yet not fall asleep not think or do anything inappropriate, stupid or harmful AND the euphoria is cleaner. I know memory-loss was not an issue. Of course, it MAY have some re-enforcing effects but it totally stopped cravings in alcohol dependant subjects.

So don't expect to see it as a street drug, expect it as a medicine to treat alcoholism and maybe, in the fullness of time, as an alcohol alternative.
 

ID Time add. Title Series Author(s) Publisher Year PagesLanguage
Drug Development Research vol. 1 iss. 1 pp.83—88
Alfentanil (R 39 209) — a particularly short-acting intravenous narcotic analgesic in rats
DOI: 10.1002/ddr.430010111 a a
C. J. E. Niemegeers; P. A. J. Janssen1981English
Drug Development Research vol. 1 iss. 2 pp.167—179
Effects of morphine, fentanyl, sufentanil, and the short-acting morphine-like analgesic alfentanil on the EEG in dogs
DOI: 10.1002/ddr.430010210 a a
Dr. A. Wauquier; W. A. E. Van Den Broeck; C. J. E. Niemegees; P. A. J. Janssen1981English
Psychopharmacology vol. 57 iss. 1 pp.21—26
Narcotic cuing and analgesic activity of narcotic analgesics: Associative and dissociative characteristics
DOI: 10.1007/bf00426952 a a
Francis C. Colpaert; Carlos J. E. Niemegeers; Paul A. J. Janssen1978English
Journal of Medicinal Chemistry vol. 29 iss. 11 pp.2290—2297
Synthetic 1,4-disubstituted 1,4-dihydro-5H-tetrazol-5-one derivatives of fentanyl: Alfentanil (R 39209), a potent, extremely short-acting narcotic analgesic
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Clinical Therapeutics vol. 32 iss. 7 pp.1427—1436
Pharmacokinetics, analgesic effect, and tolerability of a single preprocedural dose of intranasal fentanyl in patients undergoing drain removal after breast reduction or augmentation surgery: A prospective, randomized, double-blind, placebo-controlled study
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Antinociceptive activity of chemical congeners of improgan: Optimization of side chain length leads to the discovery of a new, potent, non-opioid analgesic
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Lindsay B. Hough; Iwan J.P. de Esch; Elwin Janssen; James Phillips; Konstantina Svokos; Brian Kern; Jennifer Trachler;[...]2006 SeptemberEnglish
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Receptor affinity and pharmacological potency of a series of narcotic analgesic, anti-diarrheal and neuroleptic drugs
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Kenneth D. Stahl; Willem Van Bever; Paul Janssen; Eric J. Simon1977 DecemberEnglish
Journal of Pharmacy and Pharmacology vol. 10 iss. 1 pp.14—21
A NEW SERIES OF POTENT ANALGESICS: Dextro 2:2-diphenyl-3-methyl-4-morpholinobutyrylpyrrolidine and related basic amides: Part II :Comparative analgesic activity, acute toxicity and tolerance development in rats for R875, morphine, pethidine and methadone
DOI: 10.1111/j.2042-7158.1958.tb10268.x a a
Janssen, Paul A. J.; Jageneau, Anton H.1958 SeptemberEnglish
Journal of Medicinal Chemistry vol. 21 iss. 5 pp.474—476
Synthesis and analgesic activity of some long-acting piperidinospiro derivatives of methadone
DOI: 10.1021/jm00203a014 a a
Frincke, James M.; Henderson, Gary L.; Janssen, Paul A. J.; Van der Eycken, Cyriel A. M.1978 MayEnglish
Journal of Pharmacy and Pharmacology vol. 13 iss. 1 pp.513—530
PIRINITRAMIDE (R 3365), A POTENT ANALGESIC WITH UNUSUAL CHEMICAL STRUCTURE
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Janssen, Paul A. J.1961 SeptemberEnglish
Journal of Pharmacy and Pharmacology vol. 28 iss. 3 pp.183—187
The narcotic discriminative stimulus complex: relation to analgesic activity
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Colpaert, F. C. ;Niemegeers, C. J. E. ;Janssen, P. A. J.1976 MarchEnglish
ChemInform vol. 18 iss. 16
ChemInform Abstract: Synthetic 1,4-Disubstituted-1,4-Dihydro-5H-tetrazol-5-one Derivatives of Fentanyl: Alfentanil (R 39209), a Potent, Extremely Short-Acting Narcotic Analgesic.
DOI: 10.1002/chin.198716217 a a
JANSSENS, F.; TORREMANS, J.; JANSSEN, P. A. J.1987 April 21
Chemischer Informationsdienst vol. 9 iss. 46
ChemInform Abstract: SYNTHESIS AND ANALGESIC ACTIVITY OF SOME LONG-ACTING PIPERIDINOSPIRO DERIVATIVES OF METHADONE
DOI: 10.1002/chin.197846256 a a
FRINCKE, J. M. ;HENDERSON, G. L. ;JANSSEN, P. A. J. ;VAN DER EYCKEN, C. A. M.Wiley1978 November 14

Useful papers pertaining to Jannsen's development of R4066 derivatives, dextromoramide (Palfium) and alfentanil (Alfenta).

It's worth noting that Jannsen first explored the 3,3-diphenylheptanone class and then moved to the phenylpiperidnylpropanamide class as it's simpler synthesis and higher activity would be cheaper to develop and if successful, cheaper to produce. It's worth noting that it's hard to produce very short-acting 3,3-diphenylheptanone analgesics and indeed with the ORLA derivative of R-4066 IS very potent (x212 M), it's duration of action is about 2 days.

I would certainly be interested to know if the cyclopentylamide moiety of dextromoramide is compatible with the N-substitution of R-4066 because the parent compounds both have a duration of 3 hours and a Palfium-like drug with a potency of over x100 morphine would most certainly be a VERY attractive target. Fake Palfium would sell a LOT although I hate fake pills. People have the right to know how much of what they are taking - without that, informed consent isn't.
 
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