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Name

Morphine

IUPAC names

17-Methyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α-diol
(4R,4aR,7S,7aR,12bS)-3-Methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-7,9-diol
(5α,6α)-17-Methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol

ID 9155 · Formula C₁₇H₁₉NO₃ · Molecular weight 285.338

InChI InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1

InChI Key BQJCRHHNABKAKU-KBQPJGBKSA-N This stereoisomer Any stereoisomer

SMILES O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O

ChemSpider 4450907
PubChem 5288826
Wikidata Q81225
Erowid Morphine
Wikipedia Morphine
PsychonautWiki Morphine
swgdrug.org Opium
aipsin.com Morphine (Iss. 3, Jun-Sep 2019: V-3)

Casy, AF; Beckett, AH; Hall, GH; Vallance, DK. Chemistry and pharmacology of 4-alkoxy-piperidines related to reversed esters of pethidine J. Med. Chem., 1 Dec 1961, 4 (3), 535–551. 891 kB. https://doi.org/10.1021/jm50019a012 IR,UV

Harper, NJ; Simmonds, AB. Flurocompounds related to the reversed esters of pethidine J. Med. Chem., 1 Apr 1959, 1 (2), 181–185. 291 kB. https://doi.org/10.1021/jm50003a006 #23

Vuckovic, S; Prostran, M; Ivanovic, M; Dosen-Micovic, L; Todorovic, Z; Nesic, Z; Stojanovic, R; Divac, N; Mikovic, Z. Fentanyl analogs: Structure-activity-relationship study Curr. Med. Chem., 1 Jul 2009, 16 (19), 2468–2474. 211 kB. https://doi.org/10.2174/092986709788682074 #21

Janssen, PAJ; Jageneau, AHM; Demoen, PJA; van De. Westeringh, C; Raeymaekers, AHM; Wouters, MSJ; Sanczuk, S; Hermans, BKF; Loomans, JLM. Compounds related to pethidine--I. Mannich bases derived from norpethidine and acetophenones J. Med. Chem., 1 Feb 1959, 1 (1), 105–120. 695 kB. https://doi.org/10.1021/jm50002a008 #47 UV

Brandt, SD; Kavanagh, PV. Addressing the challenges in forensic drug chemistry Drug Test. Anal., 1 Mar 2017, 9 (3), 342-346. 120 kB. https://doi.org/10.1002/dta.2169

Balayssac, S; Retailleau, E; Bertrand, G; Escot, M; Martino, R; Malet-Martino, M; Gilard, V. Characterization of heroin samples by ¹H NMR and 2D DOSY ¹H NMR Forensic Sci. Int., 1 Jan 2014, 234, 29-38. 1.4 MB. https://doi.org/10.1016/j.forsciint.2013.10.025 NMR

Chen, P; Braithwaite, RA; George, C; Hylands, PJ; Parkin, MC; Smith, NW; Kicman, AT. The poppy seed defense: a novel solution: ‘The poppy seed defense’ - a novel solution Drug Test. Anal., 1 Mar 2014, 6 (3), 194-201. 477 kB. https://doi.org/10.1002/dta.1590 MS

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

Desai, RI; Thakur, GA; Vemuri, VK; Bajaj, S; Makriyannis, A; Bergman, J. Analysis of Tolerance and Behavioral/Physical Dependence during Chronic CB1 Agonist Treatment: Effects of CB1 Agonists, Antagonists, and Noncannabinoid Drugs J. Pharmacol. Exp. Ther., 29 Nov 2012, 344 (2), 319-328. 1.1 MB. https://doi.org/10.1124/jpet.112.198374

EMCDDA. Report on the risk assessment of N-phenyl-N-[1-(2-phenylethyl)piperidin-4- yl]oxolane-2-carboxamide (THF-F), European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Jul 2018. 549 kB. #Morphine

EMCDDA. Report on the risk assessment of N-(4-fluorophenyl)-2-methyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide (4F-iBF), European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Jul 2018. 1.2 MB. #Morphine

EMCDDA. Report on the risk assessment of N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]furan-2-carboxamide (Furanylfentanyl), European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Dec 2017. 728 kB. #Morphine

EMCDDA. Report on the risk assessment of MT-45, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Oct 2015. 814 kB. #Morphine MS,IR,UV

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 #1

Ellis, CR; Kruhlak, NL; Kim, MT; Hawkins, EG; Stavitskaya, L. Predicting opioid receptor binding affinity of pharmacologically unclassified designer substances using molecular docking PLOS ONE, 24 May 2018, 13 (5), e0197734. 5.5 MB. https://doi.org/10.1371/journal.pone.0197734 #Morphine

Åstrand, A; Guerrieri, D; Vikingsson, S; Kronstrand, R; Green, H. In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT_1A, and 5-HT2_A receptors—On-target receptor potency and efficacy, and off-target effects Forensic Sci. Int., 1 Dec 2020, 317, 110553. 1.7 MB. https://doi.org/10.1016/j.forsciint.2020.110553 #Morphine

Presley, CC; Lindsley, CW. DARK classics in chemical neuroscience: Opium, a historical perspective ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2503–2518. 13.0 MB. https://doi.org/10.1021/acschemneuro.8b00459 #1

McKibben, T. Protecting group chemistry JCLIC, 1 Oct 1997, 7 (4), 30-42. 1.1 MB.

Chappell, JS. Infrared absorption properties of solid-dosage drug substances. Part II. Infrared absorption by hydrogen bonds JCLIC, 1 Mar 2014, 24 (2-3), 9-27. 1.6 MB. IR

Ujváry, I; Christie, R; Evans-Brown, M; Gallegos, A; Jorge, R; de Morais, J; Sedefov, R. DARK classics in chemical neuroscience: Etonitazene and related benzimidazoles ACS Chem. Neurosci., 7 Apr 2021, 12 (7), 1072–1092. 2.0 MB. https://doi.org/10.1021/acschemneuro.1c00037 #1

Devereaux, AL; Mercer, SL; Cunningham, CW. DARK classics in chemical neuroscience: Morphine ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2395-2407. 3.0 MB. https://doi.org/10.1021/acschemneuro.8b00150 #1

Cook, CE; Brine, DR. Pyrolysis products of heroin J. Forensic Sci., 1 Jan 1985, 30 (1), 251–261. 393 kB. https://doi.org/10.1520/JFS10990J #Morphine MS,NMR,UV

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Johnson, H. Quantitative stereo-structure activity relationships I. Opiate receptor binding In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; Vol. 22, pp 146–158. 685 kB.

Azoury, M; Zelkowicz, A; Goren, Z; Almog, J. Evaluation of ninhydrin analogues and other electron-deficient compounds as spray reagents for drugs on thin layer chromatograms Microgram J., 1 Jan 2003, 1 (1–2), 23–31. 318 kB. spot

2-MeO-Benzyl-MDMA · α-(2-Methoxybenzyl)-N-methyl-3,4-methylenedioxyphenethylamine

3-MeO-Benzyl-MDMA · α-(3-Methoxybenzyl)-N-methyl-3,4-methylenedioxyphenethylamine

4-MeO-Benzyl-MDMA · α-(4-Methoxybenzyl)-N-methyl-3,4-methylenedioxyphenethylamine

4-HOOC-A-NBOH · N-(2-Hydroxybenzyl)-4-carboxyamphetamine

Hydromorphone

Piperine

N-(2-Methoxybenzyl)-3,4-dimethylenedioxyphenethylamine · MDPEA-NBOMe

Norcodeine

7 Dec 2019 · · Isomer Design