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Names

Codeine
3-Methylmorphine

IUPAC names

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

ID 9293 · Formula C₁₈H₂₁NO₃ · Molecular weight 299.364

InChI InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1

InChI Key OROGSEYTTFOCAN-DNJOTXNNSA-N This stereoisomer Any stereoisomer

SMILES COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1O)C

ChemSpider 4447447
PubChem 5284371
Wikidata Q174723
Erowid Codeine
Wikipedia Codeine
PsychonautWiki Codeine
swgdrug.org Opium
aipsin.com Codeine (Iss. 3, Jun-Sep 2019: V-3)

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 #45 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

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 #Codeine

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 #2

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 #Codeine

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 #2

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 #2

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 #Codeine MS,NMR,UV

Søndergaard, K; Kristensen, JL; Palner, M; Gillings, N; Knudsen, GM; Roth, BL; Begtrup, M. Synthesis and binding studies of 2-arylapomorphines Org. Biomol. Chem., 1 Jan 2005, 3 (22), 4077. 166 kB. https://doi.org/10.1039/b507195j #2 MS,NMR,TLC

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

URB-532

4-Carboxy-A-NBOMe · N-(2-Methoxybenzyl)-4-carboxyamphetamine

4-HOOC-MA-NBOH · N-(2-Hydroxybenzyl)-N-methyl-4-carboxyamphetamine

25H-NBOMe imine

Hydrocodone

Metopon

Isocodeine

7 Dec 2019 · · Isomer Design