OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS
The structure of a confiscated street drug: 6-Monoacetyl morphine hydrochloride trihydrate - C19H22NO4Cl·3H2O
Matthew Wood (1) , Ivan Bernal (2) , Roger Lalancette (3,*)
(1) Carl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, 73 Warren St., Newark, NJ, 07102 USA
(2) Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, 2050 Johannesburg ZA South Africa
(3) Carl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, 73 Warren St., Newark, NJ, 07102 USA
(*) Corresponding Author
Received: 22 Jan 2021 | Revised: 10 Feb 2021 | Accepted: 18 Feb 2021 | Published: 31 Mar 2021 | Issue Date: March 2021
Since street drugs are frequently and rapidly modified, in order to circumvent the current laws that make them illicit, it is necessary to fully identify them by single crystal X-ray diffraction; subsequently, ideal powder patterns are computed for rapid identification of additional confiscations, which are mostly available in powder form. Monoacetyl morphine is found in samples of heroin as a by-product of incomplete synthesis, or from degradation of diacetyl morphine caused by heat, humidity, or pH changes. It is formed by the hydrolysis of the acetyl function on the benzene moiety of the morphine ring, thereby inserting an OH moiety at that site. This compound, 6-monoacetyl morphine, is the primary and active metabolite of heroin, rapidly hydrolyzed in the user’s blood. Herein, we describe the structure of 6-monoacetyl morphine, IUPAC name: [(4R,4aR,7S,7aR,12bS)-9-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate (A), as the trihydrated hydrochloride, whose structure has not been described previously. Our crystals belong in space group P212121 with cell parameters of a = 6.9367(2), b = 13.0374(3), c = 21.9856(6) Å, V = 1988.30 (9) Å3; its composition is C19H22NO4Cl·3H2O, and Z = 4.0. A full sphere of data was collected at 100 K using CuKα radiation (λ = 1.54178 Å), yielding 3594 unique reflections measured and a final R-factor = 4.1%, with a Flack parameter = 0.05(1).
Links for Article
| | | | | | |
| | | | | | |
| | | |
Article MetricsThis Abstract was viewed 261 times | PDF Article downloaded 74 times
Department of Chemistry, Rutgers University, 73 Warren St., Newark, NJ, 07102 USA.
. Wood, M. R.; Lalancette, R. A.; Bernal, I. Acta Crystallogr. C 2015, 71 (1), 32-38.
. Wood, M. R.; Bernal, I.; Lalancette, R. A. Acta Crystallogr. C 2016, 72 (1), 48-51.
. Wood, M. R.; Bernal, I.; Lalancette, R. A. Struct. Chem. 2017, 28 (5), 1369-1376.
. Andersen, J. M.; Ripel, A.; Boix, F.; Normann, P. T.; Morland, J. J. Pharmacol. Exp. Ther. 2009, 331 (1), 153-161.
. Boix, F.; Andersen, J. M.; Morland, J. Addiction Biology 2011, 18 (1), 1-7.
. Balchin, E.; Malcolme-Lawes, D. J.; Rowe, M. D.; S. Smith, J. A.; Bearpark, M. J.; Steed, J. W.; Wu, W.; Horsewill, A. J.; Stephenson, D. New J. Chem. 2004, 28 (11), 1309-1314.
. Cambridge Structural Database CCSD (2019), http://www.ccdc.cam.ac.uk, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
. Sonar, V. N.; Parkin, S.; Crooks, P. A. Acta Crystallogr. E 2005, 61 (8), o2579-o2581.
. Kolev, T.; Bakalska, R.; Shivachev, B.; Petrova, R. Acta Crystallogr. E 2005, 61 (8), o2582-o2584.
. Bruker (2008). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
. Bruker (2009). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
. Sheldrick, G. M. SADABS. University of Gottingen, Germany, 1996.
. Sheldrick, G. M. Acta Crystallogr. A 2015, 71 (1), 3-8.
. Sheldrick, G. M. Acta Crystallogr. C 2015, 71 (1), 3-8.
. Diamond - Crystal and Molecular Structure Visualization, Crystal Impact - H. Putz and K. Brandenburg GbR, Kreuzherrenstr. 102, 53227 Bonn, Germany
. Canfield, D.; Barrick, J.; Giessen, B. C. Acta Crystallogr. B 1979, 35 (11), 2806-2809.
. Deschamps, J. R.; George, C.; Flippen-Anderson, J. L. Acta Crystallogr. C 1996, 52 (3), 698-700.
The Supplementary Material for this article can be found online at: Supplementary files
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.12.1.52-55.2077
| | | | | | | | |
| | | | | | |
Save to Zotero Save to Mendeley
European Journal of Chemistry 2021, 12(1), 52-55 | doi: https://doi.org/10.5155/eurjchem.12.1.52-55.2077 | Get rights and content
- There are currently no refbacks.
Copyright (c) 2021 Authors
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).
© Copyright 2010 - 2021 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.