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

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The structure of a confiscated street drug: 6-Monoacetyl morphine hydrochloride trihydrate - C19H22NO4Cl·3H2O


Matthew Wood (1) orcid , Ivan Bernal (2) orcid , Roger Lalancette (3,*) orcid

(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

Abstract


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).


Keywords


Heroin; Morphine; Pi-pi bond; Water clusters; Hydrogen bonds; Water amphoterism

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DOI: 10.5155/eurjchem.12.1.52-55.2077

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Department of Chemistry, Rutgers University, 73 Warren St., Newark, NJ, 07102 USA.

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The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Wood, M.; Bernal, I.; Lalancette, R. Eur. J. Chem. 2021, 12(1), 52-55. doi:10.5155/eurjchem.12.1.52-55.2077
Wood, M.; Bernal, I.; Lalancette, R. The structure of a confiscated street drug: 6-Monoacetyl morphine hydrochloride trihydrate - C19H22NO4Cl·3H2O. Eur. J. Chem. 2021, 12(1), 52-55. doi:10.5155/eurjchem.12.1.52-55.2077
Wood, M., Bernal, I., & Lalancette, R. (2021). The structure of a confiscated street drug: 6-Monoacetyl morphine hydrochloride trihydrate - C19H22NO4Cl·3H2O. European Journal of Chemistry, 12(1), 52-55. doi:10.5155/eurjchem.12.1.52-55.2077
Wood, Matthew, Ivan Bernal, & Roger Lalancette. "The structure of a confiscated street drug: 6-Monoacetyl morphine hydrochloride trihydrate - C19H22NO4Cl·3H2O." European Journal of Chemistry [Online], 12.1 (2021): 52-55. Web. 16 Jun. 2021
Wood, Matthew, Bernal, Ivan, AND Lalancette, Roger. "The structure of a confiscated street drug: 6-Monoacetyl morphine hydrochloride trihydrate - C19H22NO4Cl·3H2O" European Journal of Chemistry [Online], Volume 12 Number 1 (31 March 2021)

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