1H-NMR and 13C-NMR dataset for some oxidative metabolites of CRA13 and their analogs
Medicinal Chemistry Laboratory, Department of Pharmacy, College of Pharmacy, Kyung Hee University, Seoul 02447, Republic of Korea
Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
Department of Life and Nanopharmaceutical Sciences, Kyung Hee University, Seoul 02447, Republic of Korea
KHU-KIST Department of Converging Science and Technology, Kyung Hee University, Seoul 02447, Republic of Korea
Abstract
CRA13 (CB-13; SAB-378) is a dual CB1R/CB2R agonist cannabinoid agent developed by Novartis Pharma. Upon administration, it undergoes metabolism to oxidative metabolites. Herein, the 1H-NMR and 13C-NMR dataset of some oxidative metabolites and analogs thereof are presented for further analysis and comparison purposes, for whom may be interested.
Article notes
Untitled section
Received 2018 Sep 7; Accepted 2018 Sep 26; Collection date 2018 Dec.
Specifications table
| Subject area | Chemistry |
| More specific subject area | Structural characterization |
| Type of data | Figures |
| How data was acquired | Nuclear magnetic resonance (NMR) spectral analyses were performed using a Brucker Avance 400 spectrometer (400 MHz for 1H-NMR) or Agilent 500 spectrometer (125 MHz for 13C-NMR). |
| Data format | Raw |
| Experimental factors | Sample solutions were prepared with deuterated CDCl3 or CD3OD. |
| Experimental features | Detection temperature was set at 25 °C. Samples were scanned 16 times for 1H-NMR spectra measurement, and scanned 1 h for 13C-NMR measurement |
| Data source location | Kyung Hee University, Seoul, Republic of Korea |
| Data accessibility | Data is provided in the article |
| Related research article | A.H.E. Hassan, M.C. Cho, H.I. Kim, J.S. Yang, K.T. Park, J.Y. Hwang, C.G. Jang, K.D. Park, Y.S. Lee, Synthesis of oxidative metabolites of CRA13 and their analogs: Identification of CRA13 active metabolites and analogs thereof with selective CB2R affinity, Bioorg. Med. Chem.26, 2018, 5069–5078, doi:10.1016/j.bmc.2018.09.007. |
Value of the data
- •CRA13 (CB-13; SAB-378) is a controlled cannabinoid substance in China and therefore a reference data for its metabolites are required.
- •The presented data provides reference that might be useful for detection of metabolites of CRA13 and related cannabinoids in biological samples.
- •In addition. It might be helpful in the assignment of signals of molecules containing di(naphthalen-1-yl)methanone moiety.
- •Also, the shown splitting and chemical shifts is helpful to structural analysis of related cannabinoids.
1.Data
The data presented herein describe the acquired for 1H-NMR and 13C-NMR spectra of hydroxy and carboxy metabolites of CRA13, as well as, methyl ester and analogs of the hydroxy, carboxy and methyl ester [1], [2]. Thus, a total of eight compounds were chemically synthesized and NMR data of pure samples were acquired in deuterated chloroform or deuterated methanol. These data might be useful for detection of metabolites of these controlled cannabinoids compounds and for structural assignment of compounds possessing di(naphthalen-1-yl)methanone moiety. The data are presented as figures with enlargement of proton peaks to clarify their splitting pattern.
2.Experimental design, materials, and methods
The compounds were chemically synthesized and purified by column chromatography as described in [1]. The samples were dissolved in CDCl3 or CD3OD then NMR spectra were acquired using a Brucker Avance 400 spectrometer (400 MHz) for 1H-NMR or Agilent 500 spectrometer (125 MHz) for 13C-NMR at 25 °C. The NMR peaks of the acquired NMR spectra are shown in Fig. 1, Fig. 2, Fig. 3, Fig. 4, Fig. 5, Fig. 6, Fig. 7, Fig. 8, Fig. 9, Fig. 10, Fig. 11, Fig. 12, Fig. 13, Fig. 14, Fig. 15, Fig. 16.
Acknowledgments
This work was supported by Korea Institute of Science and Technology (2Z05140-17-148).
Footnotes
Footnote Group
Contributor Information
Ahmed H.E. Hassan, Email: ahmed_hassan@mans.edu.eg, ahmed_hassan@khu.ac.kr.
Yong Sup Lee, Email: kyslee@khu.ac.kr.
Transparency document.Supplementary material
References
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References
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