Comparative Analysis of Theoretical and Empirical Data of Synthetic Cannabinoids

I. O. Abdulsalami; M. D. Adeoye,; K. A. Alabi; B. A. Abdulsalami; N. O. Abolurin

doi:10.53704/fujnas.v7i1.247

Authors

I. O. Abdulsalami Department of Chemical Sciences, Fountain University, Osogbo, Nigeria
M. D. Adeoye, Department of Chemical Sciences, Fountain University, Osogbo, Nigeria
K. A. Alabi Department of Chemical Sciences, Fountain University, Osogbo, Nigeria
B. A. Abdulsalami Department of Mathematical and Computer Sciences, Fountain University, Osogbo, Nigeria
N. O. Abolurin Department of Chemical Sciences, Fountain University, Osogbo, Nigeria

DOI:

https://doi.org/10.53704/fujnas.v7i1.247

Abstract

Comparative studies of spectroscopic data of indol-3-carboxylates and indazole-3-carboxylates are reported from theoretical and empirical viewpoints. Structures of indol-3-carboxylates and indazole-3-carboxylates were modeled; quantum chemical method was employed to investigate the spectroscopic (NMR and FT-IR) properties of the structures. The results obtained from the theoretical studies were compared to empirical results obtained for the spectroscopic properties of these compounds and level of agreement (or disagreement) between the results for the two studies are reported. The scope of the study is limited to the modeling, structural, and electronic and spectroscopic analyses of the modeled structures and comparative analysis of the theoretical data with published experimental data. The absorption transitions were calculated from the optimized geometry in the ground state (S₀) using TD-B3LYP/6-31G**. The energy band gaps calculated showed that Naphthalene-1-yl-(5-fluoropentyl)-1H-indazole-3-carboxylate (M5) has the lowest band gap energy, which may have a substantial influence on the intramolecular charge transfer and bioactivity of the molecule. The ¹³C and ¹HNMR chemical shifts calculated at ab initio and DFT agreed with the experimental data. DFT/6-311G** has the best correlation with fitting factor 0.9956.Thus the chemical shifts from DFT/6-311G** are very close to the experimental and can be used in the absence of experimental data. The vibrational frequency analyses by DFT/B3LYP method are in reasonable agreement with the experimental values.

Keywords: Density functional theory; Frontier molecular orbitals; Spectroscopic properties; Basis set; Indazole-3-carboxamide; N-1-methoxycarbonylalkyl group

References

Belendiuk, K. A., Baldini, L. L., & Bonn-Miller, M. O. (2015). Narrative review of the safety and efficacy of cannabis for the treatment of commonly state-approved medical and psychiatric disorders. Addictive Science Clinical Practise. 21; 10(1): 10.

Eisenberg, E., Ogintz, M., & Almog, S. (2014). The pharmacokinetics, efficacy, safety, and ease of use of a novel portable metered-dose cannabis inhaler in patients with chronic neuropathic pain: a phase 1a study. Journal of Pain Palliative Care Pharmacother. 28(3): 216-25.

Ellis, R. J., Toperoff, W., Vaida, F., Van den Brande, G., Gonzales, J., Gouaux, B., Bentley, H., & Atkinson, J. H. (2009). Smoked medicinal cannabis for neuropathic pain in HIV: a randomized, crossover clinical trial. Neuro-psycho Pharmacology. 34(3): 672-80.

Hassan, T. (2010). Quantum chemical computational studies on 2-methyl-6-[2-(trifluoromethyl) phenyl iminomethyl] phenol. Journal of Molecular Structure: Theoretical Chemistry. 950: 5-12

Hazekamp, A., Ware, M. A., Muller-Vahl, K. R., Abrams, D., & Grotenhermen, F. (2013). The medicinal use of cannabis and cannabinoids—an international cross-sectional survey on administration forms. Journal of Psychoactive Drugs 45, 199-210.

Jorge, F. E., Morigaki, M. K., & Sara, S. J. (2012) Quantum Chemical Investigation on determination of electronic, structural and electrical properties of some even carbon cage fullerenes, Indian Journal of Chemistry 51, 911-916.

Kumara, N. T. R. N., Muhammad, R. R. K., Andery, L., Mohammad, I. P., Nyuk, Y. V., Chee, M. L., & Piyasiri E. (2013). DFT/TDDFT and Experimental Studies of Natural Pigments Extracted from Black Tea Waste for DSSC Application. International Journal of Photoenergy. 1-8.

Lundqvist, M. J., Nilsing, M., Persson, P., & S. Lunell. (2006). Spacer and anchor effects on the electronic coupling in Ruthenium bis-terpyridine dye-sensitized TiO2 nanocrystals studied by DFT. International Journal of Quantum Chemistry. 106: 3214-3228.

Manhapra, A., Stefanovics, E., & Rosenheck, R. (2015). Treatment outcomes for veterans with PTSD and substance use: Impact of specific substances and achievement of abstinence. Drug Alcohol Dependence. (15) 01664-6.

Naftali, T., Bar-Lev, S. L., Dotan, I., Lansky, E. P., Sklerovsky B. F., & Konikoff F. M. (2013) Cannabis induces a clinical response in patients with Crohn's disease: a prospective placebo.

Ono M., Ogilvie J. M., Wilson, J. S., Green, H. J., Chambers, S. K., Ownsworth, T., & Shum, D. H. (2015). A meta-analysis of cognitive impairment and decline associated with adjuvant chemotherapy in women with breast cancer. Front Oncology. 50-59.

Rajal, G, Saravanan, K., & Sivakumar, S. (2015). Quantum chemical and corrosion inhibition studies of an organic compound: 2, 5-dichloroaniline. Rasayan Journal 8(1), 8-12.

Semire, B., & Adeoye I. O. (2013). Molecular Orbital Studies (Hardness, Chemical Potential and Electrophilicity) and Solvent Effect on 3-Mehtyl-, 4-Methyl and 4-Phenylpicolinic Acid: Density Functional Theory (DFT). Middle-East Journal of Scientific Research, 18 (5), 597-608.

Shafran, Y., Vadim S., Vladimir, M., Alexander, N., Oleg, B., & Alexander B. (2014). Synthetic cannabinoids as designer drugs: New representatives of indol-3-carboxylates series and indazole-3-carboxylates as novel group of cannabinoids. Identification and analytical data, Forensic Science International, 244, 263–275.

Stern, E. & Lambert, D. M. (2007). Medicinal chemistry endeavors around the phyto-cannabinoids. Chemical Biodiversity: 4, 1707-1728.

Sun, X., Xu, C. S., Chadha, N., Chen, A., & Liu, J. (2015). Marijuana for Glaucoma: A Recipe for Disaster or Treatment? Yale Journal Biological Medicine. 88(3): 265-9.

Thomas, G., Kloner, R. A., & Rezkalla, S. (2014). Adverse cardiovascular, cerebrovascular, and peripheral vascular effects of marijuana inhalation: what cardiologists need to know? American Journal of Cardiology. 113(1): 187-90.

Ware, M. A., Wang, T., Shapiro, S., Robinson, A., Ducruet, T., Huynh, T., Gamsa, A., Bennett, G. J., & Collet, J. P. (2010). Smoked cannabis for chronic neuropathic pain: a randomized controlled trial. Canadian Medical Association Journal. 182(14): E694-701.

Wilkinson, S.T., Stefanovics, E., & Rosenheck, R. A. (2015). Marijuana use is associated with worse outcomes in symptom severity and violent behaviour in patients with posttraumatic stress disorder. Journal of Clinical Psychiatry. 76(9): 1174-80.