87
Views
0
CrossRef citations to date
0
Altmetric
Research Article

The conglomerate crystal formation of methoxetamine salts in the presence of some organic achiral anions: a theoretical approach

, &
Pages 183-193 | Received 08 May 2021, Accepted 14 Jul 2021, Published online: 18 Aug 2021

References

  • Zhao YM, Sun LL, Knierman MD, et al. Fast separation and analysis of reduced monoclonal antibodies with capillary zone electrophoresis coupled to mass spectrometry. J Talanta. 2016;148:529–533.
  • Deblonde GJP, Chagnes A, Cote G, et al. Development of a capillary electrophoresis method for the analysis in alkaline media as polyoxoanions of two strategic metals: niobium and tantalum. J Chromatog A. 2016;1437:210–218.
  • Cho S, Shim J, Kim SM, et al. On-line sample cleanup and chiral separation of gemifloxacin in a urinary solution using chiral crown ether as a chiral selector in microchip electrophoresis. J Chromatog A. 2004;1055:241–245.
  • Snyder DS, Tradtrantip L, Battula S, et al. Absolute configuration and biological properties of enantiomers of CFTR inhibitor BPO-27. ACS Med Chem Lett. 2013;4:456–459.
  • Maffeia F, Brancatellib G, Barbozaa T, et al. Inherently chiral phosphonate cavitands as enantioselective receptors for mono-methylated L-amino acids. Supramol Chem. 2018;30:600–609.
  • Neale PA, Branch A, Khan SJ, et al. Evaluating the enantiospecific differences of non-steroidal anti-inflammatory drugs (NSAIDs) using an ecotoxicity bioassay test battery. Sci Total Environ. 2019;694:133659–133666.
  • Tan SC, Patel BK, Jackson SHD, et al. Stereoselectivity of ibuprofen metabolism and pharmacokinetics following the administration of the racemate to healthy volunteers. Xenobiotica. 2002;32:683–697.
  • Mori K. Bioactive natural products and chirality. Chirality. 2011;23(6):449–462.
  • Leusen FJJ. Crystal structure prediction of diastereomeric salts:  a step toward rationalization of racemate resolution. Cryst Growth Des. 2003;3:189–192.
  • Zeilhofer HU, Swandulla D, Geisslinger G, et al. Differential effects of ketamine enantiomers on NMDA receptor currents in cultured neurons. Eur J Pharmacol. 1992;213(1):155–158.
  • Rogeout C, Hein EJ. Application of continuous preferential crystallization to efficiently access enantiopure chemicals. Org Process Res Dev. 2015;19:1809–1819.
  • Liu L, Sun D, Li F, et al. Enantioselective liquid-liquid extraction of valine enantiomers in the aqueous two-phase system formed by the cholinium amino acid ionic liquid copper complexes and salt. J Mol Liq. 2019;294:111599–111606.
  • Li M, Zhang J, Ma S, et al. Chiral separation of five antihistamine drug enantiomers and enantioselective pharmacokinetic study of carbinoxamine in rat plasma by HPLC-MS/MS. New J Chem. 2020;44:5819–5827.
  • Shiomi S, Misaka R, Kanekoa M, et al. Enantioselective total synthesis of the unnatural enantiomer of quinine. Chem Sci. 2019;10:9433–9437.
  • D’Oria E, Karamertzanis PG, Price SL. Spontaneous resolution of enantiomers by crystallization: insights from computed crystal energy landscapes. Cryst Growth Des. 2010;10:1749–1756.
  • Steed JW. 21st century developments in the understanding and control of molecular solids. ChemComm. 2018;54:13175–13182.
  • Steed JW. The role of co-crystals in pharmaceutical design. Trends Pharm Sci. 2013;34(3):185–193.
  • Srisanga S, Horst JH. Racemic compound, conglomerate, or solid solution: phase diagram screening of chiral compounds. Cryst Growth Des. 2010;10:1808–1812.
  • He Q, Rohani S, Zhu J, et al. Crystallization of the racemic compound and conglomerate of (RS)-2-chloromandelic acid. Crystal Growth & Design. 2010;10(12):5136–5145.
  • Kozma D, Böcskei Z, Simon K, et al. Racemic compound formation–conglomerate formation. Part. 1. Structural and thermoanalytical study of hydrogen malonate, hydrogen phthalate and hydrogen succinate of α-phenylethylamine. J Chem Soc Perkin Trans. 1994;2(8):1883–1886.
  • Choobdari E, Fakhraian H, Peyrovi MH. Anion effect on the binary and ternary phase diagrams of chiral medetomidine salts and conglomerate crystal formation. Chirality. 2014;26(3):183–188.
  • Khavani M, Kalantarinezhad R, Izadyar M. A joint QM/MD study on α-, β- and γ-cyclodextrins in selective complexation with cathinone. Supramol Chem. 2018;30:687–696.
  • Javadi N, Aallaei M, Adib K, et al. Theoretical Investigations on the Separation of Medetomidine Enantiomers. Chem Methodol. 2020;4(6):788–797
  • Gavezzotti A, Presti LL. Theoretical study of chiral carboxylic acids. structural and energetic aspects of crystalline and liquid states. Cryst Growth Des. 2015;15:3792–3803.
  • Zarei V, Javadi N, Ghahramani Z, et al. Role of Hydrogen Transfer and Ionic Bonding on RR, SS and RS Medetomidine Conglomerates/Acids Stability: A Theoretical Study. Science. 2019;30:241–250
  • Javadi N, Habibzade S, Aallaei M, et al. Feasibility of enantiomeric separation of racemic compounds using a simple method: Theoretical investigation of anion ability to conglomerate crystal formation of ketamine salts. Eurasian Chem Commun. 2020;2:1050–1058
  • Dargan PI, Tang HC, Liang W, et al. Three months of methoxetamine administration is associated with significant bladder and renal toxicity in mice. Clin Toxicol. 2014;52:176–180.
  • Ornella C, Fabrizio S, Pierluigi S, et al. Phenomenon of new drugs on the Internet: the case of ketamine derivative methoxetamine. Hum Psychopharmacol. 2012;27:145–149.
  • Hondebrink L, Nugteren-van Lonkhuyzen JJ, Van Der Gouwe D, et al. Monitoring new psychoactive substances (NPS) in The Netherlands: data from the drug market and the Poisons Information Centre. Drug Alcohol Depend. 2015;147:109–115.
  • Lee EE, Della Selva MP, Liu A, et al. Ketamine as a novel treatment for major depressive disorder and bipolar depression: a systematic review and quantitative meta-analysis. Gen Hosp Psychiatr. 2015;37:178–184.
  • Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, Revision B.09. Wallingford CT: Gaussian, Inc; 2009.
  • Kona J, Fabian WMF. Hybrid QM/MM calculations on the first redox step of the catalytic cycle of bovine glutathione peroxidase GPX1. J Chem Theory Comput. 2011;7:2610–2616.
  • Cossi M, Barone V, Cammi R, et al. Ab initio study of solvated molecules: a new implementation of the polarizable continuum model. Chem Phys Lett. 1996;255:327–335.
  • Scalmani G, Frisch MJ. Continuous surface charge polarizable continuum models of solvation. I. general formalism. J Chem Phys. 2010;132:114110–114118.
  • Reed AE, Curtiss LA, Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev. 1988;88:899–926.
  • Lu T, Chen F. Multiwfn: a multifunctional wavefunction analyzer. J Comput Chem. 2012;33:580–592.
  • Scherer W, Sirsch P, Shorokhov D, et al. Valence charge concentrations, electron delocalization andβ-agostic bonding in d0 metal alkyl complexes. Chem Eu J. 2003;9:6057–6070.
  • Schmider H, Becke A. Chemical content of the kinetic energy density. J Mol Struc. 2000;527:51–61.
  • Chaudret R, De Courcy B, Contreras-Garcia J, et al. Unraveling non-covalent interactions within flexible biomolecules: from electron density topology to gas phase spectroscopy. Phys Chem Chem Phys. 2014;16:9876–9891.
  • Jeffrey, G.A. An Introduction to Hydrogen Bonding, Oxford University Press: New York and Oxford, 1997
  • Muzio SD, Ramondo F, Gontrani F, et al. Choline hydrogen dicarboxylate ionic liquids by X-ray scattering, vibrational spectroscopy and molecular dynamics: h-fumarate and H-maleate and their conformations. Molecules. 2020;25:4990–5010.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.