Solid-state IR-LD spectroscopy of codeine and N-norcodeine derivatives
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Linear-dichroic infrared spectra (IR-LD) of 3-ethoxy-4-(N-norcodeino-)cyclobutene-1,2-dione (1) and codeine dihydrogenphosphate (Codeinum phosphoricum) (2), oriented as solid suspensions in nematic liquid crystals, have been measured. IR characteristic band assignments were made, and used in stereo-structural predictions. The results were compared with crystallographic structures of similar organic systems, and found to be in good agreement.
1 - 9 - 2006
1 - 9 - 2006
-  H.K. Erichsen, J.X. Hao and X.J. Xu: “Comparative actions of the opioid analgesics morphine, methadone and codeine in rat models of peripheral and central neuropathic pain”, Pain, Vol. 116, (2005), pp. 347–358. http://dx.doi.org/10.1016/j.pain.2005.05.004[Crossref]
-  J. Gonenne, I. Ferber and D. Burton: “Effect of a peripheral Mu-opioid antagonist, alvimopan, on gastrointestinal transit in health: Reversal of codeine effects and stimulation of colonic transit”, Gastroenterology, Vol. 28, (2005), pp. A94–A94.
-  H.J. Gruss, A. Sutton and P. Horton: “Codeine-induced slow transit in healthy volunteers and its alteration by peripheral opiate agonists”, Gastroenterology, Vol. 128, (2005), pp. A465–A466.
-  C. Neri, M. Guarna and E. Blanchi: “Endogenous morphine and codeine in the brain of non human”, Med. Sci. Monit., Vol. 10, (2004), pp. MS1–MS5.
-  A. Joshi, E. Parara and T.V. Macfarlane: “A double-blind randomised controlled clinical trial of the effect of preoperative ibuprofen, diclofenac, paracetamol with codeine and placebo tablets for relief of postoperative pain after removal of impacted third molars”, British J. Oral Maxillofac. Surgery, Vol. 42, (2004), pp. 299–306. http://dx.doi.org/10.1016/j.bjoms.2004.02.004[Crossref]
-  D. Casassus-Builhe, P. Rey and C. Carrere: “Association of paracetamol and codeine, a rare cause of acute drug-induced pancreatitis”, Presse Medicale, Vol. 33, (2004), pp. 536–536.
-  J. DeRuiter: “Principles of drug action 2. Narcotic analgesics: morphine and “peripherally modified” morphine analogs”, Fall, 2000, pp. 1–9 (http://holivo.pharmacy.uiova.edu/morphine).
-  L.S. Harris: Drugs of Abuse: Chemistry, Pharmacology, Immunology, and AIDS, National Institute on Drug Abuse (USA) - Research monograph series, 1996, pp. 80–85.
-  G. Micali, M.R. Nasca, A. Tedeschi, F. Dall’Oglio and N. Pulvirenti: “Use of squaric acid dibutylester (SADBE) for cutaneous warts in children”, Pediatr. Dermatol., Vol 17, (2000), pp. 315–318. http://dx.doi.org/10.1046/j.1525-1470.2000.01762.x[Crossref]
-  B.C.G. Soderberg, P.S. Zehr and R. Kayali: “Synthesis of novel alkaloids using squaric acid esters”, American Chem. Soc., Vol. 228, (2004), p. U146.
-  X. Xie, A.B. Comeau and C.T. Seto: “Squaric acid derivatives: A new class of protein tyrosine phosphatases inhibitors”, American Chem. Soc., Vol. 227, (2004), p. U14.
-  E. Pena-Cabrera and L.S. Liebeskind: “Squaric acid ester-based total synthesis of echinochrome A”, J. Org. Chem., Vol. 67, (2002), pp. 1689–1691. http://dx.doi.org/10.1021/jo016034m[Crossref]
-  V. Cirimele, S. Etienne and M. Villain: “Evaluation of the One-Step (TM) ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens”, Forensic Sci. Int., Vol. 143, (2004), pp. 153–156. http://dx.doi.org/10.1016/j.forsciint.2004.02.035[Crossref]
-  C. Staub, M. Marset, A. Mino and P. Mangin: “Detection of acetylcodeine in urine as an indicator of illicit heroin use: Method validation and results of a pilot study”, Clin. Chem., Vol. 42, (2001), pp. 301–307.
-  B.B. Ivanova: “Aromatic dipeptides and their salts - solid-state linear-dichroic infrared (IR-LD) spectral analysis and ab initio calculations”, Spectrochim. Acta A, (2005), submitted.
-  B.B. Ivanova: “Stereo-structural and IR-spectral characterization of histidine containing dipeptides by means of solid state IR-LD spectroscopy and ab initio calculations”, J. Mol. Struct., Vol. 782, (2006), pp. 122–129. http://dx.doi.org/10.1016/j.molstruc.2005.08.004[Crossref]
-  B.B. Ivanova and M.G. Arnaudov: “Solid state linear-dichroic infrared spectral and theoretical analysis of methionine containing tripeptides”, Spectrochim. Acta A, (2005), in press.
-  B.B. Ivanova, M.G. Arnaudov, St. Todorov, W.S. Sheldrick and H. Mayer-Figge: “Structural analysis of the tripeptide glycyl-methionyl-glycine (H-Gly-Met-Gly-OH) and its hydrochloride”, Struct. Chem., (2005), in press.
-  B.B. Ivanova: “IR-LD spectroscopic characterization of L -Tryptophan containing dipeptides”, Spectrochim. Acta A, (2005), in press.
-  B. Ivanova, T. Kolev and R. Bakalska: “Linear-dichroic infrared spectral (IR-LD) analysis of codeine and its derivatives”, Tetrahedron, (2005), submitted.
-  T. Kolev, B.B. Ivanova and R. Bakalska: “6-O-Acetylcodeine and its hydrogen-squarate - linear-dichroic infrared (IR-LD) spectroscopy”, J. Mol. Struct., (2005), in press.
-  B.B. Ivanova, M.G. Arnaudov and P.R. Bontchev: “Linear-dichroic infrared spectral analysis of Cu(I)-homocysteine complex”, Spectrochim. Acta A, Vol. 60, (2004), pp. 855–862. http://dx.doi.org/10.1016/S1386-1425(03)00310-X[Crossref]
-  J. Michl and E.W. Thulstrup: Spectroscopy with Polarized Light. Solute alignment by photoselection, in liquid crystals, polymers, and membranes, VCH Publishers, N. Y. 1986.
-  E.W. Thulstrup and J.H. Eggers: “Moment directions of the electronic transitions of fluoranthene”, Chem. Phys. Lett., Vol. 1, (1968), pp. 690–692. http://dx.doi.org/10.1016/0009-2614(68)80122-8[Crossref]
-  B. Jordanov and B. Schrader: “Reduced IR-LD spectra of substances oriented as nematic solutions”, J. Mol. Struct., Vol. 347, (1995), pp. 389–398. http://dx.doi.org/10.1016/0022-2860(95)08561-9[Crossref]
-  B. Jordanov, R. Nentchovska and B. Schrader: “FT-IR linear dichroic solute spectra of nematic solutions as a tool for IR band assignment”, J. Mol. Struct., Vol. 297, (1993) pp. 401–406. http://dx.doi.org/10.1016/0022-2860(93)80195-2[Crossref]
-  B.B. Ivanova, D.L. Tsalev and M.G. Arnaudov: “Validation of reducing-difference procedure for the interpretation of non-polarized infrared spectra of n-component solid mixtures”, Talanta, (2006), in press. [Crossref]
-  B.B. Ivanova, V.D. Simeonov, M.G. Arnaudov and D.L. Tsalev: “Linear-dichroic infrared spectroscopy - validation and experimental design of the new orientation technique of solid samples as suspension in nematic liquid crystal”, Spectrochim. Acta A, (2006), submitted. [WoS]
-  T. Kolev, R. Petrova and M. Spiteller: “(R)-2-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]-3-phenylpropanamide hemihydrate”, Acta Crystallogr., Vol. E60, (2004), pp. 634–636
-  G. Varsanyi: Vibrational Spectra of benzene derivatives, Akademiai kiado, Budapest, 1969.
-  N.A. Roeges: A Guide to the complete interpretation of infrared spectra of organic Structures, J. Wiley, New York, 1993.
-  T. Kolev, R. Bakalska, B. Shivachev and R. Petrova: ”6-O-Acetylcodeine”, Acta Crystallogr., Vol. E61, (2005), pp. o2582–o2584.
-  D. Canfield, J. Barrick and B.C. Giessen: “Structure of diacetylmorphine (heroin)”, Acta Cryst., Vol. B35, (1979), pp. 2806–2809. [Crossref]
-  D. Canfield, J. Barrick and B.C. Giessent: “Structure of codeine”, Acta Cryst., Vol. C43, (1987), pp. 977–979.
-  L. Gylbert: “The crystal and molecular structure of morphine hydrochloride trihydrate”, Acta Cryst., Vol. B29, (1973), pp. 1630–1635. [Crossref]
-  P.C.E. Moody, N. Shikotra, C.E. French, N.C. Bruce and N.S. Scrutton: “Crystallization and preliminary diffraction studies of morphinone reductase, a flavoprotein involved in the degradation of morphine alkaloids”, Acta Cryst., Vol. D53, (1997), pp. 619–621.
-  H. Petrickova, A. Jegorov, M. Husak and I. Cisarova: “Conformation analysis of morphine alkaloids”, Acta Cryst., Vol. A58, (2002), pp. C125–C126.
-  Y.G. Gelders, C.J. de Ranter and A.R. Overbeek: “Structural studies of substituted 6,7-benzomorphan compounds. II. Absolute configurations of (-)-2-cyclobutylmethyl-5-ethyl-2’-hydroxy-9,9-dimethyl-6,7-benzomorphan hydrobromide (NCBME) and (-)-5-ethyl-2’-hydroxy-2,9,9-trimethyl-6,7-benzomorphan hydrobromide dihydrate (NME)”, Acta Cryst., Vol. B35, (1979), pp. 1111–1116.
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