72
A. Váradi et al. / European Journal of Pharmaceutical Sciences 42 (2011) 65–72
Hernández, L., Romero, A., Almela, P., García-Nogales, P., Laorden, M.L., Puig, M.M.,
2009. Tolerance to the antinociceptive effects of peripherally administered opi-
oids: Expression of -arrestins. Brain Res. 1248, 31–39.
Iorio, M.A., Disciullo, A., Mazzeo Farina, A., Frigeni, V., 1984. Diastereoisomeric qua-
ternary morphinium salts: synthesis, stereochemistry and analgesic properties.
Eur. J. Med. Chem. 19, 11–16.
Kaspersen, F.M., Van Boeckel, C.A.A., 1987. A review of the methods of chem-
ical synthesis of sulphate and glucuronide conjugates. Xenobiotica 17,
1451–1471.
d-fructopyranose 1-sulfate and 4,5-O-isopropylidene-beta-d-fructopyranose
1-sulfate. Carbohydr. Res. 337, 787–801.
Preechagoon, D., Brereton, I., Staatz, C., Prankerd, R., 1998a. Ester prodrugs of a
potent analgesic, morphine-6-sulfate: syntheses, spectroscopic and physico-
chemical properties. Int. J. Pharm. 163, 177–190.
Preechagoon, D., Smith, M.T., Prankerd, R.J., 1998b. Investigation of the antinocicep-
tive efficacy and relative potency of extended duration injectable. Int. J. Pharm.
163, 191–201.
Purdie, N., Swallows, K.A., Murphy, L.H., Purdie, R.B., 1989. Analytical application of
circular dichroism. J. Pharm. Biomed. Anal. 7, 1519–1526.
Kottayil, S. G., 1993. Ph.D. Thesis, University of Kentucky.
Linder, C., Fishman, J., 1973. Narcotic antagonists. 1. Isomeric sulfate and acetate
esters of naloxone (N-allylnoroxymorphone). J. Med. Chem. 16, 553–556.
Mazák, K., Hosztafi, S., Rácz, A., Noszál, B., 2009. Structural and physicochemical
profiling of morphine and related compounds of therapeutic interest. Mini-Rev.
Med. Chem. 9, 984–995.
McKenna, J., Norymberski, J.K., 1957. Steroid sulphates. Part I. Some solvolytic reac-
tions of the salts of steroid sulphates. J. Chem. Soc., 3889–3893.
Milne, R.W., Nation, R.L., Somogyi, A.A., 1996. The disposition of morphine and its 3-
and 6-glucuronide metabolites in humans and animals, and the importance of
the metabolites to the pharmacological effects of morphine. Drug Metab. Rev.
28, 345–472.
Mori, M.A., Oguri, K., Yoshimura, H., Shimomura, K., Kamata, O., Ueki, S., 1972. Chem-
ical synthesis and analgesic effect of morphine ethereal sulfates. Life Sci. 11,
525–533.
Obara, I., Parkitna, J.R., Korostynski, M., Makuch, W., Kaminska, D., Przewlocka, B.,
Przewlocki, R., 2009. Local peripheral opioid effects and expression of opioid
genes in the spinal cord and dorsal root ganglia in neuropathic and inflammatory
pain. Pain 141, 283–291.
Simon, C., Hosztafi, S., Makleit, S., 1991. Morphine alkaloids. III application of the Mit-
sunobu reaction for the preparation of isomorphine and isocodeine derivatives.
Synth. Commun. 21, 407–412.
Smith, H.S., 2008. Peripherally-acting opioids. Pain Phys., 11.
Visky, D., Kraszni, M., Hosztafi, S., Noszál, B., 2000. HPCE analysis of hydrolysing
morphine derivatives. Quantitation of decomposition rate and mobility. Chro-
matographia 51, 294–300.
Welsh, L.H., 1954. O3-monoacetylmorphine. J. Org. Chem. 19, 1409–1415.
Wittwer, E., Kern, S.E., 2006. Role of morphine’s metabolites in analgesia: concepts
and controversies. AAPS J. 8, E348–E352.
Wright, C.I., 1941. The enzymatic deacetylation of heroin and related morphine
derivatives by blood serum. J. Pharmacol. Exp. Ther. 71, 164–177.
Yeh, S.Y., Gorodetzky, C.W., Krebs, H.A., 1977. Isolation and identification of mor-
phine 3- and 6-glucuronides, morphine 3,6-diglucuronide, morphine 3-ethereal
sulfate, normorphine, and normorphine 6-glucuronide as morphine metabolites
in humans. J. Pharm. Sci. 66, 1288–1293.
Zheng, W., 2010. Activation of mu opioid receptor inhibits the excitatory gluta-
matergic transmission in the anterior cingulate cortex of the rats with peripheral
inflammation. Eur. J. Pharmacol. 628, 91–95.
Zuckerman, A., Bolan, E., De Paulis, T., Schmidt, D., Spector, S., Pasternak, G.W., 1999.
Pharmacological characterization of morphine-6-sulfate and codeine-6-sulfate.
Brain Res. 842, 1–5.
Ober, K.F., Fujimoto, J.M., 1972. Isolation of naloxone-3-ethereal sulfate from urine
of the cat. Proc. Soc. Exp. Biol. Med. 139, 1068–1070.
Popek, T., Lis, T., 2002. Synthesis and X-ray structures of sulfate esters of fructose
and its isopropylidene derivatives. Part 1: 2,3:4,5-di-O-isopropylidene-beta-