Endogenous morphine and its metabolites in mammals: History, synthesis, localization and perspectives

Neuroscience

Volumn 233, Issue , 2013, Pages 95-117

  Laux Biehlmann, A ^a   Mouheiche, J ^a   Veriepe J ^a   Goumon, Y ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Analgesia; Dopamine; Morphine; Morphine glucuronide; Opioid receptor

Indexed keywords

DOPAMINE; MORPHINE; NEUROTRANSMITTER; OPIATE; REACTIVE OXYGEN METABOLITE; RETICULINE; TETRAHYDROPAPAVEROLINE; THEBAINE; TOLL LIKE RECEPTOR 4; TYROSINE;

ADDICTION; ANALGESIC ACTIVITY; ANTINOCICEPTION; ASTROCYTE; BIOSYNTHESIS; BRAIN CELL; CATECHOLAMINE NERVE CELL; CENTRAL NERVOUS SYSTEM; COMPARATIVE STUDY; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; GABAERGIC TRANSMISSION; HUMAN; IMMUNE RESPONSE; MAMMAL; MEMORY; METHYLATION; NERVE CELL PLASTICITY; NERVOUS SYSTEM DEVELOPMENT; NERVOUS SYSTEM INFLAMMATION; NOCICEPTION; NONHUMAN; PARKINSON DISEASE; PATHOGENESIS; PLANT; PRIORITY JOURNAL; REVIEW; SCHIZOPHRENIA; SIGNAL TRANSDUCTION; STRESS;

ANIMALS; ASTROCYTES; DOPAMINE; HISTORY, 20TH CENTURY; MAMMALS; MORPHINE; MORPHINE DERIVATIVES; NEURONS; OPIOID PEPTIDES;

EID: 84873173202     PISSN: 03064522     EISSN: 18737544     Source Type: Journal    
DOI: 10.1016/j.neuroscience.2012.12.013     Document Type: Review

References (280)

1. Aceto M.D., Bowman E.R., Harris L.S., May E.L. Dependence studies on new compounds in the rhesus monkey, rat and mouse. NIDA Res Monogr 1989, 95:578-631.
2. Aceto M.D., Harris L.S., Abood M.E., Rice K.C. Stereoselective mu- and delta-opioid receptor-related antinociception and binding with (+)-thebaine. Eur J Pharmacol 1999, 365:143-147.
3. Al-Hasani R., Bruchas M.R. Molecular mechanisms of opioid receptor-dependent signaling and behavior. Anesthesiology 2012, 115:1363-1381.
4. Andrieux A., Salin P.A., Vernet M., Kujala P., Baratier J., Gory-Faure S., Bosc C., Pointu H., Proietto D., Schweitzer A., Denarier E., Klumperman J., Job D. The suppression of brain cold-stable microtubules in mice induces synaptic defects associated with neuroleptic-sensitive behavioral disorders. Genes Dev 2002, 16:2350-2364.
5. Arguello A.A., Harburg G.C., Schonborn J.R., Mandyam C.D., Yamaguchi M., Eisch A.J. Time course of morphine's effects on adult hippocampal subgranular zone reveals preferential inhibition of cells in S phase of the cell cycle and a subpopulation of immature neurons. Neuroscience 2008, 157:70-79.
6. Autie A., Montreuil M., Moulier V., Braha S., Wojakiewicz A., Januel D. Pain and schizophrenia: myth and reality. Encephale 2009, 35:297-303.
7. Badiani A., Robinson T.E. Drug-induced neurobehavioral plasticity: the role of environmental context. Behav Pharmacol 2004, 15:327-339.
8. Bezard E., Gross C.E. Compensatory mechanisms in experimental and human parkinsonism: towards a dynamic approach. Prog Neurobiol 1998, 55:93-116.
9. Bezard E., Gross C.E., Brotchie J.M. Presymptomatic compensation in Parkinson's disease is not dopamine-mediated. Trends Neurosci 2003, 26:215-221.
10. Bianchi E., Alessandrini C., Guarna M., Tagliamonte A. Endogenous codeine and morphine are stored in specific brain neurons. Brain Res 1993, 627:210-215.
11. Bianchi E., Guarna M., Tagliamonte A. Immunocytochemical localization of endogenous codeine and morphine. Adv Neuroimmunol 1994, 4:83-92.
12. Bilkova A., Bezakova L., Bilka F., Psenak M. An amine oxidase in seedlings of Papaver somniferum L. Biol Plant 2005, 49:389-394.
13. Bird D.A., Franceschi V.R., Facchini P.J. A tale of three cell types: alkaloid biosynthesis is localized to sieve elements in opium poppy. Plant Cell 2003, 15:2626-2635.
14. Blume A.J., Shorr J., Finberg J.P., Spector S. Binding of the endogenous nonpeptide morphine-like compound to opiate receptors. Proc Natl Acad Sci U S A 1977, 74:4927-4931.
15. Blumensohn R., Ringler D., Eli I. Pain perception in patients with schizophrenia. J Nerv Ment Dis 2002, 190:481-483.
16. Boarder M.R., Rodnight R. Tryptamine-N-methyltransferase activity in brain tissue: a re-examination. Brain Res 1976, 114:359-364.
17. Boettcher C., Fellermeier M., Boettcher C., Drager B., Zenk M.H. How human neuroblastoma cells make morphine. Proc Natl Acad Sci U S A 2005, 102:8495-8500.
18. Boettcher C., Fischer W., Zenk M.H. Comment on " human white blood cells synthesize morphine: CYP2D6 modulation" J Immunol 2006, 176:5703-5704.
19. Bonnot O., Anderson G.M., Cohen D., Willer J.C., Tordjman S. Are patients with schizophrenia insensitive to pain? A reconsideration of the question. Clin J Pain 2009, 25:244-252.
20. Borner U., Abbott S. New observations in the metabolism of morphine. The formation of codeine from morphine in man. Experientia 1973, 29:180-181.
21. Bourasset F., Cisternino S., Temsamani J., Scherrmann J.M. Evidence for an active transport of morphine-6-beta-d-glucuronide but not P-glycoprotein-mediated at the blood-brain barrier. J Neurochem 2003, 86:1564-1567.
22. Bradbury A.F., Smyth D.G., Snell C.R. Biosynthetic origin and receptor conformation of methionine enkephalin. Nature 1976, 260:165-166.
23. Brailoiu E., Hoard J., Brailoiu G.C., Chi M., Godbolde R., Dun N.J. Ultra low concentrations of morphine increase neurite outgrowth in cultured rat spinal cord and cerebral cortical neurons. Neurosci Lett 2004, 365:10-13.
24. Brefel-Courbon C., Payoux P., Thalamas C., Ory F., Quelven I., Chollet F., Montastruc J.L., Rascol O. Effect of levodopa on pain threshold in Parkinson's disease: a clinical and positron emission tomography study. Mov Disord 2005, 20:1557-1563.
25. Brix-Christensen V., Tonnesen E., Sanchez R.G., Bilfinger T.V., Stefano G.B. Endogenous morphine levels increase following cardiac surgery as part of the antiinflammatory response?. Int J Cardiol 1997, 62:191-197.
26. Brix-Christensen V., Goumon Y., Tonnesen E., Chew M., Bilfinger T., Stefano G.B. Endogenous morphine is produced in response to cardiopulmonary bypass in neonatal pigs. Acta Anaesthesiol Scand 2000, 44:1204-1208.
27. Bromek E., Haduch A., Golembiowska K., Daniel W.A. Cytochrome P450 mediates dopamine formation in the brain in vivo. J Neurochem 2011, 118:806-815.
28. Brown C.E., Roerig S.C., Burger V.T., Cody R.B., Fujimoto J.M. Analgesic potencies of morphine 3- and 6-sulfates after intracerebroventricular administration in mice: relationship to structural characteristics defined by mass spectrometry and nuclear magnetic resonance. J Pharm Sci 1985, 74:821-824.
29. Brun P., Begou M., Andrieux A., Mouly-Badina L., Clerget M., Schweitzer A., Scarna H., Renaud B., Job D., Suaud-Chagny M.F. Dopaminergic transmission in STOP null mice. J Neurochem 2005, 94:63-73.
30. Buchanan M.M., Hutchinson M., Watkins L.R., Yin H. Toll-like receptor 4 in CNS pathologies. J Neurochem 2010, 114:13-27.
31. Buckley D.B., Klaassen C.D. Tissue- and gender-specific mRNA expression of UDP-glucuronosyltransferases (UGTs) in mice. Drug Metab Dispos 2007, 35:121-127.
32. Calatozzolo C., Gelati M., Ciusani E., Sciacca F.L., Pollo B., Cajola L., Marras C., Silvani A., Vitellaro-Zuccarello L., Croci D., Boiardi A., Salmaggi A. Expression of drug resistance proteins Pgp, MRP1, MRP3, MRP5 and GST-pi in human glioma. J Neurooncol 2005, 74:113-121.
33. Casares F.M., McElroy A., Mantione K., Baggermann G., Zhu W., Stefano G.B. The American lobster, Homarus americanus, contains morphine that is coupled to nitric oxide release in its nervous and immune tissues: evidence for neurotransmitter and hormonal signaling. Neuro Endocrinol Lett 2005, 26:89-97.
34. Cashaw J.L. Determination of tetrahydropapaveroline in the urine of parkinsonian patients receiving l-dopa-carbidopa (Sinemet) therapy by high-performance liquid chromatography. J Chromatogr 1993, 613:267-273.
35. Cashaw J.L. Tetrahydropapaveroline in brain-regions of rats after acute ethanol administration. Alcohol 1993, 10:133-138.
36. Cashaw J.L., Ruchirawat S., Nimit Y., Davis V.E. Regioselective O-methylation of tetrahydropapaveroline and tetrahydroxyberbine in vivo in rat brain. Biochem Pharmacol 1983, 32:3163-3169.
37. Charlet A., Muller A.H., Laux A., Kemmel V., Schweitzer A., Deloulme J.C., Stuber D., Delalande F., Bianchi E., Van Dorsselaer A., Aunis D., Andrieux A., Poisbeau P., Goumon Y. Abnormal nociception and opiate sensitivity of STOP null mice exhibiting elevated levels of the endogenous alkaloid morphine. Mol Pain 2010, 6:96.
38. Charron G., Doudnikoff E., Laux A., Berthet A., Porras G., Canron M.H., Barroso-Chinea P., Li Q., Qin C., Nosten-Bertrand M., Giros B., Delalande D., Van Dorsselaer A., Vital A., Goumon Y., Bezard E. Endogenous morphine-like compound immunoreactivity increases in Parkinsonism. Brain 2011, 134:2321-2338.
39. Chaudhuri K.R., Odin P. The challenge of non-motor symptoms in Parkinson's disease. Prog Brain Res 2010, 184:325-341.
40. Chemuturi N.V., Donovan M.D. Role of organic cation transporters in dopamine uptake across olfactory and nasal respiratory tissues. Mol Pharm 2007, 4:936-942.
41. Chen Y., Sommer C. The role of mitogen-activated protein kinase (MAPK) in morphine tolerance and dependence. Mol Neurobiol 2009, 40:101-107.
42. Chen J.J., Chang Y.L., Teng C.M., Chen I.S. Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia. Planta Med 2000, 66:251-256.
43. Chen X.Y., Zhao L.M., Zhong D.F. A novel metabolic pathway of morphine: formation of morphine glucosides in cancer patients. Br J Clin Pharmacol 2003, 55:570-578.
44. Ciliax B.J., Heilman C., Demchyshyn L.L., Pristupa Z.B., Ince E., Hersch S.M., Niznik H.B., Levey A.I. The dopamine transporter: immunochemical characterization and localization in brain. J Neurosci 1995, 15:1714-1723.
45. Coller J.K., Christrup L.L., Somogyi A.A. Role of active metabolites in the use of opioids. Eur J Clin Pharmacol 2009, 65:121-139.
46. Cone E.J., Heit H.A., Caplan Y.H., Gourlay D. Evidence of morphine metabolism to hydromorphone in pain patients chronically treated with morphine. J Anal Toxicol 2006, 30:1-5.
47. Cone E.J., Caplan Y.H., Moser F., Robert T., Black D. Evidence that morphine is metabolized to hydromorphone but not to oxymorphone. J Anal Toxicol 2008, 32:319-323.
48. Cousins D.A., Butts K., Young A.H. The role of dopamine in bipolar disorder. Bipolar disord 2009, 11:787-806.
49. Cox B.M., Opheim K.E., Teschemacher H., Goldstein A. A peptide-like substance from pituitary that acts like morphine. 2. Purification and properties. Life Sci 1975, 16:1777-1782.
50. Dagenais C., Zong J., Ducharme J., Pollack G.M. Effect of mdr1a P-glycoprotein gene disruption, gender, and substrate concentration on brain uptake of selected compounds. Pharm Res 2001, 18:957-963.
51. Dahlin A., Xia L., Kong W., Hevner R., Wang J. Expression and immunolocalization of the plasma membrane monoamine transporter in the brain. Neuroscience 2007, 146:1193-1211.
52. Daly J., Inscoe J.K., Axelrod J. The formation of O-methylated catechols by microsomal hydroxylation of phenols and subsequent enzymatic catechol O-methylation. Substrate specificity. J Med Chem 1965, 8:153-157.
53. Davis V.E., Walsh M.J. Alcohol, amines, and alkaloids: a possible biochemical basis for alcohol addiction. Science 1970, 167:1005-1007.
54. Deitrich R., Erwin V. Biogenic amine-aldehyde condensation products: tetrahydroisoquinolines and tryptolines (beta-carbolines). Annu Rev Pharmacol Toxicol 1980, 20:55-80.
55. Dias K.L., Da Silva Dias C., Barbosa-Filho J.M., Almeida R.N., De Azevedo Correia N., Medeiros I.A. Cardiovascular effects induced by reticuline in normotensive rats. Planta Med 2004, 70:328-333.
56. Dietis N., Rowbotham D.J., Lambert D.G. Opioid receptor subtypes: fact or artifact?. Br J Anaesth 2011, 107:8-18.
57. Donnerer J., Oka K., Brossi A., Rice K.C., Spector S. Presence and formation of codeine and morphine in the rat. Proc Natl Acad Sci U S A 1986, 83:4566-4567.
58. Donnerer J., Cardinale G., Coffey J., Lisek C.A., Jardine I., Spector S. Chemical characterization and regulation of endogenous morphine and codeine in the rat. J Pharmacol Exp Ther 1987, 242:583-587.
59. Drake C.T., Milner T.A. Mu opioid receptors are in somatodendritic and axonal compartments of GABAergic neurons in rat hippocampal formation. Brain Res 1999, 849:203-215.
60. Eisenreich W.J., Hofner G., Bracher F. Alkaloids from Croton flavens L. and their affinities to GABA-receptors. Nat Prod Res 2003, 17:437-440.
61. Ekblom J., Jossan S.S., Bergstrom M., Oreland L., Walum E., Aquilonius S.M. Monoamine oxidase-B in astrocytes. Glia 1993, 8:122-132.
62. Epple A., Navarro I., Horak P., Spector S. Endogenous morphine and codeine: release by the chromaffin cells of the eel. Life Sci 1993, 52:PL117-PL121.
63. Exner M., Alt E., Hermann M., Hofbauer R., Kapiotis S., Quehenberger P., Speiser W., Minar E., Gmeiner B. P-hydroxyphenylacetaldehyde, the major product of tyrosine oxidation by the activated myeloperoxidase system can act as an antioxidant in LDL. FEBS Lett 2001, 490:28-31.
64. Facchini P.J. Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation, and metabolic engineering applications. Annu Rev Plant Physiol Plant Mol Biol 2001, 52:29-66.
65. Facchini P.J., De Luca V. Differential and tissue-specific expression of a gene family for tyrosine/dopa decarboxylase in opium poppy. J Biol Chem 1994, 269:26684-26690.
66. Facchini P.J., Park S.U. Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy. Phytochemistry 2003, 64:177-186.
67. Fang S., Takemori A.E., Portoghese P.S. Activities of morphinone and N-(cyclopropylmethyl)normorphinone at opioid receptors. J Med Chem 1984, 27:1361-1363.
68. Feng Y., He X., Yang Y., Chao D., Lazarus L.H., Xia Y. Current research on opioid receptor function. Curr Drug Targets 2012, 13:230-246.
69. Fischer S.J., Arguello A.A., Charlton J.J., Fuller D.C., Zachariou V., Eisch A.J. Morphine blood levels, dependence, and regulation of hippocampal subgranular zone proliferation rely on administration paradigm. Neuroscience 2008, 151:1217-1224.
70. Florang V.R., Rees J.N., Brogden N.K., Anderson D.G., Hurley T.D., Doorn J.A. Inhibition of the oxidative metabolism of 3,4-dihydroxyphenylacetaldehyde, a reactive intermediate of dopamine metabolism, by 4-hydroxy-2-nonenal. Neurotoxicology 2007, 28:76-82.
71. Foldes A., Meek J.L. Rat brain phenolsulfotransferase: partial purification and some properties. Biochim Biophys Acta 1973, 327:365-374.
72. Ford B. Pain in Parkinson's disease. Mov Disord 2010, 25(Suppl. 1):S98-S103.
73. Freed C., Revay R., Vaughan R.A., Kriek E., Grant S., Uhl G.R., Kuhar M.J. Dopamine transporter immunoreactivity in rat brain. J Comp Neurol 1995, 359:340-349.
74. Fricchione G., Zhu W., Cadet P., Mantione K.J., Bromfield E., Madsen J., DeGirolami U., Dworetzky B., Vaccaro B., Black P., Stefano G.B. Identification of endogenous morphine and a mu3-like opiate alkaloid receptor in human brain tissue taken from a patient with intractable complex partial epilepsy. Med Sci Monit 2008, 14:CS45-CS49.
75. Frolich N., Dees C., Paetz C., Ren X., Lohse M.J., Nikolaev V.O., Zenk M.H. Distinct pharmacological properties of morphine metabolites at G(i)-protein and beta-arrestin signaling pathways activated by the human mu-opioid receptor. Biochem Pharmacol 2011, 81:1248-1254.
76. Gaillard P.J., van der Sandt I.C., Voorwinden L.H., Vu D., Nielsen J.L., de Boer A.G., Breimer D.D. Astrocytes increase the functional expression of P-glycoprotein in an in vitro model of the blood-brain barrier. Pharm Res 2000, 17:1198-1205.
77. Gasser P.J., Orchinik M., Raju I., Lowry C.A. Distribution of organic cation transporter 3, a corticosterone-sensitive monoamine transporter, in the rat brain. J Comp Neurol 2009, 512:529-555.
78. Gerardy R., Zenk M.H. Purification and characterization of salutaridine: NADPH 7-oxidoreductase from Papaver somniferum. Phytochemistry 1993, 34:125-132.
79. Gesell A., Rolf M., Ziegler J., Diaz Chavez M.L., Huang F.C., Kutchan T.M. CYP719B1 is salutaridine synthase, the C-C phenol-coupling enzyme of morphine biosynthesis in opium poppy. J Biol Chem 2009, 284:24432-24442.
80. Gintzler A.R., Levy A., Spector S. Antibodies as a means of isolating and characterizing biologically active substances: presence of a non-peptide, morphine-like compound in the central nervous system. Proc Natl Acad Sci U S A 1976, 73:2132-2136.
81. Gintzler A.R., Mohacsi E., Spector S. Radioimmunoassay for the simultaneous determination of morphine and codeine. Eur J Pharmacol 1976, 38:149-156.
82. Gintzler A.R., Gershon M.D., Spector S. A nonpeptide morphine-like compound: immunocytochemical localization in the mouse brain. Science 1978, 199:447-448.
83. Glattard E., Welters I.D., Lavaux T., Muller A.H., Laux A., Zhang D., Schmidt A.R., Delalande F., Laventie B.J., Dirrig-Grosch S., Colin D.A., Van Dorsselaer A., Aunis D., Metz-Boutigue M.H., Schneider F., Goumon Y. Endogenous morphine levels are increased in sepsis: a partial implication of neutrophils. PLoS One 2010, 5:e8791.
84. Goldstein A., Tachibana S., Lowney L.I., Hunkapiller M., Hood L. Dynorphin-(1-13), an extraordinarily potent opioid peptide. Proc Natl Acad Sci U S A 1979, 76:6666-6670.
85. Goldstein A., Barrett R.W., James I.F., Lowney L.I., Weitz C.J., Knipmeyer L.L., Rapoport H. Morphine and other opiates from beef brain and adrenal. Proc Natl Acad Sci U S A 1985, 82:5203-5207.
86. Gong Q.L., Hedner J., Bjorkman R., Hedner T. Morphine-3-glucuronide may functionally antagonize morphine-6-glucuronide induced antinociception and ventilatory depression in the rat. Pain 1992, 48:249-255.
87. Goumon Y., Stefano G.B. Identification of morphine in the rat adrenal gland. Brain Res Mol Brain Res 2000, 77:267-269.
88. Goumon Y., Bouret S., Casares F., Zhu W., Beauvillain J.C., Stefano G.B. Lipopolysaccharide increases endogenous morphine levels in rat brain. Neurosci Lett 2000, 293:135-138.
89. Goumon Y., Casares F., Pryor S., Ferguson L., Brownawell B., Cadet P., Rialas C.M., Welters I.D., Sonetti D., Stefano G.B. Ascaris suum, an intestinal parasite, produces morphine. J Immunol 2000, 165:339-343.
90. Goumon Y., Zhu W., Weeks B.S., Casares F., Cadet P., Bougaeva M., Brownawell B., Stefano G.B. Identification of morphine in the adrenal medullary chromaffin PC-12 cell line. Brain Res Mol Brain Res 2000, 81:177-180.
91. Goumon Y., Casares F., Zhu W., Stefano G.B. The presence of morphine in ganglionic tissues of Modiolus deminissus: a highly sensitive method of quantitation for morphine and its derivatives. Brain Res Mol Brain Res 2001, 86:184-188.
92. Goumon Y., Strub J.M., Stefano G.B., Van Dorsselaer A., Aunis D., Metz-Boutigue M.H. Characterization of a morphine-like molecule in secretory granules of chromaffin cells. Med Sci Monit 2005, 11:MS31-MS34.
93. Goumon Y., Muller A., Glattard E., Marban C., Gasnier C., Strub J.M., Chasserot-Golaz S., Rohr O., Stefano G.B., Welters I.D., Van Dorsselaer A., Schoentgen F., Aunis D., Metz-Boutigue M.H. Identification of morphine-6-glucuronide in chromaffin cell secretory granules. J Biol Chem 2006, 281:8082-8089.
94. Goumon Y., Laux A., Muller A., Aunis D. Central and peripheral endogenous morphine. An R Acad Nac Farm 2009, 75:389-418.
95. Graf L., Ronai A., Bajusz S., Csheh G., Szekely J.I. Opioid agonist activity of beta-lipotropin fragments: a possible biological source of morphine-like substances in the pituitary. FEBS Lett 1976, 64:181-184.
96. Grobe N., Zhang B., Fisinger U., Kutchan T.M., Zenk M.H., Guengerich F.P. Mammalian cytochrome P450 enzymes catalyze the phenol-coupling step in endogenous morphine biosynthesis. J Biol Chem 2009, 284:24425-24431.
97. Grobe N., Lamshoft M., Orth R.G., Drager B., Kutchan T.M., Zenk M.H., Spiteller M. Urinary excretion of morphine and biosynthetic precursors in mice. Proc Natl Acad Sci U S A 2010, 107:8147-8152.
98. Grobe N., Ren X., Kutchan T.M., Zenk M.H. An (R)-specific N-methyltransferase involved in human morphine biosynthesis. Arch Biochem Biophys 2011, 506:42-47.
99. Grothe T., Lenz R., Kutchan T.M. Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. J Biol Chem 2001, 276:30717-30723.
100. Guarna M., Neri C., Petrioli F., Bianchi E. Potassium-induced release of endogenous morphine from rat brain slices. J Neurochem 1998, 70:147-152.
101. Guarna M., Bianchi E., Bartolini A., Ghelardini C., Galeotti N., Bracci L., Neri C., Sonetti D., Stefano G. Endogenous morphine modulates acute thermonociception in mice. J Neurochem 2002, 80:271-277.
102. Guarna M., Ghelardini C., Galeotti N., Bartolini A., Noli L., Neri C., Stefano G.B., Bianchi E. Effects of endogenous morphine deprivation on memory retention of passive avoidance learning in mice. Int J Neuropsychopharmacol 2004, 7:311-319.
103. Guarna M., Ghelardini C., Galeotti N., Stefano G.B., Bianchi E. Neurotransmitter role of endogenous morphine in CNS. Med Sci Monit 2005, 11:RA190-RA193.
104. Haber H., Roske I., Rottmann M., Georgi M., Melzig M.F. Alcohol induces formation of morphine precursors in the striatum of rats. Life Sci 1997, 60:79-89.
105. Hackler L., Zadina J.E., Ge L.J., Kastin A.J. Isolation of relatively large amounts of endomorphin-1 and endomorphin-2 from human brain cortex. Peptides 1997, 18:1635-1639.
106. Hagel J.M., Facchini P.J. Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy. Nat Chem Biol 2010, 6:273-275.
107. Harburg G.C., Hall F.S., Harrist A.V., Sora I., Uhl G.R., Eisch A.J. Knockout of the mu opioid receptor enhances the survival of adult-generated hippocampal granule cell neurons. Neuroscience 2007, 144:77-87.
108. Harston C.T., Morrow A., Kostrzewa R.M. Enhancement of sprouting and putative regeneration of central noradrenergic fibers by morphine. Brain Res Bull 1980, 5:421-424.
109. Hasselstrom J., Sawe J. Morphine pharmacokinetics and metabolism in humans. Enterohepatic cycling and relative contribution of metabolites to active opioid concentrations. Clin Pharmacokinet 1993, 24:344-354.
110. Hazen S.L., Heller J., Hsu F.F., d'Avignon A., Heinecke J.W. Synthesis, isolation, and characterization of the adduct formed in the reaction of p-hydroxyphenylacetaldehyde with the amino headgroup of phosphatidylethanolamine and phosphatidylserine. Chem Res Toxicol 1999, 12:19-27.
111. Hazen S.L., Gaut J.P., Crowley J.R., Hsu F.F., Heinecke J.W. Elevated levels of protein-bound p-hydroxyphenylacetaldehyde, an amino-acid-derived aldehyde generated by myeloperoxidase, are present in human fatty streaks, intermediate lesions and advanced atherosclerotic lesions. Biochem J 2000, 352(Pt. 3):693-699.
112. Heinz A., Schlagenhauf F. Dopaminergic dysfunction in schizophrenia: salience attribution revisited. Schizophr Bull 2010, 36:472-485.
113. Heller J.I., Crowley J.R., Hazen S.L., Salvay D.M., Wagner P., Pennathur S., Heinecke J.W. P-hydroxyphenylacetaldehyde, an aldehyde generated by myeloperoxidase, modifies phospholipid amino groups of low density lipoprotein in human atherosclerotic intima. J Biol Chem 2000, 275:9957-9962.
114. Heurtaux T., Benani A., Moulin D., Muller N., Netter P., Minn A. Induction of UGT1A6 isoform by inflammatory conditions in rat astrocytes. Neuropharmacology 2006, 50:317-328.
115. Hirata K., Poeaknapo C., Schmidt J., Zenk M.H. 1,2-Dehydroreticuline synthase, the branch point enzyme opening the morphinan biosynthetic pathway. Phytochemistry 2004, 65:1039-1046.
116. Hiroi T., Imaoka S., Chow T., Funae Y. Tissue distributions of CYP2D1, 2D2, 2D3 and 2D4 mRNA in rats detected by RT-PCR. Biochim Biophys Acta 1998, 1380:305-312.
117. Hiroi T., Imaoka S., Funae Y. Dopamine formation from tyramine by CYP2D6. Biochem Biophys Res Commun 1998, 249:838-843.
118. Hirrlinger J., Konig J., Dringen R. Expression of mRNAs of multidrug resistance proteins (Mrps) in cultured rat astrocytes, oligodendrocytes, microglial cells and neurones. J Neurochem 2002, 82:716-719.
119. Horak P., Haberman F., Spector S. Endogenous morphine and codeine in mice - effect of muramyl dipeptide. Life Sci 1993, 52:PL255-PL260.
120. Hughes J., Smith T., Morgan B., Fothergill L. Purification and properties of enkephalin - the possible endogenous ligand for the morphine receptor. Life Sci 1975, 16:1753-1758.
121. Hughes J., Smith T.W., Kosterlitz H.W., Fothergill L.A., Morgan B.A., Morris H.R. Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature 1975, 258:577-580.
122. Hughes M.M., Atayee R.S., Best B.M., Pesce A.J. Observations on the metabolism of morphine to hydromorphone in pain patients. J Anal Toxicol 2012, 36:250-256.
123. Hutchinson M.R., Lewis S.S., Coats B.D., Rezvani N., Zhang Y., Wieseler J.L., Somogyi A.A., Yin H., Maier S.F., Rice K.C., Watkins L.R. Possible involvement of toll-like receptor 4/myeloid differentiation factor-2 activity of opioid inactive isomers causes spinal proinflammation and related behavioral consequences. Neuroscience 2010, 167:880-893.
124. Hutchinson M.R., Loram L.C., Zhang Y., Shridhar M., Rezvani N., Berkelhammer D., Phipps S., Foster P.S., Landgraf K., Falke J.J., Rice K.C., Maier S.F., Yin H., Watkins L.R. Evidence that tricyclic small molecules may possess toll-like receptor and myeloid differentiation protein 2 activity. Neuroscience 2010, 168:551-563.
125. Hutchinson M.R., Zhang Y., Shridhar M., Evans J.H., Buchanan M.M., Zhao T.X., Slivka P.F., Coats B.D., Rezvani N., Wieseler J., Hughes T.S., Landgraf K.E., Chan S., Fong S., Phipps S., Falke J.J., Leinwand L.A., Maier S.F., Yin H., Rice K.C., Watkins L.R. Evidence that opioids may have toll-like receptor 4 and MD-2 effects. Brain Behav Immun 2010, 24:83-95.
126. Ikeda K., Kobayashi T., Kumanishi T., Niki H., Yano R. Involvement of G-protein-activated inwardly rectifying K (GIRK) channels in opioid-induced analgesia. Neurosci Res 2000, 38:113-116.
127. Ikeda H., Miyatake M., Koshikawa N., Ochiai K., Yamada K., Kiss A., Donlin M.J., Panneton W.M., Churchill J.D., Green M., Siddiqui A.M., Leinweber A.L., Crews N.R., Ezerskiy L.A., Rendell V.R., Belcheva M.M., Coscia C.J. Morphine modulation of thrombospondin levels in astrocytes and its implications for neurite outgrowth and synapse formation. J Biol Chem 2010, 285:38415-38427.
128. Ikemoto K., Kitahama K., Jouvet A., Arai R., Nishimura A., Nishi K., Nagatsu I. Demonstration of l-dopa decarboxylating neurons specific to human striatum. Neurosci Lett 1997, 232:111-114.
129. Ikemoto K., Kitahama K., Seif I., Maeda T., De Maeyer E., Valatx J.L. Monoamine oxidase B (MAOB)-containing structures in MAOA-deficient transgenic mice. Brain Res 1997, 771:121-132.
130. Ilari A., Franceschini S., Bonamore A., Arenghi F., Botta B., Macone A., Pasquo A., Bellucci L., Boffi A. Structural basis of enzymatic (S)-norcoclaurine biosynthesis. J Biol Chem 2009, 284:897-904.
131. Inazu M., Takeda H., Matsumiya T. Expression and functional characterization of the extraneuronal monoamine transporter in normal human astrocytes. J Neurochem 2003, 84:43-52.
132. Inazu M., Takeda H., Matsumiya T. Functional expression of the norepinephrine transporter in cultured rat astrocytes. J Neurochem 2003, 84:136-144.
133. Jaeger C.B. Cytoarchitectonics of substantia nigra grafts: a light and electron microscopic study of immunocytochemically identified dopaminergic neurons and fibrous astrocytes. J Comp Neurol 1985, 231:121-135.
134. Jahng J.W., Houpt T.A., Wessel T.C., Chen K., Shih J.C., Joh T.H. Localization of monoamine oxidase A and B mRNA in the rat brain by in situ hybridization. Synapse 1997, 25:30-36.
135. Jedlitschky G., Cassidy A.J., Sales M., Pratt N., Burchell B. Cloning and characterization of a novel human olfactory UDP-glucuronosyltransferase. Biochem J 1999, 340(Pt. 3):837-843.
136. Kardos J., Blasko G., Simonyi M., Szantay C. Pharmacodynamic investigation of (+/-)-salutaridine. Arzneimittelforschung 1984, 34:1758-1759.
137. Kieffer B.L., Evans C.J. Opioid tolerance-in search of the holy grail. Cell 2002, 108:587-590.
138. Kieffer B.L., Evans C.J. Opioid receptors: from binding sites to visible molecules in vivo. Neuropharmacology 2009, 56:205-212.
139. Kieffer B.L., Gaveriaux-Ruff C. Exploring the opioid system by gene knockout. Prog Neurobiol 2002, 66:285-306.
140. Killian A.K., Schuster C.R., House J.T., Sholl S., Connors M., Wainer B.H. A non-peptide morphine-like compound from brain. Life Sci 1981, 28:811-817.
141. Kim Y.M., Kim M.N., Lee J.J., Lee M.K. Inhibition of dopamine biosynthesis by tetrahydropapaveroline. Neurosci Lett 2005, 386:1-4.
142. King C.D., Rios G.R., Assouline J.A., Tephly T.R. Expression of UDP-glucuronosyltransferases (UGTs) 2B7 and 1A6 in the human brain and identification of 5-hydroxytryptamine as a substrate. Arch Biochem Biophys 1999, 365:156-162.
143. Kirby G.W. Biosynthesis of the morphine alkaloids. Science 1967, 155:170-173.
144. Kodaira H., Lisek C.A., Jardine I., Arimura A., Spector S. Identification of the convulsant opiate thebaine in mammalian brain. Proc Natl Acad Sci U S A 1989, 86:716-719.
145. Kolodziej A., Stumm R., Becker A., Hollt V. Endogenous opioids inhibit ischemia-induced generation of immature hippocampal neurons via the mu-opioid receptor. Eur J Neurosci 2008, 27:1311-1319.
146. Komatsu T., Sakurada S., Katsuyama S., Sanai K., Sakurada T. Mechanism of allodynia evoked by intrathecal morphine-3-glucuronide in mice. Adv Neuropharmacol 2009, 85:207-219.
147. Kream R.M., Sheehan M., Cadet P., Mantione K.J., Zhu W., Casares F., Stefano G.B. Persistence of evolutionary memory: primordial six-transmembrane helical domain mu opiate receptors selectively linked to endogenous morphine signaling. Med Sci Monit 2007, 13:SC5-SC6.
148. Kumar P., Sunkaraneni S., Sirohi S., Dighe S.V., Walker E.A., Yoburn B.C. Hydromorphone efficacy and treatment protocol impact on tolerance and mu-opioid receptor regulation. Eur J Pharmacol 2008, 597:39-45.
149. Laux A., Muller A.H., Miehe M., Dirrig-Grosch S., Deloulme J.C., Delalande F., Stuber D., Sage D., Van Dorsselaer A., Poisbeau P., Aunis D., Goumon Y. Mapping of endogenous morphine-like compounds in the adult mouse brain: evidence of their localization in astrocytes and GABAergic cells. J Comp Neurol 2011, 519:2390-2416.
150. Laux A., Delalande F., Mouheiche J., Stuber D., Van Dorsselaer A., Bianchi E., Bezard E., Poisbeau P., Goumon Y. Localization of endogenous morphine-like compounds in the mouse spinal cord. J Comp Neurol 2012, 520:1547-1561.
151. Laux-Biehlmann A., Grafe N., Mouheiche J., Stuber D., Welters I.D., Delalande F., Poisbeau P., Garnero P., Metz-Boutigue M.H., Schneider F., Goumon Y. Comparison of serum and lithium-heparinate plasma for the accurate measurements of endogenous and exogenous morphine concentrations. Br J Clin Pharmacol 2012, 74:381-383.
152. Lazarus L.H., Ling N., Guillemin R. Beta-lipotropin as a prohormone for the morphinomimetic peptides endorphins and enkephalins. Proc Natl Acad Sci U S A 1976, 73:2156-2159.
153. Lee E.J., Facchini P.J. Tyrosine aminotransferase contributes to benzylisoquinoline alkaloid biosynthesis in opium poppy. Plant Physiol 2011, 157:1067-1078.
154. Lee C.S., Spector S. Changes of endogenous morphine and codeine contents in the fasting rat. J Pharmacol Exp Ther 1991, 257:647-650.
155. Lenz R., Zenk M.H. Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures and differentiated plants. Eur J Biochem 1995, 233:132-139.
156. Lewis S.S., Hutchinson M.R., Rezvani N., Loram L.C., Zhang Y., Maier S.F., Rice K.C., Watkins L.R. Evidence that intrathecal morphine-3-glucuronide may cause pain enhancement via toll-like receptor 4/MD-2 and interleukin-1beta. Neuroscience 2010, 165:569-583.
157. Lewis S.S., Loram L.C., Hutchinson M.R., Li C.M., Zhang Y., Maier S.F., Huang Y., Rice K.C., Watkins L.R. (+)-Naloxone, an opioid-inactive toll-like receptor 4 signaling inhibitor, reverses multiple models of chronic neuropathic pain in rats. J Pain 2012, 13:498-506.
158. Li C.H., Chung D. Isolation and structure of an untriakontapeptide with opiate activity from camel pituitary glands. Proc Natl Acad Sci U S A 1976, 73:1145-1148.
159. Li C.H., Chung D., Doneen B.A. Isolation, characterization and opiate activity of beta-endorphin from human pituitary glands. Biochem Biophys Res Commun 1976, 72:1542-1547.
160. Loeffler S., Deus-neumann B., Zenk M.H. S-adenosyl-l-methionine: (S)-coclaurine-N-methyl-transferase from tinospora cardifolia. Phytochemistry 1995, 38:1387-1395.
161. Lotsch J., Geisslinger G. Morphine-6-glucuronide: an analgesic of the future?. Clin Pharmacokinet 2001, 40:485-499.
162. Lotsch J., Stockmann A., Kobal G., Brune K., Waibel R., Schmidt N., Geisslinger G. Pharmacokinetics of morphine and its glucuronides after intravenous infusion of morphine and morphine-6-glucuronide in healthy volunteers. Clin Pharmacol Ther 1996, 60:316-325.
163. Lowney L.I., Gentleman S.B., Goldstein A. A pituitary endorphin with novel properties. Life Sci 1979, 24:2377-2384.
164. Ludwig M., Pittman Q.J. Talking back: dendritic neurotransmitter release. Trends Neurosci 2003, 26:255-261.
165. Mackenzie P.I., Owens I.S., Burchell B., Bock K.W., Bairoch A., Belanger A., Fournel-Gigleux S., Green M., Hum D.W., Iyanagi T., Lancet D., Louisot P., Magdalou J., Chowdhury J.R., Ritter J.K., Schachter H., Tephly T.R., Tipton K.F., Nebert D.W. The UDP glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence. Pharmacogenetics 1997, 7:255-269.
166. Mackenzie P.I., Bock K.W., Burchell B., Guillemette C., Ikushiro S., Iyanagi T., Miners J.O., Owens I.S., Nebert D.W. Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 2005, 15:677-685.
167. Madbouly K.M., Senagore A.J., Delaney C.P. Endogenous morphine levels after laparoscopic versus open colectomy. Br J Surg 2010, 97:759-764.
168. Mague S.D., Blendy J.A. OPRM1 SNP (A118G): involvement in disease development, treatment response, and animal models. Drug Alcohol Depend 2010, 108:172-182.
169. Mantione K.J., Cadet P., Zhu W., Kream R.M., Sheehan M., Fricchione G.L., Goumon Y., Esch T., Stefano G.B. Endogenous morphine signaling via nitric oxide regulates the expression of CYP2D6 and COMT: autocrine/paracrine feedback inhibition. Addict Biol 2008, 13:118-123.
170. Marchitti S.A., Deitrich R.A., Vasiliou V. Neurotoxicity and metabolism of the catecholamine-derived 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde: the role of aldehyde dehydrogenase. Pharmacol Rev 2007, 59:125-150.
171. Mavrojannis M. Action cataleptique de la morphine chez les Rats. Contribution a la theorie toxique da la catalepsie. C R Soc Biol 1903, 55:1092-1094.
172. McCoy J.G., Strawbridge C., McMurtrey K.D., Kane V.B., Ward C.P. A re-evaluation of the role of tetrahydropapaveroline in ethanol consumption in rats. Brain Res Bull 2003, 60:59-65.
173. McDonough P.C., Levine B., Vorce S., Jufer R.A., Fowler D. The detection of hydromorphone in urine specimens with high morphine concentrations. J Forensic Sci 2008, 53:752-754.
174. McNicholas L.F., Martin W.R. New and experimental therapeutic roles for naloxone and related opioid antagonists. Drugs 1984, 27:81-93.
175. Medeiros M.A., Nunes X.P., Barbosa-Filho J.M., Lemos V.S., Pinho J.F., Roman-Campos D., de Medeiros I.A., Araujo D.A., Cruz J.S. (S)-reticuline induces vasorelaxation through the blockade of L-type Ca(2+) channels. Naunyn Schmiedebergs Arch Pharmacol 2009, 379:115-125.
176. Meijerink W.J., Molina P.E., Abumrad N.N. Mammalian opiate alkaloid synthesis: lessons derived from plant biochemistry. Shock 1999, 12:165-173.
177. Meissner W.G., Frasier M., Gasser T., Goetz C.G., Lozano A., Piccini P., Obeso J.A., Rascol O., Schapira A., Voon V., Weiner D.M., Tison F., Bezard E. Priorities in Parkinson's disease research. Nat Rev Drug Discov 2011, 10:377-393.
178. Mellon R.D., Bayer B.M. Evidence for central opioid receptors in the immunomodulatory effects of morphine: review of potential mechanism(s) of action. J Neuroimmunol 1998, 83:19-28.
179. Mellon R.D., Bayer B.M. Role of central opioid receptor subtypes in morphine-induced alterations in peripheral lymphocyte activity. Brain Res 1998, 789:56-67.
180. Mellon R.D., Bayer B.M. The effects of morphine, nicotine and epibatidine on lymphocyte activity and hypothalamic-pituitary-adrenal axis responses. J Pharmacol Exp Ther 1999, 288:635-642.
181. Meunier J.C., Mollereau C., Toll L., Suaudeau C., Moisand C., Alvinerie P., Butour J.L., Guillemot J.C., Ferrara P., Monsarrat B., et al. Isolation and structure of the endogenous agonist of opioid receptor-like ORL1 receptor. Nature 1995, 377:532-535.
182. Miksys S., Rao Y., Hoffmann E., Mash D.C., Tyndale R.F. Regional and cellular expression of CYP2D6 in human brain: higher levels in alcoholics. J Neurochem 2002, 82:1376-1387.
183. Misra A.L., Pontani R.B., Mule S.J. Pharmacokinetics and metabolism of (3H) thebaine. Xenobiotica 1974, 4:17-32.
184. Misra A.L., Vadlamani N.L., Pontani R.B., Mule S.J. Some physicochemical and pharmacological properties of morphine-2,3-quinone, the morphine metabolite in the rat brain. J Pharm Pharmacol 1974, 26:990-992.
185. Miyake N., Thompson J., Skinbjerg M., Abi-Dargham A. Presynaptic dopamine in schizophrenia. CNS Neurosci Ther 2011, 17:104-109.
186. Molina P.E., Hashiguchi Y., Meijerink W.J., Naukam R.J., Boxer R., Abumrad N.N. Modulation of endogenous opiate production: effect of fasting. Biochem Biophys Res Commun 1995, 207:312-317.
187. Molina R., Sanchez M., Hidalgo A., Garcia de Boto M.J. Effects of preanesthetic and anesthetic drugs on endothelium-dependent responses in the rat aorta. Gen Pharmacol 1995, 26:169-175.
188. Morais L.C., Barbosa-Filho J.M., Almeida R.N. Central depressant effects of reticuline extracted from Ocotea duckei in rats and mice. J Ethnopharmacol 1998, 62:57-61.
189. Morishige T., Tsujita T., Yamada Y., Sato F. Molecular characterization of the S-adenosyl-l-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase involved in isoquinoline alkaloid biosynthesis in Coptis japonica. J Biol Chem 2000, 275:23398-23405.
190. Muller A., Glattard E., Taleb O., Kemmel V., Laux A., Miehe M., Delalande F., Roussel G., Van Dorsselaer A., Metz-Boutigue M.H., Aunis D., Goumon Y. Endogenous morphine in SH-SY5Y cells and the mouse cerebellum. PLoS One 2008, 3:e1641.
191. Munjal I.D., Minna J.D., Manneckjee R., Bieck P., Spector S. Possible role of endogenous morphine and codeine on growth regulation of lung tissue. Life Sci 1995, 57:517-521.
192. Murray C.J.L., Lopez A.D. The global burden of disease: a comprehensive assessment of mortality and disability from diseases, injuries, and risk factors in 1990 and projected to 2020 1996, Harvard University Press, Cambridge, MA.
193. Nagano E., Yamada H., Oguri K. Characteristic glucuronidation pattern of physiologic concentration of morphine in rat brain. Life Sci 2000, 67:2453-2464.
194. Neri C., Guarna M., Bianchi E., Sonetti D., Matteucci G., Stefano G.B. Endogenous morphine and codeine in the brain of non human primate. Med Sci Monit 2004, 10:MS1-MS5.
195. Neri C., Ghelardini C., Sotak B., Palmiter R.D., Guarna M., Stefano G., Bianchi E. Dopamine is necessary to endogenous morphine formation in mammalian brain in vivo. J Neurochem 2008, 106:2337-2344.
196. Nikolaev V.O., Boettcher C., Dees C., Bunemann M., Lohse M.J., Zenk M.H. Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors. J Biol Chem 2007, 282:27126-27132.
197. Norris P.J., Hardwick J.P., Emson P.C. Regional distribution of cytochrome P450 2D1 in the rat central nervous system. J Comp Neurol 1996, 366:244-258.
198. Oka K., Kantrowitz J.D., Spector S. Isolation of morphine from toad skin. Proc Natl Acad Sci U S A 1985, 82:1852-1854.
199. Okada T., Shimada S., Sato K., Kotake Y., Kawai H., Ohta S., Tohyama M., Nishimura T. Tetrahydropapaveroline and its derivatives inhibit dopamine uptake through dopamine transporter expressed in HEK293 cells. Neurosci Res 1998, 30:87-90.
200. Osborne R., Joel S., Trew D., Slevin M. Morphine and metabolite behavior after different routes of morphine administration: demonstration of the importance of the active metabolite morphine-6-glucuronide. Clin Pharmacol Ther 1990, 47:12-19.
201. Oyler J.M., Cone E.J., Joseph R.E., Huestis M.A. Identification of hydrocodone in human urine following controlled codeine administration. J Anal Toxicol 2000, 24:530-535.
202. Perea-Sasiaín J. Biosynthesis of morphine: its importance in Parkinson's disease. Rev Fac Med Unal 2008, 56:161-189.
203. Persson A.I., Thorlin T., Bull C., Eriksson P.S. Opioid-induced proliferation through the MAPK pathway in cultures of adult hippocampal progenitors. Mol Cell Neurosci 2003, 23:360-372.
204. Persson A.I., Thorlin T., Bull C., Zarnegar P., Ekman R., Terenius L., Eriksson P.S. Mu- and delta-opioid receptor antagonists decrease proliferation and increase neurogenesis in cultures of rat adult hippocampal progenitors. Eur J Neurosci 2003, 17:1159-1172.
205. Pert C.B., Snyder S.H. Opiate receptor: demonstration in nervous tissue. Science 1973, 179:1011-1014.
206. Pert C.B., Pasternak G., Snyder S.H. Opiate agonists and antagonists discriminated by receptor binding in brain. Science 1973, 182:1359-1361.
207. Pert C.B., Pert A., Tallman J.F. Isolation of a novel endogenous opiate analgesic from human blood. Proc Natl Acad Sci U S A 1976, 73:2226-2230.
208. Poeaknapo C., Schmidt J., Brandsch M., Drager B., Zenk M.H. Endogenous formation of morphine in human cells. Proc Natl Acad Sci U S A 2004, 101:14091-14096.
209. Pryor S.C., Elizee R. Evidence of opiates and opioid neuropeptides and their immune effects in parasitic invertebrates representing three different phyla: Schistosoma mansoni, Theromyzon tessulatum, Trichinella spiralis. Acta Biol Hung 2000, 51:331-341.
210. Rein G., Glover V., Sandler M. Multiple forms of phenolsulphotransferase in human tissues: selective inhibition by dichloronitrophenol. Biochem Pharmacol 1982, 31:1893-1897.
211. Reinscheid R.K., Nothacker H.P., Bourson A., Ardati A., Henningsen R.A., Bunzow J.R., Grandy D.K., Langen H., Monsma F.J., Civelli O. Orphanin FQ: a neuropeptide that activates an opioidlike G protein-coupled receptor. Science 1995, 270:792-794.
212. Robinson T.E., Kolb B. Structural plasticity associated with exposure to drugs of abuse. Neuropharmacology 2004, 47(Suppl. 1):33-46.
213. Sagud M., Muck-Seler D., Mihaljevic-Peles A., Vuksan-Cusa B., Zivkovic M., Jakovljevic M., Pivac N. Catechol-O-methyl transferase and schizophrenia. Psychiatr Danub 2010, 22:270-274.
214. Samanani N., Facchini P.J. Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants. J Biol Chem 2002, 277:33878-33883.
215. Sango K., Maruyama W., Matsubara K., Dostert P., Minami C., Kawai M., Naoi M. Enantio-selective occurrence of (S)-tetrahydropapaveroline in human brain. Neurosci Lett 2000, 283:224-226.
216. Sargeant T.J., Miller J.H., Day D.J. Opioidergic regulation of astroglial/neuronal proliferation: where are we now?. J Neurochem 2008, 107:883-897.
217. Schestatsky P., Kumru H., Valls-Sole J., Valldeoriola F., Marti M.J., Tolosa E., Chaves M.L. Neurophysiologic study of central pain in patients with Parkinson disease. Neurology 2007, 69:2162-2169.
218. Schulz R., Wuster M., Herz A. Detection of a long acting endogenous opioid in blood and small intestine. Life Sci 1977, 21:105-116.
219. Seelbach M.J., Brooks T.A., Egleton R.D., Davis T.P. Peripheral inflammatory hyperalgesia modulates morphine delivery to the brain: a role for P-glycoprotein. J Neurochem 2007, 102:1677-1690.
220. Sery O., Prikryl R., Castulik L., St'astny F. A118G polymorphism of OPRM1 gene is associated with schizophrenia. J Mol Neurosci 2010, 41:219-222.
221. Shorr J., Foley K., Spector S. Presence of a non-peptide morphine-like compound in human cerebrospinal fluid. Life Sci 1978, 23:2057-2062.
222. Siegle I., Fritz P., Eckhardt K., Zanger U.M., Eichelbaum M. Cellular localization and regional distribution of CYP2D6 mRNA and protein expression in human brain. Pharmacogenetics 2001, 11:237-245.
223. Silber D., McLaughlin D., Sinoway L. Leg exercise conditioning increases peak forearm blood flow. J Appl Physiol 1991, 71:1568-1573.
224. Simantov R., Snyder S.H. Morphine-like peptides, leucine enkephalin and methionine enkephalin: interactions with the opiate receptor. Mol Pharmacol 1976, 12:987-998.
225. Smith M.T., Watt J.A., Cramond T. Morphine-3-glucuronide - a potent antagonist of morphine analgesia. Life Sci 1990, 47:579-585.
226. Somogyi P., Klausberger T. Defined types of cortical interneurone structure space and spike timing in the hippocampus. J Physiol 2005, 562:9-26.
227. Somogyi A.A., Barratt D.T., Coller J.K. Pharmacogenetics of opioids. Clin Pharmacol Ther 2007, 81:429-444.
228. Sonetti D., Peruzzi E., Stefano G.B. Endogenous morphine and ACTH association in neural tissues. Med Sci Monit 2005, 11:MS22-MS30.
229. Stefano G.B., Digenis A., Spector S., Leung M.K., Bilfinger T.V., Makman M.H., Scharrer B., Abumrad N.N. Opiate-like substances in an invertebrate, an opiate receptor on invertebrate and human immunocytes, and a role in immunosuppression. Proc Natl Acad Sci U S A 1993, 90:11099-11103.
230. Stefano G.B., Goumon Y., Casares F., Cadet P., Fricchione G.L., Rialas C., Peter D., Sonetti D., Guarna M., Welters I.D., Bianchi E. Endogenous morphine. Trends Neurosci 2000, 23:436-442.
231. Stefano G.B., Bianchi E., Guarna M., Fricchione G.L., Zhu W., Cadet P., Mantione K.J., Casares F.M., Kream R.M., Esch T. Nicotine, alcohol and cocaine coupling to reward processes via endogenous morphine signaling: the dopamine-morphine hypothesis. Med Sci Monit 2007, 13:RA91-RA102.
232. Stevens C.W., Aravind S., Das S., Davis R.L. Pharmacological characterization of LPS and opioid interactions at the toll-like receptor 4. Br J Pharmacol 2012, in press. 10.1111/bph.12028.
233. Stone A.N., Mackenzie P.I., Galetin A., Houston J.B., Miners J.O. Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human udp-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7. Drug Metab Dispos 2003, 31:1086-1089.
234. Suleman F.G., Abid A., Gradinaru D., Daval J.L., Magdalou J., Minn A. Identification of the uridine diphosphate glucuronosyltransferase isoform UGT1A6 in rat brain and in primary cultures of neurons and astrocytes. Arch Biochem Biophys 1998, 358:63-67.
235. Sullivan A.F., McQuay H.J., Bailey D., Dickenson A.H. The spinal antinociceptive actions of morphine metabolites morphine-6-glucuronide and normorphine in the rat. Brain Res 1989, 482:219-224.
236. Surh Y.J., Kim H.J. Neurotoxic effects of tetrahydroisoquinolines and underlying mechanisms. Exp Neurobiol 2010, 19:63-70.
237. Svingos A.L., Colago E.E., Pickel V.M. Vesicular acetylcholine transporter in the rat nucleus accumbens shell: subcellular distribution and association with mu-opioid receptors. Synapse 2001, 40:184-192.
238. Svingos A.L., Garzon M., Colago E.E., Pickel V.M. Mu-opioid receptors in the ventral tegmental area are targeted to presynaptically and directly modulate mesocortical projection neurons. Synapse 2001, 41:221-229.
239. Takeda H., Inazu M., Matsumiya T. Astroglial dopamine transport is mediated by norepinephrine transporter. Naunyn Schmiedebergs Arch Pharmacol 2002, 366:620-623.
240. Tenconi B., Lesma E., DiGiulio A.M., Gorio A. High opioid doses inhibit whereas low doses enhance neuritogenesis in PC12 cells. Brain Res Dev Brain Res 1996, 94:175-181.
241. Thompson M.A., Moon E., Kim U.J., Xu J., Siciliano M.J., Weinshilboum R.M. Human indolethylamine N-methyltransferase: cDNA cloning and expression, gene cloning, and chromosomal localization. Genomics 1999, 61:285-297.
242. Trescot A.M., Datta S., Lee M., Hansen H. Opioid pharmacology. Pain Physician 2008, 11:S133-153.
243. van de Wetering K., Zelcer N., Kuil A., Feddema W., Hillebrand M., Vlaming M.L., Schinkel A.H., Beijnen J.H., Borst P. Multidrug resistance proteins 2 and 3 provide alternative routes for hepatic excretion of morphine-glucuronides. Mol Pharmacol 2007, 72:387-394.
244. Volpe D.A., McMahon Tobin G.A., Mellon R.D., Katki A.G., Parker R.J., Colatsky T., Kropp T.J., Verbois S.L. Uniform assessment and ranking of opioid mu receptor binding constants for selected opioid drugs. Regul Toxicol Pharmacol 2011, 59:385-390.
245. von Bohlen Und Halbach O. Immunohistological markers for staging neurogenesis in adult hippocampus. Cell Tissue Res 2007, 329:409-420.
246. Wachtel S.R., Abercrombie E.D. L-3,4-dihydroxyphenylalanine-induced dopamine release in the striatum of intact and 6-hydroxydopamine-treated rats: differential effects of monoamine oxidase A and B inhibitors. J Neurochem 1994, 63:108-117.
247. Wasan A.D., Michna E., Janfaza D., Greenfield S., Teter C.J., Jamison R.N. Interpreting urine drug tests: prevalence of morphine metabolism to hydromorphone in chronic pain patients treated with morphine. Pain Med 2008, 9:918-923.
248. Wassenberg T., Willemsen M.A., Geurtz P.B., Lammens M., Verrijp K., Wilmer M., Lee W.T., Wevers R.A., Verbeek M.M. Urinary dopamine in aromatic l-amino acid decarboxylase deficiency: the unsolved paradox. Mol Genet Metab 2010, 101:349-356.
249. Weinstein D.D., Spector S., Nanney L.B., King L.E. Endogenous opiate alkaloids and human skin. J Invest Dermatol 2002, 119:709-710.
250. Weitz C.J., Lowney L.I., Faull K.F., Feistner G., Goldstein A. Morphine and codeine from mammalian brain. Proc Natl Acad Sci U S A 1986, 83:9784-9788.
251. Weitz C.J., Faull K.F., Goldstein A. Synthesis of the skeleton of the morphine molecule by mammalian liver. Nature 1987, 330:674-677.
252. Weitz C.J., Lowney L.I., Faull K.F., Feistner G., Goldstein A. 6-Acetylmorphine: a natural product present in mammalian brain. Proc Natl Acad Sci U S A 1988, 85:5335-5338.
253. Welch E.B., Thompson D.F. Opiate antagonists for the treatment of schizophrenia. J Clin Pharm Ther 1994, 19:279-283.
254. Whitman S.C., Hazen S.L., Miller D.B., Hegele R.A., Heinecke J.W., Huff M.W. Modification of type III VLDL, their remnants, and VLDL from ApoE-knockout mice by p-hydroxyphenylacetaldehyde, a product of myeloperoxidase activity, causes marked cholesteryl ester accumulation in macrophages. Arterioscler Thromb Vasc Biol 1999, 19:1238-1249.
255. Wonodi I., Adami H., Sherr J., Avila M., Hong L.E., Thaker G.K. Naltrexone treatment of tardive dyskinesia in patients with schizophrenia. J Clin Psychopharmacol 2004, 24:441-445.
256. Wuster M., Loth P., Schulz R. Characterization of opiate-like materials in blood and urine. Adv Biochem Psychopharmacol 1978, 18:313-319.
257. Yamada H., Ishii K., Ishii Y., Ieiri I., Nishio S., Morioka T., Oguri K. Formation of highly analgesic morphine-6-glucuronide following physiologic concentration of morphine in human brain. J Toxicol Sci 2003, 28:395-401.
258. Yao L., Fan P., Arolfo M., Jiang Z., Olive M.F., Zablocki J., Sun H.L., Chu N., Lee J., Kim H.Y., Leung K., Shryock J., Blackburn B., Diamond I. Inhibition of aldehyde dehydrogenase-2 suppresses cocaine seeking by generating THP, a cocaine use-dependent inhibitor of dopamine synthesis. Nat Med 2010, 16:1024-1028.
259. Yeh S.Y. Absence of evidence of biotransformation of morphine to codeine in man. Experientia 1974, 30:264-266.
260. Yeh S.Y. Urinary excretion of morphine and its metabolites in morphine-dependent subjects. J Pharmacol Exp Ther 1975, 192:201-210.
261. Yeh S.Y. Analgesic activity and toxicity of oripavine and phi-dihydrothebaine in the mouse and rat. Arch Int Pharmacodyn Ther 1981, 254:223-240.
262. Yeh S.Y., Gorodetzky C.W., Krebs H.A. Isolation and identification of morphine 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 1977, 66:1288-1293.
263. Yeh S.Y., McQuinn R.L., Gorodetzky C.W. Biotransformation of morphine to dihydromorphinone and normorphine in the mouse, rat, rabbit, guinea pig, cat, dog, and monkey. Drug Metab Dispos 1977, 5:335-342.
264. Yeh S.Y., McQuinn R.L., Gorodetzky C.W. Identification of diacetylmorphine metabolites in humans. J Pharm Sci 1977, 66:201-204.
265. Yeh S.Y., Krebs H.A., Gorodetzky C.W. Isolation and identification of morphine n-oxide alpha- and beta-dihydromorphines, beta- or gamma-isomorphine, and hydroxylated morphine as morphine metabolites in several mammalian species. J Pharm Sci 1979, 68:133-140.
266. Yoshida S., Ohta J., Yamasaki K., Kamei H., Harada Y., Yahara T., Kaibara A., Ozaki K., Tajiri T., Shirouzu K. Effect of surgical stress on endogenous morphine and cytokine levels in the plasma after laparoscopoic or open cholecystectomy. Surg Endosc 2000, 14:137-140.
267. Zadina J.E., Hackler L., Ge L.J., Kastin A.J. A potent and selective endogenous agonist for the mu-opiate receptor. Nature 1997, 386:499-502.
268. Zeng Y.S., Nie J.H., Zhang W., Chen S.J., Wu W. Morphine acts via mu-opioid receptors to enhance spinal regeneration and synaptic reconstruction of primary afferent fibers injured by sciatic nerve crush. Brain Res 2007, 1130:108-113.
269. Zhang Z., Pan Z.Z. Synaptic mechanism for functional synergism between delta- and mu-opioid receptors. J Neurosci 2010, 30:4735-4745.
270. Zhang Y., Wang Z., Cox D.P., Civelli O. Study on the activation of the opioid receptors by a set of morphine derivatives in a well-defined assay system. Neurochem Res 2012, 37:410-416.
271. Zhu W. CYP2D6: a key enzyme in morphine synthesis in animals. Med Sci Monit 2008, 14:SC15-SC18.
272. Zhu W., Baggerman G., Goumon Y., Casares F., Brownawell B., Stefano G.B. Presence of morphine and morphine-6-glucuronide in the marine mollusk Mytilus edulis ganglia determined by GC/MS and Q-TOF-MS. Starvation increases opiate alkaloid levels. Brain Res Mol Brain Res 2001, 88:155-160.
273. Zhu W., Bilfinger T.V., Baggerman G., Goumon Y., Stefano G.B. Presence of endogenous morphine and morphine 6 glucuronide in human heart tissue. Int J Mol Med 2001, 7:419-422.
274. Zhu W., Baggerman G., Secor W.E., Casares F., Pryor S.C., Fricchione G.L., Ruiz-Tiben E., Eberhard M.L., Bimi L., Stefano G.B. Dracunculus medinensis and Schistosoma mansoni contain opiate alkaloids. Ann Trop Med Parasitol 2002, 96:309-316.
275. Zhu W., Cadet P., Baggerman G., Mantione K.J., Stefano G.B. Human white blood cells synthesize morphine: CYP2D6 modulation. J Immunol 2005, 175:7357-7362.
276. Zhu W., Mantione K.J., Casares F.M., Cadet P., Kim J.W., Bilfinger T.V., Kream R.M., Khalill S., Singh S., Stefano G.B. Alcohol-, nicotine-, and cocaine-evoked release of morphine from invertebrate ganglia: model system for screening drugs of abuse. Med Sci Monit 2006, 12:BR155-BR161.
277. Zhu W., Mantione K.J., Casares F.M., Sheehan M.H., Kream R.M., Stefano G.B. Cholinergic regulation of endogenous morphine release from lobster nerve cord. Med Sci Monit 2006, 12:BR295-BR301.
278. Ziegler J., Diaz-Chavez M.L., Kramell R., Ammer C., Kutchan T.M. Comparative macroarray analysis of morphine containing Papaver somniferum and eight morphine free Papaver species identifies an O-methyltransferase involved in benzylisoquinoline biosynthesis. Planta 2005, 222:458-471.
279. Ziegler J., Facchini P.J., Geissler R., Schmidt J., Ammer C., Kramell R., Voigtlander S., Gesell A., Pienkny S., Brandt W. Evolution of morphine biosynthesis in opium poppy. Phytochemistry 2009, 70:1696-1707.
280. Zuckerman A., Bolan E., de Paulis T., Schmidt D., Spector S., Pasternak G.W. Pharmacological characterization of morphine-6-sulfate and codeine-6-sulfate. Brain Res 1999, 842:1-5.