Revisiting the controversial role of salsolinol in the neurobiological effects of ethanol: Old and new vistas

Neuroscience and Biobehavioral Reviews

Volumn 36, Issue 1, 2012, Pages 362-378

  Hipólito, Lucía ^a   Sánchez Catalán, María José ^a   Martí Prats, Lucía ^a   Granero, Luis ^a   Polache, Ana ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Mu opioids receptors; Neurobiological effects of ethanol; Salsolinol; Tetrahydroisoquinolines; VTA

Indexed keywords

ALCOHOL; DOPAMINE; SALSOLINOL;

ALCOHOL CONSUMPTION; ALCOHOL METABOLISM; ALCOHOLISM; BEHAVIOR; BLOOD BRAIN BARRIER; BLOOD LEVEL; BODY FLUID; BRAIN ELECTROPHYSIOLOGY; BRAIN LEVEL; CONDITIONING; DRINKING BEHAVIOR; DRUG SELF ADMINISTRATION; ENANTIOMER; HUMAN; IN VITRO STUDY; LOCOMOTION; MESOLIMBIC DOPAMINERGIC SYSTEM; METABOLITE; NEUROBIOLOGY; NEUROCHEMISTRY; NEUROPHYSIOLOGY; NONHUMAN; PLACE PREFERENCE; PRIORITY JOURNAL; REVIEW;

ALCOHOL DRINKING; ANIMALS; BRAIN; CONDITIONING, OPERANT; ETHANOL; HUMANS; ISOQUINOLINES; MOTOR ACTIVITY; NEUROBIOLOGY; STEREOISOMERISM;

EID: 82855178759     PISSN: 01497634     EISSN: 18737528     Source Type: Journal    
DOI: 10.1016/j.neubiorev.2011.07.007     Document Type: Review

References (156)

1. Adachi J., Mizoi Y., Fukunaga T., Kogame M., Ninomiya I., Naito T. Effect of acetaldehyde on urinary salsolinol in healthy man after ethanol intake. Alcohol (Fayetteville, N. Y.) 1986, 3:215-220.
2. Akao Y., Nakagawa Y., Maruyama W., Takahashi T., Naoi M. Apoptosis induced by an endogenous neurotoxin, N-methyl(R)salsolinol, is mediated by activation of caspase 3. Neurosci. Lett. 1999, 267:153-156.
3. Antkiewicz-Michaluk L. Endogenous risk factors in parkinson's disease: dopamine and tetrahydroisoquinolines. Pol. J. Pharmacol. 2002, 54:567-572.
4. Antkiewicz-Michaluk L., Krygowska-Wajs A., Szczudlik A., Romanska I., Vetulani J. Increase in salsolinol level in the cerebrospinal fluid of parkinsonian patients is related to dementia: Advantage of a new high-performance liquid chromatography methodology. Biol. Psychiatry 1997, 42:514-518.
5. Antkiewicz-Michaluk L., Michaluk J., Romanska I., Papla I., Vetulani J. Antidopaminergic effects of 1,2,3,4-tetrahydroisoquinoline and salsolinol. J. Neural Trans. (Vienna, Austria: 1996) 2000, 107:1009-1019.
6. Antkiewicz-Michaluk L., Romanska I., Papla I., Michaluk J., Bakalarz M., Vetulani J., Krygowska-Wajs A., Szczudlik A. Neurochemical changes induced by acute and chronic administration of 1,2,3,4-tetrahydroisoquinoline and salsolinol in dopaminergic structures of rat brain. Neuroscience 2000, 96:59-64.
7. Aragon C.M., Spivak K., Amit Z. Blockade of ethanol induced conditioned taste aversion by 3-amino-1,2,4-triazole: evidence for catalase mediated synthesis of acetaldehyde in rat brain. Life Sci. 1985, 37:2077-2084.
8. Baum S.S., Hill R., Kiianmaa K., Rommelspacher H. Effect of ethanol on (R)- and (S)-salsolinol, salsoline, and THP in the nucleus accumbens of AA and ANA rats. Alcohol 1999, 18:165-169.
9. Bembenek M.E., Abell C.W., Chrisey L.A., Rozwadowska M.D., Gessner W., Brossi A. Inhibition of monoamine oxidases A and B by simple isoquinoline alkaloids: Racemic and optically active 1,2,3,4-tetrahydro-, 3,4-dihydro-, and fully aromatic isoquinolines. J. Med. Chem. 1990, 33:147-152.
10. Blum K., Hamilton M.G., Hirst M., Wallace J.E. Putative role of isoquinoline alkaloids in alcoholism: a link to opiates. Alcohol. Clin. Exp. Res. 1978, 2:113-120.
11. Bodnar I., Mravec B., Kubovcakova L., Fekete M.I., Nagy G.M., Kvetnansky R. Immobilization stress-induced increase in plasma catecholamine levels is inhibited by a prolactoliberin (salsolinol) administration. Ann. N. Y. Acad. Sci. 2004, 1018:124-130.
12. Bondoli A., Magalini S.I., Ranieri R., Barbi S., Zanghi F. Brain lactate uptake in coma secondary to acute cerebrovascular accident. Crit. Care Med. 1978, 6:327-329.
13. Britton D.R., Rivier C., Shier T., Bloom F., Vale W. In vivo and in vitro effects of tetrahydroisoquinolines and other alkaloids on rat pituitary function. Biochem. Pharmacol. 1982, 31:1205-1211.
14. Cai, M., Liu, Y.M., 2008. Quantification of salsolinol enantiomers by stable isotope dilution liquid chromatography with tandem mass spectrometric detection. Rapid Commun. Mass Spectr.: RCM 22, 4171-4177.
15. Cederbaum A.I. The effect of cyanamide on acetaldehyde oxidation by isolated rat liver mitochondria and on the inhibition of pyruvate oxidation by acetaldehyde. Alcohol. Clin. Exp. Res. 1981, 5:38-44.
16. Church A.C., Fuller J.L., Dudek B.C. Behavioral effects of salsolinol and ethanol on mice selected for sensitivity to alcohol-induced sleep time. Drug Alcohol Depend. 1977, 2:443-452.
17. Church A.C., Fuller J.L., Dudek B.C. Salsolinol differentially affects mice selected for sensitivity to alcohol. Psychopharmacology 1976, 47:49-52.
18. Clow A., Topham A., Saunders J.B., Murray R., Sandler M. The role of salsolinol in alcohol intake and withdrawal. Prog. Clin. Biol. Res. 1985, 183:101-113.
19. Cohen G., Collins M. Alkaloids from catecholamines in adrenal tissue: possible role in alcoholism. Science (New York, N. Y.) 1970, 167:1749-1751.
20. Cohen G., Heikkila R.E., Dembiec D., Sang D., Teitel S., Brossi A. Pharmacologic activity of stereoisomers of 1-substituted 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines: Inhibition of 3H-dopamine accumulation by rat brain slices and lipolytic activity with isolated mouse fat cells. Eur. J. Pharmacol. 1974, 29:292-297.
21. Cohen G., Katz S. 6,7-dihydroxytetrahydroisoquinoline: evidence for in vivo inhibition of intraneuronal monoamine oxidase. J. Neurochem. 1975, 25:719-722.
22. Cohen G., Mytilineou G., Barrett R.E. 6,7-dihydroxytetrahydroisoquinoline: uptake and storage by peripheral sympathetic nerve of the rat. Science (New York, N. Y.) 1972, 175:1269-1272.
23. Collins M.A., Bigdeli M.G. Tetrahydroisoquinolines in vivo. I. rat brain formation of salsolinol, a condensation product of dopamine and acetaldehyde, under certain conditions during ethanol intoxication. Life Sci. 1975, 16:585-601.
24. Collins M.A., Nijm W.P., Borge G.F., Teas G., Goldfarb C. Dopamine-related tetrahydroisoquinolines: significant urinary excretion by alcoholics after alcohol consumption. Science (New York, N. Y.) 1979, 206:1184-1186.
25. Collins M.A., Ung-Chhun N., Cheng B.Y., Pronger D. Brain and plasma tetrahydroisoquinolines in rats: effects of chronic ethanol intake and diet. J. Neurochem. 1990, 55:1507-1514.
26. Correa M., Arizzi M.N., Betz A., Mingote S., Salamone J.D. Locomotor stimulant effects of intraventricular injections of low doses of ethanol in rats: acute and repeated administration. Psychopharmacology 2003, 170:368-375.
27. Costall B., Naylor R.J., Pinder R.M. Hyperactivity induced by tetrahydroisoquinoline derivatives injected into the nucleus accumbens. Eur. J. Pharmacol. 1976, 39:153-160.
28. Davis V.E., Walsh M.J. Alcohol, amines, and alkaloids: a possible biochemical basis for alcohol addiction. Science (New York, N. Y.) 1970, 167:1005-1007.
29. DeCuypere M., Lu Y., Miller D.D., LeDoux M.S. Regional distribution of tetrahydroisoquinoline derivatives in rodent, human, and parkinson's disease brain. J. Neurochem. 2008, 107:1398-1413.
30. Deng Y., Maruyama W., Dostert P., Takahashi T., Kawai M., Naoi M. Determination of the (R)- and (S)-enantiomers of salsolinol and N-methylsalsolinol by use of a chiral high-performance liquid chromatographic column. J. Chromatogr. B, Biomed. Appl. 1995, 670:47-54.
31. Deng Y., Maruyama W., Kawai M., Dostert P., Yamamura H., Takahashi T., Naoi M. Assay for the (R)- and (S)-enantiomers of salsolinols in biological samples and foods with ion-pair high-performance liquid chromatography using beta-cyclodextrin as a chiral mobile phase additive. J. Chromatogr. B, Biomed. Sci. Appl. 1997, 689:313-320.
32. Deng Y., Maruyama W., Yamamura H., Kawai M., Dostert P., Naoi M. Mechanism of enantioseparation of salsolinols, endogenous neurotoxins in human brain, with ion-pair chromatography using beta-cyclodextrin as a mobile phase additive. Anal. Chem. 1996, 68:2826-2831.
33. Dostert P., Benedetti M.S., Bellotti V., Allievi C., Dordain G. Biosynthesis of salsolinol, a tetrahydroisoquinoline alkaloid, in healthy subjects. J. Neural Trans. Gen. Sect. 1990, 81:215-223.
34. Dostert P., Strolin Benedetti M., Dordain G. Dopamine-derived alkaloids in alcoholism and in parkinson's and huntington's diseases. J. Neural Trans. 1988, 74:61-74.
35. Dufay C., Lecron J.C., Daudon F., Gombert J. Rapid and simple procedure for the determination of salsolinol in urine using high-performance liquid chromatography with electrochemical detection. J. Chromatogr. 1991, 563:224-227.
36. Duncan C., Deitrich R.A. A critical evaluation of tetrahydroisoquinoline induced ethanol preference in rats. Pharmacol. Biochem. Behav. 1980, 13:265-281.
37. Duncan M.W., Smythe G.A., Nicholson M.V., Clezy P.S. Comparison of high-performance liquid chromatography with electrochemical detection and gas chromatography-mass fragmentography for the assay of salsolinol, dopamine and dopamine metabolites in food and beverage samples. J. Chromatogr. 1984, 336:199-209.
38. Faraj B.A., Camp V.M., Davis D.C., Lenton J.D., Kutner M. Elevation of plasma salsolinol sulfate in chronic alcoholics as compared to nonalcoholics. Alcohol. Clin. Exp. Res. 1989, 13:155-163.
39. Feest U., Kemper A., Nickel B., Rabe H., Koalick F. Comparison of salsolinol excretion in alcoholics and nonalcoholic controls. Alcohol (Fayetteville, N. Y.) 1992, 9:49-52.
40. Feller D.R., Venkatraman R., Miller D.D. Comparative actions of the trimetoquinol, tetrahydropapaveroline and salsolinol isomers in beta-adrenoceptor systems. Biochem. Pharmacol. 1975, 24:1357-1359.
41. Fertel R.H., Greenwald J.E., Schwarz R., Wong L., Bianchine J. Opiate receptor binding and analgesic effects of the tetrahydroisoquinolines salsolinol and tetrahydropapaveroline. Res. Commun. Chem. Pathol. Pharmacol. 1980, 27:3-16.
42. Fish E.W., DeBold J.F., Miczek K.A. Repeated alcohol: behavioral sensitization and alcohol-heightened aggression in mice. Psychopharmacology 2002, 160:39-48.
43. Giovine A., Renis M., Bertolino A. In vivo and in vitro studies on the effect of tetrahydropapaveroline and salsolinol on COMT and MAO activity in rat brain. Pharmacology 1976, 14:86-94.
44. Guldberg H.C., Marsden C.A. Catechol-O-methyl transferase: pharmacological aspects and physiological role. Pharmacol. Rev. 1975, 27:135-206.
45. Haber H., Dumaual N., Bare D.J., Melzig M.F., McBride W.F., Lumeng L., Li T.K. The quantitative determination of R- and S-salsolinol in the striatum and adrenal gland of rats selectively bred for disparate alcohol drinking. Addict. Biol. 1999, 4:181-189.
46. Haber H., Winkler A., Putscher I., Henklein P., Baeger I., Georgi M., Melzig M.F. Plasma and urine salsolinol in humans: effect of acute ethanol intake on the enantiomeric composition of salsolinol. Alcohol. Clin. Exp. Res. 1996, 20:87-92.
47. Hamilton M.G., Hirst M., Blum K. Opiate-like activity of salsolinol on the electrically stimulated guinea pig ileum. Life Sci. 1979, 25:2205-2210.
48. Heikkila R., Cohen G., Dembiec D. Tetrahydroisoquinoline alkaloids: uptake by rat brain homogenates and inhibition of catecholamine uptake. J. Pharmacol. Exp. Ther. 1971, 179:250-258.
49. Hipolito, L., Martí-Prats, L., Sanchez-Catalan, M.J., Polache, A., Granero, L., Induction of conditioned place preference and dopamine release by salsolinol in posterior VTA of rats: involvement of mu-opioid receptors. Neurochem. Int. , in press. doi:10.1016/j.neuint.2011.04.014.
50. Hipolito L., Sanchez M.J., Polache A., Granero L. Brain metabolism of ethanol and alcoholism: an update. Curr. Drug Metab. 2007, 8. 00-00.
51. Hipolito L., Sanchez-Catalan M.J., Granero L., Polache A. Local salsolinol modulates dopamine extracellular levels from rat nucleus accumbens: shell/core differences. Neurochem. Int. 2009, 55:187-192.
52. Hipolito L., Sanchez-Catalan M.J., Polache A., Granero L. Induction of brain CYP2E1 changes the effects of ethanol on dopamine release in nucleus accumbens shell. Drug Alcohol Depend. 2009, 100:83-90.
53. Hipolito L., Sanchez-Catalan M.J., Zanolini I., Polache A., Granero L. Shell/core differences in mu- and delta-opioid receptor modulation of dopamine efflux in nucleus accumbens. Neuropharmacology 2008, 55:183-189.
54. Hipolito L., Sanchez-Catalan M.J., Zornoza T., Polache A., Granero L. Locomotor stimulant effects of acute and repeated intrategmental injections of salsolinol in rats: role of mu-opioid receptors. Psychopharmacology 2010, 209:1-11.
55. Hirose N., Murakawa K., Takada K., Oi Y., Suzuki T., Nagase H., Cools A.R., Koshikawa N. Interactions among mu- and delta-opioid receptors, especially putative delta1- and delta2-opioid receptors, promote dopamine release in the nucleus accumbens. Neuroscience 2005, 135:213-225.
56. Hirst M., Evans D.R., Gowdey C.W., Adams M.A. The influences of ethanol and other factors on the excretion of urinary salsolinol in social drinkers. Pharmacol. Biochem. Behav. 1985, 22:993-1000.
57. Homicsko K.G., Kertesz I., Radnai B., Toth B.E., Toth G., Fulop F., Fekete M.I., Nagy G.M. Binding site of salsolinol: its properties in different regions of the brain and the pituitary gland of the rat. Neurochem. Int. 2003, 42:19-26.
58. Jamal M., Ameno K., Kubota T., Ameno S., Zhang X., Kumihashi M., Ijiri I. In vivo formation of salsolinol induced by high acetaldehyde concentration in rat striatum employing microdyalisis. Alcohol Alcohol. 2003, 38:197-201.
59. Jamal M., Ameno K., Ameno S., Okada N., Ijiri I. Effect of different doses of cyanamide on striatal salsolinol formation after ethanol treatment. Legal Med. (Tokyo, Japan) 2003, 5(Suppl 1):S79-S82.
60. Jamal M., Ameno K., Ameno S., Okada N., Ijiri I. In vivo study of salsolinol produced by a high concentration of acetaldehyde in the striatum and nucleus accumbens of free-moving rats. Alcohol. Clin. Exp. Res. 2003, 27:79S-84S.
61. Jamal M., Ameno K., Kumihashi M., Ameno S., Kubota T., Wang W., Ijiri I. Microdialysis for the determination of acetaldehyde and ethanol concentrations in the striatum of freely moving rats. J. Chromatogr. B. Anal. Technol. Biomed. Life Sci. 2003, 798:155-158.
62. Johnson S.W., North R.A. Opioids excite dopamine neurons by hyperpolarization of local interneurons. J. Neurosci.: Off. J. Soc. Neurosci. 1992, 12:483-488.
63. Joyce E.M., Iversen S.D. The effect of morphine applied locally to mesencephalic dopamine cell bodies on spontaneous motor activity in the rat. Neurosci. Lett. 1979, 14:207-212.
64. Kikuchi K., Nagatsu Y., Makino Y., Mashino T., Ohta S., Hirobe M. Metabolism and penetration through blood-brain barrier of parkinsonism-related compounds. 1,2,3,4-tetrahydroisoquinoline and 1-methyl-1,2,3,4-tetrahydroisoquinoline. Drug Metab. Dispos.: Biol. Fate Chem. 1991, 19:257-262.
65. Kim H.J., Soh Y., Jang J.H., Lee J.S., Oh Y.J., Surh Y.J. Differential cell death induced by salsolinol with and without copper: possible role of reactive oxygen species. Mol. Pharmacol. 2001, 60:440-449.
66. Koob G.F., Sanna P.P., Bloom F.E. Neuroscience of addiction. Neuron 1998, 21:467-476.
67. Lee J., Huang B.X., Yuan Z., Kim H.Y. Simultaneous determination of salsolinol enantiomers and dopamine in human plasma and cerebrospinal fluid by chemical derivatization coupled to chiral liquid chromatography/electrospray ionization-tandem mass spectrometry. Anal. Chem. 2007, 79:9166-9173.
68. Lee J., Ramchandani V.A., Hamazaki K., Engleman E.A., McBride W.J., Li T.K., Kim H.Y. A critical evaluation of influence of ethanol and diet on salsolinol enantiomers in humans and rats. Alcohol. Clin. Exp. Res. 2010, 34:242-250.
69. Locke S., Cohen G., Dembiec D. Uptake and accumulation of 3H-6,7-dihydroxytetrahydroisoquinoline by peripheral sympathetic nerves in vivo. J. Pharmacol. Exp. Ther. 1973, 187:56-67.
70. Lorenc-Koci E., Antkiewicz-Michaluk L., Kaminska A., Lenda T., Zieba B., Wieronska J., Smialowska M., Schulze G., Rommelspacher H. The influence of acute and chronic administration of 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline on the function of the nigrostriatal dopaminergic system in rats. Neuroscience 2008, 156:973-986.
71. Lucchi L., Bosio A., Spano P.F., Trabucchi M. Action of ethanol and salsolinol on opiate receptor function. Brain Res. 1982, 232:506-510.
72. Maruyama W., Sobue G., Matsubara K., Hashizume Y., Dostert P., Naoi M. A dopaminergic neurotoxin, 1(R), 2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, N-methyl(R)salsolinol, and its oxidation product, 1,2(N)-dimethyl-6,7-dihydroxyisoquinolinium ion, accumulate in the nigro-striatal system of the human brain. Neurosci. Lett. 1997, 223:61-64.
73. Maruyama W., Abe T., Tohgi H., Naoi M. An endogenous MPTP-like dopaminergic neurotoxin, N-methyl(R)salsolinol, in the cerebrospinal fluid decreases with progression of parkinson's disease. Neurosci. Lett. 1999, 262:13-16.
74. Maruyama W., Dostert P., Naoi M. Dopamine-derived 1-methyl-6,7-dihydroxyisoquinolines as hydroxyl radical promoters and scavengers in the rat brain: in vivo and in vitro studies. J. Neurochem. 1995, 64:2635-2643.
75. Maruyama W., Nakahara D., Ota M., Takahashi T., Takahashi A., Nagatsu T., Naoi M. N-methylation of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, (R)-salsolinol, in rat brains: In vivo microdialysis study. J. Neurochem. 1992, 59:395-400.
76. Matsubara K., Akane A., Maseda C., Takahashi S., Fukui Y. Salsolinol in the urine of nonalcoholic individuals after long-term moderate drinking. Alcohol Drug Res. 1985, 6:281-288.
77. Matsubara K., Fukushima S., Fukui Y. A systematic regional study of brain salsolinol levels during and immediately following chronic ethanol ingestion in rats. Brain Res. 1987, 413:336-343.
78. Matsuzawa S., Suzuki T., Misawa M. Involvement of mu-opioid receptor in the salsolinol-associated place preference in rats exposed to conditioned fear stress. Alcohol. Clin. Exp. Res. 2000, 24:366-372.
79. Matsuzawa S., Suzuki T., Misawa M. Conditioned fear stress induces ethanol-associated place preference in rats. Eur. J. Pharmacol. 1998, 341:127-130.
80. McBride W.J., Li T.K., Deitrich R.A., Zimatkin S., Smith B.R., Rodd-Henricks Z.A. Involvement of acetaldehyde in alcohol addiction. Alcohol. Clin. Exp. Res. 2002, 26:114-119.
81. Melchior C.L., Myers R.D. Preference for alcohol evoked by tetrahydropapaveroline (THP) chronically infused in the cerebral ventricle of the rat. Pharmacol. Biochem. Behav. 1977, 7:19-35.
82. Melchior C.L., Simpson C.W., Myers R.D. Dopamine release within forebrain sites perfused with tetrahydroisoquinolines or tryptoline in the rat. Brain Res. Bull. 1978, 3:631-634.
83. Moser A., Kompf D. Presence of methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines, derivatives of the neurotoxin isoquinoline, in parkinsonian lumbar CSF. Life Sci. 1992, 50:1885-1891.
84. Mravec B. Salsolinol, a derivate of dopamine, is a possible modulator of catecholaminergic transmission: A review of recent developments. Physiol. Res./Acad. Sci. Bohem. 2006, 55:353-364.
85. Muller T., Przuntek H., Kuhn W., Baum S.S., Rommelspacher H. No increase of synthesis of (R)salsolinol in parkinson's disease. Move. Disord.: Off. J. Move. Disord. Soc. 1999, 14:514-515.
86. Muller T., Sallstrom Baum S., Haussermann P., Przuntek H., Rommelspacher H., Kuhn W. R- and S-salsolinol are not increased in cerebrospinal fluid of parkinsonian patients. J. Neurol. Sci. 1999, 164:158-162.
87. Musshoff F., Lachenmeier D.K., Schmidt P., Dettmeyer R., Madea B. Systematic regional study of dopamine, norsalsolinol, and (R/S)-salsolinol levels in human brain areas of alcoholics. Alcohol. Clin. Exp. Res. 2005, 29:46-52.
88. Musshoff F., Schmidt P., Dettmeyer R., Priemer F., Wittig H., Madea B. A systematic regional study of dopamine anddopamine-derived salsolinol and norsalsolinol levels in human brain areas. For. Sci. Int. 1999, 105:1-11.
89. Musshoff F., Schmidt P., Dettmeyer R., Priemer F., Jachau K., Madea B. Determination of dopamine and dopamine-derived (R)-/(S)-salsolinol and norsalsolinol in various human brain areas using solid-phase extraction and gas chromatography/mass spectrometry. Foren. Sci. Int. 2000, 113:359-366.
90. Musshoff F., Daldrup T., Bonte W., Leitner A., Lesch O.M. Salsolinol and norsalsolinol in human urine samples. Pharmacol. Biochem. Behav. 1997, 58:545-550.
91. Musshoff F., Lachenmeier D.W., Kroener L., Schmidt P., Dettmeyer R., Madea B. Simultaneous gas chromatographic-mass spectrometric determination of dopamine, norsalsolinol and salsolinol enantiomers in brain samples of a large human collective. Cell. Mol. Biol. (Noisy-Le-Grand, France) 2003, 49:837-849.
92. Myers R.D. Tetrahydroisoquinolines and alcoholism: where are we today?. Alcohol. Clin. Exp. Res. 1996, 20:498-500.
93. Myers R.D., Melchior C.L. Differential actions on voluntary alcohol intake of tetrahydroisoquinolines or a beta-carboline infused chronically in the ventricle of the rat. Pharmacol. Biochem. Behav. 1977, 7:381-392.
94. Myers R.D., Oblinger M.M. Alcohol drinking in the rat induced by acute intra-cerebral infusion of two tetrahydroisoquinolines and a beta-carboline. Drug Alcohol Depend. 1977, 2:469-483.
95. Myers W.D., Mackenzie L., Ng K.T., Singer G., Smythe G.A., Duncan M.W. Salsolinol and dopamine in rat medial basal hypothalamus after chronic ethanol exposure. Life Sci. 1985, 36:309-314.
96. Mytilineou C., Cohen G., Barrett R. Tetrahydroisoquinoline alkaloids: Uptake and release by adrenergic nerves in vivo. Eur. J. Pharmacol. 1974, 25:390-401.
97. Nagatsu T. Isoquinoline neurotoxins in the brain and parkinson's disease. Neurosci. Res. 1997, 29:99-111.
98. Nakahara D., Maruyama W., Hashiguti H., Naoi M. Characterization of the in vivo action of (R)-salsolinol, an endogenous metabolite of alcohol, on serotonin and dopamine metabolism: a microdialysis study. Brain Res. 1994, 644:226-232.
99. Naoi M., Maruyama W., Nagy G.M. Dopamine-derived salsolinol derivates as endogenous monoamine oxidase inhibitors: ocurrence, metabolism and function in human brains. NeuroToxicology 2004, 25:193-204.
100. Naoi M., Maruyama W., Akao Y., Yi H. Dopamine-derived endogenous N-methyl-(R)-salsolinol: Its role in parkinson's disease. Neurotoxicol. Teratol. 2002, 24:579-591.
101. Naoi M., Maruyama W., Dostert P., Kohda K., Kaiya T. A novel enzyme enantio-selectively synthesizes (R)salsolinol, a precursor of a dopaminergic neurotoxin, N-methyl(R)salsolinol. Neurosci. Lett. 1996, 212:183-186.
102. Naoi M., Maruyama W., Dostert P., Hashizume Y. N-methyl-(R)salsolinol as a dopaminergic neurotoxin: from an animal model to an early marker of parkinson's disease. J. Neural Trans. Suppl. 1997, 50:89-105.
103. Naoi M., Maruyama W., Matsubara K., Hashizume Y. A neutral N-methyltransferase activity in the striatum determines the level of an endogenous MPP+-like neurotoxin, 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion, in the substantia nigra of human brains. Neurosci. Lett. 1997, 235:81-84.
104. Naoi M., Maruyama W., Zhang J.H., Takahashi T., Deng Y., Dostert P. Enzymatic oxidation of the dopaminergic neurotoxin, 1(R), 2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, into 1,2(N)-dimethyl-6,7-dihydroxyisoquinolinium ion. Life Sci. 1995, 57:1061-1066.
105. Odink J., Sandman H., Schreurs W.H. Determination of free and total catecholamines and salsolinol in urine by ion-pair reversed-phase liquid chromatography with electrochemical detection after a one-step sample clean-up. J. Chromatogr. 1986, 377:145-154.
106. O'Neill P.J., Rahwan R.G. Absence of formation of brain salsolinol in ethanol-dependent mice. J. Pharmacol. Exp. Ther. 1977, 200:306-313.
107. Origitano T., Hannigan J., Collins M.A. Rat brain salsolinol and blood-brain barrier. Brain Res. 1981, 224:446-451.
108. Phillips T.J., Roberts A.J., Lessov C.N. Behavioral sensitization to ethanol: genetics and the effects of stress. Pharmacol. Biochem. Behav. 1997, 57:487-493.
109. Pianezzola E., Bellotti V., Fontana E., Moro E., Gal J., Desai D.M. Determination of the enantiomeric composition of salsolinol in biological samples by high-performance liquid chromatography with electrochemical detection. J. Chromatogr. 1989, 495:205-214.
110. Quertemont E., Grant K.A., Correa M., et al. The role of acetaldehyde in the central effects of ethanol. Alcohol. Clin. Exp. Res. 2005, 29:221-234.
111. Riggin R.M., Kissinger P.T. Letter: identification of salsolinol as a phenolic component in powdered cocoa and cocoa-based products. J. Agric. Food Chem. 1976, 24:900.
112. Rodd Z.A., Bell R.L., Zhang Y., Goldstein A., Zaffaroni A., McBride W.J., Li T.K. Salsolinol produces reinforcing effects in the nucleus accumbens shell of alcohol-preferring (P) rats. Alcohol. Clin. Exp. Res. 2003, 27:440-449.
113. Rodd Z.A., Bell R.L., Zhang Y., Murphy J.M., Goldstein A., Zaffaroni A., Li T.K., McBride W.J. Regional heterogeneity for the intracranial self-administration of ethanol and acetaldehyde within the ventral tegmental area of alcohol-preferring (P) rats: involvement of dopamine and serotonin. Neuropsychopharmacol.: Off. Publ. Am. Coll. Neuropsychopharmacol. 2005, 30:330-338.
114. Rodd Z.A., Melendez R.I., Bell R.L., Kuc K.A., Zhang Y., Murphy J.M., McBride W.J. Intracranial self-administration of ethanol within the ventral tegmental area of male wistar rats: evidence for involvement of dopamine neurons. J. Neurosci.: Off. J. Soc. Neurosci. 2004, 24:1050-1057.
115. Rodd Z.A., Oster S.M., Ding Z.M., Toalston J.E., Deehan G., Bell R.L., Li T.K., McBride W.J. The reinforcing properties of salsolinol in theVentral tegmental area: evidence for regional heterogeneity and the involvement of serotonin and dopamine. Alcohol. Clin. Exp. Res. 2008, 32:230-239.
116. Rojkovicova T., Mechref Y., Starkey J.A., Wu G., Bell R.L., McBride W.J., Novotny M.V. Quantitative chiral analysis of salsolinol in different brain regions of rats genetically predisposed to alcoholism. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2008, 863:206-214.
117. Rommelspacher H., Sllstrom Baum S., Dufeu P., Schmidt L.G. Determination of (R)- and (S)-salsolinol sulfate and dopamine sulfate levels in plasma of nonalcoholics and alcoholics. Alcohol (Fayetteville, N. Y.) 1995, 12:309-315.
118. Rubenstein J.A., Collins M.A. Tetrahydroisoquinolines derived from noradrenaline-aldehyde condensations. pyrogallol-sensitive O-methylation in rat homogenates. Biochem. Pharmacol. 1973, 22:2928-2931.
119. Sanchez-Catalan M.J., Hipolito L., Guerri C., Granero L., Polache A. Distribution and differential induction of CYP2E1 by ethanol and acetone in the mesocorticolimbic system of rat. Alcohol Alcohol. (Oxford, Oxfordshire) 2008, 43:401-407.
120. Sanchez-Catalan M.J., Hipolito L., Zornoza T., Polache A., Granero L. Motor stimulant effects of ethanol and acetaldehyde injected into the posterior ventral tegmental area of rats: role of opioid receptors. Psychopharmacology 2009, 204:641-653.
121. Sanders B. Sensitivity to low doses of ethanol and pentobarbital in mice selected for sensitivity to hypnotic doses of ethanol. J. Compar. Physiol. Psychol. 1976, 90:394-398.
122. Sasaoka T., Kaneda N. Analysis of salsolinol in human brain using high-performance liquid chromatography with electrochemical detection. J. Chromatogr. 1988, 428:152-155.
123. Sheppard H., Burghardt C.R. Effect of tetrahydroisoquinoline derivatives on the adenylate cyclases of the caudate nucleus (dopamine-type) and erythrocyte (beta-type) of the rat. Res. Commun. Chem. Pathol. Pharmacol. 1974, 8:527-534.
124. Simpson L.L. An analysis of the sympathomimetic activity of 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (TIQ). J. Pharmacol. Exp. Ther. 1975, 192:365-371.
125. Sjoquist B., Borg S., Kvande H. Salsolinol and methylated salsolinol in urine and cerebrospinal fluid from healthy volunteers. Subst. Alcohol Act. Misuse 1981, 2:73-77.
126. Sjoquist B., Eriksson A., Winblad B. Brain salsolinol levels in alcoholism. Lancet 1982, 1:675-676.
127. Sjoquist B., Liljequist S., Engel J. Increased salsolinol levels in rat striatum and limbic forebrain following chronic ethanol treatment. J. Neurochem. 1982, 39:259-262.
128. Sjoquist B., Ljungquist C. Identification and quantification of 1-carboxysalsolinol and salsolinol in biological samples by gas chromatography - mass spectrometry. J. Chromatogr. 1985, 343:1-8.
129. Sjoquist B., Magnuson E. Analysis of salsolinol and salsoline in biological samples using deuterium-labelled internal standards and gas chromatography - mass spectrometry. J. Chromatogr. 1980, 183:17-24.
130. Sjoquist B., Perdahl E., Winblad B. The effect of alcoholism on salsolinol and biogenic amines in human brain. Drug Alcohol Depend. 1983, 12:15-23.
131. Smolen T.N., Collins A.C. Behavioral effects of ethanol and salsolinol in mice selectively bred for acute sensitivity to ethanol. Pharmacol. Biochem. Behav. 1984, 20:281-287.
132. Song Y., Feng Y., Leblanc M.H., Castagloni N., Liu Y.M. 1-benzyl-1,2,3,4-tetrahydroisoquinoline passes through the blood-brain barrier of rat brain: an in vivo microdialysis study. Neurosci. Lett. 2006, 395:63-66.
133. Song Y., Xu J., Hamme A., Liu Y.M. Capillary liquid chromatography-tandem mass spectrometry of tetrahydroisoquinoline derived neurotoxins: a study on the blood-brain barrier of rat brain. J. Chromatogr. A 2006, 1103:229-234.
134. Starkey J.A., Mechref Y., Muzikar J., McBride W.J., Novotny M.V. Determination of salsolinol and related catecholamines through on-line preconcentration and liquid chromatography/atmospheric pressure photoionization mass spectrometry. Anal. Chem. 2006, 78:3342-3347.
135. Storch A., Kaftan A., Burkhardt K., Schwarz J. 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (salsolinol) is toxic to dopaminergic neuroblastoma SH-SY5Y cells via impairment of cellular energy metabolism. Brain Res. 2000, 855:67-75.
136. Strolin Benedetti M., Bellotti V., Pianezzola E., Moro E., Carminati P., Dostert P. Ratio of the R and S enantiomers of salsolinol in food and human urine. J. Neural Trans. 1989, 77:47-53.
137. Strolin Benedetti M., Dostert P., Carminati P. Influence of food intake on the enantiomeric composition of urinary salsolinol in man. J. Neural Trans. Gen. Sect. 1989, 78:43-51.
138. Szekacs D., Bodnar I., Mravec B., Kvetnansky R., Vizi E.S., Nagy G.M., Fekete M.I. The peripheral noradrenergic terminal as possible site of action of salsolinol as prolactoliberin. Neurochem. Int. 2007, 50:427-434.
139. Szekacs D., Bodnar I., Nagy G.M., Fekete M.I. Salsolinol and the peripheral sympathetic activity: The effects of hypophysectomy, adrenalectomy and adrenal medullectomy. Ideggyogya. Szem. 2007, 60:162-165.
140. Szekacs D., Bodnar I., Vizi E.S., Nagy G.M., Fekete M.I. The role of catecholamines in the prolactin release induced by salsolinol. Neurochem. Int. 2007, 51:319-322.
141. Takabe M., Itokawa Y. Thiamin depletion after ethanol and acetaldehyde administration to rabbits. J. Nutr. Sci. Vitaminol. 1983, 29:509-514.
142. Tampier L., Alpers H.S., Davis V.E. Influence of catecholamine-derived alkaloids and beta-adrenergic blocking agents on stereospecific binding of 3H-naloxone. Res. Commun. Chem. Pathol. Pharmacol. 1977, 17:731-734.
143. Tennyson V.M., Cohen G., Mytilineou C., Heikkila R. 6,7-dihydroxytetrahydroisoquinoline: electron microscopic evidence for uptake into the amine-binding vesicles in sympathetic nerves of rat iris and pineal gland. Brain Res. 1973, 51:161-169.
144. Thumen A., Behnecke A., Qadri F., Bauml E., Thumen A., Behnecke C.A., Qadri F., Bauml E., Moser A. N-methyl-norsalsolinol, a putative dopaminergic neurotoxin, passes through the blood-brain barrier in vivo. Neuroreport 2002, 13:25-28.
145. Toth B.E., Bodnar I., Homicsko K.G., Fulop F., Fekete M.I., Nagy G.M. Physiological role of salsolinol: its hypophysiotrophic function in the regulation of pituitary prolactin secretion. Neurotoxicol. Teratol. 2002, 24:655-666.
146. Toth B.E., Homicsko K., Radnai B., et al. Salsolinol is a putative endogenous neuro-intermediate lobe prolactin-releasing factor. J. Neuroendocrinol. 2001, 13:1042-1050.
147. Ung-Chhun N., Cheng B.Y., Pronger D.A., Serrano P., Chavez B., Fernandez Perez R., Morales J., Collins M.A. Alkaloid adducts in human brain: coexistence of 1-carboxylated and noncarboxylated isoquinolines and beta-carbolines in alcoholics and nonalcoholics. Prog. Clin. Biol. Res. 1985, 183:125-136.
148. Upadhya S.C., Tirumalai P.S., Boyd M.R., Mori T., Ravindranath V. Cytochrome P4502E (CYP2E) in brain: constitutive expression, induction by ethanol and localization by fluorescence in situ hybridization. Arch. Biochem. Biophys. 2000, 373:23-34.
149. Vasko M.R., Domino E.F. Tolerance development to the biphasic effects of morphine on locomotor activity and brain acetylcholine in the rat. J. Pharmacol. Exp. Ther. 1978, 207:848-858.
150. Vetulani J., Antkiewicz-Michaluk L., Nalepa I., Sansone M. A possible physiological role of cerebral tetrahydoisoquinolines. Neurotox. Res. 2003, 5:147-156.
151. Vetulani J., Nalepa I., Antkiewicz-Michaluk L., Sansone M. Opposite effect of simple tetrahydroisoquinolines on amphetamine- and morphine-stimulated locomotor activity in mice. J. Neural Trans. (Vienna, Austria: 1996) 2001, 108:513-526.
152. Vezina P., Stewart J. Conditioning and place-specific sensitization of increases in activity induced by morphine in the VTA. Pharmacol. Biochem. Behav. 1984, 20:925-934.
153. Wang W., Ameno K., Jamal M., Kumihashi M., Uekita I., Ameno S., Ijiri I. Effect of direct infusion of acetaldehyde on dopamine and dopamine-derived salsolinol in the striatum of free-moving rats using a reverse microdyalisis technique. Organ Tox. Mech. 2007, 81:121-126.
154. Weiner C.D., Collins M.A. Tetrahydroisoquinolines derived from catecholamines or DOPA: effects on brain tyrosine hydroxylase activity. Biochem. Pharmacol. 1978, 27:2699-2703.
155. Zhang W., Xie Y., Gu J., Ai S., Wang J., Yamamoto K., Jin L. Liquid chromatography with amperometric detection at a nano crystalline ce-doped lead dioxide film modified electrode for determination of (R)-salsolinol, (R)-N-methylsalsolinol and monoamine neurotransmitters in parkinsonian patients' cerebrospinal fluid. Analyst 2004, 129:229-234.
156. Zimatkin S.M., Pronko S.P., Vasiliou V., Gonzalez F.J., Deitrich R.A. Enzymatic mechanisms of ethanol oxidation in the brain. Alcohol. Clin. Exp. Res. 2006, 30:1500-1505.