3'- and 4'-chloro-substituted analogs of benztropine: Intravenous self- administration and in vitro radioligand binding studies in rhesus monkeys

Psychopharmacology

Volumn 147, Issue 4, 2000, Pages 426-435

  Woolverton, William L ^a   Rowlett, James K ^a,c   Wilcox, Kristin M ^a   Paul, Ian A ^a   Kline, Richard H ^b   Newman, Amy Hauck ^b   Katz, Jonathan L ^b  

^a UNIVERSITY OF MISSISSIPPI SCHOOL OF MEDICINE   (United States)

^b NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

^c HARVARD MEDICAL SCHOOL   (United States)

Author keywords

Cocaine; Dopamine; Drug abuse; Monoamine transport; Rhesus monkey; Self administration; Stimulant

Indexed keywords

3' CHLORO BENZTROPINE; 4' CHLORO BENZTROPINE; BENZATROPINE; CITALOPRAM; COCAINE; DOPAMINE; DOPAMINE UPTAKE INHIBITOR; MAZINDOL; SCOPOLAMINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; DOPAMINERGIC SYSTEM; DRUG BINDING SITE; DRUG DEPENDENCE TREATMENT; DRUG SELF ADMINISTRATION; FEMALE; LIGAND BINDING; MALE; MONKEY; NEUROTRANSMISSION; NONHUMAN; PRIORITY JOURNAL; PSYCHOMOTOR PERFORMANCE; REINFORCEMENT; STRUCTURE ACTIVITY RELATION;

EID: 0033958227     PISSN: 00333158     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002130050012     Document Type: Article

References (53)

1. Acri JB, Sedleck BK, Witkin JM (1996) Effects of benztropine on behavioral and toxic effects of cocaine: comparison with atropine and the selective dopamine uptake inhibitor l-[2-(diphenyknethoxy)ethyl]-4-(3-phenyl-propyl)-piperizine. J Pharmacol Exp Pharm 277:198-206
2. Agoston GE, Wu JH, Izenwasser S, George C, Katz J, Kline RH, Newman AH (1997) Novel N-substituted 4', 4"-difiuoro-3?-(diphenyknethoxy)tropane analogs: selective ligands for the dopamine transporter. J Med Chem 40:4329-4339
3. Balster RL, Schuster CR (1973a) Fixed-interval schedule of cocaine reinforcement: effect of dose and infusion duration. J Exp Anal Behav 20:119-129
4. Balster RL, Schuster CR (1973b) A comparison of d-amphetamine, l-amphetamine and methamphetamine self-administration in rhesus monkeys. Pharmacol Biochem Behav 1:67-71
5. Bennett BA, Wichems CH, Hollingsworth CK, Davies HML, Thornley C, Sexton T, Childers SR (1995) Novel 2-substituted cocaine analogs: uptake and ligand binding sites at dopamine, serotonin, and norepinephrine transport sites in the rat brain. J Pharmacol Exp Ther 272:1176-1186
6. Bergman J, Madras BK, Johnson SE, Spealman RD (1989) Effects of cocaine and related drugs in nonhuman primates. III. Self-administration by squirrel monkeys. J Pharmacol Exp Ther 251:150-155
7. Carroll FI, Lewin AH, Boja JW, Kuhar MJ (1992) Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter. J Med Chem 35:969-981
8. Carroll FI, Lewin AH, Kuhar MJ (1997) Dopamine transporter uptake blockers: structure-activity relationships. In: Reith MEA (ed) Neurotransmitter transporters: structure, functions and regulation. Humana Press, NJ, pp 263-295
9. Chait LD, Uhlenhuth EH, Johanson CE (1987) Reinforcing and subjective effects of several anorectics in normal human volunteers. J Pharmacol Exp Ther 242:777-783
10. Church WH, Justice JB, Byrd LD (1987) Extracellular dopamine in rat striatum following uptake inhibition by cocaine, nomifensine and benztropine. Eur J Pharmacol 139:345-348
11. Corwin RL, Woolverton WL, Schuster CR, Johanson CE (1987) Anorectics: effects on food intake and self-administration in rhesus monkeys. Alcohol Drug Depend 7:351-361
12. De Wit H, Bodker B, Ambre J (1992) Rate of onset influences subjective response to pentobarbital. Psychopharmacology 107:352-358
13. De Wit H, Dudish S, Ambre J (1993) Subjective and behavioral effects of diazepam depend on its rate of onset. Psychopharmacology 112:324-330
14. 3H]paroxetine binding to the 5-hydroxytryptamine uptake site in an animal model of depression. J Neurochem 56:1581-1586
15. Goldschmidt PL, Savary L, Simon P (1984) Comparison of the stimulatory effects of eight antiparkinsonian drugs. Prog Neuropsychopharmacol Biol Psychiatry 8:257-261
16. 3H]CFT binds to multiple chargestates of the solubilized dopamine transporter in primate striatum. J Pharmacol Exp Ther 273:1224-1234
17. 3H]dopamine in rat brain tissue slices. Biochem Pharmacol 24:847-852
18. Horn AS (1990) Dopamine uptake: a review of progress in the last decade. Prog Neurobiol 34:387-400
19. Jayanthi LD, Prasad PD, Ramamoorthy S, Mahesh VB, Leibach FH, Ganapathy V (1993) Sodium-and chloride-dependent, cocaine-sensitive, high affinity binding of nisoxetine to human placental norepinephrine transporter. Biochemistry 32:12178-12185
20. Johanson CE, Balster RL (1978) A summary of the results of a drug self-administration study using substitution procedures in rhesus monkeys. Bull Narc 30:43-55
21. Katz, JL (1990) Models of relative reinforcing efficacy of drugs and their predictive utility. Behav Pharmacol 1:283-301
22. Katz JL, Newman AH, Izenwasser S (1997) Relations between heterogeneity of dopamine transporter binding and function and the behavioral pharmacology of cocaine. Pharmacol Biochem Behav 57:505-512
23. Katz JL, Izenwasser S, Kline RH, Alien AC, Newman AH (1999) Novel 3-diphenylmethoxytropane analogs: selective dopamine uptake inhibitors with behavioral effects different from those of cocaine. J Pharmacol Exp Ther 288:302-315
24. Kennedy LT, Hanbauer I (1983) Sodium-sensitive cocaine binding to rat striatal membrane: possible relationship to dopamine uptake sites. J Neurochem 41:172-178
25. Kline RH, Izenwasser S, Katz JL, Joseph DB, Bowen WD, Newman AH (1997) 3'-Chloro-3-(diphenylmethoxy)tropane but not 4'-chloro-3-(diphenylmethoxy)tropane produces a cocaine-like behavioral profile. J Med Chem 40:851-857
26. 3H]2β;-carbomethoxy-3β-(4-fluorophenyl)tropane. Mol Pharmacol 36:518-524
27. 3H] Cocaine binding sites in caudate-putamen. J Pharmacol Exp Ther 251:131-141
28. McKearney JW (1982) Effects of dopamine uptake inhibitors on schedule-controlled behavior in squirrel monkeys. Psychopharmacology 78:377-379
29. Macvicar K (1977) Abuse of antiparkinsonian drugs by psychiatric patients. Am J Psychiatry 134:809-811
30. Newman AH (1998) Novel dopamine transporter ligands: the state of the art. Med Chem Res 8:1-11
31. Newman AH, Agoston GE (1998) Novel benztropine [3-(diphenylmethoxytropane)] analogs as probes for the dopamine transporter. Curr Med Chem 5:301-315
32. Newman AH, Alien AC, Izenwasser S, Katz JL (1994) Novel 3-(diphenylmethoxy) tropane analogs: potent dopamine uptake inhibitors without cocaine-like behavioral profiles. J Med Chem 37:2258-2261
33. Newman AH, Kline RH, Alien AC, Izenwasser S, George C, Katz JL (1995) Novel 4'-and 4', 4"-substituted-3-(diphenylmethoxy) tropane analogs are potent and selective dopamine uptake inhibitors. J Med Chem 38:3933-3940
34. Reith MEA, Xu C, Chen N-H (1997) Pharmacology and regulation of the neuronal dopamine transporter. Eur J Pharmacol 324:1-10
35. Ritz MC, Lamb RJ, Goldberg SR, Kuhar MJ (1987) Cocaine receptors on dopamine transporters are related to self-administration. Science 237:1219-1223
36. Scheel-Krüger J (1972) Behavioural and biochemical comparison of amphetamine derivatives, cocaine, benztropine and tricyclic anti-depressant drugs. Eur J Pharmacol 18:63-73
37. Slusher BS, Tiffany CW, Olkowski JL, Jackson PF (1997) Use of identical assay conditions for cocaine analog binding and dopamine uptake to identify potential cocaine antagonists. Drug Alcohol Depend 48:43-50
38. Smith JM (1980) Abuse of antiparkinson drugs: a review of the literature. J Clin Psychiatry 41:351-354
39. Smith PK, Krohn RI, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, Fujimoto EK, Goeke NM, Olson BJ, Klenk DC (1985) Measurement of protein using bicinchoninic acid. Ann Biochem 150:76-85
40. Snider RS, Lee JC (1961) A stereotaxic atlas of the monkey brain. University of Chicago Press, Chicago
41. 3H]Nisoxetine: a radioligand for quantitation of norepinephrine uptake sites by autoradiography or by homogenate binding. J Pharmacol Exp Ther 260:427-436
42. Tolliver BK, Ho LB, Newman AH, Fox LM, Katz JL, Berger SP (1999) Behavioral and neurochemical effects of dopamine transporter ligands alone and in combination with cocaine: characterization of 4-chlorobenztropine in vivo. J Pharmacol Exp Ther 289:110-122
43. Vaughan RA, Simantov R, Leww R, Kuhar MJ (1991) A rapid binding assay for solubilized dopamine transporters using [3H]WIN 35,428. J Neurosci Methods 40:9-16
44. Vaughan RA, Agoston GE, Lever JR, Newman AH (1999) Differential binding of tropane-based photoaffinity ligands on the dopamine transporter. J Neurosci 19:630-636
45. 3H]-N-methylscopolamine binding to muscarinic receptors in the rat central nervous system: evidence for existence of three classes of binding sites. Mol Pharmacol 30: 305-314
46. Weed MR, Woolverton WL (1995) The reinforcing effects of dopamine D1 receptor agonists in rhesus monkeys. J Pharmacol ExpTher 275:1367-1374
47. Wilcox KM, Paul IA, Woolverton WL (1999) Comparison between dopamine transporter affinity and self-administration potency of local anesthetics in rhesus monkeys. Eur J Pharmacol 367:175-181
48. Wilson MC, Schuster CR (1973) Cholinergic influence on intravenous cocaine self-administration by rhesus monkeys. Pharmacol Biochem Behav 1:643-649
49. Winger G, Stitzer ML, Woods JH (1975) Barbiturate-reinforced responding in rhesus monkeys: comparisons of drugs with different durations of actions. J Pharmacol Exp Ther 195: 505-514
50. Wise RA, Rompre PP (1989) Brain dopamine and reward. Annu Rev Psychol 40:191-225
51. Woolverton WL (1996) Intravenous self-administration of cocaine under concurrent VI schedules of reinforcement. Psychopharmacology 127:195-203
52. Woolverton WL, Johnson KM (1992) Neurobiology of cocaine abuse. Trends Neurosci 13:193-200
53. Wu Q, Coffey LL, Reith ME (1997) Cations affect [3H]mazindol and [3H]WIN 35,428 binding to the human dopamine transporter in a similar fashion. J Neurochem 69:1106-1118