Differential serotoninergic and dopaminergic activities of the (R)- and the (S)-enantiomers of 2-( di-n-propylamino) tetralin

European Journal of Pharmacology

Volumn 303, Issue 3, 1996, Pages 151-162

  Yu, Hong ^a   Liu, Ye ^b   Malmberg, Åsa ^b,c   Mohell, Nina ^c   Hacksell, Uli ^b   Lewander, Tommy ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

^c Astra Arcus AB   (Sweden)

Author keywords

(Racemate); (Rat); (Stereoisomer); 2 (Di n propylamino)tetralin; 5 HT1A receptor; Chiral compound; Dopamine D2 receptor

Indexed keywords

2 DIPROPYLAMINO 5 FLUORO 8 HYDROXYTETRALIN; 2 DIPROPYLAMINO 8 HYDROXYTETRALIN; 2 DIPROPYLAMINOTETRALIN; 3 HYDROXYBENZYLHYDRAZINE; 5 HYDROXY 2 (DIPROPYLAMINO)TETRALIN; 5 HYDROXYTRYPTOPHAN; DECARBOXYLASE INHIBITOR; DOPA; DOPAMINE 2 RECEPTOR; DOPAMINE 2 RECEPTOR BLOCKING AGENT; DOPAMINE 2 RECEPTOR STIMULATING AGENT; METIROSINE METHYL ESTER; POSTSYNAPTIC RECEPTOR; PRESYNAPTIC RECEPTOR; QUINPIROLE; RACLOPRIDE; RADIOLIGAND; RESERPINE; SEROTONIN 1A AGONIST; SEROTONIN 1A ANTAGONIST; SEROTONIN 1A RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BEHAVIOR; BODY POSTURE; BODY TEMPERATURE; BRAIN; CONTROLLED STUDY; DOPAMINERGIC SYSTEM; DRUG ANTAGONISM; DRUG RECEPTOR BINDING; ENANTIOMER; GNAWING; HYPOTHERMIA; LICKING; MALE; MONOAMINE METABOLISM; NONHUMAN; PRIORITY JOURNAL; RACEMIC MIXTURE; RAT; SEROTONINERGIC SYSTEM; SNIFFING; SUBCUTANEOUS DRUG ADMINISTRATION;

8-HYDROXY-2-(DI-N-PROPYLAMINO)TETRALIN; ANIMALS; BEHAVIOR, ANIMAL; BODY TEMPERATURE; DOPAMINE; DOPAMINE AGONISTS; MALE; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, DOPAMINE; RECEPTORS, SEROTONIN; SEROTONIN; SEROTONIN AGONISTS; STEREOISOMERISM; TETRAHYDRONAPHTHALENES;

EID: 0029951557     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/0014-2999(96)00051-9     Document Type: Article

References (40)

1. Arvidsson, L.E., U. Hacksell, J.L.G. Nilsson. S. Hjorth, A. Carlsson, P. Lindberg, D. Sanchez and H. Wikström, 1981, 8-Hydroxy-2-(di-n-propylamino)tetralin, a new centrally acting 5-hydroxytryptamine receptor agonist, J. Med. Chem. 24, 921.
2. 2 dopamine agonists, Naunyn-Schmied. Arch. Pharmacol. 336, 487.
3. Beaulieu, M., Y. Itoh, P. Tepper, A.S. Horn and J.W. Kebabian, 1984, N,N-disubstituted 2-aminotetralins are potent D-2 dopamine receptor agonists, Eur. J. Pharmacol. 105, 15.
4. 1A receptors in the brain, J. Med. Chem. 32, 779.
5. 1A receptor antagonist (S)-5-fluoro-8-hydroxy-2-(dipropylamino)tetralin: inhibition of (R)-8-hydroxy-2-(dipropylamino)tetralin-induced effects, J. Pharmacol. Exp. Ther. 258, 58.
6. Cannon, J.G., T. Lee, H.D. Goldman, B. Costall and R.J. Naylor, 1977, Cerebral dopamine agonist properties of some 2-aminotetralin derivatives after peripheral and intracerebral administration, J. Med. Chem. 20, 1111.
7. 3H]haloperidol to neuroleptic receptors in the rat striatum, Biochem. Pharmacol. 27, 1417.
8. Carlsson, A., J.N. Davis, W. Kehr, M. Lindqvist and C.V. Atack, 1972, Stimultaneous measurement of tyrosine and tryptophan hydroxylase activities in brain in vivo using an inhibitor of the aromatic amino acid decarboxylase. Naunyn-Schmied. Arch. Pharmacol. 275, 153.
9. Cloetta, M. and E. Waser, 1923, Über die Beziehungen zwischen Konstitution und Wirkung beim alizyklischen Tetrahydro-β-Naphtylamin und seinen Derivaten, Arch. Exp. Pathol. Pharmacol. 98, 198.
10. 1A receptors that are negatively coupled to adenylate cyclase, Mol. Pharmacol. 39, 780.
11. Costall, B., R.J. Naylor, J.G. Cannon and T. Lee, 1977, Differential activation by some 2-aminotetralin derivatives of the receptor mechanisms in the nucleus accumbens of rat which mediate hyperactivity and stereotyped biting, Eur. J. Pharmacol. 41, 307.
12. Feenstra, M.G.P., C. Sumners, J.H. Goedemoed, J.B. De Vries, H. Rollema and A.S. Horn, 1983, A comparison of the potencies of various dopamine receptor agonists in models for pre-and post-synaptic receptor activity, Naunyn-Schmied. Arch. Pharmacol. 324, 108.
13. Fuller, R.W. and H.D. Snoddy, 1981, Elevation of serum corticosterone concentrations in rats by pergolide and other dopamine agonists, Endocrinology 109, 1026.
14. 2 receptors produces jerks in reserpine-treated rats, J. Pharm. Pharmacol. 35, 543.
15. Hjorth, S., A. Carlsson, D. Clark, K. Svensson, H. Wikström, D. Sanchez, P. Lindberg, U. Hacksell, L.E. Arvidsson, A.M. Johansson and J.L.G. Nilsson, 1983, Central dopamine receptor agonist and antagonist actions of the enantiomers of 3-PPP, Psychopharmacology 81, 89.
16. Ilhan, M., J.P. Long and J.G. Cannon, 1984, Dopaminergic activity of a nonhydroxylated aminotetralin derivative (TL-68) on cat hearts, Arch. Int. Pharmacodyn. 271, 213.
17. Jackson, D.M., N. Mohell, J. Georgiev, A. Bengtsson, L.G. Larsson, O. Magnusson, and S.B. Ross, 1995, Time course of bromocriptine induced excitation in the rat: behavioural and biochemical studies, Naunyn-Schmied. Arch. Pharmacol. 351, 146.
18. Jacobs, B.L., 1976, An animal behaviour model for studying central serotonergic synapses, Life Sci. 19, 777.
19. Karlsson A., L. Björk, C. Pettersson, N.E. Andén and U. Hacksell, 1990, (R)- and (S)-5-Hydroxy-2-(dipropylamino)tetralin (5-OH-DPAT): assessment of optical purities and dopaminergic activities, Chirality 2, 90.
20. Lahti, R.A., L.M. Figur, M.F. Piercey, P.L. Ruppel and D.L. Evans, 1992, Intrinsic activity determinations at the dopamine D, guanine nucleotide-binding protein-coupled receptor: utilization of receptor state binding affinities, Mol. Pharmacol. 42, 432.
21. 1A receptors, J. Med. Chem. 36, 4221.
22. 3 receptors-effects of ions and guanine nucleotides, J. Pharmacol. Exp. Ther. 274, 790.
23. 3 receptors. Mol. Pharmacol. 43, 749.
24. 3 receptors, Mol. Pharmacol. 46, 299.
25. McDermed, J.D., G.M. McKenzie and A.P. Phillips, 1975, Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists, J. Med. Chem. 18, 362.
26. McDermed, J.D., G.M. McKenzie and H.S. Freeman, 1976, Synthesis and dopaminergic activity of (R,S)-, (R)-, and (S)-2-dipropylamino-5-hydroxy-1,2,3,4-tetrahydronaphthalene, J. Med. Chem. 19, 547.
27. 3 receptors, Eur. J. Pharmacol. 249, R5.
28. Munson, P.J. and D. Rodbard, 1980, LIGAND: a versatile computerized approach for characterization of ligand-binding system, Anal. Biochem. 107, 220.
29. Ortmann, R., 1985, The 5-HT syndrome and the drug discrimination paradigm in rats: application in behavioral studies on the central 5-HT system, Pharmacopsychiatry 18, 198.
30. 2 receptor antagonist raclopride discriminates between dopamine-mediated motor functions, Psychopharmacology 90, 287.
31. Rusterholz, D.B., J.P. Long, J.R. Flynn, J.G. Cannon, T. Lee, J.P. Pease, J.A. Clemens, D.T. Wong and F.P. Bymaster, 1979, Dopaminergic effects of non-hydroxylated rigid analogs of apomorphine, Eur. J. Pharmacol. 55, 73.
32. 2 receptor binding sites for agonists. A tetrahedral model, Mol. Pharmacol. 28, 391.
33. Sharabi, F.M., J.P. Long, D.B. Rusterholz, W.E. Hoffman, T. Lee, and J.G. Cannon, 1978, Centrally mediated hypotension and bradycardia induced by an aminotetralin derivative: TL-68, Res. Comm. Chem. Pathol. Pharmacol. 20, 457.
34. Sheppard, H., C.R. Burghardt and J.P. Long, 1978, The effect of dihydroxy-2-aminotetralins (DATs) on dopamine and beta type adenylate cyclases, Res. Comm. Chem. Pathol. Pharmacol. 19, 213.
35. Sokoloff, P. and J.-C. Schwartz, 1995, Novel dopamine receptors half a decade later, Trends Pharmacol. Sci. 16 270.
36. 3) as a target for neuroleptics, Nature (London) 347, 146.
37. 1 receptor and of catecholaminergic systems in the behavioural response to 8-hydroxy-2-(di-n-propylamino)tetralin in the rat, Eur. J. Pharmacol. 106, 271.
38. Van Oene, J.C., J.B. De Vries, D. Dijkstra, R.J.W. Renkema, P.G. Tepper and A.S. Horn, 1984, In vivo dopamine autoreceptor selectivity appears to be critically dependent upon the aromatic hydroxyl position in a series of N,N-disubstituted 2-aminotetralins, Eur. J. Pharmacol. 102, 101.
39. 3-receptor: a postsynaptic receptor inhibitory on rat locomotor activity, J. Neural Transm. 94, 11.
40. 1A receptor agonists, Eur. J. Pharmacol. 231, 69.