8-hydroxy-2-(di-n-propylamino)tetralin, 8-OH-DPAT, a potent and selective simplified ergot congener with central 5-HT-receptor stimulating activity

Aghajanian, G. K., Bunney, B. S., Kuhar, M. J.: Use of single unit recording in correlating transmitter turnover with impulse flow in monoamine neurons. In: New Concepts in Neurotransmitter Regulation (Mandell, A. J., ed.), pp. 119?134 and refs. cited therein. New York: Plenum Publ. Corp. 1973.

Ahlenius, S., Larsson, K., Svensson, L.: Further evidence for an inhibitory role of central 5-HT in male rat sexual behaviour. Psychopharmacol.68, 217?220 (1980 a).

Ahlenius, S., Larsson, K., Svensson, L.: Stimulating effects of lisuride on masculine sexual behaviour of rats. Eur. J. Pharmacol.64, 47?51 (1980 b).

Ahlenius, S., Larsson, K., Svensson, L., Hjorth, S., Carlsson, A., Lindberg, P., Wikström, H., Sanchez, D., Arvidsson, L.-E., Hacksell, U., Nilsson,J. L. G.: Effects of a new type of 5-HT receptor agonist on male rat sexual behavior. Pharmacol. Biochem. Behav.15, 785?792 (1981).

Andén, N.-E., Corrodi, H., Fuxe, K., Hökfelt, T.: Evidence for a central 5-hydroxytryptamine receptor stimulation by lysergic acid diethylamide. Br. J. Pharmacol.34, 1?7 (1968).

Arvidsson, L.-E., Hacksell, U., Nilsson, J. L. G., Hjorth, S., Carlsson, A., Lindberg, P., Sanchez, D., Wikström, H.: 8-hydroxy-2-(di-n-propylamino)tetralin, a new centrally acting 5-hydroxytryptamine receptor agonist. J. Med. Chem.24, 921?923 (1981).

Atack, C. V., Lindqvist, M.: Conjoint native and orthophthaldialdehyde-condensate assays for the fluorimetric determination of 5-hydroxyindoles in the brain. Naunyn-Schmiedeberg's Arch. Pharmacol.279, 267?284 (1973).

Bach, N. J., Kornfeld, E. C., Jones, N. D., Chancy, M. O., Dorman, D. E., Paschal, J. W., Clemens, J. A., Smalstig, E. B.: Bicyclic and tricyclic ergoline partial structures. Rigid 3-(2-aminoethyl)pyrroles and 3- and 4-(2-aminoethyl) pyrazoles as dopamine agonists. J. Med. Chem.23, 481?491 (1980).

Bédard, P., Carlsson, A., Lindqvist, M.: Effect of a transverse cerebral hemisection on 5-hydroxytryptamine metabolism in the rat brain. Naunyn-Schmiedeberg's Arch. Pharmacol.272, 1?15 (1972).

Camerman, N., Camerman, A.: On the stereochemistry of dopaminergic ergoline derivatives. Mol. Pharmacol.19, 517?519 (1981).

Cannon, J. G., Demopoulos, B. J., Long, J. P., Flynn, J. R., Sharabi, F. M.: Proposed dopaminergic pharmacophore of lergotrile, pergolide, and related ergot alkaloid derivatives. J. Med. Chem.24, 238?240 (1981).

Carlsson, A., Corrodi, H., Waldeck, B.:?-Substituierte Dopacetamide als Hemmer der Catechol-O-methyl-transferase und der enzymatischen Hydroxylierung aromatischer Aminosäuren. Helv. Chim. Acta46, 2271?2285 (1963).

Carlsson, A., Corrodi, H., Fuxe, K., Hökfelt, T.: Effect of antidepressant drugs on the depletion of intraneuronal brain 5-hydroxytryptamine stores caused by 4-methyl-?-ethyl-meta-tyramine. Eur. J. Pharmacol.5, 357?366 (1969).

Carlsson, A., Lindqvist, M.: The effect of L-tryptophan and some psychotropic drugs on the formation of 5-hydroxytryptophan in the mouse brainin vivo. J. Neural Transm.33, 23?43 (1972).

Carlsson, A.: Mechanism of action of neuroleptic drugs. In: Psychopharmacology: A Generation of Progress (Lipton, M. A., Killam, K. F., eds.), pp. 1057?1070. New York: Raven Press. 1978.

Cerrito, F., Raiteri, M.: Serotonin release is modulated by presynaptic autoreceptors. Eur. J. Pharmacol.57, 427?430 (1979).

Clineschmidt, B. V., Lotti, V. J.: Indolamine antagonists: Relative potencies as inhibitors of tryptamine- and 5-hydroxytryptophan-evoked responses. Br. J. Pharmacol.50, 311?313 (1974).

Feenstra, M., Rollema, H., Dijkstra, D., Grol, C. J., Horn, A. S., Westerink, B. H. C.: Effect of non-catecholic 2-aminotetralin derivatives on dopamine metabolism in the rat striatum. Naunyn-Schmiedeberg's Arch. Pharmacol.313, 213?219 (1980).

Freedman, D. X.: Effects of LSD-25 on brain serotonin. J. Pharmacol. Exp. Therap.134, 160?168 (1961).

Fuxe, K., Agnati, L., Everitt, B.: Effects of methergoline on central monoamine neurones. Evidence for a selective blockade of central 5-HT receptors. Neurosci. Lett.1, 283?290 (1975).

Gerson, S. C., Baldessarini, R. J.: Motor effects of serotonin in the central nervous system. Life Sci.27, 1435?1451 (1980).

Hacksell, U., Svensson, U., Nilsson, J. L. G., Hjorth, S., Carlsson, A., Wikström, H., Lindberg, P., Sanchez, D.: N-Alkylated 2-aminotetralins: Central dopamine receptor stimulating activity. J. Med. Chem.22, 1469?1475 (1979).

Haigler, H. J., Aghajanian, G. K.: Serotonin receptors in the brain. Fedn. Proc.36, 2159?2164 (1977).

Jacobs, B. L.: An animal behavior model for studying central serotonergic synapses. Life Sci.19, 777?786 (1976).

Kehr, W., Carlsson, A., Lindqvist, M.: Amethod for the determination of 3,4-dihydroxyphenylalanine (DOPA) in brain. Naunyn-Schmiedeberg's Arch. Pharmacol.274, 273?280 (1972).

Kehr, W.: Effects of lisuride and other ergot derivatives on monoaminergic mechanisms in rat brain. Eur. J. Pharmacol.41, 261?273 (1977).

Lloyd, K. G., Bartholini, G.: The effect of methiothepin on cerebral monoamine neurons. In: Advances in Biochemical Psychopharmacology, Vol. 10, pp. 305?309. New York: Raven Press. 1974.

McDermed, J. D., McKenzie, G. M., Phillips, A. P.: Synthesis and pharmacology of some 2-aminotetralins Dopamine receptor agonists. J. Med. Chem.18, 362?367 (1975).

McDermed, J. D., McKenzie, G. M., Freeman, H. S.: Synthesis and dopaminergic activity of (±)-, (±)-, and (?)-2-dipropylamino-5-hydroxy-1,2,3,4-tetrahydronaphthalene. J. Med. Chem.19, 547?549 (1976).

Nichols, D. E.: Structural correlation between apomorphine and LSD: Involvement of dopamine as well as serotonin in the actions of hallucinogens. J. Theor. Biol.59, 167?177 (1976).

Nichols, D. E., Pfister, W. R., Yim, G. K. W., Cosgrove, R. J.: A new view of the structural relationship between LSD and mescaline. Brain Res. Bull.2, 169?171 (1977).

Peroutka, S. J., Snyder, S. H.: Two distinct serotonin receptors: Regional variations in receptor binding in mammalian brain. Brain Res.208, 339?347 (1981).

Peroutka, S. J., Lebowitz, R. M., Snyder, S. H.: Two distinct central serotonin receptors with different physiological functions. Science212, 827?829 (1981).

Pieri, L., Keller, H. H., Burkard, W., DaPrada, M.: Effects of lisuride and LSD on cerebral monoamine systems and hallucinosis. Nature272, 278?279 (1978).

Rogawski, M. A., Aghajanian, G. K.: Response of central monoaminergic neurons to lisuride: comparison with LSD. Life Sci.24, 1289?1298 (1979).

Rosecrans, J. A., Lovell, R. A., Freedman, D. X.: Effects of lysergic acid diethylamide on the metabolism of brain 5-hydroxytryptamine. Biochem. Pharmacol.16, 2001?2021 (1967).

Sastry, B. S. R., Phillis, J. W.: Methergoline as a selective 5-hydroxytryptamine antagonist in the cerebral cortex. Can. J. Physiol. Pharmacol.55, 130?133 (1977).

Silbergeld, E. K. Hruska, R. E.: Lisuride and LSD: Dopaminergic and serotonergic interactions in the ?serotonin syndrome?. Psychopharmacol.65, 233?237 (1979).

Slaytor, M. B., Wright, S. E.: The metabolites of ergometrine and lysergic acid diethylamide in rat bile. J. Med. Pharmaceut. Chem.5, 483?491 (1962).

Tebecis, A.: Antagonism of 5-hydroxytryptamine by methiothepin shown in microelectrophoretic studies of neurones in the lateral geniculate nucleus. Nature (New Biol.)238, 63?64 (1972).

Trulson, M. E., Ross, C. A., Jacobs, B. L.: Behavioral evidence for the stimulation of CNS serotonin receptors by high doses of LSD. Psychopharmacol. Communic.2, 149?164 (1976).

Walters, J. R., Baring, M. D., Lakoski, J. M.: Effects of ergolines on dopaminergic and serotonergic single unit activity. In: Dopaminergic Ergot Derivatives and Motor Function (Fuxe, K., Calne, D. B., eds.), pp. 207?221. Oxford: Pergamon Press. 1979.

Wikström, H., Sanchez, D., Lindberg, P., Arvidsson, L.-E., Hacksell, U., Johansson, A., Nilsson, J. L. G., Hjorth, S., Carlsson, A.: Monophenolic octahydrobenzo(f)quinolines-Central dopamine- and serotonin-receptor stimulating activity. J. Med. Chem.25, 925?931 (1982).