Summary
Intraperitoneal injection of the (+)-erythro isomer of 3,4-dihydroxyphenylserine (DOPS) to rats markedly increased the concentration of cerebral noradrenaline (NA) which probably corresponds to the unnatural (+) form. In contrast, the other 3 stereoisomers of DOPS caused only a minor rise of NA. This difference is likely to be connected with the configuration of the stereoisomers at the α and β carbon which determines the rate of decarboxylation and possibly of penetration into the brain.
References
Bartholini, G., Constantinidis, J., Tissot, R., Pletscher, A.: Formation of monoamines from various amino acids in the brain after inhibition of extracerebral decarboxylase. Biochem. Pharmacol. 20, 1243–1247 (1971)
Blaschko, H., Chruściel, T. L.: The decarboxylation of amino acids related to tyrosine and their awakening action in reserpine-treated mice. J. Physiol. (Lond.) 151, 272–284 (1960)
Cahn, R. S., Ingold, C., Prelog, V.: The specification of asymmetric configuration in organic chemistry. Experientia (Basel) 12, 81–94 (1956)
Cahn, R. S., Ingold, C., Prelog, V.: Spezifikation der molekularen Chiralität. Angew. Chem. 78, 413–447 (1966)
Carlsson, A.: Functional significance of drug-induced changes in brain monoamine levels. In: Biogenic amines. H. E. Himwich and W. A. Himwich, eds. Prog. Brain Res. 8, 9–27 (1964)
Constantinidis, J., Bartholini, G., Geissbühler, F., Tissot, R.: La barrière capillaire enzymatique pour le dopa au niveau de quelques noyaux du tronc cérébral du rat. Experientia (Basel) 26, 381–383 (1970)
Constantinidis, J., Bartholini, G., Tissot, R., Pletscher, A. Accumulation of dopamine in the parenchyma after decarboxylase inhibition in the capillaries of brain. Experientia (Basel) 24, 130–131 (1968)
Creveling, C. R., Daly, J., Tokuyama, T., Witkop, B.: The combined use of α-methyltyrosine and threo-dihydroxyphenylserine. Selective reduction of dopamine levels in central nervous system. Biochem. Pharmacol. 17, 65–70 (1968)
Häggendahl, C. J.: An improved method for fluorimetric determination of small amounts of adrenaline and noradrenaline in plasma and tissues. Acta physiol. scand. 59, 242–254 (1963)
Havlíček, V.: The effect of dl-3,4-dihydroxyphenylserine (precursor of noradrenaline) on the ECoG of unrestrained rats. Int. J. Neuropharmacol. 6, 83–88 (1967)
Holtz, P., Heise, R., Lüdke, K.: Fermentationsabbau von l-dioxyphenylalanine (DOPA) durch Niere. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. 191, 87–118 (1938)
Porter, C. C., Torchiana, M. L., Stone, C. A.: (S)-norepinephrine in the tissues of mice and rats given racemic erythro-3,4-dihydroxyphenylserine (DOPS). Life Sci. 1972, 787–795.
Pratesi, P., La Manna, A., Campiglio, A., Ghislandi, V.: The configuration of noradrenaline. J. chem. Soc. 1959, 4062–4065
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Puig, M., Bartholini, G. & Pletscher, A. Formation of noradrenaline in the rat brain from the four stereoisomers of 3,4-dihydroxyphenylserine. Naunyn-Schmiedeberg's Arch. Pharmacol. 281, 443–446 (1974). https://doi.org/10.1007/BF00499439
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00499439