Skip to main content
SpringerLink
Log in

Enzymological and pharmacological aspects of monoamine oxidase

  • Chapter
IUPHAR 9th International Congress of Pharmacology

Abstract

Although inhibitors of monoamine oxidase [amine: oxygen oxido-reductase (deaminating) (flavin-containing) EC 1.4.3.4] (MAO) have been of value in the treatment of certain types of depression (see for example, Pare, 1976), their use has been limited by a range of possible adverse reactions in subjects treated with these compounds (see for instance, Dostert, 1984). Particular attention has been focused on the, potentially fatal, hypertensive effect that may result if patients treated with monoamine oxidase inhibitors ingest foodstuffs containing tyramine (the tyramine pressor response or ‘cheese reaction’ — see for example Marley, 1977).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • ASK, A.-L., FLAGERVALL, I. & ROSS, S.B. (1984). Amiflavine (FLA 336(+)), a reversible MAO-A in hibitor selective for serotoninergic neurones. In Monoamine Oxidase and Disease: Prospects for Therapy with Reversible Inhibitors. Dostert, P., Strolin Benedetti, M. & Tipton, K.F. (eds), London: Academic Press (in press).

    Google Scholar 

  • ASK, A.-L., HELLSTRÖM, W., NORRMAN, S., ÖGREN, S.- O. & ROSS, S.B. (1982). Selective inhibition of the A form of monoamine oxidase by 4-dimethylamino-a- methylphenylalkylamine derivatives in the rat. Neuropharmacology, 21, 299–308.

    Article  Google Scholar 

  • BIRKMEYER, W., RIEDERER, P., AMBROZI, L. & YOUDIM, M.B.H. (1977). Implications of combined treatment with ‘Madopar’ and 1-deprenyl in Parkinson’s disease. A long term therapy. Lancet, i, 439–443.

    Article  Google Scholar 

  • CALLINGHAM, B.A. (1981). Resolution of amine oxidase activities by irreversible inhibitors. In Monoamine Oxidase Basic and Clinical Frontiers. Kamijo, K., Usdin, E. & Nagatsu, T.(eds) pp. 100–111, Amsterdam: Excerpta Medica.

    Google Scholar 

  • CARLSSON, A., FOWLER, C.J., MAGNUSSON, T., ORELAND, L. & WIBERG, A. (1981). The activities of monoamine oxidase-A and -B, succinic dehydrogenase and acid phosphatase in the rat brain after hemitransac- tion. Naunyn-Schmiedebergs Arch. Pharmac, 316, 51–55.

    Article  Google Scholar 

  • CARMAN, J.S., GILLIN, J.C., MURPHY, D.L., WEINBER GER, D.R., KLEINMAN, J.E., BIGELOW, L.B. & WYATT, R.J. (1978). Effects of a selective inhibitor of type A monoamine oxidase — Lilly 51641 — on behaviour, sleep and circadian rhythms in depressed and schizophrenic patients. Commun. Psychopharmac, 2, 512–523.

    Google Scholar 

  • DA PRADA, M., KETTLER, R., KELLER, H.H. & HAEFELY, W.E. (1983). Neurochemical effects in vitro and in vivo of the antidepressant Ro 11–1163, a specific and short acting MAO-A inhibitor. In Monoamine Oxidase and its Selective Inhibitors. Beckmann, H. & Riederer, P. (eds) pp. 231–245, Basel: Karger.

    Google Scholar 

  • DELLA CORTE, L. & TIPTON, K.F. (1980). The turnover of the A- and B-forms of monoamine oxidase in rat liver. Biochem. Pharmac, 29, 891–895.

    Article  Google Scholar 

  • DEMAREST, KT., SMITH, D.J. & AZZARO, A.J. (1980). The presence of the type A form of monoamine oxidase within nigrostriatal dopamine-containing neurones. J. Pharmac. exp. Ther., 215, 461–468.

    Google Scholar 

  • DOSTERT, P. (1984). Myth and reality of the classical MAO inhibitors. Reasons for seeking a new generation. In Monoamine Oxidase and Disease: Prospects for Therapy with Reversible Inhibitors. Dostert, P., Strolin Benedetti, M. & Tipton, K.F. (eds), London: Academic Press (in press).

    Google Scholar 

  • ELSWORTH, J.D., GLOVER, V., REYNOLDS, G.P., SAND LER, M., LEES, A.J., PHUAPRADIT, P., SHAW, K.M., STERN, G.M. & KUMAR, P. (1978). Deprenyl administration in man. A selective MAO-B inhibitor without the ‘cheese effect’. Psychopharmacology, 57, 33–38.

    Article  Google Scholar 

  • FOWLER, C.J. & STROLIN BENEDETTI, M. (1983). Cimoxatone is a reversible tight-binding inhibitor of the A form of rat brain monoamine oxidase. J. Neurochem., 40, 510–513.

    Article  Google Scholar 

  • FOWLER, C.J. & TIPTON, K.F. (1981). Concentration dependence of the oxidation of tyramine by the two forms of rat liver mitochondrial monoamine oxidase. Biochem. Pharmac, 30, 3329–3332.

    Article  Google Scholar 

  • FOWLER, C.J. & TIPTON, K.F. (1982). Deamination of 5- hydroxytryptamine by both forms of monoamine oxidase in the rat brain. J. Neurochem., 38, 733–736.

    Article  Google Scholar 

  • FOWLER, C.J., MANTLE, T.J. & TIPTON, K.F. (1982a). The nature of the inhibition of rat liver monoamine oxidase types A and B by the acetylenic inhibitors clorgyline, 1- deprenyl and pargyline. Biochem. Pharmac, 31, 3555–3561.

    Article  Google Scholar 

  • FOWLER, C.J., TIPTON, K.F., STROLIN BENEDETTI, M. & DOW, J. (1982b). Inhibitory properties of MD 780236 and its alcohol metabolite towards monoamine oxidase- B. Acta physiol. scand., Suppl. 508, 39.

    Google Scholar 

  • FOWLER, C.J., TIPTON, K.F., MacKAY, A.V.P. & YOUDIM, M.B.H. (1982c). Human platelet monoamine oxidase — a useful enzyme in the study of psychiatric disorders? Neuroscience, 7, 1577–1594.

    Article  Google Scholar 

  • GARRICK, N.A. & MURPHY, D.L. (1982). Monoamine oxidase type A: differences in selectivity towards 1- norepinephrine compared to serotonin. Biochem. Phar mac, 31, 4061–4066.

    Article  Google Scholar 

  • GLOVER, V., SANDLER, M., OWEN, F. & RILEY, GJ. (1977). Dopamine is a monoamine oxidase B substrate in man. Nature, 265, 80–81.

    Article  Google Scholar 

  • GORIDIS, C. & NEFF, N.H. (1971). Monoamine oxidase in sympathetic nerves: a transmitter specific enzyme type. Br. J. Pharmac, 31, 4061–4066.

    Google Scholar 

  • GREEN, A.L. (1981). The kinetics of inhibition of type-B monoamine oxidase by clorgyline, pargyline and deprenyl. J. Pharm. Pharmac, 33, 798–800.

    Article  Google Scholar 

  • HALL, D.W.R., LOGAN, B.W. & PARSONS, G.H. (1969). Further studies on the inhibition of monoamine oxidase by M & B 9302 (clorgyline). I. Substrate specificity in various mammalian species. Biochem. Pharmac, 18, 1447–1454.

    Article  Google Scholar 

  • HERD, J.A. (1969). A new antidepressant M & B 9302. A pilot study and double blind controlled trial. Clin. Trials, 6, 119–126.

    Google Scholar 

  • HOUSLAY, M.D. & TIPTON, K.F. (1974). A kinetic evalua tion of monoamine oxidase activity in rat liver mitochon drial outer membranes. Biochem. J., 139, 645–652.

    Article  Google Scholar 

  • JOHNSTON, J.P. (1968). Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem. Pharmac, 17, 1285–1297.

    Article  Google Scholar 

  • KINEMUCHI, H., WAKUI, W. & KAMIJO, K. (1980). Sub strate selectivity of type A and type B monoamine oxidase in rat brain. J. Neurochem., 39,109–115.

    Article  Google Scholar 

  • LEVITT, P., PINTAR, J.E. & BREAKEFIELD, X.O. (1982). Immunocytochemical demonstration of monoamine oxidase B in brain astrocytes and serotoninergic neurons. Proc. natn. Acad. Sci. U.S.A.., 79,6385–6389.

    Article  Google Scholar 

  • LEWINSON, R., GLOVER, V. & SANDLER, M. (1980). ß- Phenylethylamine and benzylamine as substrates for human monoamine oxidase A: a source of some anomolies? Biochem. Pharmac, 29, 1221–1230.

    Article  Google Scholar 

  • MANN, J. & GERSHON, S. (1980). L-Deprenyl, a selective monoamine oxidase type B inhibitor in endogenous depression. Life Sci., 26, 877–882.

    Article  Google Scholar 

  • MANTLE, T.J., TIPTON, K.F. & GARRETT, N.J. (1976). In hibition of monoamine oxidase by amphetamine and related compounds. Biochem. Pharmac, 25, 2073–2077.

    Article  Google Scholar 

  • MARLEY, E. (1977). Monoamine oxidase inhibitors and drug interactions. In Drug Interactions. Grahame-Smith, D.G. (ed.), pp. 171–194, London: Macmillan.

    Google Scholar 

  • MENDIS, N., PARE, C.M.B., SANDLER, M., GLOVER, V. & STERN, G. (1981). (-)-Deprenyl in treatment of depression. In Monoamine Oxidase Inhibitors — The State of the Art. Youdim, M.B.H. & Paykel, E.S. (eds) pp. 171–176, Chichester: Wiley.

    Google Scholar 

  • MENDLEWICZ, J. & YOUDIM, M.B.H. (1980). Anti depressant potentiation of 5-HTP by l-deprenyl in affective illness. J. Affect. Dis., 2,137–142.

    Article  Google Scholar 

  • MURPHY, D.L., LIPPER, S., CAMPBELL, I.C., MAJOR, L.F., SLATER, S. & BUCHSBAUM, M.S. (1979). Comparative studies of MAO-A and MAO-B inhibitors in man. In Monoamine Oxidase, Structure, Function and Altered Functions. Singer, T.P., Von Korff, R.W. & Murphy, D.L. (eds) pp. 457–475, New York: Academic Press.

    Google Scholar 

  • MURPHY, D.L., ROY, B., PICKAR, D., LIPPER, S., COHEN, R.M., JIMERSON, P., LAKE, C.R., MUSCETTOLA, G., SAAVEDRA, J. & KOPIN, I.(1981). Cardiovascular changes accompanying MAO inhibition in man. In Func tion and Regulation of Monoamine Enzymes. Usdin, E., Weiner, N. & Youdim, M.B.H. (eds) pp. 549–560, Lon don: Macmillan.

    Google Scholar 

  • NEFF, N.H. & GORIDIS, C. (1972). Neuronal monoamine oxidases, specific enzyme types and their rate of formation. Adv. Biochem. Psychopharmac, 5, 307–323.

    Google Scholar 

  • NELSON, D.L., HERBERT, A., PETILLOT, Y., PICHAT, L., GLOWINSKI, J. & HAMON M., (1979). [3H]Harmaline as a specific ligand for MAO-A. Properties of the active site of MAO-A from rat and bovine brains. J. Neurochem., 32, 1817–1827.

    Article  Google Scholar 

  • O’BRIEN, R.D. (1968). Kinetics of the carbamylation of cholinesterase. Mol. Pharmac, 4, 121–130.

    Google Scholar 

  • O’CARROLL, A.-M., FOWLER, C.J., PHILLIPS, J.P., TOB-BIA, I. & TIPTON, K.F. (1983). The deamination of dopamine by human brain monoamine oxidase. Specificity for the two enzyme forms in seven brain regions. Naunyn-Schmiedebergs Arch. Pharmac, 322, 198–202.

    Article  Google Scholar 

  • PALFREYMAN, M.G., McDONALD, I., ZREIKA, M. & FOZARD, J.P. (1983). MDL 72394: the prodrug approach to monoamine oxidase inhibition. L’Encephale, 9, Suppl. 1, 55A.

    Google Scholar 

  • PARE, C.M.B. (1976). Introduction to clinical aspects of monoamine oxidase inhibitors in the treatment of depression. Ciba Found. Symp., 39, 271–280.

    Google Scholar 

  • PICKAR, D., COHEN, R.M., JIMERSON, D.L. & MURPHY, D.L. (1981). Tyramine infusions and selective monoamine oxidase inhibitor treatment. Psychophar-macology, 74, 4–7.

    Article  Google Scholar 

  • POWELL, J.F. & CRAIG, I.W. (1977). Biochemical and immunological studies of the monoamine oxidase activities of cultured human cells. Biochem. Soc Trans., 5, 180–182.

    Article  Google Scholar 

  • SMITH, T.E., WEISSBACH, H. & UDENFRIEND, S. (1963). Studies on monoamine oxidase: The mechanism of inhibition of monoamine oxidase by iproniazid. Biochemistry, 2, 746–751.

    Article  Google Scholar 

  • STROLIN BENEDETTI, M., BOUCHER, T. & FOWLER, C.J. (1983a). The deamination of noradrenaline and 5- hydroxytryptamine by rat brain and heart monoamine oxidase and their inhibition by cimoxatone, toloxatone and MD 770222. Naunyn-Schmiedebergs Arch. Pharmac, 323, 315–320.

    Article  Google Scholar 

  • STROLIN BENEDETTI, M., BOUCHER, T., CARLSSON, A. & FOWLER, C.J. (1983b). Intestinal metabolism of tyramine by both forms of monoamine oxidase in the rat. Biochem. Pharmac, 32, 47–52.

    Article  Google Scholar 

  • STUDENT, A.K. & EDWARDS, D.J. (1977). Subcellular localisation of type A and type B monoamine oxidase in rat brain. Biochem. Pharmac, 26, 2337–2342.

    Article  Google Scholar 

  • SUZUKI, O., HATTORI, H., OYA, M., KATSUMATA, Y. & MATSUMOTO, T. (1979). Oxidation of ß-phenyl- ethylamine by both types of monoamine oxidase: effects of substrate concentration and pH. Life Sci., 25, 1843–1850.

    Article  Google Scholar 

  • TIPTON, K.F. (1980). Kinetics and enzyme inhibition studies. In Enzyme Inhibitors as Drugs. Sandler, M. (ed.) pp. 1–23, London: Macmillan.

    Google Scholar 

  • TIPTON, K.F., HOUSLAY, M.D. & MANTLE, T.J. (1976). The nature and locations of the multiple forms of monoamine oxidase. Ciba Found. Symp., 39, 5–16.

    Google Scholar 

  • TIPTON, K.F., FOWLER, C.J. & HOUSLAY, M.D. (1982a). Specificities of the two forms of monoamine oxidase. In Monoamine Oxidase: Basic and Clinical Frontiers, Kamijo, K., Usdin, E. & Nagatsu, T. (eds) pp. 87–99, Amsterdam: Excerpta Medica.

    Google Scholar 

  • TIPTON, K.F., McCRODDEN, J.M., KALIR, A.S. & YOUDIM, M.B.H. (1982a). Inhibition of rat liver monamine oxidase by a-methyl- and N-propargyl-amine derivatives. Biochem. Pharmac, 31, 1251–1255.

    Article  Google Scholar 

  • TIPTON, K.F., FOWLER, C.J., McCRODDEN, J.M. & STROLIN BENEDETTI, M. (1983). The enzyme- activated irreversible inhibition of type-B monoamine oxidase by 3-[4-[(3-chlorophenyl)methoxy] phenyl]-5- [(methylamino) methyl]-2-oxazolidinone methane sulphate (compound MD 780236) and the enzyme- catalysed oxidation of this compound as competing reactions. Biochem. J., 209, 235–242.

    Article  Google Scholar 

  • TIPTON, K.F., McCRODDEN, J.M., HENEHAN, G.T.M., BOUCHER, T. & FOWLER, C.J. (1984). The formation of the acidic and alcoholic metabolites of MD 780236. Biochem. Pharmac, 33, 1377–1378.

    Article  Google Scholar 

  • VAN DER KROGT, J.A., KOOT-GRONSVELD, E. & VAN DEN BERG, C. (1983). Localization of rat striatal monoamine oxidase activities towards dopamine, serotonin and kynuramine by gradient centrifugation and nigro-striatal lesions. Life Sci., 33, 615–623.

    Article  Google Scholar 

  • WALDMEIER, P.C., FELNER, A.E. & TIPTON, K.F. (1983). The monoamine oxidase inhibiting properties of CGP 11305A. Eur. J. Pharmac, 94, 73–83.

    Article  Google Scholar 

  • WHEATLEY, D. (1970). Comparative trial of a new monoamine oxidase inhibitor in depression. Br. J. Psychiat., 117,573–574.

    Article  Google Scholar 

  • WHITE, H.L. & TANSIK, R.L. (1979). Characterization of multiple substrate binding sites of MAO. In Monoamine Oxidase Structure, Function and Altered Functions. Singer, T.P., Von Korff, R.W., & Murphy, D.L. (eds) pp. 129–144, New York: Academic Press.

    Google Scholar 

  • WILLIAMS, J.W. & MORRISON, J.F. (1979). The kinetics of reversible tight-binding inhibition. Meth. Enzymol., 63A, 437–467.

    Article  Google Scholar 

  • YANG, H.-Y.T. & NEFF, N.H. (1973). ß-Phenylethylamine: a specific substrate for type B monoamine oxidase of brain. J. Pharmac. exp. Ther., 187, 365–371.

    Google Scholar 

  • YOUDIM, M.B.H. (1983). In vivo, noradrenaline is a sub strate for rat brain monoamine oxidase A and B. Br. J. Pharmac, 79, 477–486.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Biochemistry, Trinity College, Dublin 2, Ireland

    K. F. Tipton, A. M. O’Carroll & F. Hasan

Authors
  1. K. F. Tipton
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. M. O’Carroll
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. F. Hasan
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

William Paton James Mitchell Paul Turner

Copyright information

© 1984 Macmillan Publishers Limited

About this chapter

Cite this chapter

Tipton, K.F., O’Carroll, A.M., Hasan, F. (1984). Enzymological and pharmacological aspects of monoamine oxidase. In: Paton, W., Mitchell, J., Turner, P. (eds) IUPHAR 9th International Congress of Pharmacology. Palgrave, London. https://doi.org/10.1007/978-1-349-86029-6_27

Download citation

Publish with us

Policies and ethics

Search

Navigation