메뉴 건너뛰기




Volumn 54, Issue 12, 1997, Pages 1361-1369

Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Structure-activity relationships

Author keywords

Amphetamine derivatives; Antidepressants; MAO inhibitors; Monoamine oxidase; Phenylisopropylamine derivatives; Structure activity relationships

Indexed keywords

5 HYDROXYINDOLEACETIC ACID; AMIFLAMINE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; AMPHETAMINE; AMPHETAMINE DERIVATIVE; CLORGYLINE; SELEGILINE; SEROTONIN;

EID: 0000206859     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00405-X     Document Type: Article
Times cited : (76)

References (51)
  • 1
    • 0018183281 scopus 로고
    • Substrate-selective monoamine oxidases
    • Murphy DL. Substrate-selective monoamine oxidases. Biochem Pharmacol. 27:1978;1889-1893.
    • (1978) Biochem Pharmacol , vol.27 , pp. 1889-1893
    • Murphy, D.L.1
  • 2
    • 0014314486 scopus 로고
    • Some observations upon a new inhibitor of monoamine oxidase in brain tissue
    • Johnston JP. Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem Pharmacol. 17:1968;1285-1297.
    • (1968) Biochem Pharmacol , vol.17 , pp. 1285-1297
    • Johnston, J.P.1
  • 4
    • 0020690441 scopus 로고
    • Implications of MAO-A and MAO-B inhibitors for antidepressant therapy
    • Youdim MBH. Implications of MAO-A and MAO-B inhibitors for antidepressant therapy. Mod Probl Pharmacopsychiatry. 19:1983;63-74.
    • (1983) Mod Probl Pharmacopsychiatry , vol.19 , pp. 63-74
    • Youdim, M.B.H.1
  • 5
    • 0002886610 scopus 로고
    • Monoamine oxidase inhibitors as antidepressants: Implication for the mechanism of action of antidepressants and the psychobiology of the affective disorders and some related disorders
    • H.Y. Meltzer. New York: Raven Press
    • Murphy DL, Aulakh CS, Garrik NA, Sunderland T. Monoamine oxidase inhibitors as antidepressants Implication for the mechanism of action of antidepressants and the psychobiology of the affective disorders and some related disorders . Meltzer HY. Psychopharmacology The Third Generation of Progress . 1987;545-552 Raven Press, New York.
    • (1987) Psychopharmacology: The Third Generation of Progress , pp. 545-552
    • Murphy, D.L.1    Aulakh, C.S.2    Garrik, N.A.3    Sunderland, T.4
  • 6
    • 0342680987 scopus 로고
    • Dietary issues and the "irreversible" MAOIs
    • S.H. Kennedy. Washington, DC: American Psychiatric Press
    • Shulman KI. Dietary issues and the "irreversible" MAOIs. Kennedy SH. Clinical Advances in Monoamine Oxidase Inhibitor Therapies. 1994;111-124 American Psychiatric Press, Washington, DC.
    • (1994) Clinical Advances in Monoamine Oxidase Inhibitor Therapies , pp. 111-124
    • Shulman, K.I.1
  • 8
    • 0006959229 scopus 로고
    • Pharmacology and pharmacokinetics of brofaromine and moclobemide in animals and humans
    • S.H. Kennedy. Washington, DC: American Psychiatric Press
    • Waldmeier PC, Amrein R, Schmid-Burgk W. Pharmacology and pharmacokinetics of brofaromine and moclobemide in animals and humans. Kennedy SH. Clinical Advances in Monoamine Oxidase Inhibitor Therapies. 1994;33-59 American Psychiatric Press, Washington, DC.
    • (1994) Clinical Advances in Monoamine Oxidase Inhibitor Therapies , pp. 33-59
    • Waldmeier, P.C.1    Amrein, R.2    Schmid-Burgk, W.3
  • 9
    • 0002793084 scopus 로고
    • Tyramine potentiation during treatment with MAOIs
    • S.H. Kennedy. Washington, DC: American Psychiatric Press
    • Bieck PR, Antonin K-H. Tyramine potentiation during treatment with MAOIs. Kennedy SH. Clinical Advances in Monoamine Oxidase Inhibitor Therapies. 1994;83-110 American Psychiatric Press, Washington, DC.
    • (1994) Clinical Advances in Monoamine Oxidase Inhibitor Therapies , pp. 83-110
    • Bieck, P.R.1    Antonin K-H2
  • 10
    • 0017143464 scopus 로고
    • Inhibition of monoamine oxidase by amphetamine and related compounds
    • Mantle TJ, Tipton KF, Garrett NJ. Inhibition of monoamine oxidase by amphetamine and related compounds. Biochem Pharmacol. 25:1976;2073-2077.
    • (1976) Biochem Pharmacol , vol.25 , pp. 2073-2077
    • Mantle, T.J.1    Tipton, K.F.2    Garrett, N.J.3
  • 11
    • 0017927424 scopus 로고
    • Selective MAO inhibitors. Compounds related to 4-aminophenethylamine
    • Florvall L, Ask A-L, Ögren S-O, Ross SB. Selective MAO inhibitors. Compounds related to 4-aminophenethylamine. J Med Chem. 21:1978;56-63.
    • (1978) J Med Chem , vol.21 , pp. 56-63
    • Florvall, L.1    Ask A-L2    Ögren S-O3    Ross, S.B.4
  • 12
    • 0022998222 scopus 로고
    • Selective MAO inhibitors. 4. 4-Aminophenethylamine derivatives with neuron selective action
    • Florvall L, Ask A-L, Fagervall I, Ross SB. Selective MAO inhibitors. 4. 4-Aminophenethylamine derivatives with neuron selective action. J Med Chem. 29:1986;2250-2256.
    • (1986) J Med Chem , vol.29 , pp. 2250-2256
    • Florvall, L.1    Ask A-L2    Fagervall, I.3    Ross, S.B.4
  • 14
    • 0020316166 scopus 로고
    • Influence of ring and side chain substituents on the selectivity of amphetamine as a monoamine oxidase inhibitor
    • Fuller RW, Hemrick-Luecke SK. Influence of ring and side chain substituents on the selectivity of amphetamine as a monoamine oxidase inhibitor. Res Commun Subst Abuse. 3:1982;159-164.
    • (1982) Res Commun Subst Abuse , vol.3 , pp. 159-164
    • Fuller, R.W.1    Hemrick-Luecke, S.K.2
  • 15
    • 0025369020 scopus 로고
    • Inhibition of brain type A monoamine oxidase and 5-hydroxytryptamine uptake by two amphetamine metabolites, p-hydroxyamphetamine and p-hydroxynorephedrine
    • Arai Y, Kim SK, Kinemuchi H, Tadano T, Satoh S-E, Satoh N, Kisara K. Inhibition of brain type A monoamine oxidase and 5-hydroxytryptamine uptake by two amphetamine metabolites, p-hydroxyamphetamine and p-hydroxynorephedrine. J Neurochem. 55:1990;403-408.
    • (1990) J Neurochem , vol.55 , pp. 403-408
    • Arai, Y.1    Kim, S.K.2    Kinemuchi, H.3    Tadano, T.4    Satoh S-E5    Satoh, N.6    Kisara, K.7
  • 16
    • 0019191223 scopus 로고
    • P-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo
    • Green AL, El Hait MAS. p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo. J Pharm Pharmacol. 32:1980;262-266.
    • (1980) J Pharm Pharmacol , vol.32 , pp. 262-266
    • Green, A.L.1    El Hait, M.A.S.2
  • 17
    • 0021022469 scopus 로고
    • Selective monoamine oxidase inhibitors. Compounds derived from phenethylamine and 1-phenoxy-2-aminopropane
    • Kumar Y, Florvall L, Ask A-L, Ross SB, Holm A-C, Ögren S-O. Selective monoamine oxidase inhibitors. Compounds derived from phenethylamine and 1-phenoxy-2-aminopropane. Acta Pharm Suec. 20:1983;349-364.
    • (1983) Acta Pharm Suec , vol.20 , pp. 349-364
    • Kumar, Y.1    Florvall, L.2    Ask A-L3    Ross, S.B.4    Holm A-C5    Ögren S-O6
  • 18
    • 0021075106 scopus 로고
    • Selective monoamine oxidase inhibitors. II. 4-Aminophenylalkylamine derivatives
    • Florvall L, Ask A-L, Ross SB, Ögren S-O, Holm A-Ch. Selective monoamine oxidase inhibitors. II. 4-Aminophenylalkylamine derivatives. Acta Pharm Suec. 20:1983;255-270.
    • (1983) Acta Pharm Suec , vol.20 , pp. 255-270
    • Florvall, L.1    Ask A-L2    Ross, S.B.3    Ögren S-O4    Holm A-Ch5
  • 19
    • 0022456375 scopus 로고
    • Selective MAO inhibitors. 3. Cyclic compounds related to 4-aminophenethylamine. Preparation and neuron selective action of some 5-(2-aminoethyl)-2,3-dihydroindoles
    • Florvall L, Kumar Y, Ask A-L, Fagervall I, Ross SB. Selective MAO inhibitors. 3. Cyclic compounds related to 4-aminophenethylamine. Preparation and neuron selective action of some 5-(2-aminoethyl)-2,3-dihydroindoles. J Med Chem. 29:1986;1406-1412.
    • (1986) J Med Chem , vol.29 , pp. 1406-1412
    • Florvall, L.1    Kumar, Y.2    Ask A-L3    Fagervall, I.4    Ross, S.B.5
  • 20
    • 0021845521 scopus 로고
    • Inhibition of MAO in 5-hydroxytryptaminergic neurons by substituted p-aminophenylalkylamines
    • Ask A-L, Fagervall I, Florvall L, Ross SB, Ytterborn S. Inhibition of MAO in 5-hydroxytryptaminergic neurons by substituted p-aminophenylalkylamines. Br J Pharmacol. 85:1985;683-690.
    • (1985) Br J Pharmacol , vol.85 , pp. 683-690
    • Ask A-L1    Fagervall, I.2    Florvall, L.3    Ross, S.B.4    Ytterborn, S.5
  • 23
    • 0002467903 scopus 로고
    • Medicinal chemistry and structure-activity relationships
    • A.K. Cho, & D.S. Segal. San Diego, CA: Academic Press
    • Nichols DE. Medicinal chemistry and structure-activity relationships. Cho AK, Segal DS. Amphetamine and Its Analogs. Psychopharmacology, Toxicology and Abuse. 1994;3-41 Academic Press, San Diego, CA.
    • (1994) Amphetamine and Its Analogs. Psychopharmacology, Toxicology and Abuse , pp. 3-41
    • Nichols, D.E.1
  • 26
    • 0015322949 scopus 로고
    • Potential psychotomimetics. New bromoalkoxy-amphetamines
    • Sepúlveda S, Valenzuela R, Cassels BK. Potential psychotomimetics. New bromoalkoxy-amphetamines. J Med Chem. 15:1972;413-415.
    • (1972) J Med Chem , vol.15 , pp. 413-415
    • Sepúlveda, S.1    Valenzuela, R.2    Cassels, B.K.3
  • 27
    • 0023628951 scopus 로고
    • A quantum-chemical and experimental study on the hallucinogen (±)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON)
    • Gómez-Jeria JS, Cassels BK, Saavedra-Aguilar JC. A quantum-chemical and experimental study on the hallucinogen (±)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON). Eur J Med Chem. 22:1987;433-437.
    • (1987) Eur J Med Chem , vol.22 , pp. 433-437
    • Gómez-Jeria, J.S.1    Cassels, B.K.2    Saavedra-Aguilar, J.C.3
  • 28
    • 0028349504 scopus 로고
    • Some fluoro and nitro analogues of hallucinogenic amphetamines
    • Jara AN, Torres MA, Cassels BK, Rezende MC. Some fluoro and nitro analogues of hallucinogenic amphetamines. Synth Commun. 24:1994;417-426.
    • (1994) Synth Commun , vol.24 , pp. 417-426
    • Jara, A.N.1    Torres, M.A.2    Cassels, B.K.3    Rezende, M.C.4
  • 32
    • 0028360365 scopus 로고
    • 4-Dimethylaminophenethylamine, a sensitive, specific, electrochemically detectable monoamine oxidase-B substrate
    • Reyes-Parada M, Scorza MC, Silveira R, Dajas F, Cassels BK. 4-Dimethylaminophenethylamine, a sensitive, specific, electrochemically detectable monoamine oxidase-B substrate. Life Sci. 54:1994;1955-1963.
    • (1994) Life Sci , vol.54 , pp. 1955-1963
    • Reyes-Parada, M.1    Scorza, M.C.2    Silveira, R.3    Dajas, F.4    Cassels, B.K.5
  • 34
    • 0016802875 scopus 로고
    • Comparison of 4-chloro-, 4-bromo-, and 4-fluoroamphetamine in rats: Drug levels in brain and effects on brain serotonin metabolism
    • Fuller RW, Baker JC, Perry KW, Molloy BB. Comparison of 4-chloro-, 4-bromo-, and 4-fluoroamphetamine in rats Drug levels in brain and effects on brain serotonin metabolism . Neuropharmacology. 14:1975;483-488.
    • (1975) Neuropharmacology , vol.14 , pp. 483-488
    • Fuller, R.W.1    Baker, J.C.2    Perry, K.W.3    Molloy, B.B.4
  • 36
    • 0026014834 scopus 로고
    • Synthesis, biological evaluation and quantitative structure activity relationship analysis of nuclear-substituted pargylines as competitive inhibitors of MAO-A and MAO-B
    • Ali A, Robinson JB. Synthesis, biological evaluation and quantitative structure activity relationship analysis of nuclear-substituted pargylines as competitive inhibitors of MAO-A and MAO-B. J Pharm Pharmacol. 43:1991;750-757.
    • (1991) J Pharm Pharmacol , vol.43 , pp. 750-757
    • Ali, A.1    Robinson, J.B.2
  • 37
    • 0028329424 scopus 로고
    • A PLS quantitative structure-activity relationship study of some monoamine oxidase inhibitors of phenylalkylamine type
    • Norinder U, Florvall L, Ross SB. A PLS quantitative structure-activity relationship study of some monoamine oxidase inhibitors of phenylalkylamine type. Eur J Med Chem. 29:1994;191-195.
    • (1994) Eur J Med Chem , vol.29 , pp. 191-195
    • Norinder, U.1    Florvall, L.2    Ross, S.B.3
  • 38
    • 0021646446 scopus 로고
    • 2 involvement in the mechanism of action of hallucinogenic agents
    • 2 involvement in the mechanism of action of hallucinogenic agents. Life Sci. 35:1984;2505-2511.
    • (1984) Life Sci , vol.35 , pp. 2505-2511
    • Glennon, R.A.1    Titeler, M.2    McKenney, J.D.3
  • 39
    • 0023882042 scopus 로고
    • 2 receptor as a site of action for LSD and phenylisopropylamine hallucinogens
    • 2 receptor as a site of action for LSD and phenylisopropylamine hallucinogens. Psychopharmacology. 94:1988;213-216.
    • (1988) Psychopharmacology , vol.94 , pp. 213-216
    • Titeler, M.1    Lyon, R.A.2    Glennon, R.A.3
  • 42
    • 0026748823 scopus 로고
    • Effects of p-chloroamphetamine on brain serotonin neurons
    • Fuller RW. Effects of p-chloroamphetamine on brain serotonin neurons. Neurochem Res. 17:1992;449-456.
    • (1992) Neurochem Res , vol.17 , pp. 449-456
    • Fuller, R.W.1
  • 43
    • 0023803409 scopus 로고
    • Evidence for dual serotonergic projections to neocortex: Axons from the dorsal and median raphe nuclei are differentially vulnerable to the neurotoxin p-chloroamphetamine (PCA)
    • Mamounas LA, Molliver ME. Evidence for dual serotonergic projections to neocortex Axons from the dorsal and median raphe nuclei are differentially vulnerable to the neurotoxin p-chloroamphetamine (PCA) . Exp Neurol. 102:1988;23-36.
    • (1988) Exp Neurol , vol.102 , pp. 23-36
    • Mamounas, L.A.1    Molliver, M.E.2
  • 44
    • 0023735752 scopus 로고
    • Methylenedioxyamphetamine (MDA) and methylenedioxymethamphetamine (MDMA) cause selective ablation of serotonergic axon terminals in forebrain: Immunocytochemical evidence for neurotoxicity
    • O'Hearn E, Battaglia G, De Souza EB, Kuhar MJ, Molliver ME. Methylenedioxyamphetamine (MDA) and methylenedioxymethamphetamine (MDMA) cause selective ablation of serotonergic axon terminals in forebrain Immunocytochemical evidence for neurotoxicity . J Neurosci. 8:1988;2788-2803.
    • (1988) J Neurosci , vol.8 , pp. 2788-2803
    • O'Hearn, E.1    Battaglia, G.2    De Souza, E.B.3    Kuhar, M.J.4    Molliver, M.E.5
  • 45
    • 0026545692 scopus 로고
    • P-Methylthioamphetamine is a potent new non-neurotoxic serotonin-releasing agent
    • Huang X, Marona-Lewicka D, Nichols DE. p-Methylthioamphetamine is a potent new non-neurotoxic serotonin-releasing agent. Eur J Pharmacol. 229:1992;31-38.
    • (1992) Eur J Pharmacol , vol.229 , pp. 31-38
    • Huang, X.1    Marona-Lewicka, D.2    Nichols, D.E.3
  • 46
    • 0029078456 scopus 로고
    • The monoamine oxidase-B inhibitor l-deprenyl protects against 3,4-methylenedioxymethamphetamine-induced lipid peroxidation and long-term serotonergic deficits
    • Sprague JE, Nichols DE. The monoamine oxidase-B inhibitor l-deprenyl protects against 3,4-methylenedioxymethamphetamine-induced lipid peroxidation and long-term serotonergic deficits. J Pharmacol Exp Ther. 273:1995;667-673.
    • (1995) J Pharmacol Exp Ther , vol.273 , pp. 667-673
    • Sprague, J.E.1    Nichols, D.E.2
  • 47
    • 0028949807 scopus 로고
    • Inhibition of MAO-B protects against MDMA-induced neurotoxicity in the striatum
    • Sprague JE, Nichols DE. Inhibition of MAO-B protects against MDMA-induced neurotoxicity in the striatum. Psychopharmacology. 118:1995;357-359.
    • (1995) Psychopharmacology , vol.118 , pp. 357-359
    • Sprague, J.E.1    Nichols, D.E.2
  • 48
    • 0028308447 scopus 로고
    • The MAO-B inhibitor deprenyl, but not the MAO-A inhibitor clorgyline, potentiates the neurotoxicity of p-chloroamphetamine
    • Benmansour S, Brunswick DJ. The MAO-B inhibitor deprenyl, but not the MAO-A inhibitor clorgyline, potentiates the neurotoxicity of p-chloroamphetamine. Brain Res. 650:1994;305-312.
    • (1994) Brain Res , vol.650 , pp. 305-312
    • Benmansour, S.1    Brunswick, D.J.2
  • 50
    • 0029658459 scopus 로고    scopus 로고
    • (±)-1-(2,5-Dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors
    • Reyes-Parada M, Scorza C, Romero V, Silveira R, Medina JH, Andrus D, Nichols DE, Cassels BK. (±)-1-(2,5-Dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors. Naunyn-Schmiedebergs Arch Pharmacol. 354:1996;579-585.
    • (1996) Naunyn-Schmiedebergs Arch Pharmacol , vol.354 , pp. 579-585
    • Reyes-Parada, M.1    Scorza, C.2    Romero, V.3    Silveira, R.4    Medina, J.H.5    Andrus, D.6    Nichols, D.E.7    Cassels, B.K.8
  • 51
    • 0002353477 scopus 로고
    • Clinical pharmacology of anxiolytics and antidepressants: A psychopharmacological perspective
    • S.E. File. New York: Pergamon Press
    • Nutt DJ, Glue P. Clinical pharmacology of anxiolytics and antidepressants A psychopharmacological perspective . File SE. Psychopharmacology of Anxiolytics and Antidepressants. 1991;1-28 Pergamon Press, New York.
    • (1991) Psychopharmacology of Anxiolytics and Antidepressants , pp. 1-28
    • Nutt, D.J.1    Glue, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.