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Volumn 36, Issue 23, 1993, Pages 3700-3706

Synthesis and Pharmacological Examination of Benzofuran, Indan, and Tetralin Analogues of 3,4-(Methylenedioxy)amphetamine

Author keywords

[No Author keywords available]

Indexed keywords

3,4 METHYLENEDIOXYAMPHETAMINE; 3,4 METHYLENEDIOXYMETHAMPHETAMINE; AMPHETAMINE; BENZOFURAN DERIVATIVE; DOPAMINE; DRUG ANALOG; INDAN DERIVATIVE; LYSERGIDE; NEUROTRANSMITTER; NORADRENALIN; OXYGEN; PARGYLINE; SEROTONIN; SODIUM CHLORIDE; TETRALIN DERIVATIVE;

EID: 0027135576     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00075a027     Document Type: Article
Times cited : (78)

References (33)
  • 2
    • 0027410102 scopus 로고
    • Interactions of Methylenedioxymetham-phetamine with Monoamine Transmitter Release Mechanisms in Rat Brain Slices
    • Fitzgerald, J. L.; Reid, J. J. Interactions of Methylenedioxymetham-phetamine with Monoamine Transmitter Release Mechanisms in Rat Brain Slices. Naunyn-Schmiedeberg'sArch. Pharmacol. 1993, 347, 313–323.
    • (1993) Naunyn-Schmiedeberg'sArch. Pharmacol. , vol.347 , pp. 313-323
    • Fitzgerald, J.L.1    Reid, J.J.2
  • 4
    • 0022874762 scopus 로고
    • Derivatives of 1-(1,3-Benzodioxol-5-yl)-2-butanamine: Representatives of a Novel Therapeutic Class
    • Nichols, D. E.; Hoffman, A. J.; Oberlender, R. A.; Jacob, P., III; Shulgin, A. T. Derivatives of 1-(1,3-Benzodioxol-5-yl)-2-butanamine: Representatives of a Novel Therapeutic Class. J. Med. Chem. 1986, 29, 2009–2015.
    • (1986) J. Med. Chem. , vol.29 , pp. 2009-2015
    • Nichols, D.E.1    Hoffman, A.J.2    Oberlender, R.A.3    Jacob, P.4    Shulgin, A.T.5
  • 5
    • 0022838197 scopus 로고
    • Differences Between the Mechanism of Action of MDMA, MBDB, and the Classic Hallucinogens. Identification of a New Therapeutic Class: Entactogens
    • Nichols, D. E. Differences Between the Mechanism of Action of MDMA, MBDB, and the Classic Hallucinogens. Identification of a New Therapeutic Class: Entactogens. J. Psychoact. Drugs 1986, 18, 305–313.
    • (1986) J. Psychoact. Drugs , vol.18 , pp. 305-313
    • Nichols, D.E.1
  • 6
    • 0025652948 scopus 로고
    • Structure-Activity Relationships of MDMA and Related Compounds: A New Class of Psychoactive Drugs?
    • Nichols, D. E.; Oberlender, R. Structure-Activity Relationships of MDMA and Related Compounds: A New Class of Psychoactive Drugs? Ann. N.Y. Acad. Sci. 1990, 600, 613–625.
    • (1990) Ann. N.Y. Acad. Sci. , vol.600 , pp. 613-625
    • Nichols, D.E.1    Oberlender, R.2
  • 7
    • 0023920316 scopus 로고
    • Drug Discrimination Studies With MDMA and Amphetamine
    • Oberlender, R.; Nichols, D. E. Drug Discrimination Studies With MDMA and Amphetamine. Psychopharmacology 1988, 95, 71–76.
    • (1988) Psychopharmacology , vol.95 , pp. 71-76
    • Oberlender, R.1    Nichols, D.E.2
  • 8
    • 0025650302 scopus 로고
    • (+)-N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a Discriminative Stimulus in Studies of 3,4-Methylenedioxymethamphetamine-Like Behavioral Activity
    • Oberlender, R.; Nichols, D. E. (+)-N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a Discriminative Stimulus in Studies of 3,4-Methylenedioxymethamphetamine-Like Behavioral Activity. J. Pharmacol. Exp. Ther. 1990, 255, 1098–1106.
    • (1990) J. Pharmacol. Exp. Ther. , vol.255 , pp. 1098-1106
    • Oberlender, R.1    Nichols, D.E.2
  • 9
    • 0022839628 scopus 로고
    • The Background and Chemistry of MDMA
    • Shulgin, A. T. The Background and Chemistry of MDMA. J. Psychoact. Drugs 1986, 18, 291–304.
    • (1986) J. Psychoact. Drugs , vol.18 , pp. 291-304
    • Shulgin, A.T.1
  • 10
    • 0023228746 scopus 로고
    • Stereochemical Effects of 3,4-Methylenedioxymethamphetamine (MDMA) and Related Amphetamine Derivatives on Inhibition of Uptake of [3H]-Monoamines into Synaptosomes from Different Regions of Rat Brain
    • Steele, T. D.; Nichols, D. E.; Yim, G. K. W. Stereochemical Effects of 3,4-Methylenedioxymethamphetamine (MDMA) and Related Amphetamine Derivatives on Inhibition of Uptake of [3H]-Monoamines into Synaptosomes from Different Regions of Rat Brain. Biochem. Pharmacol. 1987, 36, 2297–2303.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 2297-2303
    • Steele, T.D.1    Nichols, D.E.2    Yim, G.K.W.3
  • 11
    • 0024241851 scopus 로고
    • Subjective Effects of 3,4-Methylenedioxymethamphetamine in Recreational Users
    • Peroutka, S. J.; Newman, H.; Harris, H. Subjective Effects of 3,4-Methylenedioxymethamphetamine in Recreational Users. Neu-ropsychopharmacology 1988, 1, 273–277.
    • (1988) Neu-ropsychopharmacology , vol.1 , pp. 273-277
    • Peroutka, S.J.1    Newman, H.2    Harris, H.3
  • 12
    • 0344594694 scopus 로고
    • Letters from Andrew Weil. The Love Drug
    • Weil, A. T. Letters from Andrew Weil. The Love Drug. J. Psychedelic Drugs 1976, 8, 335–337.
    • (1976) J. Psychedelic Drugs , vol.8 , pp. 335-337
    • Weil, A.T.1
  • 13
    • 0022838801 scopus 로고
    • Subjective Reports of the Effects of MDMA in a Clinical Setting
    • Greer, G.; Tolbert, R. Subjective Reports of the Effects of MDMA in a Clinical Setting. J. Psychoact. Drugs 1986, 18, 319–327.
    • (1986) J. Psychoact. Drugs , vol.18 , pp. 319-327
    • Greer, G.1    Tolbert, R.2
  • 14
    • 84989037778 scopus 로고
    • A Place for Ecstasy in Psychotherapy?
    • Trager, J. A Place for Ecstasy in Psychotherapy? Med. Tribune 1988, 29, 12–14.
    • (1988) Med. Tribune , vol.29 , pp. 12-14
    • Trager, J.1
  • 15
    • 0022845199 scopus 로고
    • Meetings at the Edge with Adam: A Man for All Seasons
    • Wolfson, P. E. Meetings at the Edge with Adam: A Man for All Seasons. J. Psychoact. Drugs 1986, 18, 329–333.
    • (1986) J. Psychoact. Drugs , vol.18 , pp. 329-333
    • Wolfson, P.E.1
  • 16
    • 0022486506 scopus 로고
    • Methylenedioxy-methamphetamine: A Potentially Neurotoxic Amphetamine Analogue
    • Schmidt, C. J.; Wu, L.; Lovenberg, W. Methylenedioxy-methamphetamine: A Potentially Neurotoxic Amphetamine Analogue. Eur. J. Pharmacol. 1986, 124, 175–178.
    • (1986) Eur. J. Pharmacol. , vol.124 , pp. 175-178
    • Schmidt, C.J.1    Wu, L.2    Lovenberg, W.3
  • 17
    • 0022911033 scopus 로고
    • The Effects of 3,4-Methylenedioxymethamphetamine (MDMA) and 3,4-Methylenedioxyamphetamine (MDA) on Monoaminergic Systems in the Rat Brain
    • Stone, D. A.; Stahl, D. C.; Hanson, G. R.; Gibb, J. W. The Effects of 3,4-Methylenedioxymethamphetamine (MDMA) and 3,4-Methylenedioxyamphetamine (MDA) on Monoaminergic Systems in the Rat Brain. Eur. J. Pharmacol. 1986, 128, 41–48.
    • (1986) Eur. J. Pharmacol. , vol.128 , pp. 41-48
    • Stone, D.A.1    Stahl, D.C.2    Hanson, G.R.3    Gibb, J.W.4
  • 19
    • 0023902232 scopus 로고
    • Toxic Effects of MDMA on Central Serotonergic Neurons in the Primate: Importance of Route and Frequency of Drug Administration
    • Ricaurte, G.; Delanney, L. E.; Irwin, I.; Langsten, J. W. Toxic Effects of MDMA on Central Serotonergic Neurons in the Primate: Importance of Route and Frequency of Drug Administration. Brain Res. 1988, 446, 165–168.
    • (1988) Brain Res. , vol.446 , pp. 165-168
    • Ricaurte, G.1    Delanney, L.E.2    Irwin, I.3    Langsten, J.W.4
  • 20
    • 0026322365 scopus 로고
    • Serotonin Neurotoxicity in Rats After Combined Treatment With a Dopaminergic Agent Followed by a Nonneurotoxic 3,4-Methylenedioxymethamphet-amine (MDMA) Analogue
    • Johnson, M. P.; Huang, X.; Nichols, D. E. Serotonin Neurotoxicity in Rats After Combined Treatment With a Dopaminergic Agent Followed by a Nonneurotoxic 3,4-Methylenedioxymethamphet-amine (MDMA) Analogue. Pharmacol. Biochem. Behau. 1991, 40, 915–922.
    • (1991) Pharmacol. Biochem. Behau. , vol.40 , pp. 915-922
    • Johnson, M.P.1    Huang, X.2    Nichols, D.E.3
  • 22
    • 0025739285 scopus 로고
    • Synthesis and Pharmacological Examination of 1-(3-Methoxy-4-methylphenyl)-2-aminopropane and 5-Methoxy-6-methyl-2-aminoindan: Similarities to 3,4-(Methylenedioxy)methamphet-amine (MDMA)
    • Johnson, M. P.; Frescas, S. P.; Oberlender, R.; Nichols, D. E. Synthesis and Pharmacological Examination of 1-(3-Methoxy-4-methylphenyl)-2-aminopropane and 5-Methoxy-6-methyl-2-aminoindan: Similarities to 3,4-(Methylenedioxy)methamphet-amine (MDMA). J. Med. Chem. 1991, 34, 1662–1668.
    • (1991) J. Med. Chem. , vol.34 , pp. 1662-1668
    • Johnson, M.P.1    Frescas, S.P.2    Oberlender, R.3    Nichols, D.E.4
  • 23
    • 0025918369 scopus 로고
    • 3H]Monoamine Releasing and Uptake Inhibition Properties of 3,4-Methylene-dioxymethamphetamine and p-Chloroamphetamine analogues
    • 3H]Monoamine Releasing and Uptake Inhibition Properties of 3,4-Methylene-dioxymethamphetamine and p-Chloroamphetamine analogues. Eur. J. Pharmacol. 1991, 200, 9–16.
    • (1991) Eur. J. Pharmacol. , vol.200 , pp. 9-16
    • Johnson, M.P.1    Conarty, P.F.2    Nichols, D.E.3
  • 24
    • 0025063946 scopus 로고
    • Nonneurotoxic Tetralin and Indan Analogues of 3,4-(Methylenedioxy)amphetamine (MDA)
    • Nichols, D. E.; Brewster, W. K.; Johnson, M. P.; Oberlender, R.; Riggs, R. M. Nonneurotoxic Tetralin and Indan Analogues of 3,4-(Methylenedioxy)amphetamine (MDA). J. Med. Chem. 1990, 33, 703–710.
    • (1990) J. Med. Chem. , vol.33 , pp. 703-710
    • Nichols, D.E.1    Brewster, W.K.2    Johnson, M.P.3    Oberlender, R.4    Riggs, R.M.5
  • 25
    • 0012733678 scopus 로고
    • Exclusive Ortho α-Chlo-roacetylation of Phenols
    • Toyoda, T.; Sasakura, K.; Sugasawa, T. Exclusive Ortho α-Chlo-roacetylation of Phenols. J. Org. Chem. 1981, 46, 189–191.
    • (1981) J. Org. Chem. , vol.46 , pp. 189-191
    • Toyoda, T.1    Sasakura, K.2    Sugasawa, T.3
  • 27
    • 0003135197 scopus 로고
    • Structure-activity Relationships of MDMA and Related Compounds, a New Class of Psychoactive Agents
    • Peroutka, S. J., Eds.; Kluwer Academic Publishers: Boston
    • Nichols, D. E.; Oberlender, R. Structure-activity Relationships of MDMA and Related Compounds, a New Class of Psychoactive Agents. In Ecstasy: The Clinical, Pharmacological, and Neurotoxicological Effects of the Drug MDMA; Peroutka, S. J., Eds.; Kluwer Academic Publishers: Boston, 1990.
    • (1990) Ecstasy: The Clinical, Pharmacological, and Neurotoxicological Effects of the Drug MDMA
    • Nichols, D.E.1    Oberlender, R.2
  • 28
    • 0027337064 scopus 로고
    • 2 Receptor-mediated Potentiation of Dopamine Synthesis and Serotonergic Neurotoxicity
    • in press
    • 2 Receptor-mediated Potentiation of Dopamine Synthesis and Serotonergic Neurotoxicity. Eur. J. Pharmacol. 1993, in press.
    • (1993) Eur. J. Pharmacol.
    • Huang, X.1    Nichols, D.E.2
  • 30
    • 85013226206 scopus 로고
    • Hypoglycemic Thiazolidineones
    • United States Patent 4,703,052, October 27
    • Eggler, J. F.; Holland, G. F.; Johnson, M. R.; Volkmann, R. A. Hypoglycemic Thiazolidineones. United States Patent 4,703,052, October 27, 1987.
    • (1987)
    • Eggler, J.F.1    Holland, G.F.2    Johnson, M.R.3    Volkmann, R.A.4
  • 31
    • 0342426589 scopus 로고
    • Chloromethylation of Ortho-Disubstituted Benzenes. A Simple Preparation of Some Useful α Isomers of Indan, Tetralin, and Benzosuberane
    • Wightman, R. H.; Laycock, D. E.; Avdovich, H. W. Chloromethylation of Ortho-Disubstituted Benzenes. A Simple Preparation of Some Useful α Isomers of Indan, Tetralin, and Benzosuberane. J. Org. Chem. 1978, 43, 2167–2170.
    • (1978) J. Org. Chem. , vol.43 , pp. 2167-2170
    • Wightman, R.H.1    Laycock, D.E.2    Avdovich, H.W.3
  • 32
    • 84951384024 scopus 로고
    • A Simplified Method of Evaluating Dose-Effect Experiments
    • Litchfield, J. T.; Wilcoxon, F. A Simplified Method of Evaluating Dose-Effect Experiments. J. Pharmacol. Expt. Ther. 1949, 96, 99–113.
    • (1949) J. Pharmacol. Expt. Ther. , vol.96 , pp. 99-113
    • Litchfield, J.T.1    Wilcoxon, F.2
  • 33
    • 0022005744 scopus 로고
    • Analysis of Radioligand Binding Experimente: A Collection of Computer Programs for the IBM PC
    • McPherson, G. A. Analysis of Radioligand Binding Experimente: A Collection of Computer Programs for the IBM PC. J. Pharmacol. Methods 1985, 14, 213–228.
    • (1985) J. Pharmacol. Methods , vol.14 , pp. 213-228
    • McPherson, G.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.