2,3-Dihydroxy-9-amino-9,10-dihydrophenanthrene, a rigid congener of dopamine and isoapomorphine.

PubWeight™: 0.91‹?›

🔗 View Article (PMID 650669)

Published in J Med Chem on April 01, 1978

Authors

D E Nichols, J E Toth, J D Kohli, C K Kotake

Articles by these authors

Brine shrimp: a convenient general bioassay for active plant constituents. Planta Med (1982) 6.46

Brine shrimp: a convenient general bioassay for active plant constituents. Planta Med (1982) 3.45

Differences between the mechanism of action of MDMA, MBDB, and the classic hallucinogens. Identification of a new therapeutic class: entactogens. J Psychoactive Drugs (1987) 1.68

Evaluation of new anticancer agents against the MIA PaCa-2 and PANC-1 human pancreatic carcinoma xenografts. Oncol Res (1993) 1.67

A comparison of the vascular dopamine receptor with other dopamine receptors. Annu Rev Pharmacol Toxicol (1978) 1.41

Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines. J Med Chem (2000) 1.33

Studies on the mechanism of phosphatidylinositol 3-kinase inhibition by wortmannin and related analogs. J Med Chem (1996) 1.18

trans-10,11-dihydroxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine: a highly potent selective dopamine D1 full agonist. J Med Chem (1990) 1.14

Serotonergic basis of antipsychotic drug effects in schizophrenia. Biol Psychiatry (1998) 1.11

Behavioral effects of selective dopaminergic compounds in rats discriminating cocaine injections. J Pharmacol Exp Ther (1991) 1.11

Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups. J Med Chem (1996) 1.11

Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J Med Chem (1993) 1.08

Selective DA2 versus DA1 antagonist activity of domperidone in the periphery. Eur J Pharmacol (1983) 1.07

Modification and evaluation of the potato disc assay and antitumor screening of euphorbiaceae seeds. J Nat Prod (1983) 1.06

Effects of the enantiomers of MDA, MDMA and related analogues on [3H]serotonin and [3H]dopamine release from superfused rat brain slices. Eur J Pharmacol (1986) 1.06

Asymmetric synthesis of psychotomimetic phenylisopropylamines. J Med Chem (1973) 1.06

Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists. J Med Chem (2001) 1.05

An integrated hypothesis for the serotonergic axonal loss induced by 3,4-methylenedioxymethamphetamine. Neurotoxicology (1998) 1.05

Conformational analysis of D1 dopamine receptor agonists: pharmacophore assessment and receptor mapping. J Med Chem (1996) 1.02

D1 and D2 dopamine receptors independently regulate spontaneous blink rate in the vervet monkey. J Pharmacol Exp Ther (1991) 1.02

[125I]-2-(2,5-dimethoxy-4-iodophenyl)aminoethane ([125I]-2C-I) as a label for the 5-HT2 receptor in rat frontal cortex. Pharmacol Biochem Behav (1990) 1.01

Excitatory action of sympathomimetic amines on 5-hydroxytryptamine receptors of gut. Br J Pharmacol (1969) 1.01

Peripheral pre- and post-synaptic dopamine receptors: are they different from dopamine receptors in the central nervous system? Commun Psychopharmacol (1979) 1.00

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) 0.99

Locomotor inhibition, yawning and vacuous chewing induced by a novel dopamine D2 post-synaptic receptor agonist. Eur J Pharmacol (1997) 0.99

Binding to the serotonin 5-HT2 receptor by the enantiomers of 125I-DOI. Neuropharmacology (1987) 0.98

Effect of the R(-) and S(+) isomers of MDA and MDMA on phosphatidyl inositol turnover in cultured cells expressing 5-HT2A or 5-HT2C receptors. Neurosci Lett (1994) 0.98

A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor. J Med Chem (1998) 0.98

[3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues. Eur J Pharmacol (1991) 0.98

Comparison of biochemical and histochemical techniques for estrogen receptor analyses in mammary carcinoma. Cancer (1980) 0.97

Dihydrexidine, a full dopamine D1 agonist, reduces MPTP-induced parkinsonism in monkeys. Eur J Pharmacol (1991) 0.97

Structures of three inhibitor complexes provide insight into the reaction mechanism of the human methylenetetrahydrofolate dehydrogenase/cyclohydrolase. Biochemistry (2000) 0.97

9-Dihydroxy-2,3,7,11b-tetrahydro-1H-naph[1,2,3-de]isoquinoline: a potent full dopamine D1 agonist containing a rigid-beta-phenyldopamine pharmacophore. J Med Chem (1996) 0.96

Serotonin neurotoxicity in rats after combined treatment with a dopaminergic agent followed by a nonneurotoxic 3,4-methylenedioxymethamphetamine (MDMA) analogue. Pharmacol Biochem Behav (1991) 0.95

Social reactivity and D1 dopamine receptors: studies in mice selectively bred for high and low levels of aggression. Neuropsychopharmacology (1994) 0.95

Effects of certain hallucinogenic amphetamine analogues on the release of [3H]serotonin from rat brain synaptosomes. J Med Chem (1982) 0.94

3,3',5'-Tri-O-methylpiceatannol and 4,3',5'-tri-O-methylpiceatannol: improvements over piceatannol in bioactivity. J Nat Prod (1987) 0.94

Dihydrexidine, a novel selective high potency full dopamine D-1 receptor agonist. Eur J Pharmacol (1989) 0.94

MDMA transiently alters biogenic amines and metabolites in mouse brain and heart. Pharmacol Biochem Behav (1989) 0.93

Adrenoceptive receptors in the duodenum, aorta and atria of the rabbit. J Pharm Pharmacol (1967) 0.92

Homologous desensitization of the D1A dopamine receptor: efficacy in causing desensitization dissociates from both receptor occupancy and functional potency. J Pharmacol Exp Ther (1998) 0.92

Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes. J Med Chem (1995) 0.92

Regional variation in the alpha-adrenergic receptors in the canine resistance vessels. Naunyn Schmiedebergs Arch Pharmacol (1982) 0.92

Dihydrexidine, a novel full efficacy D1 dopamine receptor agonist. J Pharmacol Exp Ther (1992) 0.91

Characteristics of the vascular dopamine receptor: comparison with other receptors. Fed Proc (1978) 0.91

Drug discrimination studies with MDMA and amphetamine. Psychopharmacology (Berl) (1988) 0.91

Quantitative structure-activity relationship modeling of dopamine D(1) antagonists using comparative molecular field analysis, genetic algorithms-partial least-squares, and K nearest neighbor methods. J Med Chem (1999) 0.91

Synthesis and evaluation of 6,7-dihydroxy-2,3,4,8,9,13b-hexahydro-1H- benzo[6,7]cyclohepta[1,2,3-ef][3]benzazepine, 6,7-dihydroxy- 1,2,3,4,8,12b-hexahydroanthr[10,4a,4-cd]azepine, and 10-(aminomethyl)-9,10- dihydro-1,2-dihydroxyanthracene as conformationally restricted analogs of beta-phenyldopamine. J Med Chem (1995) 0.91

Reinforcing effects of certain serotonin-releasing amphetamine derivatives. Pharmacol Biochem Behav (1996) 0.91

Distinct recognition of substrates by the human and Drosophila serotonin transporters. J Pharmacol Exp Ther (2003) 0.91

Parkinson's disease and D1 dopamine receptors. Curr Opin Investig Drugs (2001) 0.91

Common receptors for hallucinogens in rat brain: a comparative autoradiographic study using [125I]LSD and [125I]DOI, a new psychotomimetic radioligand. Brain Res (1989) 0.90

Absorption and excretion of 2,4-dichlorophenoxyacetic acid in man. Xenobiotica (1974) 0.90

Hallucinogenic and stimulatory amphetamine derivatives: fingerprinting DOM, DOI, DOB, MDMA, and MBDB by spectral analysis of brain field potentials in the freely moving rat (Tele-Stereo-EEG). Psychopharmacology (Berl) (1989) 0.89

Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine. J Med Chem (1999) 0.88

A comparative study of dopamine and noradrenaline on the rabbit aorta. Can J Physiol Pharmacol (1969) 0.88

Synthesis and molecular modeling of 1-phenyl-1,2,3,4-tetrahydroisoquinolines and related 5,6,8,9-tetrahydro-13bH-dibenzo[a,h]quinolizines as D1 dopamine antagonists. J Med Chem (1994) 0.88

Stereoselective LSD-like activity in d-lysergic acid amides of (R)- and (S)-2-aminobutane. J Med Chem (1992) 0.87

LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors. Psychopharmacology (Berl) (1995) 0.87

Dinapsoline: characterization of a D1 dopamine receptor agonist in a rat model of Parkinson's disease. J Pharmacol Exp Ther (2001) 0.87

Spare receptors and intrinsic activity: studies with D1 dopamine receptor agonists. Synapse (1995) 0.87

Structural correlation between apomorphine and LSD: involvement of dopamine as well as serotonin in the actions of hallucinogens. J Theor Biol (1976) 0.87

D1 dopamine receptors. Int Rev Neurobiol (2001) 0.87

Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA). J Med Chem (1991) 0.87

Separation of peripheral dopamine receptors by a selective DA1 antagonist, SCH 23390. Hypertension (1984) 0.86

Mechanisms mediating the positive inotropic and chronotropic changes induced by dopexamine in the anesthetized dog. J Pharmacol Exp Ther (1987) 0.86

Cardiovascular effects of 2, 5-dimethoxy-4-methylamphetamine (DOM, STP). J Pharmacol Exp Ther (1973) 0.86

Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives. J Med Chem (1997) 0.86

LSD and phenethylamine hallucinogens: new structural analogy and implications for receptor geometry. Life Sci (1978) 0.86

Cardiovascular effects of (--)-cathinone in the anaesthetized dog: comparison with (+)-amphetamine. J Pharm Pharmacol (1982) 0.86

Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)cyclopropylamine derivatives. J Med Chem (1998) 0.86

Behavioral effects in the rat of dihydrexidine, a high-potency, full-efficacy D1 dopamine receptor agonist. Neuropsychopharmacology (1991) 0.86

Relative activities of SCH 23390 and its analogs in three tests for D1/DA1 dopamine receptor antagonism. Eur J Pharmacol (1986) 0.85

"Full" dopamine D1 agonists in human caudate: biochemical properties and therapeutic implications. Neuropharmacology (1995) 0.85

Correlation of psychotomimetic activity of phenethylamines and amphetamines with 1-octanol-water partition coefficients. J Med Chem (1975) 0.85

Alpha-adrenergic blocking action of propranolol. J Pharm Pharmacol (1967) 0.85

Structure activity relationships of N-substituted dopamine derivatives as agonists of the dopamine vascular and other cardiovascular receptors. J Pharmacol Exp Ther (1980) 0.85

Structure-activity studies of 20-deoxo-20-amino derivatives of tylosin-related macrolides. J Antibiot (Tokyo) (1989) 0.84

Effect of beta-alkyl substitution on D-1 dopamine agonist activity: absolute configuration of beta-methyldopamine. J Med Chem (1987) 0.84

Dopamine agonist properties of N-alkyl-4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines. J Med Chem (1981) 0.84

Resolution and absolute configuration of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, a potent hallucinogen analogue. J Med Chem (1979) 0.84

The monoamine oxidase-B inhibitor L-deprenyl protects against 3,4-methylenedioxymethamphetamine-induced lipid peroxidation and long-term serotonergic deficits. J Pharmacol Exp Ther (1995) 0.84

The antiproliferative and cell cycle effects of 5,6,7, 8-tetrahydro-N5,N10-carbonylfolic acid, an inhibitor of methylenetetrahydrofolate dehydrogenase, are potentiated by hypoxanthine. J Pharmacol Exp Ther (1998) 0.84

Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class. J Med Chem (1986) 0.84

Synthesis, antimicrobial evaluation and structure-activity relationships within 23-modified derivatives of 5-O-mycaminosyltylonolide. J Antibiot (Tokyo) (1987) 0.83

Alpha-adrenoceptor blocking activity of fenoldopam (SK&F 82526), a selective DA1 agonist. J Pharm Pharmacol (1986) 0.83

(+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxy-methamphetamine-like behavioral activity. J Pharmacol Exp Ther (1990) 0.82

Native fluorescence and hallucinogenic potency of some amphetamines. Experientia (1971) 0.82

Psychostimulant-like effects of p-fluoroamphetamine in the rat. Eur J Pharmacol (1995) 0.82

D1 and functionally selective dopamine agonists as neuroprotective agents in Parkinson's disease. CNS Neurol Disord Drug Targets (2006) 0.82

Microdialysis studies on 3,4-methylenedioxyamphetamine and structurally related analogues. Eur J Pharmacol (1991) 0.82

Dopamine D1 receptors: efficacy of full (dihydrexidine) vs. partial (SKF38393) agonists in primates vs. rodents. Eur J Pharmacol (1993) 0.81

Dopaminergic benzo[a]phenanthridines: resolution and pharmacological evaluation of the enantiomers of dihydrexidine, the full efficacy D1 dopamine receptor agonist. J Med Chem (1994) 0.81

Dopamine D1 receptor agonists as antiparkinson drugs. Trends Pharmacol Sci (1998) 0.81

Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA). J Med Chem (1998) 0.81

Inhibition of MAO-B protects against MDMA-induced neurotoxicity in the striatum. Psychopharmacology (Berl) (1995) 0.81

Benzofuran bioisosteres of hallucinogenic tryptamines. J Med Chem (1992) 0.81

Sulpiride: a weak antagonist of norepinephrine and 5-hydroxytryptamine. Eur J Pharmacol (1979) 0.81

Receptors for sympathomimetic amines in the rabbit aorta: differentiation by specific antagonists. Br J Pharmacol Chemother (1968) 0.81