Page last updated: 2024-09-03

3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole and nicotine

3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole has been researched along with nicotine in 29 studies

Compound Research Comparison

Studies
(3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole)
Trials
(3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole)
Recent Studies (post-2010)
(3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole)
Studies
(nicotine)
Trials
(nicotine)
Recent Studies (post-2010) (nicotine)
6821828,5192,2809,302

Protein Interaction Comparison

ProteinTaxonomy3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole (IC50)nicotine (IC50)
Neuronal acetylcholine receptor subunit alpha-4Mus musculus (house mouse)0.0055
Acetylcholine receptor subunit alphaTetronarce californica (Pacific electric ray)0.0025
Acetylcholine receptor subunit betaTetronarce californica (Pacific electric ray)0.0025
Acetylcholine receptor subunit gammaTetronarce californica (Pacific electric ray)0.0025
Acetylcholine receptor subunit deltaTetronarce californica (Pacific electric ray)0.0025
Neuronal acetylcholine receptor subunit alpha-3Rattus norvegicus (Norway rat)0.005
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)0.0046
Neuronal acetylcholine receptor subunit alpha-2Rattus norvegicus (Norway rat)0.005
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)0.0046
Neuronal acetylcholine receptor subunit beta-3Rattus norvegicus (Norway rat)0.005
Neuronal acetylcholine receptor subunit beta-4Rattus norvegicus (Norway rat)0.005
Neuronal acetylcholine receptor subunit beta-2Homo sapiens (human)0.3256
Neuronal acetylcholine receptor subunit alpha-5Rattus norvegicus (Norway rat)0.005
Acetylcholine receptor subunit beta-like 2Drosophila melanogaster (fruit fly)4
Neuronal acetylcholine receptor subunit beta-4Homo sapiens (human)0.43
Neuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)0.1866
Neuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)7.6
Neuronal acetylcholine receptor subunit alpha-6Rattus norvegicus (Norway rat)0.005
Neuronal acetylcholine receptor subunit alpha-9Rattus norvegicus (Norway rat)0.0041
Neuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)0.3456
Neuronal acetylcholine receptor subunit alpha-7Mus musculus (house mouse)0.004
Neuronal acetylcholine receptor subunit beta-3Homo sapiens (human)0.0848
Neuronal acetylcholine receptor subunit alpha-7Rattus norvegicus (Norway rat)0.0087
Neuronal acetylcholine receptor subunit alpha-6Homo sapiens (human)0.0848
Neuronal acetylcholine receptor subunit alpha-5Mus musculus (house mouse)0.004
Liver carboxylesterase B-1Rattus norvegicus (Norway rat)0.045
Neuronal acetylcholine receptor subunit beta-3Mus musculus (house mouse)0.004
Neuronal acetylcholine receptor subunit beta-4Mus musculus (house mouse)0.004
Neuronal acetylcholine receptor subunit alpha-3Mus musculus (house mouse)0.004
Neuronal acetylcholine receptor subunit alpha-2Mus musculus (house mouse)0.004
Neuronal acetylcholine receptor subunit beta-2Mus musculus (house mouse)0.004
Neuronal acetylcholine receptor subunit alpha-10Rattus norvegicus (Norway rat)0.005
Neuronal acetylcholine receptor subunit alpha-6Mus musculus (house mouse)0.004

Research

Studies (29)

TimeframeStudies, this research(%)All Research%
pre-19900 (0.00)18.7374
1990's21 (72.41)18.2507
2000's3 (10.34)29.6817
2010's4 (13.79)24.3611
2020's1 (3.45)2.80

Authors

AuthorsStudies
Anderson, DJ; Carrera, GM; Elliott, RL; Garvey, DS; He, Y; Hettinger, AM; Holladay, MW; Lebold, SA; Lin, NH; Wasicak, JT1
Arneric, SP; Brioni, JD; Buckley, MJ; Carrera, GM; Decker, MW; Garvey, DS; Holladay, MW; Sullivan, JP; Wasicak, JT; Williams, M1
Anderson, DJ; Arneric, SP; Brioni, JD; Buccafusco, JJ; Buckley, MJ; Decker, MW; Donnelly-Roberts, DL; Garvey, DS; Gunn, DE; Holladay, MW; Lin, NH; Marsh, KG; Prendergast, MA; Rodrigues, AD; Ryther, KB; Sullivan, JP; Williams, M1
Dart, MJ; Holladay, MW; Lynch, JK1
Begtrup, M; Christensen, B; Ehrbar, U; Hansen, JB; Olesen, PH; Pettersson, I; Rimvall, K; Tønder, JE1
Bolchi, C; Clementi, F; Fumagalli, L; Gotti, C; Moroni, B; Pallavicini, M; Vailati, S; Valoti, E; Villa, L1
Clementi, F; Dallanoce, C; De Amici, M; De Micheli, C; Gotti, C; Lo Presti, L; Magrone, P; Matera, C; Riganti, L1
Brunner, D; Caldarone, B; Eaton, JB; Fedolak, A; Hanania, T; Kozikowski, AP; Lukas, RJ; Tückmantel, W; Yu, LF1
Curtis, MA; Lin, SX; Sperry, J1
Arneric, SP; Brioni, JD; Brodie, MS; Decker, MW; Kim, DJ1
Adams, P; Anderson, DJ; Arneric, SP; Briggs, CA; Cadman, ED; Donnelly-Roberts, D; Garvey, DS; Hughes, ML; Raszkiewicz, JL; Sullivan, JP1
Holley, LA; Sarter, M; Turchi, J1
Brioni, JD; Buckley, MJ; Decker, MW; Giardina, WJ; Kang, CH; Kim, DJ; Radek, RJ; Raszkiewicz, JL; Sullivan, JP; Wasicak, JT1
Arneric, SP; Brioni, JD; Buckley, MJ; Decker, MW; Kim, DJ; O'Neill, AB1
Arneric, SP; Buccafusco, JJ; Decker, MW; Jackson, WJ; Marsh, KC; Terry, AV1
Arneric, SP; Bannon, AW; Briggs, CA; Brioni, JD; Decker, MW; Donnelly-Roberts, D; Kyncl, J; Marsh, KC; Radek, RJ; Sullivan, JP1
Aceto, MD; Creasy, KR; Damaj, MI; Martin, BR; Rosecrans, JA; Welch, SP1
Nordberg, A; Warpman, U1
Badio, B; Daly, JW; Garraffo, HM; Padgett, WL; Plummer, CV1
Imoto, M; Ohno, T; Saito, K; Tani, Y; Tsuneyoshi, A1
Stevens, KE; Wear, KD1
Arneric, SP; Donnelly-Roberts, DL; Manelli, AM; Puttfarcken, PS1
Arneric, SP; Buccafusco, JJ; Decker, MW; Jackson, WJ; Prendergast, MA; Terry, AV1
Bergström, M; Bivehed, H; Fasth, KJ; Långström, B; Nordberg, A; Ogren, M; Sihver, W; Watanabe, Y1
Bergström, M; Fasth, KJ; Långström, B; Lundqvist, H; Nordberg, A; Ogren, M; Sihver, W; Watanabe, Y1
Bubl, B; Feuerstein, TJ; Hubbe, U; Huethe, F; Jackisch, R; Löffler, M; McIntosh, JM1
Barr, JD; Bevins, RA; Murray, JE; Reichel, CM1
Geyer, MA; Meves, JM; Young, JW1

Reviews

2 review(s) available for 3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole and nicotine

ArticleYear
Neuronal nicotinic acetylcholine receptors as targets for drug discovery.
    Journal of medicinal chemistry, 1997, Dec-19, Volume: 40, Issue:26

    Topics: Acetylcholine; Animals; Binding Sites; Dopamine; Drug Design; Humans; Molecular Structure; Nervous System; Neurons; Nicotine; Nicotinic Agonists; Nicotinic Antagonists; Receptors, Nicotinic; Structure-Activity Relationship

1997
Pyridine alkaloids with activity in the central nervous system.
    Bioorganic & medicinal chemistry, 2020, 12-15, Volume: 28, Issue:24

    Topics: Alkaloids; Amphibians; Animals; Bacteria; Central Nervous System Diseases; Fungi; Nicotine; Plants; Pyridines; Receptors, Nicotinic

2020

Other Studies

27 other study(ies) available for 3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole and nicotine

ArticleYear
Ligands for brain cholinergic channel receptors: synthesis and in vitro characterization of novel isoxazoles and isothiazoles as bioisosteric replacements for the pyridine ring in nicotine.
    Journal of medicinal chemistry, 1994, Dec-23, Volume: 37, Issue:26

    Topics: Animals; Brain; Dopamine; Isoxazoles; Ligands; Nicotinic Agonists; Rats; Receptors, Nicotinic; Structure-Activity Relationship; Thiazoles

1994
Novel isoxazoles which interact with brain cholinergic channel receptors have intrinsic cognitive enhancing and anxiolytic activities.
    Journal of medicinal chemistry, 1994, Apr-15, Volume: 37, Issue:8

    Topics: Alkaloids; Animals; Anti-Anxiety Agents; Azocines; Binding Sites; Brain; Bungarotoxins; Cognition; Isoxazoles; Mice; Molecular Structure; Motor Activity; Nicotine; Quinolizines; Rats; Receptors, Cholinergic; Receptors, Nicotinic; Stereoisomerism

1994
Structure-activity studies on 2-methyl-3-(2(S)-pyrrolidinylmethoxy) pyridine (ABT-089): an orally bioavailable 3-pyridyl ether nicotinic acetylcholine receptor ligand with cognition-enhancing properties.
    Journal of medicinal chemistry, 1997, Jan-31, Volume: 40, Issue:3

    Topics: Administration, Oral; Alkaloids; Animals; Anti-Anxiety Agents; Azocines; Biological Availability; Bungarotoxins; Cell Line; Cognition; Dogs; Haplorhini; Humans; Hypothermia; Isoxazoles; Ligands; Maze Learning; Mice; Molecular Structure; Psychomotor Performance; Pyrrolidines; Quinolizines; Receptors, Nicotinic; Rubidium; Structure-Activity Relationship

1997
Improving the nicotinic pharmacophore with a series of (Isoxazole)methylene-1-azacyclic compounds: synthesis, structure-activity relationship, and molecular modeling.
    Journal of medicinal chemistry, 1999, Dec-02, Volume: 42, Issue:24

    Topics: Animals; Cerebral Cortex; Chemical Phenomena; Chemistry, Physical; Hydrogen Bonding; Isoxazoles; Male; Models, Molecular; Molecular Conformation; Molecular Structure; Nicotine; Nitrogen; Quinuclidines; Rats; Rats, Wistar; Receptors, Muscarinic; Receptors, Nicotinic; Static Electricity; Structure-Activity Relationship; Thermodynamics

1999
Synthesis and alpha4beta2 nicotinic affinity of 2-pyrrolidinylmethoxyimines and prolinal oxime ethers.
    Bioorganic & medicinal chemistry letters, 2004, Dec-06, Volume: 14, Issue:23

    Topics: Animals; Cerebral Cortex; Imines; Proline; Protein Binding; Pyrrolidines; Rats; Receptors, Nicotinic

2004
Synthesis of novel chiral Δ2-isoxazoline derivatives related to ABT-418 and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes.
    European journal of medicinal chemistry, 2010, Volume: 45, Issue:12

    Topics: Crystallography, X-Ray; Isoxazoles; Models, Molecular; Molecular Conformation; Neurons; Pyrrolidines; Receptors, Nicotinic; Stereoisomerism; Structure-Activity Relationship

2010
Identification of novel α4β2-nicotinic acetylcholine receptor (nAChR) agonists based on an isoxazole ether scaffold that demonstrate antidepressant-like activity.
    Journal of medicinal chemistry, 2012, Jan-26, Volume: 55, Issue:2

    Topics: Animals; Antidepressive Agents; Blood Proteins; Cytochrome P-450 Enzyme Inhibitors; ERG1 Potassium Channel; Ether-A-Go-Go Potassium Channels; HEK293 Cells; Humans; Isoxazoles; Male; Mice; Mice, Inbred BALB C; Microsomes, Liver; Nicotinic Agonists; Protein Binding; Radioligand Assay; Rats; Receptors, Nicotinic; Stereoisomerism; Structure-Activity Relationship

2012
ABT-418: discriminative stimulus properties and effect on ventral tegmental cell activity.
    Psychopharmacology, 1995, Volume: 119, Issue:4

    Topics: Animals; Anti-Anxiety Agents; Behavior, Animal; Discrimination, Psychological; Dose-Response Relationship, Drug; Electrophysiology; Isoxazoles; Male; Mecamylamine; Nicotine; Pyrrolidines; Rats; Rats, Wistar; Time Factors; Ventral Tegmental Area

1995
(S)-3-methyl-5-(1-methyl-2-pyrrolidinyl) isoxazole (ABT 418): a novel cholinergic ligand with cognition-enhancing and anxiolytic activities: I. In vitro characterization.
    The Journal of pharmacology and experimental therapeutics, 1994, Volume: 270, Issue:1

    Topics: Alkaloids; Animals; Anti-Anxiety Agents; Azocines; Binding, Competitive; Cognition; Corpus Striatum; Dopamine; Ion Channels; Isoxazoles; Kinetics; Male; Mice; Nicotine; Parasympathomimetics; PC12 Cells; Pyrrolidines; Quinolizines; Rats; Rats, Sprague-Dawley; Receptors, Cholinergic; Receptors, Nicotinic; Rubidium; Rubidium Radioisotopes; Tritium

1994
Effects of nicotinic acetylcholine receptor ligands on behavioral vigilance in rats.
    Psychopharmacology, 1995, Volume: 118, Issue:2

    Topics: Animals; Anti-Anxiety Agents; Arousal; Attention; Behavior, Animal; Isoxazoles; Ligands; Lobeline; Mecamylamine; Nicotine; Pyrrolidines; Rats; Receptors, Nicotinic; Time Factors

1995
(S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole (ABT 418): a novel cholinergic ligand with cognition-enhancing and anxiolytic activities: II. In vivo characterization.
    The Journal of pharmacology and experimental therapeutics, 1994, Volume: 270, Issue:1

    Topics: Alzheimer Disease; Animals; Anti-Anxiety Agents; Anticonvulsants; Avoidance Learning; Behavior, Animal; Body Temperature; Brain; Cerebrovascular Circulation; Cognition; Electroencephalography; Isoxazoles; Male; Mice; Mice, Inbred Strains; Motor Activity; Nicotine; Nociceptors; Pyrrolidines; Rats; Rats, Wistar; Receptors, Cholinergic; Seizures; Vomiting

1994
Anxiolytic-like effects of the novel cholinergic channel activator ABT-418.
    The Journal of pharmacology and experimental therapeutics, 1994, Volume: 271, Issue:1

    Topics: Administration, Oral; Animals; Anti-Anxiety Agents; Cognition Disorders; Diazepam; Isoxazoles; Male; Maze Learning; Mecamylamine; Mice; Nicotine; Pyrrolidines; Rats; Rats, Wistar; Substance Withdrawal Syndrome

1994
Improvement in performance of a delayed matching-to-sample task by monkeys following ABT-418: a novel cholinergic channel activator for memory enhancement.
    Psychopharmacology, 1995, Volume: 120, Issue:3

    Topics: Animals; Anti-Anxiety Agents; Behavior, Animal; Dose-Response Relationship, Drug; Isoxazoles; Learning; Macaca mulatta; Male; Memory; Nicotine; Pyrrolidines; Receptors, Nicotinic; Task Performance and Analysis; Time Factors

1995
Potential treatment of Alzheimer disease using cholinergic channel activators (ChCAs) with cognitive enhancement, anxiolytic-like, and cytoprotective properties.
    Alzheimer disease and associated disorders, 1995, Volume: 9 Suppl 2

    Topics: Alzheimer Disease; Animals; Anti-Anxiety Agents; Avoidance Learning; Cognition; Dose-Response Relationship, Drug; Isoxazoles; Nicotine; Nicotinic Agonists; Pyrrolidines; Rats

1995
Comparative pharmacology of nicotine and ABT-418, a new nicotinic agonist.
    Psychopharmacology, 1995, Volume: 120, Issue:4

    Topics: Animals; Anti-Anxiety Agents; Binding, Competitive; Discrimination, Psychological; Dose-Response Relationship, Drug; Isoxazoles; Locomotion; Male; Mice; Mice, Inbred ICR; Nicotine; Pyrrolidines; Rats; Rats, Sprague-Dawley; Time Factors

1995
Epibatidine and ABT 418 reveal selective losses of alpha 4 beta 2 nicotinic receptors in Alzheimer brains.
    Neuroreport, 1995, Nov-27, Volume: 6, Issue:17

    Topics: Aged; Aged, 80 and over; Alkaloids; Alzheimer Disease; Animals; Anti-Anxiety Agents; Azocines; Binding, Competitive; Bridged Bicyclo Compounds, Heterocyclic; Cells, Cultured; Humans; Isoxazoles; Kinetics; Mice; Nicotine; Nicotinic Agonists; Pyridines; Pyrrolidines; Quinolizines; Receptors, Nicotinic; Temporal Lobe; Transfection

1995
Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine.
    European journal of pharmacology, 1997, Feb-26, Volume: 321, Issue:2

    Topics: Animals; Anti-Anxiety Agents; Cerebral Cortex; Ganglia; Isoxazoles; Kinetics; Male; Mice; Nicotine; Nicotinic Agonists; Nociceptors; PC12 Cells; Pyrrolidines; Rats; Receptors, Nicotinic; Tritium

1997
Nicotinic acetylcholine receptor (nACh-R) agonist-induced changes in brain monoamine turnover in mice.
    Psychopharmacology, 1997, Volume: 129, Issue:3

    Topics: Alkaloids; Animals; Azocines; Binding, Competitive; Brain; Dopamine; Isoxazoles; Male; Mecamylamine; Mice; Mice, Inbred Strains; Nicotine; Nicotinic Agonists; Nicotinic Antagonists; Norepinephrine; Pyrrolidines; Quinolizines; Serotonin; Tacrine

1997
Normalizing effects of nicotine and a novel nicotinic agonist on hippocampal auditory gating in two animal models.
    Pharmacology, biochemistry, and behavior, 1997, Volume: 57, Issue:4

    Topics: Acoustic Stimulation; Animals; Anti-Anxiety Agents; Conditioning, Psychological; Evoked Potentials, Auditory; Female; Hippocampus; Isoxazoles; Male; Mice; Mice, Inbred DBA; Microelectrodes; Nicotine; Nicotinic Agonists; Pyrrolidines; Rats; Rats, Sprague-Dawley

1997
Evidence for nicotinic receptors potentially modulating nociceptive transmission at the level of the primary sensory neuron: studies with F11 cells.
    Journal of neurochemistry, 1997, Volume: 69, Issue:3

    Topics: Analgesics, Non-Narcotic; Analysis of Variance; Animals; Bridged Bicyclo Compounds, Heterocyclic; Cytosine; Dimethylphenylpiperazinium Iodide; Ganglia, Spinal; Hybrid Cells; Isoxazoles; Mice; Neuroblastoma; Neurons, Afferent; Nicotine; Nicotinic Agonists; Nicotinic Antagonists; Pain; Pyridines; Pyrrolidines; Rats; Receptors, Nicotinic; Rubidium; Substance P; Synaptic Transmission

1997
Central nicotinic receptor agonists ABT-418, ABT-089, and (-)-nicotine reduce distractibility in adult monkeys.
    Psychopharmacology, 1998, Volume: 136, Issue:1

    Topics: Animals; Anti-Anxiety Agents; Attention; Cholinergic Agents; Dose-Response Relationship, Drug; Female; Isoxazoles; Macaca mulatta; Macaca nemestrina; Male; Mental Recall; Nicotine; Nicotinic Agonists; Photic Stimulation; Pyridines; Pyrrolidines; Receptors, Nicotinic

1998
In vitro evaluation of 11C-labeled (S)-nicotine, (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole, and (R,S)-1-methyl-2-(3-pyridyl)azetidine as nicotinic receptor ligands for positron emission tomography studies.
    Journal of neurochemistry, 1998, Volume: 71, Issue:4

    Topics: Animals; Azetidines; Binding Sites; Brain; Carbon Radioisotopes; Isoxazoles; Ligands; Male; Nicotine; Pyrrolidines; Rats; Rats, Sprague-Dawley; Receptors, Nicotinic; Tomography, Emission-Computed

1998
In vivo positron emission tomography studies on the novel nicotinic receptor agonist [11C]MPA compared with [11C]ABT-418 and (S)(-)[11C]nicotine in rhesus monkeys.
    Nuclear medicine and biology, 1999, Volume: 26, Issue:6

    Topics: Animals; Azetidines; Brain; Carbon Radioisotopes; Cerebellum; Isoxazoles; Macaca mulatta; Nicotine; Organ Specificity; Pyrrolidines; Radiopharmaceuticals; Temporal Lobe; Thalamus; Tomography, Emission-Computed

1999
Health news. The sleeper syndrome.
    Harvard health letter, 2001, Volume: 26, Issue:3

    Topics: Alzheimer Disease; Cacao; Humans; Hygiene; Isoxazoles; Margarine; Nicotine; Parkinson Disease; Pyrrolidines; Superoxides

2001
Dopamine release in human neocortical slices: characterization of inhibitory autoreceptors and of nicotinic acetylcholine receptor-evoked release.
    Brain research bulletin, 2006, Jan-30, Volume: 68, Issue:5

    Topics: 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine; Adolescent; Adult; Aged; Alkaloids; Analysis of Variance; Animals; Autoreceptors; Azocines; Calcium; Child; Child, Preschool; Domperidone; Dopamine; Dopamine Antagonists; Dose-Response Relationship, Drug; Drug Interactions; Electric Stimulation; Feedback; Female; Fluvoxamine; Humans; In Vitro Techniques; Isoxazoles; Male; Maprotiline; Mice; Middle Aged; Neocortex; Nicotine; Nicotinic Antagonists; Potassium; Pyrrolidines; Quinolizines; Rats; Receptors, Nicotinic; Sulpiride; Time Factors; Tritium

2006
Extinction with varenicline and nornicotine, but not ABT-418, weakens conditioned responding evoked by the interoceptive stimulus effects of nicotine.
    Neuropharmacology, 2010, Volume: 58, Issue:8

    Topics: Animals; Benzazepines; Conditioning, Classical; Discrimination, Psychological; Extinction, Psychological; Generalization, Psychological; Isoxazoles; Ligands; Male; Nicotine; Nicotinic Agonists; Pyrrolidines; Quinoxalines; Rats; Rats, Sprague-Dawley; Varenicline

2010
Nicotinic agonist-induced improvement of vigilance in mice in the 5-choice continuous performance test.
    Behavioural brain research, 2013, Mar-01, Volume: 240

    Topics: alpha7 Nicotinic Acetylcholine Receptor; Animals; Attention; Behavior, Animal; Benzamides; Bridged Bicyclo Compounds; Choice Behavior; Cholinergic Antagonists; Isoxazoles; Male; Mice; Mice, Inbred C57BL; Nicotine; Nicotinic Agonists; Psychomotor Performance; Pyrrolidines; Receptors, Nicotinic; Scopolamine

2013