NIMH Chemical Synthesis and Drug Supply Program
Publications: NIMH Chemical Synthesis and Drug Supply Program
The NIMH is eager to be made aware of publications resulting from the use of the compounds it has supplied. In light of budgetary restrictions, it is frequently necessary and appropriate for a program to justify its existence. If you find this service useful, please take the extra time to keep us informed of your published results. Please send reprints of published work to Jamie Driscoll (NIMH)
Please indicate in the Materials & Methods section of your publication that the compounds were obtained from the National Institute of Mental Health's Chemical Synthesis and Drug Supply Program.
Researchers have provided publications resulting from the compounds provided in the NIMH Inventory, which is maintained and supplied by RTI International. The following publications have been reported.
C. Jin, L. D. Mayer, A. H. Lewin, K. S. Rehder and G. A. Brine, Practical Synthesis of p-aminophen-ethyl-spiperone (NAPS), a High -Affinity, Selective D2-dopamine Receptor Antagonist, Synth. Commun., 38 (5), 816-823 (2008).
M. R. Kilbourn, Brian Hockley, Lihsueh Lee, Catherine Hou, Rjech Goswami, D. E. Ponde, M.-P. Kung and H. F. Kung, Pharmacokinetics of [18F]fluoroalkyl derivatives of dihydrotetrabenazine in rat and monkey brain, Nuclear Medicine and Biology, 34, 233-237 (2007).
I. J. Lever, T. M. Pheby and A. S. C Rice, Continuous infusion of the cannabinoid WIN 55,212-2 to the site of a peripheral nerve injury reduces mechanical and cold hypersensitivity, British Journal of Pharmacology, 151, 292-302 (2007).
W. M. Caudle, J. R. Richardson, M. Z. Wang, T. N. Taylor, T. S. Guillot, A. L. McCormack, R. E. Colebrooke, D. A. DiMone, P. C. Emson and G. W. Miller, Reduced Vesicular Storage of Dopamine Causes Progressive Nigrostriatal Neurodegeneration, The Journal of Neuroscience, 27 (30), 8138-8148 (2007).
L. Zhao, C. Jin, Z. Mao, M. B. Gopinathan, K. Rehder and R. D. Brinton, Design, Synthesis, and Estrogenic Activity of a Novel Estrogen Receptor Modulator–A Hybrid Structure of 17beta-Estradio and Vitamin E in Hippocampal Neurons, J. Med. Chem., 50, 4471-4481 (2007).
C. Jin, K. G. Boldt, K. S. Rehder, and G. A. Brine, Improved Syntheses of N-Desmethylcitalopram and N,N-Didesmethylcitalopram, Synth. Commun., 37 (6), 901-908 (2007).
Jaime M. Hatcher, Jason R. Richardson, Thomas S. Guillot, Alison L. McCormack, Donato A. DiMonte, Dean P. Jones, Kurt D. Pennell and Gary W. Miller, Dieldrin exposure induces oxidative damage in the mouse nigrostriatal dopamine system, Experimental Neurology, 204, 619-630 (2007).
D. Feifel. Method of inhibiting neural transmission mediated by serotonin-2a and enhancing sensorimotor gating, U.S. Patent Application 20060179492, (2006).
Xiaohua Li, Kelley M. Rosborough, Ari B. Friedman, Wawa Zhu and Kevin A. Roth, Regulation of mouse brain glycogen synthase kinase-3 by atypical antipsychotics, The International Journal of Neuropsychopharmacology, Cambridge Univ. Press, (2006).
R. K. McNamara, B. Levant, B. Taylor, R. Ahlbrand, Y. Liu, J. R. Sullivan, K. Stanford, and N. M. Richtand, C57BL/6J Mice exhibit reduced Dopamine D3 receptor-mediated locomotor-inhibitory function relative to DBA/2J mice, Neuroscience, 143 (1), 141-153 (2006).
C. Jin, J. P. Burgess, K. S. Rehder and G. A. Brine, Synthesis of N6-[endo-2'-(endo-5'-Hydroxy)norbornyl]-8-(N-methylisopropylamino)-9-methyladenine (WRC-0571): A potent and selective adenosine A1 receptor antagonist, Synthesis, (2), 219-224 (2007).
Leah N. Squires, Jennifer A. Jakubowski, Jeffrey N. Stuart, Stanislav S. Rubakhin, Nathan G. Hatcher, Won-Suk Kim, Kevin Chen, Jean C. Shih, Isabelle Seif and Jonathan V. Sweedler, Serotonin Catabolism and the Formation and Fate of 5-Hydroxyindole Thiazolidine Carboxylic Acid The Journal of Biological Chemistry, 281 (19), 13463-13470 (2006).
Yolanda Zea-Ponce, Ronald M. Baldwin, Richard A. Miliust, Venkatesalu Bakthavachalam and Robert B. Innis, [123I]iodomethane, a main product in the synthesis of 5-[123I]iodo-6-nitroquipazine by iododestannylation, Journal of Labelled Compounds and Radiopharmaceuticals, 36 (4), 331-337 (2006).
Chunyang Jin, Jason P. Burgess, Madathil B. Gopinathan and George A. Brine, Chemical synthesis and structural elucidation of a new serotonin metabolite: (4R)-2-[(5'-hydroxy-1'H-indol-3'-yl)methyl]thiazolidine-4-carboxylic acid, Tetrahedron Letters, 47, 943-946 (2006).
Rajesh Goswami, Dattaq E. Ponde, Mei-Ping Kung, Catherine Hou, Mike R. Kilbourn, Hank F. Kung, Fluoroalkyl derivatives of dihydrotetrabenazine as positron emission tomography imaging agents targeting vesicular monoamine transporters, Science Direct, 33, 685-694, (2006).
Matthew L. MacDonald, Molly E. Eaton, Joshua T. Dudman and Christine Konradi, Antipsychotic drugs elevate mRNA levels of presynaptic proteins in the frontal cortex of the rat, Biol. Psychiatry, 57 (9), 1041-1051 (2005).
Paula R. Powell, Tracy L. Paxon, Kyung-An Han and Andrew G. Ewing, Analysis of biogenic amine variability among individual fly heads with micellar electrokinetic capillary chromatography-electrochemical detection, Anal Chem., 77 (21), 6902-6908 (2005).
Tracy L. Paxon, Paula R. Powell, Hyun-Gwan Lee, Kyung-An Han and Andrew G. Ewing, Microcolumn Separation of Amine Metabolites in the Fruit Fly, Anal Chem., 77 (16), 5349-5355 (2005).
Sandra Panchalingam and Ashiwel S. Undie, Physicochemical modulation of agonist-induced [35S]GTPyS Binding: Implications for Coexistence of Multiple Functional Conformatios of Dopamine D1-like Receptors, Journal of Receptors and Signal Transduction, 25 (2), 125-146 (2005).
Klaus Becker, Matthias Eder, Walter Zieglgansberger, Hans-Ulrich Dodt, WIN 55,212-2 Decreases the spatial spread of neocortical excitation in vitro, NeuroReport, 16 (9), 993-996 (2005).
T. J. Price, A. M. Patwardhan, C. M. Flores and K. M. Hargreaves, A Role for the anandamide membrane transporter in TRPV1-mediated neurosecretion from trigeminal sensory neurons, Neuropharmacology, 49 (1), 25-39 (2005).
Katsura Nozawa; et al., Novel potassium-dependent sodium-calcium exchanger, U.S. Patent Application 20050119173, (2005).
Gerard J. O'Sullivan, Anthony Kinsella, David R. Sibley, Orna Tighe, David T. Croke and John L. Waddington, Ethological resolution of behavioural topography and D1-like versus D2-like agonist responses in congenic D5 dopamine receptor mutants: Identification of D5:D2-like interactions, Synapse, 55 (4), 202-211 (2005).
M. Panjehpour, M. Castro and K. -N. Klotz, Human breast cancer cell line MDA-MB-231 expresses endogenous A 2B adenosine receptors mediating a Ca 2+ signal, British Journal of Pharmacology, 145 (2), 211-218 (2005).
T. J. Price, A. Patwardhan, A. N. Akopian and K. M. Hargreaves, Modulation of trigeminal sensory neuron activity by the dual cannabinoid-vanilloid agonists, British Journal of Pharmacology, 141, 1118-1130 (2004).
Peter S. Talbot, W. Godon Frankie, Dah-Ren Hwang, Yiyun Huang, Raymond F. Suckow, Mark Slifstein, Anissa Abi-Dargham and Marc Laruelle, Effects of reduced endogenous 5-HT on the in vivo binding of the serotonin transporter radioligand 11C-DASB in healthy humans, Synapse, 55 (3), 164-175 (2004).
D. P. Finn, S. R. G. Beckett, D. Richardson, D. A. Kendall, C. A. Marsden and V. Chapman, Evidence for differential modulation of coniditioned aversion and fear-conditioned analgesia by CB1 receptors, European Journal of Neuroscience, 20 (3), 848-852 (2004).
Kimberly A. Petrie, Michael Bubser, Cheryl D. Casey, M. Duff Davis, Bryan L. Roth and Ariel Y. Deutch, The Neurotensin Agonist PD14913 Increases Fos Expression in the Prefrontal Cortex of the Rat, Neuropsychopharmacology, 29, 1878-1888 (2004).
P. D. Shilling, G. Melendez, K. Priebe, E. Richelson and D. Feifel, Neurotensin agonists block the prepulse inhibition deficits produced by a 5-HT 2A and an a1 agonist, Psychopharmacology, 175 (3), 353-359 (2004).
P. Alexander Arguello and J. David Jentsch, Cannabinoid CB1 receptor-mediated impairment of visuospatial attention in the rat, Psychopharmacology, 177 (1-2), 141-150 (2004).
Yasuyuki Makihara, Hiroshi Yamamoto, Mai Inoue, Katsunori Tomiyama, Noriaki Koshikawa and John L. Waddington, Topographical effects of D1-like dopamine receptor agonistson orofacial movements in mice and their differential regulation via oppositional versus synergistic D1-like: D2-like interactions: cautionary observations on SK&F 82958 as an anomalous agent, Journal of Psychopharmacology, 18 (4), 484-495 (2004).
M. Soaje and R. P. Deis, Involvement of Opioid Receptor Subtypes in Both Stimulatory and Inhibitory Effects of the Opioid Peptides on Prolactin Secretion During Pregnancy, Biomedical and Life Sciences, 24 (2), 193-204 (2004).
David Feifel, Gilia Melendez and Paul D. Shilling, Reversal of Sensorimotor Gating Deficits in Brattleboro Rats by Acute Administration of Clozapine and a Neurotensin Agonist, but not Haloperidol: a Potential predictive model for novel antipsychotic effects, Neuropsychopharmacology, 29, 731-738 (2004).
Theodore J. Price, Amol Patwardhan, Armen N. Akopian, Kenneth M. Hargreaves and Christopher M. Flores Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons, British Journal of Pharmacology, 142, 257-266 (2004).
Jennifer Ronesi, Gregory L. Gerdeman and David M. Lovinger, Disruption of Endocannabinoid Release and Striatal Long-Term Depression by Postsynaptic Blockage of Endocannabinoid Membrane Transport, J. Neurosci., 24 (7), 1673-1679 (2004).
Z. Cao, S. Hallur, H. Z. Qiu, X. Peng and Y. Li, Induction of endogenous glutathione by the chemoprotective agent, 3H-1,2-dithiole-3-thione, in human neuroblastoma SH-SY5Y cells affords protection against peroxynitrite-induced cytotoxicity, Biochem. Biophys. Res. Comm., 316, 1043-1049 (2004).
G. J. O'Sullivan, B. L. Roth, A. Kinsella and J. L. Waddington, SF&F 83822 distinguishes adenylyl cyclase from phospholipase C-coupled dopamine D1-like receptors: behavioural topography, Eur. J. Pharmacol., 486, 273-280 (2004).
Margaret I. Davis, Jennifer Ronesi and David M. Lovinger, A Predominant Role for Inhibition of the Adenylate Cyclase/Protein Kinase A Pathway in ERK Activation by Cannabinoid Receptor 1 in N1E-115 Neuroblastoma Cells, J. Biol. Chem., 278 (49), 48973-48980 (2003).
Barbara J. Ebersole, Irache Visiers, Harel Weinstein and Stuart C. Sealfon Molecular Basis of Partial Agonism: Orientation of Indoleamine ligands in the binding pocket of the human serotonin 5-HT2A receptor determines relative efficacy, Molecular Pharmacology, 63, (1), 36-43 (2003).
Katsunori Tomiyama, Fergal N. McNamara, Jeremiah H. Clifford, Anthony Kinsella, John Drago, Sara Fuchs, David K. Grandy, Malcolm J. Low, Marcelo Rubinstein, Orna Tighe, David T. Croke, Noriaki Koshikawa and John L. Waddington, Comparative phenotypic resolution of spontaneous, D2-like and D1-like agonist-induced orofacial movement topographies in congenic mutants with dopamine D2 vs. D3 receptor "knockout", Synapse, 51 (1), 71-81 (2003).
Shahnaz Christina Azad, Matthias Eder, Giovanni Marsicano, Beat Lutz, Walter Zieglgansberger and Gerhard Rammes, Activation of the Cannabinoid Receptor Type 1 Decreases Glutamatergic and GABAergic Synaptic Transmission in the Lateral Amygdala of the Mouse, Learning & Memory, 10l, 116-128 (2003).
R. J. Rodgers, J. Haller, J. Halasz and E. Mikics, 'One-trial sensitization' to the anxiolytic-like effects of cannabinoid receptor antagonist SR141716A in the mouse elevatec plus-maze, European Journal of Neuroscience, 17 (6), 1279-1286 (2003).
Daniela Cota, Giovanni Marsicano, Matthias Tschop, Yvonne Grubler, Cornelia Flachskamm, Mirjam Schubert, Dorothee Auer, Alexander Yassouridis, Christa Thone-Reineke, et. al..., The endogenous cannabinoid system affects energy balance via central orexigenic drive and peripheral lipogenesis, J. Clinical Investigation, 112, 423-431 (2003).
Christopher D. Verrico, J. David Jentsch, Laura Dazzi and Robert H. Roth, Systemic, but not local, administration of cannabinoid CB1 receptor agonists modulate prefrontal cortical acetylcholine efflux in the rat, Synapse, 48 (4), 178-183 (2003).
K. Tomiyama, F. N. McNamara, J. J. Clifford, A. Kinsella, J. Drago, O. Tighe, D. T. Croke, N. Koshikawa and J. L. Waddington, Phenotypic resolution of spontaneous and D (1)-like agonist-induced orofacial movement topographies in congenic dopamine D receptor ..., Neuropharmacology, 42, 644-652 (2002).
M. Soaje, EG de Di Nasso and R. P. Deis, Regulation by endogenous opioids of suckling-induced prolactin secretion in pregnant and lactating rats: role of ovarian steroids, Journal of Endocrinology, 172 (2), 255-261 (2002).
Giovanni Marsicano, Carsten T. Wotjak, Shahnaz C. Azad, Tiziana Bisogno, Gerhard Rammes, Maria Grazia Cascio, Heike Hermann, Jianrong Tang, Clementine Hofmann, et. al., The endogenous cannabinoid system controls extinction of aversive memories, Nature, 418, 530-534 (2002).
Gregory L. Gerdeman, Jennifer Ronesi and David M. Lovinger, Postsynaptic endocannabinoid release is critical to long-term depression in the striatum, Nature Neuroscience, 5, 446-451 (2002).
Fergal N. McNamara, Jeremiah J. Clifford, Orna Tighe, Anthony Kinsella, John Drago, Sara Fuchs, David T. Croke and John L. Waddington, Phenotypic, ethologically based resolution of spontaneous and D2-like vs. D1-like agonist-induced behavioural topography in mice with congenic D3 dopamine receptor "knockout", Synapse, 46 (1), 19-31 (2002).
Carol A. Tamminga, Charles B. Nemeroff, Randy D. Blakely, Linda Brady, Cameron S. Carter, Kenneth L. Davis, Raymond Dingledine, Jack M. Gorman, Dimitri E. Grigoriadis, et. al., Developing Novel Treatments for Mood Disorders: Accelerating Discovery, Biol. Psychiatry, 52 (6), 589-609 (2002).
Gregory L. Gerdeman, Jennifer Ronesi and David M. Lovinger, Postsynaptic endocannabinoid release is critical to long-term depression in the striatum, Nature Neuroscience, 5 (5), 446-451 (2002).
T. J. DeVries, Y. Shaham, J. R. Homberg, H. Crombag, K. Schurman, J. Dieben, L.J.M.J. Vanderschuren, and A.N.M. Schoffelmeer A cannabinoid mechanism in relapse to cocaine seeking Nature Med 7, 1151 (2001).
S. Panchalingam and A. S. Undie, SKF83959 exhibits biochemical agonism by stimulating [ S]GTP ?S binding and phosphoinositide hydrolysis in rat and monkey brain, Neuropharmacology, 40, 826-837 (2001).
A. K. Patni, S. Gupta, A. Sharma, A. K. Tiwary, and S. K. Garg Role of intracellular calcium in the spermicidal action of 2',4'-dichlorobenzamil, a novel contract spermicide, J. Pharm. Pharmacol. 53, 1387-1392 (2001).
P. R. Reddy, A. Patni, A. Sharma, S. Gupta, and A. K. Tiwary Effect of 2',4'-dichlorobenzamil hydrochloride, a Na +-Ca 2+ exchange inhibitor, on human spermatozoa Eur. J. Pharmacol. 418, 153-155 (2001).
N. Safran, V. Shneyvays, N. Balas, K. A. Jacobson, H. Nawarth, and A. Shainberg Cardioprotective effects of adenosine A1 and A3 receptor activation during hypoxia in isolated rat cardiac myocytes Mol. Cell. Biochem 217, 143-152 (2001).
V. Shneyvays, L. Mamedova, T. Zinman, K. Jacobson, and A. Shainberg Activation of A 3adenosine receptor protects against doxorubicin-induced cardiotoxicity J. Mol. Cell Cardiol 33, 1249-1261 (2001).
D. Bridges, K. Ahman and A. S.C. Rice, The Synthetic Cannabinoid WIN55, 212-2 attenuates hyperalgesia and allodynia in a rat model of ...., British Journal of Pharmacology, 133, 586-594 (2001).
Gregory Gerdeman and David M. Lovinger, CB1 Cannabinoid Receptor Inhibits Synaptic Release of Glutamate in Rat Dorsolateral Striatum, Journal of Neurophysiology, 85 (1), 468-471 (2001).
T. Obsil, R. Ghirlando, D. Klein, S. Ganguly and F. Dyda, Crystal Structure of the 14-3-3?: Serotonin N-acetyltransferase Complex A role for scaffolding in enzyme regulation, Cell, 105 (2), 257-267 (2001).
I. A. Antonijevic, J. A. Russell, R. J. Bicknell, G. Leng and A. J. Douglas, Effect of progesterone on the activation of neurones of the supraoptic nucleis during parturition, Journal of Reproduction and Fertility, 120, 367-376 (2000).
F. Dyda, D. C. Klein, and A. B. Hickman. GCN5-related N-acetyltransferases: A structural overview. Annu. Rev. Biophys. Biomol. Struct. 29, 81-103 (2000).
S. W. Rhee and M. J. Tanga Synthesis of tritium labelled 4P-PDOT, a selective melatonin receptor antagonist J. Labelled Cpd. Radiopharm 43, 925-932 (2000)
V. Shneyvays, K. A. Jacobson, A.-H. Li, H. Nawrath, T. Zinman, A. Issac, and A. Shainberg Induction of apoptosis in rat cardiocytes by A3 adenosine receptor activation and its suppression by isoproterenol Exp. Cell Res 257, 111-126 (2000).
T. V. Dunwiddie, K. A. Jacobson, and L. Diao. An adenosine A 3receptor-selective agonist does not modulate calcium-activated potassium currents in hippocampal CA1 pyramidal neurons. Progr. Brain Res. 120, 275-285 (P. Illes and H. Zimmermann, Eds.), (1999).
A. B. Hickman, M. A. A. Namboodiri, D. C. Klein and F. Dyda, The structural basis of ordered substrate binding by serotonin N-acetyltransferase: Enzyme complex at 1.8 Angstrom resolution with a bisubstrate analog, Cell, 97, 361-369 (1999).
W. Xu, S. Leung, J. Wright and S. E. Guggino, Expression of Cyclic Nucleotide-Gated Cation Channels in Airway Epithelial Cells, Journal of Membrane Biology, 171 (2), 117-126 (1999).
K.-N. Klotz, E. Camaioni, R. Volpini, S. Kachler, S. Vittori and G. Cristalli, 2-Substituted N-ethylcarboxamidoadenosine derivatives as high-affinity agonists at human A3 adenosine receptors, Naunyn-Schmiedeberg's Archives of Pharmacology, 360 (2), 103-108 (1999).
W. J. Murdoch, Perturbation of Sheep Ovarian Surface Epithelial Cells by Ovulation: Evidence for roles of progesterone and poly(ADP-ribose) polymerase in the restoration of DNA integrity, Journal of Endocrinology, 156 (3), 503-508 (1998).
David Fulton and John Quilley Evidence against Anandamide as the Hyperpolarizing Factor Mediating the Nitric Oxide-Independent Coronary Vasodilator Effect of Bradykinin in the Rat, J. Pharmacology and Experimental Therapeutics, 286 (3), 1146-1151 (1998).
M. Soaje and R. P. Deis, Opioidergic Regulation of Prolactin Secretion During Pregnancy: role of ovarian hormones, Journal of Endocrinology, 155 (1), 99-106 (1997).
David R. Wallace, Charles F. Mactutus and Rosemarie M. Booze, Repeated Intravenous cocaine administration: Locomotor activity and dopamine D2/D3 receptors, Synapse, 23 (3), 152-163 (1996).
Steven D. Wyrick, Raymond G. Booth, Andrew M. Myers, Constance E. Owens, Ehren C. Bucholtz, Phillip C. Hooper, Nora S. Kula, Ross J. Baldessarini and Richard B. Mailman, 1-Phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes and related derivatives as ligands for the neuromodulatory s3 receptor: Further structure-activity relationships, J. Med. Chem., 38, 3857-3864 (1995).
J. Eric Ahiskog, Ryan J. Uitti, Phillip A. Low, Gertrude M. Tyce, Kim K. Nickander, Ronald C. Petersen and Emre Kokmen, No evidence for systemic oxidant stress in Parkinson's or alzheimer's disease, Movement Disorders, 10 (5), 566-573 (1995).
Brian Duff Sloley, y-Glutamyl conjugation of 5-hydroxytryptamine (serotonin) in the earthworm (Lumbricus terrestris), Neurochemical Research, 19 (2), 217-222 (1994).
Nora S. Kula, Ross J. Baldessarini, John W. Kebabian and John L. Neumeyer, S-(+)-aporphines are not selective for human D3 dopamine receptors, Cellular and Molecular Neurobiology, 14 (2), 185-191 (1994).
P. S. Puttfarcken, J. S. Handen, D. T. Montgomery, J. T. Coyle and L. L. Werling, N-acetyl-aspartylglutamate modulation of N-methyl-D-aspartate-stimulated [3H]norepinephrine release from rat hippocampal slices, Journal of Pharmacology and Experimental Therapeutics, 266 (2), 796-803 (1993).
Thomas A. Cawley Jr. and Timothy J. Shickley, The Potential Neurotoxin 2-OH-Dopamine is an Inhibitor of Arylsulfatase, Annals of the New York Academy of Sciences, 648 (1), 256-259 (1992).
B.-A. Battelle, S. C. Edwards, L. Kass, H. M. Maresch, S. K. Pierce and A. C. Wishart, Identification and Function of Octopamine and Tyramine Conjugates in the Limulus Visual System, Journal of Neurochemistry, 51 (4), 1240-1251 (1988).
G. Manikumar, C. Jin and K. S. Rehder, Convenient Synthesis of Tolcapone, a Selective Catechol-O-methyltransferase Inhibitor, Synth. Commun., 38 (5), 810-815 (2008).
G. Roussy, M.-A. Dansereau, L. Dore-Savard, K. Belleville, N. Beaudet, E. Richelson and P. Sarret, Spinal NTS1 receptors regulate nociceptive signaling in a rat formalin tonic pain model, Journal of Neurochemistry, 105 (4), 1100-1114 (2008).