Journal ArticleDOI
Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an ecuadoran poison frog
Thomas F. Spande,H. M. Garraffo,M. W. Edwards,Herman J. C. Yeh,Lewis K. Pannell,John W. Daly +5 more
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TLDR
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane represents a unique new class of alkaloids.Abstract:
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane. It represents a unique new class of alkaloidsread more
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Journal Article
Development of Muscarinic Analgesics Derived from Epibatidine: Role of the M4 Receptor Subtype
James L. Ellis,Dean Harman,Javier Gonzalez,Michael L. Spera,Ronggang Liu,T. Y. Shen,Donna M. Wypij,Fangming Zuo +7 more
TL;DR: Results demonstrate that the antinociception elicited by these epibatidine analogs is mediated via muscarinic M4 receptors located in the spinal cord, and compounds that specifically target the M4 receptor therefore may be of substantial value as alternative analgesics to the opiates.
Journal ArticleDOI
Discovery of 4-(5-Methyloxazolo[4,5-b]pyridin-2-yl)-1,4-diazabicyclo[3.2.2]nonane (CP-810,123), a Novel α7 Nicotinic Acetylcholine Receptor Agonist for the Treatment of Cognitive Disorders in Schizophrenia: Synthesis, SAR Development, and in Vivo Efficacy in Cognition Models
Christopher J. O’Donnell,Bruce N. Rogers,Bronk Brian Scott,Dianne K. Bryce,Jotham Wadsworth Coe,Karen K. Cook,Allen J. Duplantier,Edelweiss Evrard,Mihály Hajós,William E. Hoffmann,Raymond S. Hurst,Noha Maklad,Robert J. Mather,Stafford McLean,Frank M. Nedza,Brian T. O’Neill,Langu Peng,Weimin Qian,Melinda M. Rottas,Steven B. Sands,Anne W. Schmidt,Alka Shrikhande,Douglas K. Spracklin,Diane F. Wong,Andy Q. Zhang,Lei Zhang +25 more
TL;DR: The structural diversity of this compound and its preclinical in vitro and in vivo package support the hypothesis that alpha 7 nAChR agonists may have potential as a pharmacotherapy for the treatment of cognitive deficits in schizophrenia.
Journal ArticleDOI
Total synthesis of epibatidine
TL;DR: The first total synthesis of (+)-epibatidine from the skin of an Ecuadoran frog was described in this article, which is a putative nonopioid analgesic.
Journal ArticleDOI
Neurochemical Evidence of Heterogeneity of Presynaptic and Somatodendritic Nicotinic Acetylcholine Receptorsa
TL;DR: Since Langley’ first reported the existence of a “receptive substancc” for nicotine in skeletal muscle that could mediatc the effccts of nicotine, evidence was obtained that acetylcholinc receptors (AChRs) could be involved in synaptic transmission in many parts of the central nervous systcm (CNS), and also could be responsible for signal transmission through autonomic ganglia.
Journal ArticleDOI
Synthesis of a fluorine-18 labeled derivative of epibatidine for in vivo nicotinic acetylcholine receptor PET imaging.
Lilian Dolci,Frédéric Dollé,Héric Valette,Françoise Vaufrey,Chantal Fuseau,Michel Bottlaender,Christian Crouzel +6 more
TL;DR: Its specific regiodistribution and its high ratio of specific-to-nonspecific binding confirm the ideal profile of [18F]norchlorofluoroepibatidine as a suitable radioligand for PET imaging of nAChRs in the brain.