E1145
(±)-Epibatidine dihydrochloride hydrate
≥98% (HPLC), powder
Sinónimos:
exo-(±)-2-(6-Chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane dihydrochloride hydrate
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About This Item
Fórmula empírica (notación de Hill):
C11H13ClN2 · 2HCl · xH2O
Peso molecular:
281.61 (anhydrous basis)
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77
Productos recomendados
Nivel de calidad
Ensayo
≥98% (HPLC)
Formulario
powder
condiciones de almacenamiento
desiccated
color
off-white
solubilidad
DMSO: >4 mg/mL
methanol: 4 mg/mL
cadena SMILES
Cl[H].Cl[H].[H]O[H].Clc1ccc(cn1)[C@H]2CC3CCC2N3
InChI
1S/C11H13ClN2.2ClH.H2O/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8;;;/h1,4,6,8-10,14H,2-3,5H2;2*1H;1H2/t8?,9-,10?;;;/m1.../s1
Clave InChI
AXWYRFKDLRSESC-VAGRNHIFSA-N
Acciones bioquímicas o fisiológicas
Epibatidine is most potent nicotinic acetylcholine receptor agonist known; non-opioid analgesic.
The activity of epibatidine at neuronal and neuromuscular nicotinic acetylcholine receptors was compared with the activity of nicotine and suxamethonium. Activation of ganglionic nicotinic receptors by epibatidine was shown in the guinea-pig ileum (contraction mediated by the cholinergic neurons of the ileum) and in pithed and atropinized rats (rise in blood pressure). Epibatidine also activated nicotinic receptors at the peripheral terminals of afferent C-fibres (rabbit ear) and in the brain (antidiuresis in rats). The agonistic effects of epibatidine were followed by long-lasting receptor desensitization. No antinociceptive effect of epibatidine was seen in rats at a dose free of motor impairment. On muscle end plate nicotinic receptors of the rat diaphragm (not responding to depolarizing agents by contraction), epibatidine was equipotent with suxamethonium in causing neuromuscular inhibition. On an extraocular muscle of the rabbit (responding to depolarizing agents by contraction) epibatidine in vitro and in situ caused a contraction at a 100-fold lower dose than suxamethonium. The Straub tail reaction in mice to epibatidine could be attributed to the sustained stimulation of motor end plate receptors of the "slow contracting" type of muscle fibres by epibatidine. Epibatidine was the most potent agonist on all neuronal and neuromuscular nicotinic receptors examined.
Características y beneficios
This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Palabra de señalización
Danger
Frases de peligro
Consejos de prudencia
Clasificaciones de peligro
Acute Tox. 2 Dermal - Acute Tox. 2 Oral
Código de clase de almacenamiento
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
Clase de riesgo para el agua (WGK)
WGK 3
Punto de inflamabilidad (°F)
Not applicable
Punto de inflamabilidad (°C)
Not applicable
Equipo de protección personal
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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Aurora Alvarez-Buylla et al.
eLife, 12 (2024-01-11)
Alkaloids are important bioactive molecules throughout the natural world, and in many animals they serve as a source of chemical defense against predation. Dendrobatid poison frogs bioaccumulate alkaloids from their diet to make themselves toxic or unpalatable to predators. Despite
M W Decker et al.
Biochemical pharmacology, 58(6), 917-923 (1999-10-06)
Pharmacological treatments for pain have come largely from two classes of compounds--the opioids and the nonsteroidal anti-inflammatory drugs (NSAIDs). Because of deficiencies associated with these two classes of compounds, exploration of novel approaches to pain relief has intensified of late.
F Lembeck
Naunyn-Schmiedeberg's archives of pharmacology, 359(5), 378-385 (1999-09-25)
The activity of epibatidine at neuronal and neuromuscular nicotinic acetylcholine receptors was investigated in several in situ and in vitro systems and compared with the activity of nicotine and suxamethonium. Activation of ganglionic nicotinic receptors by epibatidine was shown in
Ali Yehia et al.
Current protocols in pharmacology, 88(1), e73-e73 (2020-02-19)
Automated patch-clamp (APC) systems have become indispensable tools of drug-discovery programs by allowing high-throughput electrophysiology-based screening of ion channel compounds. The recent development and introduction of microfluidics-based APC systems have made it possible to study the interactions of ligand-gated ion
W Sihver et al.
Neuroscience, 94(3), 685-696 (1999-12-01)
The laminar binding distribution of three nicotinic receptor agonists, [3H](-)nicotine, [3H]cytisine, and [3H]epibatidine, and their relation to the [3H]vesamicol binding, which is known to represent the vesicular acetylcholine transport sites, was performed employing in vitro autoradiography on the medial temporal
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