E1145
(±)-Epibatidine dihydrochloride hydrate
≥98% (HPLC), nicotinic acetylcholine receptor agonist, powder
Synonym(s):
exo-(±)-2-(6-Chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane dihydrochloride hydrate
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Product Name
(±)-Epibatidine dihydrochloride hydrate, ≥98% (HPLC), powder
Quality Level
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
off-white
solubility
DMSO: >4 mg/mL, methanol: 4 mg/mL
SMILES string
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
InChI key
AXWYRFKDLRSESC-VAGRNHIFSA-N
Biochem/physiol Actions
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.
Features and Benefits
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 2 Dermal - Acute Tox. 2 Oral
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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Alexandra Gribizis et al.
Neuron, 104(4), 711-723 (2019-09-29)
Visual spatial perception in the mammalian brain occurs through two parallel pathways: one reaches the primary visual cortex (V1) through the thalamus and another the superior colliculus (SC) via direct projections from the retina. The origin, development, and relative function
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