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E1145

Sigma-Aldrich

(±)-Epibatidine dihydrochloride hydrate

≥98% (HPLC), powder

Synonym(s):

exo-(±)-2-(6-Chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane dihydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C11H13ClN2 · 2HCl · xH2O
Molecular Weight:
281.61 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
24894390
NACRES:
NA.77

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

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.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

E1145-BULK:
E1145-VAR:
E1145-5MG:
E1145-1MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M W Decker et al.
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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
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
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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