(2R)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane hydrate dihydrochloride

• ChemBase ID: 155275
• Molecular Formular: C11H17Cl3N2O
• Molecular Mass: 299.62448
• Monoisotopic Mass: 298.04064621
• SMILES: c1cc(ncc1[C@H]1CC2CCC1N2)Cl.O.Cl.Cl
• Canonical SMILES: Clc1ccc(cn1)[C@H]1CC2NC1CC2.O.Cl.Cl
• InChI: 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
• InChIKey: AXWYRFKDLRSESC-VAGRNHIFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane hydrate dihydrochloride
• IUPAC Traditional name: (2R)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane hydrate dihydrochloride
• Synonyms: exo-(±)-2-(6-Chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane dihydrochloride hydrate; (±)-Epibatidine dihydrochloride hydrate

Database IDs

• PubChem SID: 162249413; 24894390
• PubChem CID: 16219300

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.3915857
• LogD (pH = 7.4): -1.0436354
• Log P: 1.8435768
• Molar Refractivity: 57.3916 cm^3
• Polarizability: 22.39249 Å^3
• Polar Surface Area: 24.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >4 mg/mL; methanol: soluble4 mg/mL
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 27/28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310
• GHS Precautionary statements: P264-P280-P301 + P310-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H13ClN2 · 2HCl · xH2O

DETAILS

Sigma Aldrich - E1145

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.