Epiboxidine hydrochloride

Names

[ Name ]:
Epiboxidine hydrochloride

[Synonym ]:
7-Azabicyclo(2.2.1)heptane,2-(3-methyl-5-isoxazolyl)-,exo
(+-)-Epiboxidine
exo-2-(3-Methyl-5-isoxazolyl)-7-azabicyclo(2.2.1)heptane

Biological Activity

[Description]:

Epiboxidine is a potent and selective neural nAChR agonist with Kis of 0.46 nM and 1.2 nM for rat and human α4β2 nAChRs, respectively. Epiboxidine is a methylisoxazole analog of the alkaloid Epibatidine, and is also an analog of another nAChR agonist, ABT 418[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR

Signaling Pathways >> Neuronal Signaling >> nAChR

Research Areas >> Neurological Disease

[Target]

Ki: 0.46 nM (rat α4β2 nAChR) and 1.2 nM (human α4β2 nAChR)[1]

[In Vitro]

Epiboxidine has affinity and functional at central neuronal α4β2 receptors, with Kis of 0.46 and 1.2 in rat and humen[1]. Epiboxidine has activity at ganglionic-type α3β4*-nicotinic receptors of PC12 cells, with a Ki of 19[1]. Epiboxidine is much less toxic than Epibatidine[1]. Epiboxidine stimulates sodium-22 influx in PC12 and TE671 cells, with EC50s of 0.18 and 2.6 µM[2].

[In Vivo]

Epiboxidine (20 μg/kg; ip; once) treatment shows marked analgetic activity in mice[1]. Epiboxidine (50 and 100 mg/kg; intraperitoneal injected; once) causes marked antinociception as measured in the hot-plate assay[2]. Epiboxidine inhibits [3H]nicotine binding in rat cerebral cortical membranes, with a Ki of 0.6 nM[2]. Animal Model: Adult male NIH Swiss strain mice (25-30 g)[2] Dosage: 50 and 100 mg/kg Administration: I.p.; once Result: Caused a dose-related Straub tail, hypomotility, hypoventilation and piloerection.

[References]

[1]. Fitch RW, et al. Homoepiboxidines: further potent agonists for nicotinic receptors. Bioorg Med Chem. 2004;12(1):179-190.

[2]. Badio B, et al. Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine. Eur J Pharmacol. 1997;321(2):189-194.

Chemical & Physical Properties

[ Density]:
1.13g/cm3

[ Boiling Point ]:
313.1ºC at 760mmHg

[ Molecular Formula ]:
C₁₀H₁₄N₂O

[ Molecular Weight ]:
178.23

[ Flash Point ]:
143.2ºC

[ Exact Mass ]:
214.08700

[ PSA ]:
38.06000

[ LogP ]:
2.72170

[ Vapour Pressure ]:
0.000507mmHg at 25°C

[ Index of Refraction ]:
1.53

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CL5446415

Articles

Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine.

Eur. J. Pharmacol. 321 , 189-194, (1997)

Synthetic (+/-)-epiboxidine (exo-2-(3-methyl-5-isoxazolyl)-7-azabicyclo[2.2.1]heptane) is a methylisoxazole analog of the alkaloid epibatidine, itself a potent nicotinic receptor agonist with antinoci...

Dithiothreitol causes HIV-1 integrase dimer dissociation while agents interacting with the integrase dimer interface promote dimer formation.

Biochemistry 50 , 1567-81, (2011)

We have developed a homogeneous time-resolved fluorescence resonance energy transfer (FRET)-based assay that detects the formation of HIV-1 integrase (IN) dimers. The assay utilizes IN monomers that e...

Related Compounds

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