Epiboxidine is a potent and specific neural nAChR agonist/activator with Ki of 0.46 nM and 1.2 nM for rat and human α4β2 nAChR, respectively. Epiboxidine is a methylisoxazole analog of the alkaloid Epibatidine and an analog of ABT 418, another nicotinic receptor agonist.

Physicochemical Properties

Molecular Formula	C10H14N2O
Molecular Weight	178.23
Exact Mass	214.087
CAS #	188895-96-7
Related CAS #	Epiboxidine hydrochloride;862909-67-9
PubChem CID	5747670
Appearance	Typically exists as solid at room temperature
Density	1.13g/cm3
Boiling Point	313.1ºC at 760mmHg
Flash Point	143.2ºC
Vapour Pressure	0.000507mmHg at 25°C
Index of Refraction	1.53
LogP	2.721
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Heavy Atom Count	13
Complexity	209
Defined Atom Stereocenter Count	3
SMILES	CC1=NOC([C@H]2C[C@@H]3CC[C@H]2N3)=C1
InChi Key	GEEFPQBPVBFCSD-XHNCKOQMSA-N
InChi Code	InChI=1S/C10H14N2O/c1-6-4-10(13-12-6)8-5-7-2-3-9(8)11-7/h4,7-9,11H,2-3,5H2,1H3/t7-,8-,9+/m0/s1
Chemical Name	5-[(1R,2S,4S)-7-azabicyclo[2.2.1]heptan-2-yl]-3-methyl-1,2-oxazole
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Ki: 0.46 nM (rat α4β2 nAChR) and 1.2 nM (human α4β2 nAChR)[1]
ln Vitro	Epiboxidine has affinity and functional at central neuronal α4β2 receptors, with a Ki of 0.46 and 1.2 in rat and humen[1]. Epiboxidine shows action at ganglionic-type α3β4*-nicotinic receptors of PC12 cells, with a Ki of 19[1]. Epiboxidine is considerably less hazardous than Epibatidine[1]. Epiboxidine stimulates sodium-22 influx in PC12 and TE671 cells, with EC50s of 0.18 and 2.6 µM[2].
ln Vivo	Mice treated with epiboxidine (20 μg/kg; ip; once) exhibit pronounced analgesic activity[1]. The hot-plate assay indicates that epiboxidine (50 and 100 mg/kg; intraperitoneal administered; once) significantly reduces pain[2]. With a Ki of 0.6 nM, epiboxidine inhibits the binding of [3H]nicotine in the cerebral cortical membranes of rats[2].
Animal Protocol	Animal/Disease Models: Adult male NIH Swiss strain mice (25-30 g)[2] Doses: 50 and 100 mg/kg Route of Administration: Ip; once Experimental Results: Caused a dose-related Straub tail, hypomotility, hypoventilation and piloerection.
References	[1]. Homoepiboxidines: further potent agonists for nicotinic receptors. Bioorg Med Chem. 2004;12(1):179-190. [2]. Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine. Eur J Pharmacol. 1997;321(2):189-194.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.6107 mL	28.0536 mL	56.1073 mL
	5 mM	1.1221 mL	5.6107 mL	11.2215 mL
	10 mM	0.5611 mL	2.8054 mL	5.6107 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.