Physicochemical Properties
| Molecular Formula | C9H15CLN2O2 |
| Exact Mass | 218.082 |
| Elemental Analysis | C, 49.43; H, 6.91; Cl, 16.21; N, 12.81; O, 14.63 |
| CAS # | 178419-42-6 |
| Related CAS # | 178419-47-1; 178419-42-6 (HCl); |
| PubChem CID | 9859263 |
| Appearance | White to off-white solid powder |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 14 |
| Complexity | 248 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | Cl.O=C1NC[C@@]2(CN3CCC2CC3)O1 |
| InChi Key | XGLBLUBBDSJBIU-FVGYRXGTSA-N |
| InChi Code | InChI=1S/C9H14N2O2.ClH/c12-8-10-5-9(13-8)6-11-3-1-7(9)2-4-11;/h7H,1-6H2,(H,10,12);1H/t9-;/m0./s1 |
| Chemical Name | (3S)-Spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidine]-2'-one hydrochloride |
| Synonyms | AR-R-17779 AR-R 17779 AR-R17779AR-R17779 hydrochloride |
| 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
| ln Vitro | When it comes to α7 nicotinic receptors, AR-R17779 is 35,000 times more selective and 5 times more powerful than (-)-nicotine [1]. Macrophages' production of TNF is inhibited by AR-R17779 (200 nM; 24 hours) in response to LPS [4]. |
| ln Vivo | AR-R17779 (intraperitoneally twice daily for seven days; 1–5 mg/kg) ameliorates arthritis, lowers synovial inflammation, postpones the development of the disease, and stops joint deterioration [3]. In rats, AR-R17779 (1–10 mg/kg; subcutaneously administered for 3 weeks) cures working memory deficit caused by fimbria-fornix hippocampal slices and enhances learning in two radial arm maze tasks [2]. |
| Animal Protocol |
Animal/Disease Models: Male DBA/1 mice (8-10 weeks) underwent unilateral cervical vagotomy or sham surgery, and then induced arthritis with type II collagen [3] Doses: 1, 2.5, 5 mg/kg administered Method: intraperitoneal (ip) injection twice (two times) daily from day 20 to day 26. Experimental Results: Improvement of arthritis and delay of disease onset. Reduces erosive disease, cartilage degeneration and synovial inflammation. TNFα levels were diminished in plasma and synovial tissue. |
| References |
[1]. (-)-Spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] a conformationally restricted analogue of acetylcholine, is a highly selective full agonist at the alpha 7 nicotinic acetylcholine receptor. J Med Chem. 2000 Nov 2;43(22):4045-. [2]. AR-R17779, and alpha7 nicotinic agonist, improves learning and memory in rats. Behav Pharmacol. 1999 Nov;10(6-7):675-80. [3]. Stimulation of nicotinic acetylcholine receptors attenuates collagen-induced arthritis in mice. Arthritis Rheum. 2009 Jan;60(1):114-22. [4]. Involvement of Mast Cells in α7 Nicotinic Receptor Agonist Exacerbation of Freund's Complete Adjuvant-Induced Monoarthritis in Mice. |
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.) |