Physicochemical Properties
| Molecular Formula | C21H34O3 |
| Molecular Weight | 334.49 |
| CAS # | 567-01-1 |
| Appearance | Typically exists as solids at room temperature |
| LogP | 3.568 |
| SMILES | CC12CCC3C(CCC4CC(O)CCC34C)C1CCC2C(=O)CO |
| Synonyms | 5α,3β-THDOC; 567-01-1; 3-beta,5-alpha-TETRAHYDRODEOSOXYCORTICOSTERONE; CHEMBL2057971; 2-hydroxy-1-[(3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone; 3b,5a-Tetrahydrodeoxycorticosterone; SCHEMBL10381095; |
| 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 | GABAA receptors; NMDA receptor |
| ln Vivo |
Epiallopregnanolone (5α,3β-THDOC; 1-100 mg/kg; ip) inhibits pilocarpine-induced epileptic seizures in mice (ED50 is 45.9 mg/kg) [2]. Ethanol had similar discriminative ED50s (0.5 g/kg) in both groups; however rats trained with the lower ethanol dose were more sensitive to rate-decreasing effects of ethanol. Alphaxalone occasioned ethanol-appropriate responding in both training groups, although less effectively in rats trained on the lower ethanol dose (maximum 65% versus 80% ethanol-appropriate responding). No difference in sensitivity to the rate-decreasing effects of alphaxalone was present between groups. Epiallopregnanolone did not reliably occasion ethanol-appropriate responding in either training group, and rats trained on the lower ethanol dose were slightly more sensitive to epiallopregnanolone rate decreasing effects. Epiallopregnanolone did not alter any effects of ethanol or alphaxalone. Conclusions: Our results agree with previous reports that 3 alpha-hydroxy neurosteroids occasion ethanol-appropriate responding, while 3beta-hydroxy neurosteroids do not; as well as reports showing no antagonism of the discriminative stimulus or rate-suppressant effects of ethanol or 3 alpha-hydroxy neurosteroids by 3beta-hydroxy neurosteroids. Results of the present study demonstrate that ethanol and 3 alpha-hydroxy neurosteroids share discriminative stimulus effects. However, these results are inconsistent with the hypothesis that such neurosteroids mediate the discriminative stimulus of ethanol. |
| Animal Protocol |
Animal/Disease Models: Male Swiss mice (25-30 g) injected with Pilocarpine[2] Doses: 1-100 mg/kg Route of Administration: ip; once Experimental Results: Inhibited seizures induced by Pilocarpine. Epiallopregnanolone was suspended in a60% (w/v) solution of saline and THBP in a heated sonicator (60°C). Epiallopregnanolone was soluble in the THBP solu-tion at doses up to 10 mg/ml. All drugs were administered IP. Ethanol wasadministered 10 minutes before the session started (immediately beforethe 10-minute presession wait period), and neurosteroids were adminis-tered 30-min before the session started (20 minutes before the presessionwait period). |
| References |
[1]. Alphaxalone and epiallopregnanolone in rats trained to discriminate ethanol. Alcohol Clin Exp Res. 2005 Sep;29(9):1621-9. |
| Additional Infomation | It is possible that peripherally administered Epiallopregnanolone is converted to other compounds in brain or doesnot penetrate the central nervous system. Interconversionof epiallopregnanolone and its active isomer allopreg-nanolone, readily occurs in brain (Rupprecht, 1999). Sucha conversion would likely produce effects similar to thoseseen in subjects after alphaxalone administration. The mar-ginal ethanol-appropriate responding seen after adminis-tration of high doses of epiallopregnanolone, especially inthe group trained with a 1.2 g/kg ethanol dose, could be dueto such conversion. However, it is important to note thatthis effect was neither substantial nor dose-related. Furtherstudies performed with specific antagonists of steroid con-verting enzymes could address this concern. Because epi-allopregnanolone was inactive after most doses tested inboth groups, it is possible that appreciable levels did notreach the brain. Although the formulation was the same asthat of alphaxalone which certainly did produce centraleffects, the chiral configuration of epiallopregnanolonemay have prevented epiallopregnanolone entry into thebrain. Future studies with direct administration to or sam-pling of epiallopregnanolone from the brain could addressthis concern.In summary, after ethanol doses of 0.8 g/kg and 1.2 g/kgwere established as discriminative stimuli, alphaxalone oc-casioned ethanol-appropriate responding while epiallo-pregnanolone did not. The effects of alphaxalone weresimilar to those reported by others and are similar to resultsof experiments with other 3-hydroxy neurosteroids. Al-phaxalone appeared to occasion ethanol-appropriate re-sponding more readily in subjects trained to discriminatethe higher dose of ethanol. Epiallopregnanolone waslargely inactive, and was unable to alter the discriminativestimulus effects of ethanol or alphaxalone, in contrast withprevious in vitro reports of antagonism. [1] |
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 | 2.9896 mL | 14.9481 mL | 29.8963 mL | |
| 5 mM | 0.5979 mL | 2.9896 mL | 5.9793 mL | |
| 10 mM | 0.2990 mL | 1.4948 mL | 2.9896 mL |