Physicochemical Properties
| Molecular Formula | C21H27NO4 |
| Molecular Weight | 357.44 |
| Exact Mass | 357.194 |
| CAS # | 65150-66-5 |
| PubChem CID | 131667957 |
| Appearance | Typically exists as solid at room temperature |
| LogP | 1.558 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 26 |
| Complexity | 597 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | O1C2=C(OC)C=CC3C[C@@H]4[C@]5(O)CC[C@@H](O)[C@@]1([H])[C@]5(CCN4CC1CC1)C2=3 |
| InChi Key | UOUQRGSISDNGKD-GQHLEUQBSA-N |
| InChi Code | InChI=1S/C21H27NO4/c1-25-15-5-4-13-10-16-21(24)7-6-14(23)19-20(21,17(13)18(15)26-19)8-9-22(16)11-12-2-3-12/h4-5,12,14,16,19,23-24H,2-3,6-11H2,1H3/t14-,16-,19+,20+,21-/m1/s1 |
| Chemical Name | (4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-9-methoxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7-diol |
| Synonyms | 65150-66-5; Methyl-6_-Naltrexol; 3-O-Methyl-6; A-naltrexone; 3-O-Methyl-6??-naltrexone; ARD181365; |
| 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 | Naltrexone metabolite |
| Enzyme Assay |
1. Metabolite identification method:
-High performance liquid chromatography ultraviolet detection (HPLC-UV) was used to separate 3-O-Mmethyl-6 β - naltrexone. The chromatographic column was C18 (25 cm × 4.6 mm, 5 μ m), the mobile phase was methanol water acetic acid (60:40:0.1, v/v/v), the flow rate was 1 mL/min, and the detection wavelength was 280 nm. This method can distinguish 3-O-Mmethyl-6 β - naltrexone from other naltrexone metabolites (such as 6 β - naltrexone), with a retention time of 10.2 minutes (compared to 6 β - naltrexone, which is 8.2 minutes) [1] |
| Animal Protocol |
1. Biological sample collection:
-After oral administration of naltrexone (50 mg/kg) to rats, plasma, urine, and bile samples were collected at different time points. Plasma samples were precipitated with acetonitrile and centrifuged (3000 × g, 15 minutes), and the supernatant was directly injected for HPLC analysis; Urine and bile samples need to be hydrolyzed by β - glucuronidase to detect bound metabolites [1] |
| References |
[1]. Wall ME, Brine DR. Analytical methods for quantitative and qualitative analysis of naltrexone and metabolites in biological fluids. NIDA Res Monogr. 1981;28:52-65. PMID: 6791013. |
| Additional Infomation | Analytical procedures for the determination of naltrexone and metabolites have been presented. The basic procedure involves the use of radiolabeled drugs and thin layer chromatography. Naltrexone, 6 beta-naltrexol and 2-hydroxy-3-O-methyl-6 beta-naltrexol were found by both the TLC procedure and combined gas chromatography-mass spectrometry. The presence of 3-O-methyl-6 beta-naltrexol was indicated by the TLC method, but this metabolite could not be found by mass spectrometry. [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 | 2.7977 mL | 13.9884 mL | 27.9767 mL | |
| 5 mM | 0.5595 mL | 2.7977 mL | 5.5953 mL | |
| 10 mM | 0.2798 mL | 1.3988 mL | 2.7977 mL |