Physicochemical Properties
| Molecular Formula | C20H15NO |
| Molecular Weight | 285.34 |
| CAS # | 80749-33-3 |
| Appearance | Typically exists as solids at room temperature |
| SMILES | CC1=C(C2=CC=CC=C2N1)C(=O)C3=CC=CC4=CC=CC=C43 |
| Synonyms | 80749-33-3; (2-Methyl-1H-indol-3-yl)(naphthalen-1-yl)methanone; DTXSID70472432; DTXCID10423246; (2-methyl-1h-indol-3-yl)-naphthalen-1-ylmethanone; (2-Methyl-1H-indol-3-yl)-1-naphthalenylmethanone; 2-methyl-3-(naphthalene-1-carbonyl)-1H-indole; 1'-Naphthoyl-2-methylindole; |
| 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 |
Cannabinoid Receptor (CB1) (Ki = 3.2 nM) [1] |
| ln Vitro |
1'-Naphthoyl-2-methylindole exhibited high affinity for rat forebrain cannabinoid receptors with Ki = 3.2 nM in competitive binding assays using [³H]CP-55,940. This represented a >10-fold improvement over the lead compound pravadoline (Ki = 34 nM). [1] In isolated mouse vas deferens preparations, Compound 88 (10–100 nM) dose-dependently inhibited electrically evoked contractions (IC₅₀ = 42 nM), an effect fully blocked by the CB1 antagonist SR141716A. [1] |
| ln Vivo |
Compound 88 (0.3–10 mg/kg, i.v.) produced classic cannabinoid behavioral effects in mice: dose-dependent hypomotility (ED₅₀ = 1.2 mg/kg), catalepsy (ED₅₀ = 2.8 mg/kg), and hypothermia (ED₅₀ = 1.5 mg/kg) at 30 min post-administration. Effects persisted for >90 min at higher doses (10 mg/kg). [1] |
| Enzyme Assay |
Cannabinoid receptor binding assays used rat forebrain membranes incubated with [³H]CP-55,940 (0.5 nM) and varying concentrations of Compound 88 in Tris-HCl buffer (50 mM, pH 7.4) containing 5 mM MgCl₂ and 0.1% BSA. After 90 min at 30°C, bound radioactivity was separated by filtration and quantified. Ki values were calculated using Cheng-Prusoff equation. [1] |
| Animal Protocol |
Binding assay: Rat forebrains were homogenized in ice-cold Tris-HCl buffer and centrifuged. Membrane pellets were resuspended for radioligand binding studies. [1] Mouse behavioral tests: Male mice received intravenous injections of Compound 88 (0.3–10 mg/kg) dissolved in ethanol:emulphor:saline (1:1:18). Hypomotility (open-field test), catalepsy (bar test), and rectal temperature were measured at 30, 60, and 90 min post-dose. [1] Vas deferens bioassay: Mouse vasa deferentia were mounted in organ baths with Krebs solution. Electrical stimulation (0.1 Hz, 0.3 ms pulse) induced contractions. Compound 88 was cumulatively added to assess inhibition. [1] |
| References |
[1]. Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics. J Med Chem. 1995 Aug 4;38(16):3094-105. |
| Additional Infomation |
Compound 88 established critical SAR insights: 1-Naphthoyl substitution at C3' combined with 2-methylindole core maximized CB1 affinity. Its full agonist profile was confirmed by reversal with SR141716A in functional assays. [1] This compound became a structural prototype for aminoalkylindole-derived synthetic cannabinoids, demonstrating nanomolar potency in both binding and functional assays. [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 | 3.5046 mL | 17.5230 mL | 35.0459 mL | |
| 5 mM | 0.7009 mL | 3.5046 mL | 7.0092 mL | |
| 10 mM | 0.3505 mL | 1.7523 mL | 3.5046 mL |