Physicochemical Properties
| Molecular Formula | C22H24CL3N3OS |
| Molecular Weight | 484.87 |
| Exact Mass | 483.07 |
| CAS # | 155512-52-0 |
| PubChem CID | 45073425 |
| Appearance | Off-white to light yellow solid powder |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 30 |
| Complexity | 595 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | CN([C@H](CN1CCCC1)C2=CC(=CC=C2)N=C=S)C(=O)CC3=CC(=C(C=C3)Cl)Cl.Cl |
| InChi Key | BNWYENYHNOESCX-ZMBIFBSDSA-N |
| InChi Code | InChI=1S/C22H23Cl2N3OS.ClH/c1-26(22(28)12-16-7-8-19(23)20(24)11-16)21(14-27-9-2-3-10-27)17-5-4-6-18(13-17)25-15-29;/h4-8,11,13,21H,2-3,9-10,12,14H2,1H3;1H/t21-;/m1./s1 |
| Chemical Name | 2-(3,4-dichlorophenyl)-N-[(1S)-1-(3-isothiocyanatophenyl)-2-pyrrolidin-1-ylethyl]-N-methylacetamide;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
| Targets | κ Opioid Receptor/KOR |
| ln Vivo | In Wistar Kyoto rats, DIPPA (2.5 and 5 mg/kg; sc) hydrochloride reduces the latency to feed; however, therapy had no effect on approach latencies in SD rats[2]. The high dose of DIPPA (1 and 5 mg/kg; sc) hydrochloride causes an increase in immobility in SD rats as compared to the group of rats treated with saline[2]. Compared to the 5 mg/kg group of Wistar Kyoto rats, SD rats consume less DIPPA (5 mg/kg) hydrochloride. In both strains, DIPPA hydrochloride dramatically reduces burying time. Burying is reduced in both strains by DIPPA hydrochloride (5 mg/kg) as compared to the within-strain control groups. In SD rats, DIPPA hydrochloride tends to reduce consumption in the home cage but dramatically boosts feeding in the novel cage, where possible anxiolytic-like effects of the substance may counteract its hypophagic effects[2]. |
| Animal Protocol |
Animal/Disease Models: Wistar Kyoto rats and SD rats (250–300 g)[2] Doses: 2.5 and 5 mg/kg Route of Administration: Sc Experimental Results: diminished the latency to feed in Wistar Kyoto rats, but treatment did not alter approach latencies in SD rats. Animal/Disease Models: Wistar Kyoto rats and SD rats (250–300 g)[2] Doses: 1 and 5 mg/kg Route of Administration: Sc Experimental Results: High dose increased immobility in SD rats compared to the saline-treated strain control group. |
| References |
[1]. Identification of a κ-opioid agonist as a potent and selective lead for drug development against human African trypanosomiasis. Biochem Pharmacol. 2010;80(10):1478-1486. [2]. Comparison of the kappa-opioid receptor antagonist DIPPA in tests of anxiety-like behavior between Wistar Kyoto and Sprague Dawley rats. Psychopharmacology (Berl). 2010;210(2):295-302. [3]. 2-(3,4-Dichlorophenyl)-N-methyl-N-[2-(1-pyrrolidinyl)-1-substituted- ethyl]-acetamides: the use of conformational analysis in the development of a novel series of potent opioid kappa agonists. J Med Chem. 1991;34(1):181-189. [4]. kappa Opioid receptor selective affinity labels: electrophilic benzeneacetamides as kappa-selective opioid antagonists. J Med Chem. 1994;37(26):4490-4498. |
Solubility Data
| 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 | 2.0624 mL | 10.3120 mL | 20.6241 mL | |
| 5 mM | 0.4125 mL | 2.0624 mL | 4.1248 mL | |
| 10 mM | 0.2062 mL | 1.0312 mL | 2.0624 mL |