| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
kappa-opioid receptor/KOR( Kd = 2.2 nM); μ-opioid receptor/MOR (Kd = 430 nM)
|
|---|---|
| ln Vitro |
(+)-U-50488 (hydrochloride) (+)-Trans-(1R,2R)-U-50488 hydrochloride) is the (-)-Trans-(1S,2S)-U-50488[1] enantiomer.
The enantiomers of U50,488, ligands highly selective for kappa-opioid receptors, have been prepared by a refined procedure and their optical purity demonstrated. The absolute configuration of (+)-trans-2-pyrrolidinyl-N-methylcyclohexylamine, a chemically versatile intermediate for synthesis of analogs of kappa-opioid receptor ligands with defined chirality, has been determined to be 1S,2S by X-ray crystallographic analysis. This intermediate has been used to synthesize the optically pure U50,488 enantiomers with known absolute configuration[2]. |
| References | |
| Additional Infomation |
Objective: This article provides a detailed review of the chemical and pharmacological properties of novel non-fentanyl synthetic opioid receptor agonists, particularly N-substituted benzamides and acetamides (commonly known as U-class drugs) and 4-aminocyclohexanols developed by Upjohn in the 1970s and 1980s. Methods: This article tracks the emergence of these drugs as substances of abuse using peer-reviewed literature, patents, professional literature, data from international early warning systems, and discussion posts on drug user forums. Results: In terms of impact on the drug market, prevalence, and harm, the most influential compound to date is U-47700 (trans-3,4-dichloro-N-[2-(dimethylamino)cyclohexyl]-N-methylbenzamide), which users report producing transient euphoria and inducing relapse. Since U-47700 was internationally regulated in 2017, a series of structurally similar related compounds (derived from the original patented compound) have appeared on the illicit drug market. Interest appears to be increasing in a structurally unrelated opioid developed by Upjohn (now known as BDPC/bromadol), and should be closely monitored. Conclusion: International early warning systems are an important component of tracking emerging psychoactive substances and help in taking countermeasures and collecting relevant data for detailed risk assessment. It is recommended that preliminary studies be conducted on the most likely new compounds to provide drug metabolism and pharmacokinetic data to ensure early detection of new substances in toxicological samples. Since these compounds are chiral, stereochemistry has a significant impact on their potency, so configuration determination should be considered in the detection methods. [1]
|
| Molecular Formula |
C19H26CL2N2O
|
|---|---|
| Molecular Weight |
369.33
|
| Exact Mass |
404.119
|
| CAS # |
67198-17-8
|
| Related CAS # |
(1R,2R)-U-50488 hydrochloride;109620-49-7;(-)-U-50488 hydrochloride;114528-79-9;(±)-U-50488 hydrochloride;67197-96-0;(±)-U-50488 hydrate hydrochloride;(+)-U-50488 hydrochloride;114528-81-3
|
| PubChem CID |
19872097
|
| Appearance |
Typically exists as solid at room temperature
|
| LogP |
5.141
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
25
|
| Complexity |
428
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CN(C1CCCCC1N2CCCC2)C(=O)CC3=CC(=C(C=C3)Cl)Cl.Cl
|
| InChi Key |
KGMMGVIYOHGOKQ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C19H26Cl2N2O.ClH/c1-22(19(24)13-14-8-9-15(20)16(21)12-14)17-6-2-3-7-18(17)23-10-4-5-11-23;/h8-9,12,17-18H,2-7,10-11,13H2,1H3;1H
|
| Chemical Name |
2-(3,4-dichlorophenyl)-N-methyl-N-(2-pyrrolidin-1-ylcyclohexyl)acetamide;hydrochloride
|
| Synonyms |
67198-17-8; (+/-)-U-50488 hydrochloride; (+)-U-50488Hydrochloride; 2-(3,4-dichlorophenyl)-N-methyl-N-(2-pyrrolidin-1-ylcyclohexyl)acetamide;hydrochloride; 67198-19-0; SCHEMBL7115845; 3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclo-hexyl] benzeneacetamide 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)
|
| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7076 mL | 13.5380 mL | 27.0761 mL | |
| 5 mM | 0.5415 mL | 2.7076 mL | 5.4152 mL | |
| 10 mM | 0.2708 mL | 1.3538 mL | 2.7076 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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