CAS Number158681-13-1
SynonymsRimonabant hydrochloride; MFCD04034714; Rimonabant (Hydrochloride)
Molecular FormulaC22H22O1N4Cl4
Molecular Weight500.25
Purity98%
Boiling Point627.6ºC at 760 mmHg
Melting Point230-240ºC
AppearanceOff-white to white crystalline powder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 158681-13-1 |
| Catalog No. | 2A-9012311 |
| Chinese Name | 盐酸利莫那班 |
| Synonyms | Rimonabant hydrochloride; MFCD04034714; Rimonabant (Hydrochloride) |
| Molecular Formula | C22H22O1N4Cl4 |
| Molecular Weight | 500.25 |
| Purity | 98 |
| Boiling Point | 627.6ºC at 760 mmHg |
| Melting Point | 230-240ºC |
| Appearance | Off-white to white crystalline powder |
| Storage Condition | -20°C Freezer |
| Application | Rimonabant hydrochloride is a cannabinoid receptor (CB) antagonist that selectively binds CB1 with a Ki of 2 nM. |
| MDL Number | MFCD00934884 |
| SMILES | Cc1c(C(=O)NN2CCCCC2)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1.Cl |
| InChI | InChI=1S/C22H21Cl3N4O.ClH/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15;/h5-10,13H,2-4,11-12H2,1H3,(H,27,30);1H |
| InChI Key | REOYOKXLUFHOBV-UHFFFAOYSA-N |
| Hazard Symbols | Transport |
| MSDS | msds/12311_1_158681_13_1.pdf |
| Bioactivity | Rimonabant hydrochloride is a cannabinoid receptor (CB) antagonist which binds selectively to CB1 with a Ki of 2 nM. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Research Areas >> Metabolic Disease Target Ki: 2 nM (CB1 receptor)[1] In Vitro Rimonabant hydrochloride (SR 141716A) binds selectively to central cannabinoid receptors (CB1) with high affinity (Ki=2 nM), and blocks the inhibitory effects of cannabinoid receptor agonists in the mouse vas deferens, dopamine-stimulated adenylyl cyclase and WIN 55212-stimulated GTPγS binding[1]. Rimonabant dose-dependently inhibited CO synthesis in Raw 264.7 macrophages, with 1 µM producing a significant (~40%) decrease compared to untreated controls and concentrations ≥ 5 µM producing near complete inhibition. A small, but significant, reduction of TG and DG synthesis is also observed with Rimonabant at concentrations ≥ 10 µM. Inhibition of CO synthesis in Raw 264.7 macrophages by Rimonabant (IC50 value 2.9±0.38 µM) is very similar to that of AM251 and SR144528 (IC50 value 2.6±0.26 µM and 2.5±0.32 µM, respectively), two related compounds previously demonstrated to be potent ACAT inhibitors. Mouse peritoneal macrophages also displayed significantly reduced CO synthesis in response to Rimonabant treatment. Rimonabant at concentrations ≥ 1 µM significantly inhibits CO synthesis in CHO-ACAT1 and CHO-ACAT2 cells in a concentration-dependent manner with similar efficiency (IC50s of 1.5±1.2 µM and 2.2±1.1 µM, respectively)[2]. In Vivo Pretreatment with Rimonabant hydrochloride (SR 141716A) blocks the antinociceptive, discriminative stimulus, memory impairing and hypolocomotor effects produced by Δ-9-THC. SR 141716A also precipitates a withdrawal syndrome in rats treated chronically with Δ-9-THC[1]. Pretreatment of mice with 0.1 mg/kg of WIN 55212-2 is effective in increasing the CPP induced by MDMA , while 1 mg/kg of Rimonabant specifically blocks CB1 receptors and does not act as an inverse agonist[3]. Kinase Assay Raw 264.7 cells (2×106/well) in 12-well plates are rinsed with PBS and refed culture media supplemented with varying amounts of Rimonabant 1h prior to supplementation with 7-ketocholesterol (7KC). All wells are adjusted to receive equal amounts of vehicle. Following a 16 h incubation, caspase-3 and caspase 3-like activity is determined[2]. Animal Admin Mice[3] A total of 250 male mice of the OF1 strain (21 days of age) are used. Animals are injected i.p. with cocaine hydrochloride, WIN 55212-2, or Rimonabant (SR 141716A) in a volume of 0.01 mL/g. Control groups are injected with the physiological saline used to dissolve cocaine (NaCl 0.9%) or with Tween-80, which is used to dissolve WIN 55212-2 and Rimonabant (0.01%, 0.01 mL of Tween dissolved in 100 mL of saline). The doses of cocaine administered are selected on the basis of previous studies showing that 1 mg/kg is a subthreshold dose for inducing CPP in naïve mice, while 6 mg/kg is effective in inducing CPP acquisition but not in producing reinstatement after extinction of CPP. Similarly, the doses of cannabinoid drugs administered are selected on the basis of previous studies on the effects of WIN 55212-2 in the CPP paradigm and on the effects of cannabinoid pretreatment on the CPP induced by other drugs of abuse. References [1]. Vivian JA, et al. Analgesic, respiratory and heart rate effects of cannabinoid and opioid agonists in rhesus monkeys: antagonist effects of SR 141716A. J Pharmacol Exp Ther. 1998 Aug;286(2):697-703. [2]. Netherland C, et al. Rimonabant is a dual inhibitor of acyl CoA:cholesterol acyltransferases 1 and 2. Biochem Biophys Res Commun. 2010 Aug 6;398(4):671-6. [3]. Rodríguez-Arias M, et al. Effects of Cannabinoid Exposure during Adolescence on the Conditioned Rewarding Effects of WIN 55212-2 and Cocaine in Mice: Influence of the Novelty-Seeking Trait. Neural Plast. 2016;2016:6481862. Chemical & Physical Properties Boiling Point 627.6ºC at 760 mmHg Melting Point 230-240ºC Molecular Formula C22H22Cl4N4O Molecular Weight 500.248 Flash Point 333.3ºC Exact Mass 498.054779 PSA 50.16000 LogP 7.06940 InChIKey REOYOKXLUFHOBV-UHFFFAOYSA-N SMILES Cc1c(C(=O)NN2CCCCC2)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1.Cl Storage condition -20°C Freezer |
| Use of | Rimonabant hydrochloride is a cannabinoid receptor (CB) antagonist which binds selectively to CB1 with a Ki of 2 nM. Properties Articles27 Name Rimonabant Hydrochloride Synonym More Synonyms SR 141716A Biological Activity Description Rimonabant hydrochloride is a cannabinoid receptor (CB) antagonist which binds selectively to CB1 with a Ki of 2 nM. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Research Areas >> Metabolic Disease Ki: 2 nM (CB1 receptor)[1] References [1]. Vivian JA, et al. Analgesic, respiratory and heart rate effects of cannabinoid and opioid agonists in rhesus monkeys: antagonist effects of SR 141716A. J Pharmacol Exp Ther. 1998 Aug;286(2):697-703. [2]. Netherland C, et al. Rimonabant is a dual inhibitor of acyl CoA:cholesterol acyltransferases 1 and 2. Biochem Biophys Res Commun. 2010 Aug 6;398(4):671-6. [3]. Rodríguez-Arias M, et al. Effects of Cannabinoid Exposure during Adolescence on the Conditioned Rewarding Effects of WIN 55212-2 and Cocaine in Mice: Influence of the Novelty-Seeking Trait. Neural Plast. 2016;2016:6481862. Chemical & Physical Properties Exact Mass 498.054779 PSA 50.16000 LogP 7.06940 InChIKey REOYOKXLUFHOBV-UHFFFAOYSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Dangerous Regulations for land transport: 2811 International Dangerous Regulations for sea transport: 2811 International Dangerous Regulations for air transport: 2811 14.2 United Nations shipping name European Land Transport Dangerous Regulations: TOXIC SOLID, ORGANIC, N.O.S. (5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1- piperidinyl-1H-pyrazole-3-carboxamide hydrochloride) IMDG: TOXIC SOLID, ORGANIC, N.O.S. (5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1- piperidinyl-1H-pyrazole-3-carboxamide hydrochloride) International air transport hazard regulations: Toxic solid, organic, n.o.s. (5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1- piperidinyl-1H-pyrazole-3-carboxamide hydrochloride) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
| Related Products in Specialty Chemicals | ||
|---|---|---|
| Rilmenidine | 54187-04-1 | 2A-9012306 |
| Rilozarone | 79282-39-6 | 2A-9012307 |
| Rimantadine | 13392-28-4 | 2A-9012308 |
| Rimantadine hydrochloride | 1501-84-4 | 2A-9012309 |
| Rimonabant | 168273-06-1 | 2A-9012310 |
| Ripisartan | 148504-51-2 | 2A-9012313 |
| Risotilide | 120688-08-6 | 2A-9012315 |
| Risperidal | 106266-06-2 | 2A-9012316 |
| Ristianol | 78092-65-6 | 2A-9012317 |
| Ritanserin | 87051-43-2 | 2A-9012318 |
| Browse all Specialty Chemicals products » | ||
Phone:
630-322-8886
630-322-8887
Email:
Office Locations:
Chicago, IL, USA
San Francisco, CA, USA
EN
SDS