Related CAS #
75859-04-0 (free base)
Synonym
BW 234U; Rimcazole dihydrochloride, Rimcazole 2HCl
IUPAC/Chemical Name
9-[3-(cis-3,5-Dimethyl-1-piperazinyl)propyl]-9H-carbazole Dihydrochloride
InChi Key
ZWHRZGHGYMUSRM-VWDRLOGHSA-N
InChi Code
InChI=1S/C21H27N3.2ClH/c1-16-14-23(15-17(2)22-16)12-7-13-24-20-10-5-3-8-18(20)19-9-4-6-11-21(19)24;;/h3-6,8-11,16-17,22H,7,12-15H2,1-2H3;2*1H/t16-,17+;;
SMILES Code
C[C@H]1N[C@@H](C)CN(CCCN2C3=C(C4=C2C=CC=C4)C=CC=C3)C1.[H]Cl.[H]Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in water
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in water
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Rimcazole dihydrochloride is an antagonist at σ receptors (IC50 values 1480 and 386 nM at σ1 and σ2 receptors, respectively). Rimcazole dihydrochloride binds to the dopamine transporter (IC50 = 57.6 nM) and inhibits dopamine uptake. Reduces the stimulatory effects of cocaine in vivo.
In vitro activity:
The induction of HIF-1alpha by rimcazole contributes to tumor cell killing. HIF-1alpha levels are consistently higher after rimcazole treatment in HCT-116p53+/+ cells. Rimacazole has a potent apoptosis-inducing effect in HCT-116p53+/+ cells.
Reference: Oncogene. 2007 Feb 22;26(8):1137-46. https://pubmed.ncbi.nlm.nih.gov/16924239/
In vivo activity:
Rimcazole strongly inhibited the growth of A375M melanoma xenografts. This growth inhibition is accompanied by an early increase of (18)F-FDG uptake in the tumor.
Reference: J Nucl Med. 2013 Sep;54(9):1613-20. https://pubmed.ncbi.nlm.nih.gov/23940303/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
3.9 |
10.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
394.38
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Achison M, Boylan MT, Hupp TR, Spruce BA. HIF-1alpha contributes to tumour-selective killing by the sigma receptor antagonist rimcazole. Oncogene. 2007 Feb 22;26(8):1137-46. doi: 10.1038/sj.onc.1209890. Epub 2006 Aug 21. PMID: 16924239.
2. Rybczynska AA, de Bruyn M, Ramakrishnan NK, de Jong JR, Elsinga PH, Helfrich W, Dierckx RA, van Waarde A. In vivo responses of human A375M melanoma to a σ ligand: 18F-FDG PET imaging. J Nucl Med. 2013 Sep;54(9):1613-20. doi: 10.2967/jnumed.113.122655. Epub 2013 Aug 12. PMID: 23940303.
3. Borowicz KK, Wilczyński PM, Kleinrok Z, Czuczwar SJ. Rimcazole, a sigma receptor ligand, and the anticonvulsive action of convention
In vitro protocol:
1. Achison M, Boylan MT, Hupp TR, Spruce BA. HIF-1alpha contributes to tumour-selective killing by the sigma receptor antagonist rimcazole. Oncogene. 2007 Feb 22;26(8):1137-46. doi: 10.1038/sj.onc.1209890. Epub 2006 Aug 21. PMID: 16924239.
In vivo protocol:
1. Rybczynska AA, de Bruyn M, Ramakrishnan NK, de Jong JR, Elsinga PH, Helfrich W, Dierckx RA, van Waarde A. In vivo responses of human A375M melanoma to a σ ligand: 18F-FDG PET imaging. J Nucl Med. 2013 Sep;54(9):1613-20. doi: 10.2967/jnumed.113.122655. Epub 2013 Aug 12. PMID: 23940303.
2. Borowicz KK, Wilczyński PM, Kleinrok Z, Czuczwar SJ. Rimcazole, a sigma receptor ligand, and the anticonvulsive action of convention
Matsumoto, R. R., Hewett, K. L., Pouw, B., Bowen, W. D., Husbands, S. M., Cao, J. J., & Newman, A. H. (2001). Rimcazole analogs attenuate the convulsive effects of cocaine: correlation with binding to sigma receptors rather than dopamine transporters. Neuropharmacology, 41(7), 878-886.
Eaton, M. J., Lookingland, K. J., & Moore, K. E. (1996). The σ ligand rimcazole activates noradrenergic neurons projecting to the paraventricular nucleus and increases corticosterone secretion in rats. Brain research, 733(2), 162-166.
