Rimcazole (BW 234U) di-HCl is a carbazole analogue that acts partially as a sigma receptor antagonist. Rimcazole di-HCl binds dopamine transporters with moderate affinity and inhibits dopamine uptake. Rimcazole di-HCl may reduce motor activity and sensitization. Rimcazole di-HCl is also used in cancer research.

Physicochemical Properties

Molecular Formula	C21H29CL2N3
Molecular Weight	394.38
Exact Mass	393.174
CAS #	75859-03-9
Related CAS #	Rimcazole;75859-04-0
PubChem CID	53388
Appearance	White to off-white solid powder
Boiling Point	499.1ºC at 760 mmHg
Flash Point	255.7ºC
LogP	5.737
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Heavy Atom Count	26
Complexity	380
Defined Atom Stereocenter Count	2
SMILES	C[C@@H]1CN(C[C@@H](N1)C)CCCN2C3=CC=CC=C3C4=CC=CC=C42.Cl.Cl
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+;;
Chemical Name	9-[3-[(3R,5S)-3,5-dimethylpiperazin-1-yl]propyl]carbazole;dihydrochloride
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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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	sigma (σ) receptor[1] dopamine transporter[1]
ln Vitro	HCT-116p53+/+ cell counts are lowered concentration-dependently by rimcazole (1–50 μM; 24-48 hours) [2]. In cancer cells (HCT-116p53+/+ and MDA-MB-231 cells), rimcazole (50 μM; 1–24 hours) causes a transitory increase of HIF-1α protein, but not in normal human dermal fibroblasts [2].
Cell Assay	Western Blot Analysis[2] Cell Types: HCT-116p53+/+ cells Tested Concentrations: 50 μM Incubation Duration: 1, 2, 3, 5, 6, 24 hrs (hours) Experimental Results: Accumulation of HIF-1α protein, maximal at 6 h. No change in p53 protein levels. HIF-1α protein levels returned to normal steady-state levels within 24 h.
References	[1]. Review of the pharmacological and clinical profile of rimcazole. CNS Drug Rev. Spring 2004;10(1):1-22. [2]. HIF-1alpha contributes to tumour-selective killing by the sigma receptor antagonist rimcazole. Oncogene. 2007 Feb 22;26(8):1137-46. [3]. Rimcazole analogs attenuate the convulsive effects of cocaine: correlation with binding to sigma receptors rather than dopamine transporters. Neuropharmacology. 2001 Dec;41(7):878-86. [4]. A behavioral economic analysis of the effects of rimcazole on reinforcing effects of cocaine injection and food presentation in rats. Psychopharmacology (Berl). 2019 Dec;236(12):3601-3612.

Solubility Data

Solubility (In Vitro)

DMSO: 12.5 mg/mL (31.70 mM) H2O: < 0.1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 1.25 mg/mL (3.17 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.25 mg/mL (3.17 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 1.25 mg/mL (3.17 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.5356 mL	12.6781 mL	25.3563 mL
	5 mM	0.5071 mL	2.5356 mL	5.0713 mL
	10 mM	0.2536 mL	1.2678 mL	2.5356 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.