Synonym
BIII-890; BIII-890-CL; BIII-890 CL
IUPAC/Chemical Name
(2R,6S)-3-((S)-2-(benzyloxy)propyl)-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro 2,6-methanobenzo[d]azocin-10-ol hydrochloride
InChi Key
UWKTVIXWZRROOI-VLIWAZBPSA-N
InChi Code
InChI=1S/C25H33NO2.ClH/c1-18(28-17-19-9-6-5-7-10-19)16-26-14-13-25(4)21-11-8-12-22(27)20(21)15-23(26)24(25,2)3;/h5-12,18,23,27H,13-17H2,1-4H3;1H/t18-,23+,25-;/m0./s1
SMILES Code
OC1=C2C([C@]3(C)CCN(C[C@@H](OCC4=CC=CC=C4)C)[C@](C3(C)C)([H])C2)=CC=C1.[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 DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
More Info
Related CAS #
221019-25-6 (Crobenetine free base)
Preparing Stock Solutions
The following data is based on the
product
molecular weight
416.00
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 |
1: Carter AJ, Grauert M, Pschorn U, Bechtel WD, Bartmann-Lindholm C, Qu Y, Scheuer T, Catterall WA, Weiser T. Potent blockade of sodium channels and protection of brain tissue from ischemia by BIII 890 CL. Proc Natl Acad Sci U S A. 2000 Apr 25;97(9):4944-9. PubMed PMID: 10781102; PubMed Central PMCID: PMC18337.
2: Grauert M, Bechtel WD, Weiser T, Stransky W, Nar H, Carter AJ. Synthesis and structure-activity relationships of 6,7-benzomorphan derivatives as use-dependent sodium channel blockers for the treatment of stroke. J Med Chem. 2002 Aug 15;45(17):3755-64. PubMed PMID: 12166948. 1: Meythaler J. BIII-890-CL. Boehringer Ingelheim. Curr Opin Investig Drugs. 2002 Dec;3(12):1733-5. Review. PubMed PMID: 12528308.
3: Carter AJ, Grauert M, Pschorn U, Bechtel WD, Bartmann-Lindholm C, Qu Y, Scheuer T, Catterall WA, Weiser T. Potent blockade of sodium channels and protection of brain tissue from ischemia by BIII 890 CL. Proc Natl Acad Sci U S A. 2000 Apr 25;97(9):4944-9. PubMed PMID: 10781102; PubMed Central PMCID: PMC18337.
4: Dekker LV, Daniels Z, Hick C, Elsegood K, Bowden S, Szestak T, Burley JR, Southan A, Cronk D, James IF. Analysis of human Nav1.8 expressed in SH-SY5Y neuroblastoma cells. Eur J Pharmacol. 2005 Dec 28;528(1-3):52-8. PubMed PMID: 16325806.
5: Laird JM, Carter AJ, Grauert M, Cervero F. Analgesic activity of a novel use-dependent sodium channel blocker, crobenetine, in mono-arthritic rats. Br J Pharmacol. 2001 Dec;134(8):1742-8. PubMed PMID: 11739251; PubMed Central PMCID: PMC1572907.
6: Grauert M, Bechtel WD, Weiser T, Stransky W, Nar H, Carter AJ. Synthesis and structure-activity relationships of 6,7-benzomorphan derivatives as use-dependent sodium channel blockers for the treatment of stroke. J Med Chem. 2002 Aug 15;45(17):3755-64. PubMed PMID: 12166948.
