Stereochemistry | ABSOLUTE |
Molecular Formula | C23H26N2O4 |
Molecular Weight | 394.4635 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1OC)[C@@]34CCN5CC6=CCO[C@H]7CC(=O)N2[C@H]3[C@H]7[C@H]6C[C@@H]45
InChI
InChIKey=RRKTZKIUPZVBMF-IBTVXLQLSA-N
InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1
Molecular Formula | C23H26N2O4 |
Molecular Weight | 394.4635 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Brucine is an alkaloid resembling strychnine but it is much less potent than strychnine. Brucine was first discovered in 1819 by Pelletier and Caventou in the bark of the Strychnos nux vomica tree. Brucine causes paralysis of the peripheral nerve endings and produces violent convulsions. Since brucine is a large chiral molecule, it has been used as an enantioselective recognition agent using in chiral resolution. While brucine has been shown to have good anti-tumor effects, on both hepatocellular carcinoma and breast cancer, its narrow therapeutic window has limited its use as a treatment for cancer. Brucine is also used in traditional Chinese medicine as an anti-inflammatory and analgesic agent, as well as in some Ayurveda and homeopathy drugs. Like strychnine, brucine also functions as antagonist at the glycine receptor and paralyzes the inhibitory neurons
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
three transdermal doses (10, 20 and 40 mg/kg) were administered to mice to evaluate pharmacological activity
Route of Administration:
Transdermal