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Details

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
Structure of BRUCINE

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

HIDE SMILES / InChI

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency
1.7 µM [Ki]
1.4 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
three transdermal doses (10, 20 and 40 mg/kg) were administered to mice to evaluate pharmacological activity
Route of Administration: Transdermal
In Vitro Use Guide
Brucine could inhibit the THP-1 cell growth in concentration and time-dependent manners at the range of 50 to 400 ug/ml.
Substance Class Chemical
Record UNII
6NG17YCK6H
Record Status Validated (UNII)
Record Version