brodifacoum

Also known as 3-(3-(4'-Bromo-(1,1'-biphenyl)-4-yl)-1,2,3,4-tetrahydro-1-naphthyl)-4-hydroxy-2H-1-benzopyran-2-one, 3-(3-(4'-Bromo-(1,1'-biphenyl)-4-yl)-1,2,3,4-tetrahydro-1-napthalenyl)-4-hydroxycoumarin

Brodifacoum is a highly lethal 4-hydroxycoumarin vitamin K antagonist anticoagulant poison. In recent years, it has become one of the world's most widely used pesticides. It is typically used as a rodenticide, but is also used to control larger pests such as possums.

Chemical data

Formula: C31H23BrO3
Molecular weight: 523.4 g/mol
IUPAC name: 3-[3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-4-hydroxychromen-2-one
SMILES: C1C(CC2=CC=CC=C2C1C3=C(C4=CC=CC=C4OC3=O)O)C5=CC=C(C=C5)C6=CC=C(C=C6)Br
InChIKey: VEUZZDOCACZPRY-UHFFFAOYSA-N
XLogP: 7.6
Polar surface area: 46.5 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

473 papers

via PubMed

~11 min read

Encyclopedic overview

10 sections

Contents

Chemical synthesis
Toxicology
Brand names
Human poisoning
Treatment
Case reports
Recreational drug use
See also
References
Further reading

Brodifacoum has an especially long half-life in the body, which ranges up to nine months, requiring prolonged treatment with antidotal vitamin K for both human and pet poisonings. It has one of the highest risks of secondary poisoning to both mammals and birds. Significant experience in brodifacoum poisonings has been gained in many human cases where it has been used in attempted suicides, necessitating long periods of vitamin K treatment. In March 2018, cases of severe coagulopathy and bleeding associated with synthetic cannabinoid use contaminated with brodifacoum were reported in five states of the US.

Excerpted from Wikipedia’s “brodifacoum” article, available under the CC BY-SA 4.0 licence.