Nux Vomica Alkaloids

Strychnine and Brucine

Biosynthetic Origin

terpenoid indole alkaloids from Trp (from shikimate pathway via anthranilic acid) have a tryptamine fragment and a C9 or C10 residue 3 types of indole alkaloids: Corynanthe, Aspidosperma and Iboga

Biosynthetic Origin

Biosynthetic Origin

Biosynthetic Origin

Biosynthetic Origin

Biosynthetic Origin

Natural Source

found in Strychnos nuxvomica (Fam. Loganiaceae) strychnine (1.2 % ), brucine (1.6 %) also contains igasuric acid & loganin, a glycoside Strychnos ignatia more strychnine

Pharmaceutical Applications: Strychnine

appetite stimulant and general tonic in small doses Specific Medicine Nux Vomica and Tinctura Nucis Vomicae pesticide/ vermin killer used in synthetic chemistry as optically-active bases to achieve optical resolution of racemic acids (along with brucine)

Mechanism of Action

an antagonist of glycine, a major inhibitory neurotransmitter in the mammalian nervous system

Mechanism of Action

increased reflex action, increased rate of respiration, and enlargement of the capacity of the lungs increased force, rate, and volume of the pulse, raised arterial pressure, increased sharpness to sight, hearing, and smell, and general irritation

Side Effects

extremely poisonous (100 mg is fatal ) uneasiness and restlessness, suffocation, tremors, convulsions, risus sardonicus, opisthotonos, pain, weariness, spasms death usually taking place after three or four convulsions death may occur during the interval from exhaustion, or paralytic asphyxia, or during the grip upon the respiratory muscles and the heart from cramp asphyxia

Side Effects

Analogues

Strychnine: -- brucine, dimethoxy analogue -- bisquaternary dimers Brucine: