[IPS1] PCOG - Part 8: Alkaloids

Proverbs 16:3

Robiquet

isolated the alkaloids narcotine in 1803

Serturner

investigated opium and isolated morphine in 1806.

Pelletier and Caventou

Isolated strychnine in 1817

Nitrogen

Alkaloids are secondary metabolites containing organic ______ within their chemical structure

Alkaloid

An ________ is a nitrogenous organic molecule that has a pharmacological effect on humans and other animals. The name derives from the word alkaline; originally, the term was used to describe any nitrogen-containing base (an amine in modern terms)

Amino acids

The basic unit in the biogenesis of the true alkaloids are ___________

Terpene units or Acetate

The non-nitrogen containing rings or side chains of true alkaloids are derived from _____ or ______

Methionine

The chemical group responsible for the addition of methyl groups to nitrogen atoms in true alkaloids

Pyridine alkaloids

[Classifications] piperine

Pyridine alkaloids

[Classifications] coniine

Pyridine alkaloids

[Classifications] trigonelline

Pyridine alkaloids

[Classifications] arecoline

Pyridine alkaloids

[Classifications] arecaidine

Pyridine alkaloids

[Classifications] guvacine

Pyridine alkaloids

[Classifications] cytisine

Pyrrolidine alkaloids

[Classifications] hygrine

Pyrrolidine alkaloids

[Classifications] cuscohygrine

Pyrrolidine alkaloids

[Classifications] nicotine

Tropane alkaloids

[Classifications] atropine

Tropane alkaloids

[Classifications] cocaine

Tropane alkaloids

[Classifications] ecgonine

Tropane alkaloids

[Classifications] scopolamine

Tropane alkaloids

[Classifications] catuabine

Quinoline alkaloids

[Classifications] quinine

Quinoline alkaloids

[Classifications] quinidine

Quinoline alkaloids

[Classifications] dihydroquinine

Quinoline alkaloids

[Classifications] dihydroquinidine

Quinoline alkaloids

[Classifications] strychnine

Quinoline alkaloids

[Classifications] brucine

Quinoline alkaloids

[Classifications] veratrine

Quinoline alkaloids

[Classifications] cevadine

Isoquinoline alkaloids

[Classifications] opium alkaloids (papaverine, narcotine, narceine)

Isoquinoline alkaloids

[Classifications] sanguinarine

Isoquinoline alkaloids

[Classifications] hydrastine

Isoquinoline alkaloids

[Classifications] berberine

Isoquinoline alkaloids

[Classifications] berbamine

Isoquinoline alkaloids

[Classifications] emetine

Isoquinoline alkaloids

[Classifications] oxyacanthine

Phenantrine Alkaloids

[Classifications] opium alkaloids (morphine, codeine, thebaine).

Phenethylamine alkaloids

[Classifications] mescaline

Phenethylamine alkaloids

[Classifications] ephedrine

Phenethylamine alkaloids

[Classifications] dopamine

Indole (Tryptamines)

serotonin

Indole (Tryptamines)

DMT, 5-MeO-DMT

Indole (Tryptamines)

bufotenine

Indole (Tryptamines)

psilocybin

Indole (Ergolines)

ergine, ergotamine, lysergic acid, LSD

Indole (Beta-carbolines)

harmine, harmaline, tetrahydroharmine

Indole (Yohimbans)

reserpine

Indole (Yohimbans)

yohimbine

Indole (Vinca alkaloids)

Vinblastine, Vincristine

Indole (Mitragyna speciosa)

mitragynine, 7-hydroxymitragynine

Indole (Tabernanthe iboga)

ibogaine

Indole (Tabernanthe iboga)

voacangine

Indole (Tabernanthe iboga)

coronaridine

Indole (Tabernanthe iboga)

18-methoxycoronaridine

Purine (Xanthines)

caffeine, theobromine, theophylline

Amandarin

Newt alkaloids

Terpenoid (aconite)

aconitine

Terpenoid (steroids)

Solanum alkaloids: solanidine, solanine, chaconine

Terpenoids (steroids)

Veratrum alkaloids: veratramine, cyclopamine, cycloposine, jervine, muldamine

Quaternary Ammonium Compounds

muscarine

Quaternary Ammonium Compounds

neurine

Quaternary Ammonium Compounds

Choline

Alkalis

Alkaloids are liberated from aqueous solution of their salts by (acids/alkalis)

Valser's Reagent

[Tests] Mercuric Iodide T.S

Valser's Reagent

[Tests] prepared by slowly adding a 10% solution of Potassium iodide to red mercuric iodide until all is dissolved

White precipitate

[Tests] Valser's Reagent Positive Result

Wagner's reagent

[Tests] Iodine in Potassium Iodide

Wagner's reagent

[Tests] Is a solution containing 1.275 g of iodine and 3.6 g Potassium iodide dissolved in sufficient distilled water to make 100 mL

Reddish or Red-brown Precipitate

[Tests] Wagner's reagent Positive Result

Mayer's reagent

[Tests] Mercuric Potassium Iodide

Mayer's reagent

[Tests] A solution of 1.3558 g of Mercuric Chloride in 60 mL of water and mixed with 5 g of Potassium Iodide in 10 mL of water and the mixture diluted to 100 mL with water

White or slightly yellow ppt

[Tests] Mayer's reagent Positive Result

Draggendorff's Reagent

[Tests] Potassium bismuth iodide

Orange precipitate

[Tests] Draggendorff's Reagent Positive Result

Proximate Assay

Alkaloidal assay in which the percent of extractive represents the total of a class of plant principles, such as alkaloids, glycosides, etc.

Ultimate Assay

Alkaloidal assay in which the percent of extractive from a crude drug represents a single chemical species such as morphine.