Alkaloids Flashcards

Vocabulary flashcards for Alkaloids lecture notes.

Alkaloids

Basic nitrogenous compounds with physiological activity.

Physical Properties of Alkaloids

Bitter taste and mostly colorless.

Alkaloids that are not crystalline solids

Coniine, Arecoline, Nicotine, and Sparteine

Ranunculaceae

Buttercup Family

Rubiaceae

Coffee Family (extract: caffeine)

Papaveraceae

Morphine Derivatives (e.g., Codeine/Hydroxymorphone)

Solanaceae

Nightshade Family

Berberidaceae

Berberine Alkaloids (w/ antimicrobial property)

Fabaceae

Legume Family

Free Alkaloids

Soluble in NON-POLAR solvents

Free Alkaloids

Water insoluble / sparingly soluble

Remedy for insoluble alkaloids

Addition of acid (usually HCl) → Alkaloidal salt (Water Soluble)

The Stats Otto Process

One of the most common methods employed in alkaloidal extraction

Defatting agent used in The Stats Otto Process

Acetone

Alkali used to liberate the free alkaloid from their salts

NH3 or NH4OH with lime solution

Aqueous acid used to convert the alkaloid into a salt

HCl or H2SO4

Reagents used during precipitation

NaHCO3 or NH3

Alkaloidal test

From double salts with salts of heavy metals (eg. Hg, Au, Pt) except Caffeine

AKA (+) precipitate – complexation

General Test for Alkaloids

Dragendorff ’s / Krauts Potassium Bismuth Iodide

Orange precipitate

Mayer’s Mercuric KI

Cream precipitate

Wagner’s (Bouchardat’s – Most sensitive) Iodine in KI

Reddish brown precipitate

Valser’s Mercuric Iodide

White precipitate

Marme’s Potassium Cadmium Iodide

White precipitate

Hager’s Picric acid

Yellow precipiate

Sonnenchein’s Phosphomolybdic acid

Blue / Green precipitate

Scheibler’s Phosphotungstic acid

Characteristic color

Glod chloride

Yellow precipitate

Tannic acid (5%, freshly prepared)

Buff precipitate, insoluble in NH3

Vitali – Morin test

Atropine, Purple color

Gerard’s test

Atropine, Red color

Gerard’s test

Hyoscyamine, Red color after warming

Gerard’s test

Hyoscine, White precipitate

Van- Urks test

Ergot alkaloids, Blue color

Thalleiquin test

Quinine, Quinidine, Purple color

Mandelin’s test

Strychnine, Violet color

Murexide test

Caffeine, Pink color

True Alkaloids

N-atom with the ring

Non-heterocyclic Alkaloids

No N-atom within the ring

Protoalkaloid (eg Biogenic/ alkaloidal amine)

Derived from amino acid / anthranilic acid + heterocyclic ring

Alkaloids derived from Ornithine

Pyridine – Piperidine, Tropane

Alkaloids derived from Tyrosine

Isoquinoline

Alkaloids derived from Tryptophan

Indole

Alkaloids derived from Histidine

Imidazole

Alkaloids derived from Anthranilic acid

Quinoline, Quinazoline

Protoalkaloids

Derived from Amino acid + Non-heterocyclic ring

Pseudo Alkaloids

NOT derived from Amino acid + Heterocyclic ring

Source of Nicotine

Tobacco leaves : Nicotiana tabacum , Solanaceae

Use of Nicotine

CNS stimulant; smoking deterrent

Source of Arecoline

Areca / betel nut (Ripe seed, dried): Areca catechu

Use of Arecoline

Anthelmintic (taenicide), Stimulatory masticatory (chewed with lime and Piper betel leaves)

Source of Lobeline

Indian tobacco leaves: Lobelia inflata

Use of Lobeline

Tobacco substitute (weaker effect), CNS stimulant; smoking deterrent

Tropane

Dicyclic from Ornithine

Source of Atropine

Deadly nightshade : Atropa belladonna

Use of Atropine

Anticholinergic - causes dilation of eyes, used for bradycardia

Source of Hyoscyamine

Henbane leaves : Hyoscyamus niger

Source of Hyoscine / Scopolamine

Jimson weed : Datura stromonium

Use of Hyoscine / Scopolamine

Treatment for motion sickness, anticholinergic , calming delirium

Source of Mandragorine

European mandrake / mayapple : Mandragora officinarum

Use of Mandragorine

Emetic

Cocaine / Methylbenzoylecgonine

“Crack/coke”; Divine plant of Incas

Use of Cocaine / Methylbenzoylecgonine

CNS stimulant, local anesthetic, (+) Brompton’s cocktail

Source of Quinine

Red cinchona bark : Cinchona succiruba

Use of Quinine

Antimalaria

Source of Emetic / Methylcephaline

Ipecac dried rhizome/root

Use of Emetic / Methylcephaline

Antiembic (former use), Emetic (syrup)

Source of Sanguinarine

Sanguinaria/ Bloodroot rhizome (dried)

Use of Sanguinarine

Stimulant, emetic, expectorant

Source of Hydrastine, Berberine

Goldenseal: Hydrastis canadensis

Use of Hydrastine, Berberine

Astringent, Antimicrobial (used in skin care production)

Source of Tubocurarine

Curare/ South American Arrow Poison

Use of Tubocurarine

Skeletal Muscle Relaxant

Opium Alkaloids

Air-dried milky exudate of unripe seed capsule of Papaver somniferum (Opium poppy)

Use of Opium Alkaloids

Narcotic Analgesic

Morphine

Most important & abundant narcotic analgesic; habit forming

Codeine

Widely used; antitussive; less habit forming than Morphine; contains additional methyl at C3

Thebaine

CNS stimulant

Benzylisoquinoline

Non-Narcotic Opium, Antitussive (Noscapine; Papaverine - Smooth Muscle Relaxant)

Heroin

More potent, +habit forming than morphine

Apomorphine

Condensation of morphine w/ HCl, emetic, amorphous version

Hydromorphone

More potent narcotic analgesic, less habit forming, constipation

Hydrocodone

Antitussive

Source of Reserpine

Dried roots of Rauwolfia serpentina

Use of Reserpine

Hypotensive

Source of Physostigmine

Calabar, Ordeal/ Esere Bean: Physostigma venenosum

Use of Physostigmine

AChE inhibitor (cholinergic), Treatment for Glaucoma

Source of Strychnine

Dried ripe seed of Strychnos nux vomica

Use of Strychnine

CNS stimulant, rat killer

Source of Yohimbine

Bark of Pausinystalia yohimbe (Rubiaceae)

Use of Yohimbine

Alpha 2 blocker (sympatholytic), mydriatic, Temporary treatment for impotence

Source of Vinca Alkaloid (Vincristine and Vinblastine)

Periwinkle whole plant: Catharanthus roseus (Apocynaceae)

Use of Vinca Alkaloid (Vincristine and Vinblastine)

Anticancer

Source of Ergot Alkaloids

Dried Sclerotium of Ergot Rye found in Rye (Secale cereale)

Ergotamine

DOC: Migraine

Ergonovine / Ergometrine

Oxytocic for labor

Ergonovine

For contraction of uterine

Methysergide

Prophylactic treatment for migraine

Lysergic acid diethylamide (LSD)

Hallucinogen (psychomimetic); habit forming

Source of Pilocarpine

Leaflets of Pilocarpus jaborandi