Pharmacognosy and Plant Chemistry - Alkaloids Part 1 Flashcards

Flashcards for reviewing Alkaloids Part 1 lecture notes.

Who isolated narcotine in 1803?

Derosne, a French chemist

Who isolated morphine from opium in 1816?

Serturner

Who isolated strychnine, emetine, brucine, piperine, caffeine, quinine, colchicine, and coniine between 1817-1826?

Pelletier and Caventou

Who established the structure of coniine, the first alkaloid, found in hemlock?

Schiff

Why are amines often called 'organic bases'?

Due to the universal presence of nitrogen.

In what states can alkaloids exist?

Free state as salts or N-oxides

Name three alkaloids that are liquids at room temperature.

Sparteine, coniine and arecoline, nicotine

Give an example of an alkaloid that has color.

Berberine (yellow) or sanguinarine (red)

Are free bases soluble in H2O?

Sparingly soluble in H2O, soluble in organic solvents

What taste do alkaloids have?

Bitter

What part(s) of the Datura plant are used?

All parts

What part of the Cinchona plant is used?

Bark

What part of the Nux Vomica plant is used?

Seeds

Give an example of a primary amine alkaloid.

Mescaline

Give an example of a secondary amine alkaloid.

Ephedrine

Give an example of a tertiary amine alkaloid.

Atropine

Give an example of a quaternary amine alkaloid.

Tubocurarine

Which alkaloids have their nitrogen atoms enclosed within a ring system?

True Alkaloids

Give an example of where true alkaloids can be found in other organisms.

Fungi (lysergic acid derivatives), Amphibians (antimicrobial)

Are pseudoalkaloids derived from amino acids?

No

Do protoalkaloids have nitrogenous heterocycles?

No

Describe Process A for extracting alkaloids.

Powdered material is moistened with water, mixed with lime Ca(OH)2. Extraction is done with organic solvents like ether or petroleum spirit. Organic liquid is shaken with aq. acid and allowed to separate. Alkaloid salts now in aqueous liquid, impurities are in organic liquid.

Describe Process B for extracting alkaloids.

Powdered material is extracted with water or aqueous alcohol containing dilute acid. Pigments and other unwanted materials are removed by shaking with chloroform or other organic solvents. Free alkaloids are precipitated with sodium bicarbonate or ammonia and separated by filtration.

From what amino acid is pyridine derived?

Ornithine/Aspartate

From what amino acid is piperidine derived?

Lysine

From what amino acid is pyrrolidine derived?

Ornithine/Aspartate

From what amino acid is pyrrolizidine derived?

Ornithine

What is the scientific name for Tobacco?

Nicotiana tabacum

What is the family of Tobacco?

Solanaceae

What are the constituents of Tobacco?

Nicotine

What is Tobacco used for?

Smoking cessation (Can cause lung cancer)

What is the scientific name for Indian Tobacco?

Lobelia inflata

What is the family of Indian Tobacco?

Lobeliaceae

What are the constitiuents of Indian Tobacco?

0.25% alkaloids, esp. lebline

Name a use for Indian Tobacco.

Smoking cessation, neuromuscular stimulation, for spasmodic asthma and chronic bronchitis, Anti Smoking preparations, Resuscitation of newborn infants

What is the scientific name for Broom?

Cytisus scoparius

What is the family of Broom?

Fabaceae

What are the constituents of Broom?

Sparteine, cytisine

What is Broom used for?

Mild diuretic and cathartic

What is the scientific name for Poison Hemlock?

Conium maculatum

What is the family of Poison Hemlock?

Apiaceae

What is the constituent of Poison Hemlock?

Coniine

What is Poison Hemlock used for?

Used by Geeks for preparing a draught by means of which criminals were put to death

What is the scientific name for Betel Nut?

Areca catechu

What is the family of Betel Nut?

Araceae

What are the constituents of Betel Nut?

Arecoline, guavacine

What is Betel Nut used for?

Chewed with leaves of Piper betle and lime, taenicide in the east

What is the scientific name for Pomegranate?

Punica granatum

What is the family of Pomegranate?

Punicaceae

What are the constituents of Pomegranate?

Pelletierine, Isopelletierine

What is Pomegranate used for?

Anthelmintic, for hemorrhoids

What is the scientific name for Black Pepper?

Piper nigrum

What is the family of Black Pepper?

Piperaceae

What are the constituents of Black Pepper?

Piperine, Piperettine

What is Black Pepper used for?

Treatment of gonorrhea and chronic bronchitis

What is the scientific name for Clubmoss?

Lycopodium clavulatum

What is the family of Clubmoss?

Lycopodiaceae

What are the constituents of Clubmoss?

Lycopodiumoleic acid, lycopodine

What is Clubmoss used for?

Limited extent in dusting powders and medicated snuffs, and as dusting powder for pills, used in quantitative microscopy

What are pyrrolizidine alkaloids used for?

Hepatotoxic alkaloids, some are also carcinogenic or mutagenic

What is the scientific name for Deadly Nightshade?

Atropa belladonna

What is the family of Deadly Nightshade?

Solanaceae

What are the constituents of Deadly Nightshade?

0.30% of total alkaloids calculated as hyoscyamine/atropine

What is another name for Jimsonweed?

Thornapple, Angel's Trumpet

What is the scientific name for Jimsonweed?

Datura stramonium

What is the family of Jimsonweed?

Solanaceae

Name an allied drug to Jimsonweed.

D. innoxia, D. metel, D. fastuose

What is the scientific name for Henbane?

Hyoscyamus niger

What is another name for Henbane?

Stinking nightshade

What are the constituents of Henbane?

0.05% alkaloids calculated as hyoscyamine

What is Henbane used for?

Used in preparations intended to burn (for relief of asthma)

What is the scientific name for Duboisia?

Duboisia myoporoides, D. hopwoodii (Pituri)

What is the family of Duboisia?

Solanaceae

What are the constituents of Duboisia?

Hyoscine and hyoscyamine

What is Duboisia used for?

A good source of atropine

What is the scientific name for Aswagandha?

Withania somnifera

What is the family of Aswagandha?

Solanaceae

What are the constituents of Aswagandha?

Tropine, hygrine

What is Aswagandha used for?

Sedative

What is the scientific name for Coca?

Erythroxylum coca

What is the family of Coca?

Erythroxylaceae

What are the constituents of Coca?

0.7%-1.5% alkaloids (Cocaine, ecgonine, cuscohygrine)

What is Coca used for?

Local anesthetic, used in Brompton's cocktail (along with morphine), an analgesic in terminal cancer

Where do the uses of Belladonna alkaloids root from?

Their anticholinergic property

Give an example of a Belladonna alkaloid used for asthma.

Henbane, ipratropium, tiotropium

Give an example of a Belladonna alkaloid used for motion sickness.

Scopolamine (hyoscine N-butylbromide)

What alkaloid is used for control of secretions pre-op?

Hyoscine HBr

Which alkaloid is mydriatic and what does that mean?

Atropine, dilates the pupil of the eye

What is atropine used as an antidote for?

Organophosphate poisoning

What is the scientific name for Jaborandi?

Pilocarpus jaborandi

What is the family of Jaborandi?

Rutaceae

What are the constituents of Jaborandi?

Pilocarpine, pilosine

What is Jaborandi used for?

Ophthalmic practice, irrigation of eye and relieve pressure in early glaucoma, dry mouth

From what amino acid is dopamine derived?

Tyrosine

What is the scientific name for Opium?

Papaver somniferum

What is the family of Opium?

Papaveraceae

What are the constituents of Opium?

0.18-0.28% morphine

What is Prepared Opium BP/EP?

Contains 10% morphine and minimum 1% codeine, thebaine limited to 3.0%

Who discovered morphine?

Serturner

What is morphine used for?

Opioid analgesic