ALKALOIDS

Wilhelm Meissner

The term alkaloid was coined by ________, a German pharmacist

Algali

substance that has been roasted from ashes/ashes of plants

Alqali

plant from which soda/sodium carbonate was 1st isolated from

Alkaloids

are basic nitrogenous compounds contain one or more nitrogen in heterocyclic ring system having marked physiological action on humans and animals

alkaloid (alkali-like)

is commonly used to designate basic heterocyclic nitrogenous compounds of plant and animal origin that are physiologically active

Nicotine, Coniine, Sparteine

Liquid Alkaloids

Conium maculatum

poison hemlock

Aethusa cynapium

dog parsley

Cytisus scoparius

common broom/scotch broom

Lupinus mutabilis

tarwi

Pilocarpine and Hyoscine

Non Volatile Alkaloids

Pilocarpus jaborandi

Pilocarpine from

Pilocarpine

relaxes muscle spasms, treats eye conditions like glaucoma, xerostomia

Xerostomia

Dry mouth

Hyoscine

aka Scopolamine, N&V (nausea & vomiting), motion sickness

Berberine

Colored Alkaloids

Berberine

bright crystal yellow color, isolated from Common Barberry (Berberis vulgaris)

Berberis vulgaris

Common Barberry

Alcohol

Both alkaloidal bases and their salts are soluble in

organic solvents

Alkaloid bases dissolve in

water

Alkaloid salts dissolve in

alkaloid-based meds

↑ solubility, stability, bioavailability

morphine sulfate & codine phosphate

Alkaloids used in salt forms

Phenol

= weakly acidic = allow morphine to form salts

Carboxylic acid

= strong acid = allows narceine to form salts when reacted with bases

Strychnine and Caffeine

Alkaloids are decomposed by heat, except

Sublimable

Alkaloids are decomposed by heat, except Strychnine and Caffeine because?

>70 degrees C

Temperature of decomposition

Wagner’s test – Reddish Brown precipitate

iodine in potassium iodide soln.

Reddish Brown precipitate

Wagner’s test result

Mayer’s Test – Creamy precipitate with true alkaloid

mercuric potassium iodide

Creamy precipitate with true alkaloid

Mayer’s Test result

Dragendorff’s Test – Reddish Brown Precipitate

potassium bismuth iodide

Reddish Brown Precipitate

Dragendorff’s Test result

True Alkaloids

• Derived from amino acids and have nitrogen in a heterocyclic ring • Aka Typical Alkaloids
• Ex. Atropine

Proto Alkaloids

• Derived from amino acids but no not have a nitrogen in a heterocyclic ring
• Ex. Ephedrine

Pseudo Alkaloids

• Aka Amino Alkaloids
• Not derived from amino acids but have a nitrogen in a heterocyclic ring
• Ex. Caffeine

False Alkaloids

• Non alkaloids that give a false positive reaction with alkaloidal reagents
• Ex. Capsaicin

Ephedra sinica

Ephedra Sci name

Ephedraceae

Ephedra fam

Ma Huang

Synonym of ephedra

Ephedra

o Sympathomimetic effects

o Bronchodilator in asthma, colds, flu

o Used as a weight loss agent

o Corrects low blood pressure conditions

Ephedrine and Pseudoephedrine

Alkaloids in Ephedra

1-2.5% ephedrine; 80% psuedoephedrine

Amount of alkaloids in ephdra

Colchicaceae

Colchicum Fam

Colchicum

Colchicum autumnale

Colchicum

Meadow saffron, Autumn crocus

Colchicum

o Antitumor activity
o Relieves gout (colchicine)

Sterculiaceae

Cocoa Fam

Cocoa

Theobroma cacao

Cocoa

Cocoa bean

Cocoa

Nutritive, Stimulant, Diuretic

Theobroma oil

is used as a suppository base and as chocolates.

Theobromine

3,7-dimethylxanthine; vasodilator, bronchodilator, diuretic, stimulant muscles (diuretic & stimulant to a lesser extent than theophylline)

Theaceae

Tea fam

Tea

Camellia sinensis

Tea

Thea

Tea

CNS Stimulant, beverages, diuretic

Theophylline

1,3-dimethylxanthine

Rubiaceae

Coffee Fam

Coffee

Coffea arabica and Coffea liberica

Coffee

Coffee beans

Coffee

Source of caffeine, CNS stimulant and diuretic

Caffeine

1,3,7-trimethylxanthine

Sterculiaceae

Cola Fam

Cola

Cola nitida

Cola

Kola, Kola nut, Bitter kola

Cola

Preparation of carbonated beverages and as a stimulant

Kolacetchin

Formed when KolaNut is dry

theobromine and caffeine

when the kola nut is dry, it produces

Campanulaceae

Lobelia Fam

Lobelia

Lobelia nicotianifolia

Lobelia

Wild tobacco

Lobeline

anti-depressant, emetic, respiratory stimulant, aid to smoking cessation, tx for methamphetamine abuse

Lobelanidine & Lobelanine

less studies; emetic

Piperaceae

Black pepper fam

Black Pepper

Piper nigrum

Black Pepper

For gonorrhea, chronic bronchitis, condiments

Piperaceae

Long pepper fam

Long pepper

Piper longum

Long pepper

Anti-atherosclerotic

Solanaceae

Tobacco Fam

Tobacco

Nicotiana tabacum

Tobacco

Pesticidal, insecticidal

Nicotine

95% of alkaloid content; makes smoking addictive; natural insecticide

Nornicotine & Anatabine

most abundant minor alkaloids

Nornicotine

demethylated form of nicotine; lacks N-methyl group = less potent

Anatabine

anti-inflammatory; being studied for possible use for Alzheimer’s disease

Anabasine

insecticide

Solanaceae

Belladona fam

Beladonna

Atropa belladonna

Beladonna

Deadly Nightshade

Beladonna

Parasympatholytic drug, anticholinergic, reduce secretions, reduce spasm

Atropine

relaxing muscles; regulating HR (when slow = bradycardia = <60 bpm); dilating pupils (eye exam/surgery); poisoning by chloroform & opium

Solanaceae

Datura Stramonium Fam

Datura Stramonium

Thornapple, Jamestown weed, Jimsonweed

Datura Stramonium

Asthma, controls salivation, muscular rigidity, tremors

Henbane

Hyoscyamus niger

Solanaceae

Henbane Fam

Erythroxylaceae

Coca fam