Source: Ephedra Herb (Ma Huang, Yellow Hemp).

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Presentation transcript:

Source: Ephedra Herb (Ma Huang, Yellow Hemp). Alkaloids with Exocyclic Nitrogen (Protoalkaloids- Phenylalkylamines- Biological amines) 1- Ephedra Alkaloids Source: Ephedra Herb (Ma Huang, Yellow Hemp). Ephedra used as remedy for Asthma in Chinese medicine. (-)-Ephedrine is the major Alkaloid in Ephedra. Ephedrine is a phenylalkylamine with N atom in the side chaine

Ephedrine is similar to adrenaline in structures. Advantages of Ephedrine over adrenaline: 1- Orally active. 2- Prolonged action

Isomers: Two Chairal centers → 4 Isomres. Most active is (-)-Ephedrine. (+)-Ephedrine have 1/3 the activity. Pseudoephedrine much less active.

Properties: Soluble in water and organic solvents Steam volatile Negative reaction with Mayer’s reagent. React with Chloroform to produce Ephedrine HCl and phosogen Ephedrine HCl in 25% HCl isomerizes to Pseudoephedrine.

Test for Identity: Chen’s test: Ephedrine HCl in water + 0.1 ml CuSO4 + 1ml NaOH → Violet colour, shake with Ether → Ether layer → purple Aqueous layer → blue Uses: 1- Asthma. 2- Hey fever. 3- Mydriatic. 4- Nasal decongestant. 5- Certain allergic conditions.

2- Cathe Alkaloids (Kat القاط) CNS stimulant activity Abused drug.

3- Peyote Alkaloids Hallucinogenic Alkaloid

Tropolone Alkaloids Colchicum Alkaloids Source: Colchicum Corm. Constituents: Colchicine. Properties: 1- Neutral Alkaloid. 2- Amid function. Test: 1- Red colour with FeCl3. 2- Yellow colour with dil. Mineral acids. Uses: 1- Treatment of Gout. 2- Anticancer in vitro. 3- Treatment of Mediterranean Sea fever. 4- Polyploidy in Plants.

Imidazole Alkaloids Pilocarpus Alkaloids Source: Jaborandi leaves (Pilocarpus jaborandi). Constituents: (+)-Pilocarpine. Properties: 1- Oily liquid miscible with water. 2- Non-volatile liquid alkaloid. 3- Lactone function. Test: Helche’s test: Alkaloid + Dil acid + K2CrO7 → violet colour (Pilocarpine dichromate) Uses: 1- Miotic. 2- Diaphoretic. 3- Hair preparations.

Pyridine Alkaloids Tobacco Alkaloids Source: Tobacco leaves. Constituents: 1- Nicotine (75%). 2- Nornicotine. 3- Anabasine. Properties: 1- The 3 alkaloids are volatile liquids. 2- Nicotine is tertiary alkaloid while the others are secondary. 3- Nicotine has some miscibility with water.

1- Insecticide & Pesticide. 2- No medicinal use due to toxicity. Test for Nicotine: 1- Aqueous Solution + p-dimethylaminobenzaldehyde in HCl → Rose Red Colour → Violet 2- Aqueous Solution + Vanillin HCl → Red Colour 3- Solution in Ether + I2 in Ether → deep red colourd needles of nicotine periodate Uses: 1- Insecticide & Pesticide. 2- No medicinal use due to toxicity.

Piperidine Alkaloids 1- Conium Alkaloids Source: Hemlock fruits. Constituents: Coniine. Properties: 1- Volatile liquid. 2- Free from Oxygen. 3- CNS stimulant. Uses: 1- Local analgesic so used for Hemorrhoids and anal fissures.

2- Lobelia Alkaloids Source: Lobelia Herb (Indian Tobacco). Constituents: 1- Lobeline (50%). 2- Lobelanine. 3- Lobelanidine.

1- Lobeline is sparingly soluble in water. Test: Properties: 1- Lobeline is sparingly soluble in water. 2- Lobeline HCl is soluble in CHCl3. Test: 1- Lobeline + Marqui’s reagent → Red colour 2- Lobeline + Froehd’s reagent → Red colour → Blue Uses: 1- Lobelia extract is used as expectorant. 2- Lobeline is respiratory stimulant. 3- Lobeline is used to break tobacco habits in the form of tablets or lozenges.

3- Pomegranate Alkaloids Source: Pomegranate barks. Constituents: 1- Pelletierine. 2- Isopelletierine. 3- Methylpelletierine. Properties: 1- Volatile liquid Alkaloids. Uses: 1- Taeniafuge and Vermifuge.