Pharmcognosy II. Tropane Alkaloids
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1 Pharmcognosy II Tropane Alkaloids
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6 Tropane alkaloids Many of these psychoactive alkaloids
7 Tropane Alkaloids They are ester alkaloids resulted from the coupling of organic acids with amino alcohol (Base). Derived from tropine and consist of mandelic, tropic or benzoic acid esters of tropine. The parent base is the Tropane base. 7 H N 1 2 NH Tropane Alkaloids are classified into: 1- Solanaceous Tropane Alkaloids. 2- Erythroxylon (Coca) Alkaloids.
8 1- Solanaceous Tropane Alkaloids Occurrence: Atropa, Datura, Hyoscyamus, Duboisia spp. Main Alkaloids are: 1 Atropine. 2 Hyoscyamine. 3. Hyoscine (Scopolamine).
9 Atropine & Hyoscyamine Hyoscyamine is the major natural alkaloid with negative optical rotation (l- form). During extraction hyoscyamine racemizes to the optically inactive dl Atropine. Both alkaloids composed of tropine base and tropic acid. NCH 3 Tropine base O Tropic Acid * O OH Me N O O H CH 2 OH Me N O O CH 2 OH (-)-Hyoscyamine Atropine
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11 Atropine Atropine is a core medicine in the World Health Organization's "Essential Drugs List", which is a list of minimum medical needs for a basic health care system. Atropine is a racemic mixture of D-hyoscyamine and L- hyoscyamine. The most common atropine compound used in medicine is atropine sulfate. Atropine sulfate Injection, USP 0.1 mg/mi (Adult) 0.05 mg/ml (Pediatric)
12 Pharmacological Action of Atropine A mydriatic (causes dilatation of the eye pupil). An antispasmodic (relaxes the intestinal and bronchial smooth muscles). A preanesthetic medication to stop body secretions. A CNS stimulant. An antidote to organophosphorus insecticides.
13 Side Effects of Atropine Adverse reactions to atropine include: ventricular fibrillation. tachycardia. dizziness. nausea. blurred vision & dilated pupils loss of balance, & confusion.
14 Solanaceous Alkaloids H 3 C N O HO H 3 C N O H CH 2 OH O O (-)-Hyoscyamine Atropine (-)-Hyoscine
15 Natural Source of Atropine & Hyoscine Atropine & Hyoscine are tropane alkaloids extracted from deadly nightshade (Atropa belladonna), jimsonweed (Datura stramonium), Duboisia(Duboisia myobroides), henbane (hyoscyamus niger & hyoscyamus muticus) and other plants of the family Solanaceae.
16 Natural Sources of Atropine & Hyoscine Atropa belladonna ( Solanaceae) Hyoscyamus niger ( Solanaceae) Datura stramonium
17 Hyoscine (Scopolamine) Hyoscine is an ester of l-tropic acid with scopoline base. Hyoscine is a syrupy liquid. Tropic Acid O NCH 3 O Scopoline base O OH
18 Hyoscine (Scopolamine) Hyoscine is an ester of l-tropic acid with scopoline base. Hyoscine is a syrupy liquid. Hyoscine
19 Plant material and solvent Organic solvent dissove Alkaloids Extract Organic solvent dissove Impurities Concentration Acidification Alkalinization Acidified Extract (Alk. as salts) Alkaline aqueous layer
20 Separation of the Alkaloidal mixtures: Alkaloids in the form of HCl salts 1- Alkalinize by NaHCO 3 ph Extract with Ether Ether Hyoscine free base (pka = 6.2) Aqueous layer Atropine & Hyoscyamine HCl (pka = 9.3) Convert to oxalate salts, Fractional Crystallization (Acetone/ Ether) Atropine Oxalate Crystals Hyoscyamine Oxalate Solution
21 Atropine & Hyoscyamineine Oxalates Crystallization from Acetone/Ether Atropine Oxalate Crystals Hyoscyamine Oxalate Solution
22 Chemical tests: Vitali-Morin s test: Solid alkaloid + fuming HNO 3 Evaporate to dryness, dissolve residue in acetone, add methanolic solution of KOH Violet colour. P-dimethylaminobenzaldehyde: Alkaloid + reagent in porcelain dish and heat on boiling water path Intense Red Colour Cherry Red after cooling. Gerrard s test: Alkaloid + 2% HgCl 2 in 50% Ethanol Red colour Atropine Red after warming Hyoscyamine White ppt Hyoscine
23 Pharmacological actions and uses: The three Alkaloids are anticholinergic agents: Decrease saliva and GIT secretions so used preoperative. Decrease motility of smooth muscles so used as antispasmodics. Stimulate respiratory system. A mydriatic (causes dilatation of the eye pupil). An antidote to organophosphorus insecticides. Hyoscine has more central effect so it is sedative and hypnotic. Hyoscine is mainly used as antiemetic.
24 Synthetic and Semisynthetic Derivatives: Homatropine: Synthetic drug prepared by passing HCl gas in a mixture of tropine base and mandelic acid in the presence of water. Homatropine is less toxic than Atropine. It is hypnotic in small doses. Homatropine is used as Mydriatic with shorter effect than Atropine. NCH 3 O O OH
25 Hyoscine butyl bromide: Quaternary Semisynthetic derivative of Hyscine. It is used as antispasmodic and antiemetic. Br - O Bu NCH 3 + O O OH
26 2- Erythroxylon (Coca) Alkaloids Occurrence: Coca leaves contain about 2% total alkaloids. Main Alkaloids are: 1 Cocaine. 2 Cinnamylcocaine truxilline. H 3 C The base for Coca Alakloid is called Ecogonine N O C OH Ecogonine OH
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28 Erythroxylon cocca
29 Erythroxylon cocca
30 Cocaine It is the major Alkaloid in Coca leaves. Cocaine is diester Alkaloid. Heating at C in conc. HCl leads to hydrolyses of cacaine to MeOH, Benzoic acid and Ecogonine base. COOMe NCH 3 O Benzoic acid Ecgonine base O
31 Production of Cocaine commercially: The total Alkaloids are hydrolysed to obtain the free base. The base is then Methylated with HCl in MeOH. The Methylated base is then esterified with Benzoly chloride. Cinnamylcocaine COOMe NCH 3 O Cinnamic acid Ecgonine base O
32 Uses: Cocaine was used as local anesthetic. Cocaine has a CNS stimulant activity so is one of the widely abused drugs.
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34 Datura stramonium - Solanaceae Definition: Stramonium Leaf consists of the dried leaves or dried leaves and flowering tops of Datura stramonium. The drug should contain at least 0.25% alkaloids calculated as hyoscyamine. Common names: Stramonium leaf, Thornapple, Jimson or Jamestown weed
35 Datura stramonium - Constituents Main (Tropane) Alkaloids * Hyoscyamine Hyoscine (2:1) Younger plants: hyoscine predominant alkaloid Also contains Atropine Larger stems contain little alkaloid, and drug should contain no more than 3% of stems with a diameter >5mm
36 Datura stramonium Allied Drugs & Adulterants ALLIED DRUGS Datura innoxia Datura metel (dried leaves are also curled and twisted like D. stramonium), but are browner in colour. Datura sanguinea ADULTERANTS Xanthium, Carthamus and Chenopodium leaves (easily distinguished from original herb)
37 Uses of Datura stramonium Atropine: Stimulant on CNS Depresses nerve endings on the secretory glands and smooth muscle Hyoscine: lacks CNS stimulant action of atropine Sedative motion sickness Atropine & Hyoscine: used in opthalmic practice to dilate the pupil of the eye.
38 Hyoscyamus niger - Solanaceae Definition: Hyoscyamus leaf consists of the dried leaves or dried leaves and flowering tops of Hyoscyamus niger. It should contain at least 0.05% alkaloids hyoscyamine.
39 Hyoscyamus niger - Constituents Tropane Alkaloids Mainly Hyoscyamine Hyoscine (main constituent)
40 Hyoscyamus niger - Uses Resembles belladonna and stramonium in action only weaker. Higher hyoscine content less likely to cause cerebral stimulation. Used to relieve spasm of the urinary tract
41 Atropa belladonna - Solanaceae Definition: Belladonna herb consists of the dried leaves and flowering tops of Atropa belladonna, containing at least 0.3% alkaloids (hyoscyamine). Should not contain >3% stem >5mm in diameter. USP also allows A. acuminata in the Belladonna Leaf monograph.
42 Atropa belladonna - Constituents Main (Tropane) alkaloid Hyoscyamine Also contains Scopoletin Calcium oxalate
43 Atropa belladonna - Uses Used as a sedative To stop bodily secretions (e.g. saliva) Root preparations are used externally
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