Tropane Alkaloids – PST05210 Basic Pharmacognosy
NTA Level 5 • Semester 2 • PST05210 Tropane Alkaloids Basic Pharmacognosy • Source Session/Topic 20 Full source-text version: all educational wording from the extracted learning source is retained; only presenter/tutor metadata and web-layout noise are removed, while formatting is improved for readability. Session 20: Tropane Alkaloids Total Session Time: 120 minutes Prerequisites • None Learning Tasks By the end of this session students are expected to be able to: • Define tropane alkaloids • Explain natural sources and uses of tropane alkaloids Resources Needed: • Flip charts, marker pens, and masking tape • Black/white board and chalk/whiteboard markers • LCD projector and Laptop SESSION OVERVIEW |Step |Time |Activity/ |Content | | | |Method | | |1 |05 minutes |Presentation |Introduction, Learning Objectives | |2 |20 minutes |Presentation |Introduction to Tropane Alkaloids | | | |Buzzing | | |3 |20 minutes |Presentation |Natural Sources and Uses of | | | |Brainstorming |Stramonium | |4 |25 minutes |Presentation |Natural Sources and Uses of | | | | |Belladonna | |5 |20 minutes |Presentation |Natural Sources and Uses of | | | | |Hyocyamus | |6 |20 minutes |Presentation |Natural Sources and Uses of Coca | |7 |05 minutes |Presentation |Key Points | |8 |05 minutes |Presentation |Evaluation | SESSION CONTENTS STEP 1: Presentation of Session Title and Learning Objectives (5 minutes) READ or ASK students to read the learning objectives and clarify ASK students if they have any questions before continuing. STEP 2: Introduction to Tropane Alkaloids (20 minutes) • Tropane alkaloids are derived from tropine and consist of mandelic, tropic or benzoic acid esters of tropine • Chemically they are formed by fusion of pyrrolidine and piperidine ring with a common methylated nitrogen o Tropane alkaloids are very closely related to each other • All tropane alkaloids have pronounced physiological actions • Tropane alkaloids include: o Hyoscyamine o Hyoscine o Atropine o Cocaine • They all occur within the Solanaceae family (except cocaine which occurs in Erythroxylaceae family) STEP 3: Natural Sources and Uses of Stramonium (20 minutes) • Definition o Stramonium is defined as dried leaves and flowering tops of Datura stramonium and its varieties, family Solanaceae o Its synonyms are thornapple, jimson or Jamestown weed o Drug is required to contain not less than 0.25% of alkaloid calculated as hyocyamine o Drug is widely distributed in Africa, Germany, France, Hungary o Adulterant: Solanum nigrum o Allied Drugs are Datura inoxia, Datura metel and Datura sanguinea • Constituents o Contain 0.2 – 0.45% alkaloids, the major alkaloids are; ▪ Hyoscyamine ▪ Hyoscine ▪ Small quantities of atropine o Hyoscyamine and hyoscine are found in the ration 2:1 (hyoscyamine: hyoscine) o Younger plants contain hyoscine, atropine is little and is formed from racemization of hyoscyamine o These alkaloids test positive for Vitali-Morin test • Uses of Stramonium; o Hyoscyamine is used to treat urinary tract disorders o It is used to treat spasms of the bladder o Hyoscyamine preparations are also used as antispasmodics in the therapy of peptic ulcers o Hyoscine hydrobromide is used in pre-operative medication 30 – 60 minutes before induction of anaesthesia o Hyoscine butylbromide used in irritable bowel syndrome to relief pain due to abdominal cramps o It is also used in dysmenorrhea STEP 4: Natural Sources and Uses of Belladonna (25 minutes) • Definition o Consist of the dried leaves and flowering tops of Atropa belladonna ▪ Its synonym is deadly night shade ▪ Family: Solanaceae ▪ Contains not less than 0.3% of total alkaloids calculated as hyoscyamine o Adulterant: Phytolacca dodecandra o Allied drugs are Indian belladonna and Atropa acuminata • Constituents o Contains 0.3 – 0.6% of Tropane alkaloids, the chief of which is hyoscyamine o Belladonin o Small quantities of volatile bases e.g. pyridine and N- methylpyrroline are present • Pharmacological Actions o Atropine ▪ Stimulant on CNS ▪ Dilates eye pupils ▪ Decreases sweating ▪ Produces stomach acid and saliva and relaxes smooth muscle (asthma and colic) o Hyoscine ▪ lacks CNS stimulant action of atropine ▪ Sedative – motion sickness o Atropine and Hyoscine ▪ Used in ophthalmic practice to dilate pupil • Uses of Belladonna o Belladonna leaves are used for internal preparations o Used as sedative, antispasmodic and to check secretions o Roots are used for external preparations o Atropine is indicated in organophosphates and carbamate insecticides poisoning o It produces mydriatic effect by paralyzing the iris and the ciliary muscles o Is it used as an antispasmodic to lessen smooth muscle spasm/griping o Used to treat some types of arrhythmias STEP 5: Natural Sources and Uses of Hyocyamus (20 minutes) • Definition o Hyoscyamus leaf consists of the dried leaves or dried leaves and flowering tops of Hyoscyamus niger, family Solanaceae o Common name: Henbane • Constituents: o Tropane alkaloids mainly: ▪ Hyoscyamine in small amount ▪ Hyoscine (main constituent) o Allied Drugs are Hyoscyamus albus, Hyosycamus muticus, Hyoscyamus pusillus, Hyoscyamus aureus • Uses of Hyocyamus o Resembles belladonna and stramonium in action but weaker ▪ Higher hyoscine content hence less likely to cause cerebral stimulation o Used to relieve spasm of the urinary tract o Used as a sedative o Used as an expectorant o Anti-asthmatic STEP 6: Natural Sources and Uses of Coca (20 minutes) • Definition o Coca is derived from dried leaves of Erythroxylum coca (Bolivian or Huanuco) and E. truxillense (Peruvian or Truxillo), cultivated in Peru, Bolivia, Colombia and Indonesia, family Erythroxylaceae ▪ Coca leaves have been used in South America as a masticatory from very early times ▪ The leaves are artificially or sun-dried and packed in bags. o Constituents ▪ Coca leaves contain about 0.7 to 1.5% of total alkaloids, of which cocaine, cinnamylcocaine and α-truxilline are the most important. ▪ These alkaloids occur in different proportions in different commercial varieties ▪ Other substances are hygrine, hygroline, tropacocaine o Uses ▪ Local anaesthetic agent ▪ Stimulan STEP 6: Key Points (5 minutes) • Tropane alkaloids are very closely related to each other • Belladonna consists of dried leaves