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 and flowering tops of Atropa

belladonna

• Stramonium is defined as dried leaves and flowering tops of Datura

stramonium and its varieties

• Hyoscyamus leaf consists of the dried leaves or dried leaves and

flowering tops of Hyoscyamus niger

STEP 7: Evaluation (5 minutes)

• What is the source of hyoscyamus?
• What are the uses of atropine?
• What is the use of hyocyamus?

References

Trease, G. E., Evans, W. C., & Evans, D. (2009). Trease and Evans

pharmacognosy. London: Saunders.

Joanne Barnes et al (2002), Herbal medicines 3rd Edition: Pharmaceutical

Press

Wallis, T. E. (2005). Textbook of pharmacognosy. New Delhi: CBS.

Robbers, J. E., Speedie, M. K., Tyler, V. E., & Tyler, V. E. (1996).

Pharmacognosy and pharmacobiotechnology. Baltimore: Williams &

Wilkins.

Heinrich, M., Kinghorn, A. D., Maizels, D., Gibbons, S., & Phillipson, J.

D. (2012). Fundamentals of pharmacognosy and phytotherapy. Edinburgh:

Churchill Livingstone/Elsevier.

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