[6117 Lec] Alkaloids Family

Name all 10 classes of Alkaloids

Pyridine-Piperidine

Tropane

Imidazole

Isoquinoline

Quinoline

Indole

Steroidal

Amines

Purine/Xanthines

Miscellaneous

Pyridine-Piperidine are categorized based on what?

monocyclic structures

What are the 4 categories of Pyridine-Piperidine class of alkaloids?

Pyridine

Piperidine

Pyrrolidine

Pyrrolizidine

Pyridine Structure

Piperidine Structure

Pyrrolidine Structure

Pyrrolizidine Structure

What is Pyridine chemically?

an aza-arene comprising of a benzene core in which 1 CH group is replaced by nitrogen atom

What is Pyrrolizidine chemically?

a bicyclic organo nitrogen heterocyclic compound composed of 2 ortho fused pyrrolidine structure that share a common nitrogen atom

What is Pyrrolidine chemically?

cyclic amine whose 5 membered ring contains four carbon atoms and one nitrogen atom

What is Piperadine chemically?

a cycloalkane that is cyclohexane in which one of the carbon is replaced by nitrogen

Where does Pyridine and Pyrrolidine come from?

ornithine/aspartate

Where does Pyrrolizidine come from?

ornithine

Where does Piperidine come from?

lysine

Pyridine chemical formula

C5H5N

Tobacco Scientific Name

Nicotiana tabacum

Tobacco Family

Solanaceae

Solanaceae is also known as what?

Nightshade family

Tobacco Constituents

Nicotine

Describe Nicotine function in the CNS

addictive central nervous system stimulant that causes either ganglionic stimulation in low doses or ganglionic blockage in high doses

Describe Nicotine as an Alkaloid

natural alkaloid that is a major component of cigarettes and used therapeutically to help with smoking cessation

Nicotine CNS stimulating activities may be mediated by what actions?

release of several neurotransmitters that includes acetylcholine, beta endorphin, dopamine, norepinephrine, and serotonin

Nicotine can cause what disease?

Lung Cancer

Structure of Nicotine?

Indian Tobacco Scientific Name

Lobelia inflata

Indian Tobacco Family

Lobeliaceae

Indian Tobacco Active Constituent

0.25% alkaloids, esp. Lobeline

Is Indian Tobacco connected to Tobacco?

No

Lobeline is commonly employed as what?

emetic, antidepressant, respiratory stimulant smoking cessation

spasmodic asthma

chronic bronchitis

Lobeline can treat what drug abuse?

treatment of methamphetamine abused

Is Lobeline structurally related to nicotine?

No

What type of interaction does Lobeline produce to the nicotinic receptors?

agonist and antagonist

What happens when Lobeline is given at toxic doses?

paralytic (can cause mouth dryness, nausea, vomiting, diarrhea, abdominal pain, dizziness, headache, sometime respiratory difficulties and death due to respiratory paralysis

Broom Scientific Name

Cytisus scoparius

Broom Family

Fabaceae

Broom Constituents

Sparteine, cytisine

Sparteine Structure

What is Sparteine chemically?

lupine alkaloid containing a tetracyclic bis quinolicidines ring system derived from the 3C5 chain of lysine.

Sparteine is dervied from which optical rotation of lysine?

L-lysine derived alkaloid

It is the best known of the naturally occurring lupine alkaloids isolated from leguminous plants.

Sparteine

Is Sparteine a cardiovascular agent?

Yes

Describe the interaction of Cytisine towards the nicotinic receptors.

α4β2 partial agonist nicotinic acetylcholine receptor responsible for central effects of nicotine

Describe the effects of Varenicline.

reduces the craving for it and decreases pleasurable effects of nicotine from cigarettes and other tobacco products

This structure inspired the development of an antismoking preparation known as varenicline

cytisine

Cytisine has been used for in what area for smoking cessation?

eastern europe

Poison Hemlock Scientific Name

Conium maculatum

Poison Hemlock Family

Apiaceae

Poison Hemlock Constituents

Coniine

Poison Hemlock is easily mistaken for what fruit?

anise fruit

What would be the effect when poison hemlock and anise fruit have been mixed up?

serious poisoning

What type of p alkaloid is Coniine?

piperidine alkaloid

Coniine is related to what group of alkaloids?

N-methyl coniine

Is Coniine poisonous?

Yes

How is qualitative determination of coniine done?

potassium hydroxide

Positive Result of Coniine with KOH

develops strong, mouse-like odor due to liberation of coniine

Exposure to coniine affects which parts of the body?

periphery, blocking neuromuscular transmission onto skeletal and smooth muscles

Dose of coniine that can cause delitirious effects?

0.5 to 1 gram of coniine

What are the symptoms of coniine exposure?

drowsiness, burning of the mouth and throat, gradual aspasia, ascending paralysis and death

What famous tea was made from Poison Hemlock?

Hemlock Tea

What was the historic significance of hemlock tea?

used for execution in ancient Greece and the decoction used to put the philosopher Socrates to death

Varenicline Structure

Cystisine Structure

Betel Nut Scientific Name

Areca catechu

Betel Nut Family

Araceae

Betel Nut Constituents

Arecoline and Guvacine

Betel Nut is commonly known in the Philippines as?

Bunga or Nganga

Betel nut is sourced from what tree?

seed of the fruit of the oriental palm Areca catechu

It is the basic ingredient of a variety of widely used chewed products.

Betel nut

Is Betel Nut botanically correct?

No

Why Betel Nut not botanically correct?

If the fruit is from the family arecaceae or palm family it is called fibrous drupe, not a nut

Arecoline Structure

active constituent of a betel hut

Arecoline

It is commonly chewed with leaves of Piper betle and lime.

Betel Nut

Are all betel quid products chewed in different places? If not, how is it consumed?

placed in the mouth or applied to the oral cavity and remain in contact with the oral mucosa.

Describe Arecoline as an alkaloids and its implications.

natural alkaloid and has a psycho-modulating effects and has been implicated in the pathogenesis of oral cancer and oral submucous fibrosis

Arecoline together with this alkaloid can cause oropharyngeal and esophageal cancer.

Arecatannins

It is an old anthelmintic that has been used as a taenicide for cats, dogs and poultry since 1921.

Arecoline

What is taenicide?

meds that kills tapeworms

Pomegranate Scientific Name

Punica granatum

Pomegranate Family

Punicaceae

Pomegranate Constituents

Pelletierine, isopelleireine

In which part of pomegranate can we source an alkaloid that is structurally related to arecoline? What is that alkaloid?

Root bark and Pelletierine

Pelletierine Structure

Pomegranate Uses

anthelmintic, for hemorrhoids

It is employed as an anthelmintic for tapeworms (tenicide).

Pelletierine tannate

Black Pepper Scientific Name

Piper nigrum

Black Pepper Family

Piperaceae

Black Pepper Constituents

Piperine, piperettine

Piperine Structure

In which part of the black pepper plant can piperine be abstracted from?

fruits and seeds of Piper nigrum

It is the cause of black pepper pungency.

piperine

Uses of black pepper before

treatment of gonorrhea and chronic bronchitis

Name the 3 allied drugs of black pepper

Long Pepper

Cubeb

Guineesine

Which among the allied drugs of black pepper can be a potential antihypercholesterolemic?

Guineesine

Cubeb Scientific Name

Piper cubeba

Long pepper Scientific Name of both variations

Piper retrofractum, P. longum

What makes Guineesine a potential antihypercholesterolemic?

presence of cholesterol acyltransferase inhibitor

Clubmoss Scientific Name

Lycopodium clavatum

Clubmoss Family

Lycopodiaceae

Clubmoss Constituents

Lycopodium Oleic acid, lycopodine