F: Steroidal Alkaloids and Alkaloidal Amines

What alkaloid group was discussed previously before steroidal alkaloids?

Purine alkaloids

What is the similarity between purine alkaloids and steroidal alkaloids?

Neither is derived from amino acids

How are purine alkaloids and steroidal alkaloids distinguished?

By their specific structural characteristics

What is the classification of alkaloid groups based on?

The ring structure or nucleus of the chief alkaloid group in the plant drug

What are the nine classes of alkaloids based on ring structure or nucleus?

Pyridine and piperidine, Tropane, Quinoline, Isoquinoline, Indole, Imidazole, Purine, Steroidal, Alkaloidal Amines

What backbone distinguishes steroidal alkaloids?

Tetracyclic cyclopentanophenanthrene backbone

What does "tetracyclic" mean regarding the steroidal alkaloid structure?

It contains four rings

What does the tetracyclic cyclopentanophenanthrene backbone mark a close relationship with?

Sterols and cardiac glycosides

What is the backbone or basic nucleus of sterols, such as cholesterol?

Tetracyclic cyclopentanophenanthrene structure

What is the backbone or basic nucleus of cardiac glycosides, such as digoxin and digitoxin?

Tetracyclic cyclopentanophenanthrene structure

Are steroidal alkaloids derived from amino acids?

No

What is the botanical source of green hellebore?

Dried rhizome and roots of Veratrum viride

What is the scientific name of green hellebore or American hellebore?

Veratrum viride

To what family does green hellebore belong?

Liliaceae / Lily family

What are the pharmacological properties possessed by green hellebore?

Hypotensive, cardiac depressant, and sedative properties

What does possessing hypotensive properties mean for green hellebore?

It can decrease blood pressure

For what medical condition has green hellebore been used in treatment?

Hypertension

What does possessing cardiac depressant properties indicate for green hellebore?

Negative inotropism (it can decrease the pumping force of the heart)

Why is green hellebore utilized as a pest plant by farmers?

It is extremely toxic

What is green hellebore used to kill when utilized as a pest plant by farmers?

Insects and pests

How did some tribes historically use the green hellebore plant?

To elect a new leader

What part of the green hellebore plant would candidates eat to elect a new leader?

The root

Who would become the new leader after eating the green hellebore root?

The last to start vomiting

What is a rhizome (also known as rootstocks)?

A type of plant stem situated either at the soil surface or underground

What is an example of a plant that utilizes rhizomes?

Ginger or Zingiber officinale (Family: Zingiberaceae)

What are the parts of the green hellebore plant usually utilized?

The rhizomes and the roots

What is the botanical source of white hellebore?

Dried rhizome of Veratrum album

What is the scientific name of white hellebore or European hellebore?

Veratrum album

What does the term "album" in Veratrum album mean?

White

To what family does white hellebore belong?

Liliaceae / Lily family

What pharmacological properties does white hellebore possess?

Hypotensive properties

What property makes white hellebore useful as a pesticide?

It is poisonous

Against what insect was white hellebore briefly used as a pesticide in Colorado, USA?

Colorado potato beetle

What agricultural use is common to both white and green hellebores?

Employed as insecticides

What is the scientific name of black false hellebore?

Veratrum nigrum

To what family does Veratrum nigrum belong?

Melanthiaceae

Is Veratrum nigrum closely related to or does it resemble true hellebores?

No

What is the scientific name of California corn lily, white or California false hellebore?

Veratrum californicum

To what family does Veratrum californicum belong?

Melanthiaceae

What toxicity level characterizes Veratrum californicum?

An extremely poisonous plant

What characterizes the section on steroidal alkaloids?

Their tetracyclic cyclopentanophenanthrene structure

What is the final type of alkaloids to be discussed?

The alkaloidal amines

Unlike purine alkaloids and steroidal alkaloids, what are alkaloidal amines derived from?

Amino acids

What are the nine classes of alkaloids based on the ring structure or nucleus?

Pyridine and piperidine, Tropane, Quinoline, Isoquinoline, Indole, Imidazole, Purine, Steroidal, Alkaloidal Amines

What is the main difference of alkaloidal amines from other classes of alkaloid?

The nitrogenous portion (or the amine) is not part of the cyclic ring

Where is the nitrogen atom (the NH2 or amine portion) located in alkaloidal amines?

Outside the cyclic ring structure

What are examples of alkaloidal amines?

Mescaline, peyote, and ephedra

What specific essential amino acid are alkaloidal amines derived from?

Phenylalanine

What specific non-essential amino acid are alkaloidal amines derived from?

Tyrosine

What other essential amino acid are other alkaloidal amines biosynthesized from?

Tryptophan

What is the tryptophan-derived alkaloidal amine in Barley (Hordeum vulgare, Poaceae)?

Gramine

What is the tryptophan-derived alkaloidal amine in the Mexican hallucinogenic mushroom, Psilocybe semperviva (Hymenogastraceae)?

Psilocybin

What tryptophan-derived alkaloidal amines are found in a number of plant and animal species?

Serotonin and bufotenine

What is bufotenine (bufotenin)?

A tryptamine derivative related to serotonin

Where is the alkaloid bufotenine found?

In some species of toads (skin), mushrooms, and higher plants

What are the common names for ephedrine?

Ephedra or ma huang

What is the primary botanical source of ephedrine?

Ephedra sinica (Fam. Gnetaceae)

What are other botanical sources of ephedrine aside from E. sinica?

E. equisetina and E. distachya

What does the Chinese character “ma” mean?

Astringent

What does the Chinese character “huang” mean?

Yellow

What do the Chinese characters “ma huang” probably refer to?

The taste and color of the drug

In what year did the use of ephedrine in modern medicine begin?

1923

What is Lianhua Qingwen (LHQW)?

A classical Chinese medical preparation with controversial use for COVID-19

Why is Lianhua Qingwen hazardous?

It contains ephedrine, which is classified as a dangerous drug

What licenses and prescriptions are required for ephedrine?

An S2 license and a yellow prescription from a physician

Who frequently abuses ephedrine?

Athletes

What is the clinical value of ephedrine itself?

No clinical use

In what supplements and preparations is ephedrine found as an ingredient?

Many dietary supplements (“Energy-Boosters”, Diet pills like Metabolife®) and herbal preparations

Since 1994, how many reports of adverse effects associated with ephedrine alkaloid has the FDA received?

More than 800

What are the serious adverse effects associated with the use of products containing ephedrine alkaloid?

Hypertension, palpitations, neuropathy, myopathy, psychosis, stroke, memory loss, heart rate irregularities, insomnia, nervousness, tremors, seizures, heart attacks, and death

What is hypertension in the context of ephedrine adverse effects?

Elevated blood pressure

What is palpitations in the context of ephedrine adverse effects?

Rapid heart rate

What is neuropathy in the context of ephedrine adverse effects?

Nerve damage

What is myopathy in the context of ephedrine adverse effects?

Muscle injury

Why must patients with high blood pressure be extremely careful if taking preparations like Lianhua Qingwen?

It could spike their blood pressure further

What action did the US FDA take regarding supplements containing ephedrine alkaloids in 2004?

Banned the sale

Why is ephedrine classified as an alkaloidal amine?

Because its nitrogen atom is located outside the ring structure

What drug class is ephedrine sulfate used as?

A sympathomimetic (alpha- and beta-Adrenergic Agonists)

What does a sympathomimetic mimic?

The action of catecholamines (like norepinephrine, epinephrine, and dopamine)

What do catecholamines cause as known vasoconstrictors?

An increase in blood pressure

What states is ephedrine sulfate used to combat due to its ability to increase blood pressure?

Hypotensive states

What allergic disorders is ephedrine sulfate used for?

Bronchial asthma

What receptor does ephedrine sulfate act on when treating allergic disorders like bronchial asthma?

Beta-2 agonist

What condition is ephedrine sulfate used for when vasodilation occurs in the blood vessels of the nose?

Nasal congestion

What receptor does ephedrine sulfate act on to cause vasoconstriction and reverse nasal congestion?

Alpha agonist

What drug class is ephedrine hydrochloride?

A sympathomimetic (alpha- and beta-Adrenergic Agonists)

What is ephedrine hydrochloride used for during anesthesia?

Hypotension

What is ephedrine hydrochloride used as for the symptomatic treatment of asthma?

A bronchodilator

Why is the use of ephedrine hydrochloride limited in the treatment of depressive states or narcolepsy?

Due to dangerous cardiovascular side effects

What are the dangerous cardiovascular side effects that limit the use of ephedrine hydrochloride for depressive states or narcolepsy?

Palpitations, heart attacks, stroke, and irregular heart rates

What does narcolepsy mean?

Excessive sleepiness

Why was ephedrine hydrochloride historically used for self-medication in the management of obesity?

Its CNS stimulant properties keep the user awake and suppress appetite, leading to weight loss

Is ephedrine hydrochloride used for the management of obesity still commercially available in the US?

No

What is the value of ephedrine hydrochloride used as a nasal decongestant?

Of doubtful value

What is the terminology distinction regarding nasal decongestion for ephedrine hydrochloride?

The condition is "congestion" (a blockage), and the drug "decongests" or reverses this state via its alpha-agonist-induced vasoconstriction

Who has misused and abused ephedrine hydrochloride?

Athletes, bodybuilders, weight lifters, and others, including high school- and college-aged individuals engaged in sports

What is the other known name for Colchicine?

“Colchicum seed”

What is the botanical source of colchicine?

Dried, ripe seed of Colchicum autumnale (Colchicaceae)

What other family has colchicine also been found in?

The Lily family / Liliaceae

What is Colchicum corm?

The dried corm of the same species