José G. López
Natural Products
Dr. J. B. Freisen
Shared Homework #3
Ephedrine
- Structure and structural features
What
is its structure and chemical formula?- What are its physical and chemical characteristics?
- What heterocyclic rings does it contain?
Chemical Formula: C10H15NO
Boiling point: 253-255ºC
Melting point: 37-39ºC
Solubility: Soluble in alcohol, water, ether and oils
Optical rotation: A Benzene ring attached with an alcohol and amine on a propyl strand.
Heterocyclic rings: One aromatic ring, phenylethanamine.
- Source and Isolation
- What plant/organism produces the alkaloid? Where does the plant grow? Under what conditions does it grow?
- What part of the plant/organism is the best source of the alkaloid?
- In what form is the alkaloid used?
Ephedrine is a stimulant to the central nervous system obtained from the plant Ephedra equisetina. Ephedrine is also produced synthetically as a salt form, ephedrine sulfate. It is native to the United States, where it grows as a shrub or vines in the southwestern states. It has also been known to grow in parts of Europe such as England and Germany. It can be found growing on sandy plains, canyons, deserts and other dry areas like hills and rocky places. The plant prefers sandy (dry), sunny positions and cannot grow in the shade. It reaches heights from 2 to 3 feet with no leaves. The stems are smooth and green with many joints. At the site of these joints in the stems there appear small yellow-green buds when the plant is in bloom.
Ephedrine itself is located in the stems of the plant. The alkaloid is useful for treating asthma ad other respiratory conditions. The alkaloid is also useful as an antispasmodic (relieving spasms), diaphoretic (produces perspiration), vasodilator (causes dilation of certain blood vessels), stimulant, diuretic, anti-viral, and blood purifier.
- Related alkaloids
- What other alkaloids are in the same “family?”
- What is a common structural characteristic of this family?
- How has the alkaloid been synthetically modified or mimicked to enhance its activity?
Ephedrine’s chemical structure is similar to:
Methamphetamine
Epinephrine
The common structural characteristic of this family is the phenylethanamine ring.
One form of a synthetic ephedrine is called pseudoephedrine that has similar but weaker effects of ephedrine.
- Discovery and traditional use.
- How did the alkaloid become internationally renown?
- What is the history of its use?
- What effect does the alkaloid have on the human system?
Ephedrine gained popularity when it was presented as an aid for weight loss and as an energy booster. These weight loss and energy-boosting products often contain other stimulating elements such as caffeine. It also came to media attention because ephedrine was found in a new form of hallucinogenic drug called “ecstasy”. Ephedra was found in a grave dating back 60,000 years. It was used in traditional Chinese Medicine, known as Ma Huang, over 5,000 years ago. Traditionally it was used as both a stimulant and bronchodilator. Since the early 1900’s it has been used to treat ailments such as asthma and prescribed for allergies.
Ephedrine is a stimulant that works on the body’s sympathetic nervous system. It causes stimulation of the beta and alpha-receptors causing the release of norepinephrine. Norepinephrine in turn stimulates the body to respond by increasing heart rate, dilation of the bronchioles and constriction of blood vessels.
- References: