Epinephrine

= Epinephrine =

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 * by: Liz **

Reference Facts:

 * IUPAC Name: (R)-4-(1-hydroxy-2-ethyl)benzene-1,2-diol **
 * Formula: Cmedia type="custom" key="7295991"Hmedia type="custom" key="7295995"NOmedia type="custom" key="7296001" **
 * Molar Mass: 183.204 g/mol **
 * Density: No data found **
 * Melting Point: 211.5° C **
 * Boiling Point: Decomposes. 215°C **
 * Solubility: Soluble in aqueous solutions of inorganic acids **
 * Other Names: 3,4 Dihydroxy-1-[1-hydroxy-2-(methylamino)ethyl]benzene, Adrenaline , and Lyophrine. **
 * Toxicity: Highly toxic; fatal if inhaled or swallowed in large doses. When heated, it can produce carbon monoxide. **
 * Stability: Sensitive to light, usually stable. **
 * Physical State: White or yellow crystalline powder **


 * Epinephrine is a hormone, neurotransmitter, and is also used as a drug. It increases heart rate, dilates air passages, and contracts blood vessels. **
 * It is also categorized as a [|catecholamine], and is produced in the adrenal glands. In the human body, it is used in many different ways. **
 * For instance, epinephrine in the body is triggered by excitement, threat, terror, and other emotions that get the heart racing. It is used in hospitals for patients who undergo cardiac arrest or any type of problem that would slow down or speed up a person's heart rate immensely, such as asthma and [|anaphylaxis] . As a drug, this can also cause many side-effects; such as palpitations, [|tachycardia], [|cardiac dysrhythmia], anxiety, headache, and [|hypertension]. **



History

 * In 1886, William Bates reported to the New York Medical Journal, of an unknown substance that was produced in the adrenal gland. Later on, it was discovered by **** Polish physiologist, [|Napoleon Cybulski], and he **** called it "nadnerczyna." which, in Polish translates to "adrenal." They were a combination of epinephrine and other [|catecholamines] **** which are synthesized in the adrenal glands, and goes from being tyrosine to adrenaline. **** In the 1900's, a Japanese chemist by the name of [|Jokichi Takamine] and his assistant modified these and made them into pure epinephrine and in 1901, extracted it and purified it from the glands of sheep. This organic compound was also first synthesized in 1904 by a [|Friedrich Stolz]. **


 * The terminology of "adrenaline" is derived from Latin roots "ad-" wihich means "to or toward," and "renes-," which means "kidney." So, together it literally means to or toward the kidney. The same goes for the terminology of "Epinephrine." "Epi-" meaning "on" and "Nephros," which means "kidney" as well. **


 * Epinephrine is synthesized in the adrenal gland in a ** [|metabolic pathway] **that allows ** [|tyrosine] ** to undergo a series of multiple-step processes to ultimately become epinephrine. Tyrosine is first oxidized and becomes ** [|L-DOPA], ** an isomer of Dopamine, and is then decarboxylated to become ** [|dopamine] . ** When the dopamine is oxidized, your result is **[|norepinephrine] , ** which then undergoes a process called ** __ methylation. __ ** This adds one carbon and two hydrogens to produce the final product, thus being epinephrine. **


 * Click [[file:Catecholamines_biosynthesis1.svg]] to see a diagram of how Epinephrine is made in the adrenal glands. **

**Uses**


 * In the hospital, epinephrine is used as a drug for patients that undergo cardiac arrest, or any other [|cardiac dysrhythmias]. It is used for these specific reasons: One, because it can increase heart rate, and in the lungs it increases the respiratory rate. Also, it can help open up air passages, which is why it is sometimes used as a medicine for people with bronchitis and asthma. Because of its constricting effects on the blood vessels and arteries, epinephrine is used as a treatment for [|anaphylaxis], and also [|sepsis]. It can be synthesized to a liquid and mixed with other isomers of epinephrine to create a medicine for [|Croup] cough, which is a severe cough that makes the victim sound as if they are barking. This treatment is called Racemic epinephrine. It relaxes the smooth muscles in the bronchial tubes, and stimulates the airways to relieve the patient of this ailment. **

Percent Composition And Structure

 * Epinephrine contains one benzene ring, three hydroxyl groups, one trigonal pyramidal methyl group and one nitrogen atom, all bonded together as you can see in Figure 3 below: **




 * Below is a table of the % composition by moles and by mass of each of the elements in this organic compound: **


 * ** Element ** || ** % Composition by Moles ** || ** % Composition by Mass ** ||
 * Hydrogen || 7.512%  ||  0.074%  ||
 * Carbon || 59.003%  ||  59%  ||
 * Oxygen || 7.645%  ||  26%  ||
 * Nitrogen || 26.1699%  ||  0.076%  ||

3-D Model

 * Save this ** [[file:epinephrine.bio]] ** file and open with iMol to see a 3-D model! **

How Does It Work In The Body?

 * Epinephrine is well-known as the "fight or flight" response hormone, because of its rapid response to changing in the body. As a hormone, epinephrine will either increase or decrease the heart rate, and how controlled your breathing is, in times of streee, excitement, or in a time of fear. As a neurotransmitter, it is triggered in the adrenal glands, ** **and attaches to other** **[|adrenergic receptors] and binding to them can trigger many different metabolic changes in the human body, such as a **** threatening, stressful, or exciting situation. It will increase the heart rate, boost the production of sugars and oxygen to the brain and its muscles, thus suppressing other non-emergency bodily functions. **