(R)-(−)-L-Epinephrine or (R)-(−)-L-adrenaline
|Systematic (IUPAC) name|
|ATC code||A01 B02BC09 C01CA24 R01AA14 R03AA01 S01EA01|
|Mol. mass||183. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug ATC code A01 is a division of the Anatomical Therapeutic Chemical Classification System and part of the A Alimentary tract and metabolism section A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 204 g/mol|
|Metabolism||adrenergic synapse (MAO and COMT)|
|Half life||2 minutes|
|Routes||IV, IM, endotracheal|
Epinephrine (usually referred to as adrenaline; see Terminology) is a hormone and neurotransmitter. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems Chemical synapses are specialized junctions through which Neurons signal to each other and to non-neuronal cells such as those in Muscles or Glands Catechol- O -methyl transferase ( COMT;) is one of several Enzymes that degrade Catecholamines such as Dopamine, Epinephrine The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during For a topic outline on this subject see List of basic Australia topics. The United States of America —commonly referred to as the The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. For a topic outline on this subject see List of basic Australia topics. A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom, the UK or Britain,is a Sovereign state located A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained The United States of America —commonly referred to as the In Pharmacology and Toxicology, a route Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. Intramuscular injection is the injection of a substance directly into a Muscle. Hormones (from Greek ὁρμή - "impetus" are chemicals released by cells that affect cells in other parts of the body See Chemical synapse for an introduction to concepts and terminology used in this article It is a catecholamine, a sympathomimetic monoamine derived from the amino acids phenylalanine and tyrosine. Sympathomimetic drugs are substances that mimic the effects of the Catecholamines Epinephrine (adrenaline Norepinephrine (noradrenaline and/or In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this Phe redirects here For the BitTorrent feature see PHE. For the constellation see Phoenix (constellation. Tyrosine (abbreviated as Tyr or Y) or 4-hydroxyphenylalanine, is one of the 20 Amino acids that are used by cells to synthesize The Latin roots ad-+renes and the Greek roots epi-+nephros both literally mean "on/to the kidney" (referring to the adrenal gland, which sits atop the kidneys and secretes epinephrine). Latin ( lingua Latīna, laˈtiːna is an Italic language, historically spoken in Latium and Ancient Rome. Greek (el ελληνική γλώσσα or simply el ελληνικά — "Hellenic" is an Indo-European language, spoken today by 15-22 million people mainly The kidneys are complicated organs that have numerous biological roles In Mammals the adrenal glands (also known as suprarenal glands) are the triangle-shaped Endocrine glands that sit on top of the Kidneys their Epinephrine is often shortened to epi or to EP in American medical jargon. For Wikipedia jargon see WikipediaGlossary. For hacker slang see Jargon File.
In May 1886, William Bates reported the discovery of a substance produced by the adrenal gland in the New York Medical Journal. William Horatio Bates ( December 23, 1860 - July 10, 1931) was an American Physician who practiced ophthalmology and developed what Epinephrine was isolated and identified in 1895 by Napoleon Cybulski, a Polish physiologist. Napoleon Cybulski ( September 13, 1854 - April 26, 1919) - Polish physiologist, discoverer of Adrenaline, one Poland (Polska officially the Republic of Poland Physiology (from Greek grc φύσις physis, "nature origin" and grc -λογία -logia) is the study of the mechanical physical The discovery was repeated in 1897 by John Jacob Abel. John Jacob Abel ( May 19, 1857 – May 26, 1938) was a significant American biochemist and pharmacologist. 
Jokichi Takamine, a Japanese chemist, independently discovered the same hormone in 1900. was a Japanese Chemist. Early Life and Education He was born in Takaoka, Toyama Prefecture, Japan the son of a physician moved to  In 1901 he isolated and purified the hormone adrenaline from cow glands.
It was first artificially synthesized in 1904 by Friedrich Stolz. Friedrich Stolz (1860&mdash1936 was a German chemist and in 1904 the first person to artificially synthesize Epinephrine ( Adrenaline)
Epinephrine is a "fight or flight" hormone, and plays a central role in the short-term stress reaction. The fight-or-flight response', also called the fright, fight or flight response, hyperarousal or the acute stress response, was first It is released from the adrenal glands when danger threatens or in an emergency. Such triggers may be threatening, exciting, or environmental stressor conditions such as high noise levels, or bright light (see Fight-or-flight response). In chemistry a stressor is something that either speeds up a Reaction rate or keeps the reaction rate the same Noise health effects are the Health consequences of elevated Sound levels Elevated workplace or other Noise can cause Hearing impairment Over-illumination is the presence of lighting intensity ( Illuminance) beyond that required for a specified activity The fight-or-flight response', also called the fright, fight or flight response, hyperarousal or the acute stress response, was first
An example of noise-induced trigger of epinephrine release is tinnitus. Tinnitus (tɪˈnaɪtəs or /ˈtɪnɪtəs/ from the Latin word for " Ringing " is the perception of sound within the human ear in the absence of corresponding The fight-or-flight response caused by tinnitus is a contributor to physical stress seen in tinnitus patients, exacerbating the case.
When secreted into the bloodstream, it rapidly prepares the body for action in emergency situations. The hormone boosts the supply of oxygen and glucose to the brain and muscles, while suppressing other non-emergency bodily processes (digestion in particular). Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Glucose (Glc a Monosaccharide (or simple Sugar) also known as grape sugar, is an important Carbohydrate in Biology. The brain is the center of the Nervous system in animals All Vertebrates and the majority of Invertebrates have a brain Muscle (from Latin musculus, diminutive of mus "mouse" is contractile tissue of the body and is derived from the Digestion is the breaking down of chemicals in the body into a form that can be absorbed
It increases heart rate and stroke volume, dilates the pupils, and constricts arterioles in the skin and gut while dilating arterioles in skeletal muscles. Measuring heart rate The Pulse rate (which in most people is identical to the heart rate can be measured at any point on the body where an Artery 's pulsation Stroke volume (SV is the volume of Blood pumped by the right/ Left ventricle of the heart in one contraction. The pupil is the hole that is located in the center of the iris of the eye and that controls the amount of light that enters the Eye. An arteriole is a small diameter Blood vessel that extends and branches out from an Artery and leads to capillaries. Skeletal muscle is a type of Striated muscle, which usually attaches to tendons It elevates the blood sugar level by increasing catalysis of glycogen to glucose in the liver, and at the same time begins the breakdown of lipids in fat cells. Blood sugar, used in a physiological context is a misnomer and misleading Catalysis is the process in which the rate of a Chemical reaction is increased by means of a Chemical substance known as a catalyst Glycogen is a Polysaccharide of Glucose (Glc which functions as the secondary short term energy storage in Animal cells Lipids are broadly defined as any fat- Soluble ( lipophilic) naturally-occurring Molecule, such as fats oils waxes cholesterol sterols fat-soluble Adipocytes are the cells that primarily compose Adipose tissue, specialized in storing energy as Fat. Like some other stress hormones, epinephrine has a suppressive effect on the immune system. An immune system is a collection of mechanisms within an Organism that protects against Disease by identifying and killing Pathogens and Tumor 
Although epinephrine does not have any psychoactive effects, stress or arousal also releases norepinephrine in the brain. Norepinephrine ( INN) (abbreviated norepi or NE) or noradrenaline ( BAN) (abbreviated NA or NAd) is a Norepinephrine has similar actions in the body, but is also psychoactive.
The type of action in various cell types depends on their expression of adrenergic receptors. A cell type is a distinct morphological or functional form of cell.
Epinephrine's actions are mediated through adrenergic receptors:
β2 receptors are found primarily in skeletal muscle blood vessels where they trigger vasodilation. Skeletal muscle is a type of Striated muscle, which usually attaches to tendons However, α-adrenergic receptors are found in most smooth muscles and splanchnic vessels, and epinephrine triggers vasoconstriction in those vessels. Smooth muscle is a type of non- Striated muscle, found within the Tunica media layer of large and small Arteries and Veins, the bladder In Anatomy, the intestine is the segment of the alimentary canal extending from the Stomach to the Anus and in humans and other mammals consists Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels particularly the large Arteries, Arterioles
Epinephrine is used as a drug to treat cardiac arrest and other cardiac dysrhythmias resulting in diminished or absent cardiac output; its action is to increase peripheral resistance via α1-adrenoceptor vasoconstriction, so that blood is shunted to the body's core, and the β1-adrenoceptor response which is increased cardiac rate and output (the speed and pronouncement of heart beats). Medication, also referred to as medicine, can be loosely defined as any substance intended for use in the diagnosis cure mitigation treatment or prevention of disease A cardiac arrest, also known as cardiorespiratory arrest, cardiopulmonary arrest or circulatory arrest, is the abrupt cessation of normal circulation of Dysrhythmia redirects here For the American band see Dysrhythmia (band. Cardiac output (Q is the volume of blood being pumped by the Heart, in particular by a ventricle in a minute The adrenergic receptors (or adrenoceptors) are a class of G protein-coupled receptors that are targets of the Catecholamines Adrenergic receptors Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels particularly the large Arteries, Arterioles The adrenergic receptors (or adrenoceptors) are a class of G protein-coupled receptors that are targets of the Catecholamines Adrenergic receptors This beneficial action comes with a significant negative consequence—increased cardiac irritability—which may lead to additional complications immediately following an otherwise successful resuscitation. Alternatives to this treatment include vasopressin, a powerful antidiuretic which also increases peripheral vascular resistance leading to blood shunting via vasoconstriction, but without the attendant increase in myocardial irritability. Arginine vasopressin ( AVP) also known as vasopressin, argipressin or antidiuretic hormone ( ADH) is a Hormone found in An antidiuretic is an Agent or Drug that administered to an Organism, helps control body water balance through its effects on the urine output and kidneys 
Because of its suppressive effect on the immune system, epinephrine is used to treat anaphylaxis and sepsis. Anaphylaxis is an acute systemic (multi-system and severe Type I Hypersensitivity allergic reaction in humans and other Mammals Sepsis is a serious medical condition characterized by a whole-body inflammatory state (called a Systemic inflammatory response syndrome or SIRS caused Allergy patients undergoing immunotherapy may receive an epinephrine rinse before the allergen extract is administered, thus reducing the immune response to the administered allergen. Immunotherapy in medicine refers to an array of treatment strategies based upon the concept of modulating the Immune system to achieve a prophylactic and/or It is also used as a bronchodilator for asthma if specific beta2-adrenergic receptor agonists are unavailable or ineffective. A bronchodilator is a substance that dilates the bronchi and Bronchioles decreasing airway resistance and thereby facilitating airflow Asthma is a chronic Condition involving the Respiratory system in which the airways occasionally constrict become inflamed, and are Beta2-adrenergic agonists, also known as Beta2-adrenergic receptor agonists, are a class of drugs used to treat Asthma and other Adverse reactions to epinephrine include palpitations, tachycardia, anxiety, headache, tremor, hypertension, and acute pulmonary edema. A palpitation (medical term ectopic heart beat) is an abnormal awareness of the beating of the Heart, whether it is too slow too fast irregular Hypertension, also referred to as high blood pressure, HTN or HPN, is a medical condition in which the Blood pressure is chronically elevated Pulmonary Edema (American English or oedema (British English is swelling and/or fluid accumulation in the Lungs It leads to impaired gas exchange and may cause 
Because of various expression of α1 or β2-receptors, depending on the patient, administration of epinephrine may raise or lower blood pressure, depending whether or not the net increase or decrease in peripheral resistance can balance the positive inotropic and chronotropic effects of epinephrine on the heart, effects which respectively increase the contractility and rate of the heart. An inotrope (ˈaɪnətroʊp is an agent that alters the force or energy of Muscular contractions Negatively inotropic agents weaken the force of muscular contractions Chronotropic effects (from chrono-, meaning time are those that change the Heart rate. Myocardial contractility is a term used in Physiology to describe the performance of cardiac muscle Measuring heart rate The Pulse rate (which in most people is identical to the heart rate can be measured at any point on the body where an Artery 's pulsation
Epinephrine is synthesized from norepinephrine in a synthetic pathway shared by all catecholamines, including L-dopa, dopamine, norepinephrine, and epinephrine. Norepinephrine ( INN) (abbreviated norepi or NE) or noradrenaline ( BAN) (abbreviated NA or NAd) is a Dopamine is a Hormone and Neurotransmitter occurring in a wide variety of animals including both vertebrates and invertebrates
Epinephrine is synthesized via methylation of the primary distal amine of norepinephrine by phenylethanolamine N-methyltransferase (PNMT) in the cytosol of adrenergic neurons and cells of the adrenal medulla (so-called chromaffin cells). Norepinephrine ( INN) (abbreviated norepi or NE) or noradrenaline ( BAN) (abbreviated NA or NAd) is a Phenylethanolamine N-methyltransferase ( PNMT) is an Enzyme found in the Adrenal medulla that converts Norepinephrine (Noradrenalin to Epinephrine The cytosol or intracellular fluid (or cytoplasmic matrix) is the liquid found inside cells. The adrenal medulla is part of the Adrenal gland. It is located at the center of the gland being surrounded by the Adrenal cortex. Chromaffin cells are Neuroendocrine cells found in the medulla of the Adrenal gland (suprarenal gland - located above the kidneys and in other ganglia PNMT is only found in the cytosol of cells of adrenal medullary cells. PNMT uses S-adenosylmethionine (SAMe) as a cofactor to donate the methyl group to norepinephrine, creating epinephrine. S -Adenosyl methionine (SAM is a Coenzyme involved in Methyl group transfers In Chemistry, a methyl group is a Hydrophobic Alkyl Functional group named after Methane (4
For norepinephrine to be acted upon by PNMT in the cytosol, it must first be shipped out of granules of the chromaffin cells. Chromaffin cells are Neuroendocrine cells found in the medulla of the Adrenal gland (suprarenal gland - located above the kidneys and in other ganglia This may occur via the catecholamine-H+ exchanger VMAT1. VMAT1 ( Vesicular monoamine transporter 1 is a protein that transports the Monoamine neurotransmitters into Synaptic vesicles In Chromaffin cells VMAT1 is also responsible for transporting newly synthesized epinephrine from the cytosol back into chromaffin granules in preparation for release.
Epinephrine synthesis is solely under the control of the central nervous system (CNS). In Vertebrates the central nervous system ( CNS) is the part of the Nervous system which is enclosed in the Meninges. Several levels of regulation dominate epinephrine synthesis.
Adrenocorticotropic hormone (ACTH) and the sympathetic nervous system stimulate the synthesis of epinephrine precursors by enhancing the activity of enzymes involved in catecholamine synthesis. Adrenocorticotropic hormone ( ACTH or corticotropin) is a Polypeptide Hormone produced and secreted by the Pituitary gland The Sympathetic Nervous System ( SNS) is a branch of the Autonomic nervous system along with the Enteric nervous system and Parasympathetic nervous The specific enzymes are tyrosine hydroxylase in the synthesis of dopa and enzyme dopamine-β-hydroxylase in the synthesis of norepinephrine. Tyrosine hydroxylase or tyrosine 3-monooxygenase is the Enzyme responsible for catalyzing the conversion of the Amino acid L-tyrosine to Dopamine β-hydroxylase (DBH is an Enzyme that converts Dopamine to Norepinephrine:Synonyms Aromatic L-amino acid decarboxylase ( Tryptophan Norepinephrine ( INN) (abbreviated norepi or NE) or noradrenaline ( BAN) (abbreviated NA or NAd) is a
ACTH also stimulates the adrenal cortex to release cortisol, which increases the expression of PNMT in chromaffin cells, enhancing epinephrine synthesis. Situated along the perimeter of the Adrenal gland, the adrenal cortex mediates the stress response through the production of Mineralocorticoids and Glucocorticoids Cortisol is a Corticosteroid Hormone produced by the Adrenal gland (in the Zona fasciculata of the Adrenal cortex) This is most often done in response to stress.
The sympathetic nervous system, acting via splanchnic nerves to the adrenal medulla, stimulates the release of epinephrine. The splanchnic nerves are paired nerves that contribute to the Innervation of the viscera, carrying fibers of the Autonomic nervous system (visceral efferent fibers Acetylcholine released by preganglionic sympathetic fibers of these nerves acts on nicotinic acetylcholine receptors, causing cell depolarization and an influx of calcium through voltage-gated calcium channels. The Chemical compound acetylcholine (often abbreviated ACh) is a Neurotransmitter in both the Peripheral nervous system (PNS and Central Structure Nicotinic receptors with a molecular mass of 290 kDa, are made up of five subunits arranged symmetrically around the central pore. Calcium (ˈkælsiəm is the Chemical element with the symbol Ca and Atomic number 20 Voltage-dependent calcium channels (VDCC are a group of voltage-gated Ion channels found in excitable cells ( e Calcium triggers the exocytosis of chromaffin granules and thus the release of epinephrine (and norepinephrine) into the bloodstream.
Epinephrine (as with norepinephrine) does exert negative feedback to down-regulate its own synthesis at the presynaptic alpha-2 adrenergic receptor. Negative Feedback feeds part of a System 's output inverted into the system's input generally with the result that fluctuations are attenuated WikipediaWikipedia is not a dictionary ---> Downregulation is the process by which
A pheochromocytoma is a tumor of the adrenal gland (or, rarely, the ganglia of the sympathetic nervous system), which results in the uncontrolled secretion of catecholamines, usually epinephrine. A phaeochromocytoma ( pheochromocytoma in the US is a Neuroendocrine tumor of the medulla of the Adrenal glands (originating in the Chromaffin The Sympathetic Nervous System ( SNS) is a branch of the Autonomic nervous system along with the Enteric nervous system and Parasympathetic nervous
In liver cells, epinephrine binds to the β-Adrenergic receptor which changes conformation and helps Gs, a G protein, exchange GDP to GTP. This trimeric G protein dissociates to Gs alpha and Gs beta/gamma subunits. Gs alpha binds to adenyl cyclase thus converting ATP into Cyclic AMP. Cyclic AMP binds to the regulatory subunit of Protein Kinase A: Protein kinase A phosphorylates Phosphorylase Kinase. Meanwhile, Gs beta/gamma binds to the calcium channel and allows calcium ions to enter the cytoplasm. Calcium ions bind to calmodulin proteins, a protein present in all eukaryotic cells, which then binds to Phosphorylase Kinase and finishes its activation. Phosphorylase Kinase phosphorylates Phosphorylase which then phosphorylates glycogen and converts it to glucose-6-phosphate.
Although widely referred to as adrenaline outside of the US, and the lay public worldwide, the USAN and INN for this chemical is epinephrine because adrenaline bore too much similarity to the Parke, Davis & Co trademark Adrenalin (without the "e") which was registered in the U. In religious organizations the laity comprises all persons who are not Clergy. United States Adopted Names are unique nonproprietary names assigned to Pharmaceuticals marketed in the United States. An International Nonproprietary Name ( INN; also known as rINN, for recommended International Nonproprietary Name or pINN for proposed Parke-Davis is a Subsidiary of the Pharmaceutical company Pfizer. S. The BAN and EP term for this chemical is adrenaline, and is indeed now one of the few differences between the INN and BAN systems of names. A British Approved Name ( BAN) is the official non-proprietary or generic name given to a Pharmaceutical Substance, as defined in the British Pharmacopoeia The European Pharmacopoeia of the Council of Europe is a listing of a wide range of Active substances and Excipients used to prepare Pharmaceutical
Amongst U. S. health professionals, the term epinephrine is used over adrenaline. However, it should be noted that universally, pharmaceuticals that mimic the effects of epinephrine are called adrenergics, and receptors for epinephrine are called adrenoceptors.
It can also be spelled epinephrin (without the "e").
Natural epinephrine is the (R)-(−)-L-epinephrine stereoisomer. Stereoisomers are isomeric molecules that have the same molecular formula and sequence of bonded atoms (constitution but which differ in the three dimensional orientations
Epinephrine is now also used in EpiPens and Twinjects. EpiPen is a registered trademark for the most commonly used Autoinjector of Epinephrine (a Twinject is the registered trademark of the first Epinephrine Autoinjector that contains two doses EpiPens are long narrow autoinjectors that administer epinephrine, Twinjects are similar but contain two doses of epinephrine. An autoinjector (or auto-injector) is a Medical device designed to deliver a single Dose of a particular (typically life-saving drug. Twinject is the registered trademark of the first Epinephrine Autoinjector that contains two doses It is also used in medicines and usually the Epinephrine is extracted from adrenal glands of hogs, cattle, and sheep.
Though both EpiPen and Twinject are trademark names, common usage of the terms are drifting toward the generic context of any epinephrine autoinjector. A genericized trademark (also known as a generic trademark or proprietary eponym) is a Trademark or Brand name that has become the colloquial
Aqueous preparations of adrenaline are obtained by use of HCL or tartaric acid we should use only acids because in the absence of acid medium , it undergoes oxidation. Tartaric acid is a white crystalline Organic acid. It occurs naturally in many plants particularly Grapes Bananas and Tamarinds and is
Borate salt is used in opthalmolgy