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Barbituric acid, the basic structure of all barbiturates
Barbituric acid, the basic structure of all barbiturates

Barbiturates are drugs that act as central nervous system depressants, and by virtue of this they produce a wide spectrum of effects, from mild sedation to anesthesia. Barbituric acid or malonylurea or 4-hydroxyuracil is an Organic compound based on a Pyrimidine Heterocyclic skeleton 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 Depressant is a chemical agent that diminishes the function or activity of a specific part of the body (see also Sedative) Sedation is a Medical procedure involving the administration of Sedative drugs generally to facilitate a medical procedure with Local anaesthesia. Anesthesia, or anaesthesia (see spelling differences; from Greek grc αν- an-, "without" and grc αἲσθησις Some are also used as anticonvulsants. The anticonvulsants, also called antiepileptic drugs (abbreviated "AEDs" are a diverse group of pharmaceuticals used in the treatment of epileptic

Barbiturates are derivatives of barbituric acid. Barbituric acid or malonylurea or 4-hydroxyuracil is an Organic compound based on a Pyrimidine Heterocyclic skeleton

Contents

History

Barbituric acid, was first synthesised on December 4, 1864, by German researcher Adolf von Baeyer. Barbituric acid or malonylurea or 4-hydroxyuracil is an Organic compound based on a Pyrimidine Heterocyclic skeleton "December 4th" redirects here For the song by Jay-Z, see December 4th (song. Year 1864 ( MDCCCLXIV) was a Leap year starting on Friday (link will display the full calendar of the Gregorian Calendar (or a Leap year Germany, officially the Federal Republic of Germany ( ˈbʊndəsʁepuˌbliːk ˈdɔʏtʃlant is a Country in Central Europe. Johann Friedrich Wilhelm Adolf von Baeyer (ˈbaɪɐ October 31, 1835 - August 20, 1917) was a German chemist who This was done by condensing urea (an animal waste product) with diethyl malonate (an ester derived from the acid of apples). A condensation reaction is a Chemical reaction in which two Molecules or moieties ( Functional groups) combine to form one single molecule together with Urea is an Organic compound with the Chemical formula ( N[[hydrogen H]]22 C[[oxygen O]] Malonic acid ( IUPAC Systematic name: propanedioic acid) is a Dicarboxylic acid with structure C[[hydrogen H]]2( Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. There are several stories about how the substance got its name. The most likely story is that von Baeyer and his colleagues went to celebrate their discovery in a tavern where the town's artillery garrison were also celebrating the day of Saint Barbara — the patron saint of artillerists. A tavern or pot-house is loosely a place of Business where people gather to drink Alcoholic beverages and more than likely also be served Food Artillery (from French artillerie) is a military Combat Arm which employs any apparātus machine Garrison (various spellings (from the French garnison, itself from the verb garnir, "to equip" is the collective term for a body of Troops Saint Barbara, known in the Eastern Orthodox Church as the Great Martyr Barbara, was a Christian Saint and Martyr. An artillery officer is said to have christened the new substance by amalgamating Barbara with urea. [1]

Barbituric acid itself does not have any effect on the CNS (Central Nervous System), however to date chemists have derived over 2,500 compounds that do possess pharmacologically active qualities. The broad class of Barbiturates is broken down further and classified according to speed of onset and duration of action. Ultra-Short acting Barbiturates are commonly used for anesthesia because their extremely short duration of action allows for greater control. These properties allow doctors to rapidly put a patient "under" in emergency surgery situations. Doctors can also bring a patient out of anesthesia just as quickly should complications arise during surgery. The middle two classes of Barbiturates are often combined under the title Short-Intermediate acting. These Barbiturates are also employed for anesthetic purposes, and are also sometimes prescribed for anxiety or insomnia. This is not a common practice anymore however, due to the addiction liablity associated with Barbiturates, they have been replaced by the Benzodiazepines for these purposes. The final class of Barbiturates are known as Long acting Barbiturates (most notably phenobarbital, which has a half-life of roughly 92 hours). This class of Barbiturates is used almost exclusively as anticonvulsants, although on rare occasions they are sometimes prescribed for daytime sedation. Barbiturates in this class are not used for insomnia, because due to their extremely long half-life, patients would awake with a residual "hang-over" effect and feel groggy. No substance of medical value was discovered, however, until 1903 when two German chemists working at Bayer, Emil Fischer and Joseph von Mering, discovered that barbital was very effective in putting dogs to sleep. For other uses see Bayer (disambiguation or Beyer or Buyer. Bayer AG (German ˈbaɪə () is a German Barbital (marketed under the brand name Veronal) also called barbitone was the first commercially marketed Barbiturate. Barbital was then marketed by Bayer under the trade name Veronal. A trade name, also known as a trading name or a business name, is the name which a Business trades under for commercial purposes although its registered Barbital (marketed under the brand name Veronal) also called barbitone was the first commercially marketed Barbiturate. It is said that Von Mering proposed this name because the most peaceful place he knew was the Italian city of Verona. Italy (Italia officially the Italian Republic, (Repubblica Italiana is located on the Italian Peninsula in Southern Europe, and on the two largest Verona is a city and provincial capital in Veneto, Northern Italy. [1]

Barbiturates can in most cases be used as either the free acid or as salts of sodium, calcium, potassium, magnesium, lithium etc. Codeine- and Dionine-based salts of barbituric acid have been developed. Codeine ( INN) or methylmorphine is an Opiate used for its Analgesic, antitussive and antidiarrheal properties Ethylmorphine (also known as codethyline, Dionine®, and ethyl morphine) is a drug in the class of both Opiates (representing a minor synthetic

In 1912, Bayer introduced another barbituric acid derivative, phenobarbital, under the trade name Luminal, as a sedative-hypnotic. Phenobarbital ( INN) or phenobarbitone (former BAN) is a Barbiturate, first marketed as Luminal by Friedr

In the 1950s and 1960s, reports began to be published about side effects and dependence related to barbiturates. In Medicine, an adverse effect is a harmful and undesired effect resulting from a medication or other intervention such as Chemotherapy or Surgery.

In 1970 several barbiturates were designated in the United States as controlled substances with the passage of the American Controlled Substances Act of 1970. The United States of America —commonly referred to as the The Controlled Substances Act ( CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Pentobarbital, secobarbital and amobarbital were designated schedule II drugs, butabarbital schedule III, and barbital and phenobarbital schedule IV. Pentobarbital is a short-acting Barbiturate that is available as both a Free acid and a Sodium salt, the former of which is only slightly soluble in water Secobarbital (marketed by Eli Lilly and Company under the brand name Seconal) is a Barbiturate derivative drug Amobarbital (formerly known as amylobarbitone is a drug that is a Barbiturate derivative The Controlled Substances Act ( CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Butabarbital (trade name Butisol) is a prescription Barbiturate sleep aid.

In 1971 the Convention on Psychotropic Substances was signed in Vienna. The Convention on Psychotropic Substances is a United Nations Treaty designed to control Psychoactive drugs such as Amphetamines Barbiturates Vienna ( in Wien; see also other names) is the Capital of Austria, and is also one of the nine States of Austria. Designed to regulate amphetamines, barbiturates, and other synthetics, the treaty today regulates secobarbital (III), amobarbital (schedule III), butalbital (III), cyclobarbital (III), pentobarbital (III), allobarbital (IV), methylphenobarbital (IV), phenobarbital (IV), and vinylbital (IV) as scheduled substances. Amphetamine, and related drugs such as Methamphetamine are a group of drugs that act by increasing levels of Norepinephrine, Serotonin, and Dopamine A Treaty is an agreement under International law entered into by actors in international law namely States and International organizations. Secobarbital (marketed by Eli Lilly and Company under the brand name Seconal) is a Barbiturate derivative drug Amobarbital (formerly known as amylobarbitone is a drug that is a Barbiturate derivative Butalbital, 5-allyl-5-isobutylbarbituric acid is a Barbiturate with an intermediate duration of action Cyclobarbital, also known as cyclobarbitol or cyclobarbitone, is a Drug which is a Barbiturate derivative. Allobarbital is a Barbiturate derivative invented in 1912 by Ernst Preiswerk and Ernst Grether working for CIBA. Methylphenobarbital, also known as mephobarbital, (marketed in the US under the brand name Mebaral by Ovation) is a drug which is a Barbiturate Phenobarbital ( INN) or phenobarbitone (former BAN) is a Barbiturate, first marketed as Luminal by Friedr Vinylbital, also known as butylvinyl, is a drug which is a Barbiturate derivative The Convention on Psychotropic Substances is a United Nations Treaty designed to control Psychoactive drugs such as Amphetamines Barbiturates

Table of Barbiturates


Barbiturates
Short NameR5R5Full Name
AllobarbitalCH2CHCH2CH2CHCH25,5-diallylbarbiturate
AmobarbitalCH2CH3CH2CH2CH(CH3)25-ethyl-5-isopentyl-barbiturate
AprobarbitalCH2CHCH2CH(CH3)25-allyl-5-isopropyl-barbiturate
AlphenalCH2CHCH2C6H55-allyl-5-phenyl-barbiturate
BarbitalCH2CH3CH2CH35,5-diethylbarbiturate
BrallobarbitalCH2CHCH2CH2CBrCH25-allyl-5-(2-bromo-allyl)-barbiturate
PhenobarbitalCH2CH3C6H55-phenyl-5-ethylbarbiturate


Mechanism of action

The principal mechanism of action of barbiturates is believed to be their affinity for the GABAA receptor (Acts on GABA : BDZ receptor cl- channel complex). Allobarbital is a Barbiturate derivative invented in 1912 by Ernst Preiswerk and Ernst Grether working for CIBA. An allyl group is an Alkene Hydrocarbon group with the formula H2C=CH-CH2- An allyl group is an Alkene Hydrocarbon group with the formula H2C=CH-CH2- Amobarbital (formerly known as amylobarbitone is a drug that is a Barbiturate derivative In Organic chemistry, pentyl is a five- Carbon Alkyl substituent with Chemical formula -C5H11. Aprobarbital (Oramon is a Barbiturate derivative invented in the 1920s by Ernst Preiswerk An allyl group is an Alkene Hydrocarbon group with the formula H2C=CH-CH2- In Organic chemistry, isopropyl is a substituent form of Propane, the three- Carbon Alkyl Functional group. Alphenal is a Barbiturate derivative invented in the 1960s It has primarily Anticonvulsant properties and was used occasionally for the treatment of Epilepsy An allyl group is an Alkene Hydrocarbon group with the formula H2C=CH-CH2- In Organic chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the Functional group with the formula - Barbital (marketed under the brand name Veronal) also called barbitone was the first commercially marketed Barbiturate. Brallobarbital is a Barbiturate derivative invented in 1964 It has Sedative and Hypnotic properties and was used for the treatment of Insomnia An allyl group is an Alkene Hydrocarbon group with the formula H2C=CH-CH2- An allyl group is an Alkene Hydrocarbon group with the formula H2C=CH-CH2- Phenobarbital ( INN) or phenobarbitone (former BAN) is a Barbiturate, first marketed as Luminal by Friedr In Organic chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the Functional group with the formula - GABA is the principal inhibitory neurotransmitter in the mammalian Central Nervous System (CNS). Gamma-aminobutyric acid (GABA is the chief inhibitory Neurotransmitter in the Mammalian Central nervous system. Mammals ( class Mammalia) are a class of Vertebrate Animals characterized by the presence of Sweat glands, including sweat glands In Vertebrates the central nervous system ( CNS) is the part of the Nervous system which is enclosed in the Meninges. Barbiturates bind to the GABAA receptor at the alpha subunit, which are binding sites distinct from GABA itself and also distinct from the benzodiazepine binding site. Gamma-aminobutyric acid (GABA is the chief inhibitory Neurotransmitter in the Mammalian Central nervous system. The benzodiazepines (pronounced, often abbreviated to "benzos") are a class of Psychoactive drugs with varying Hypnotic Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor. In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. The alpha- a mino-3-hydroxy-5- m ethyl-4-isoxazole' p' ropionic a cid receptor (also known as AMPA receptor Glutamate receptors are Transmembrane receptors located on Neuron membranes Glutamate is the principal excitatory neurotransmitter in the mammalian CNS. Taken together, the findings that barbiturates potentiate inhibitory GABAA receptors and inhibit excitatory AMPA receptors can explain the CNS-depressant effects of these agents. At higher concentration they inhibit the Ca2+ dependent release of neurotransmitters. [2]

Therapeutic use

Barbiturates like pentobarbital and phenobarbital were long used as anxiolytics and hypnotics. An anxiolytic is a drug prescribed for the treatment of Symptoms of Anxiety. For the state of mind see Hypnosis. Hypnotic drugs induce Sleep (which differentiates them from the Sedative Today benzodiazepines have largely supplanted them for these purposes, because benzodiazepines have less potential for abuse and less danger of lethal overdose. The benzodiazepines (pronounced, often abbreviated to "benzos") are a class of Psychoactive drugs with varying Hypnotic The term drug overdose (or simply overdose or OD) describes the Ingestion or application of a Drug or other substance in quantities Today, fewer than 10 percent of all sedative/hypnotic prescriptions in the United States are for barbiturates.

Barbiturates are still widely used in surgical anesthesia, especially to induce anesthesia. Surgery (from the χειρουργική cheirourgikē, via chirurgiae meaning "hand work" is a medical specialty that uses operative manual and instrumental Anesthesia, or anaesthesia (see spelling differences; from Greek grc αν- an-, "without" and grc αἲσθησις

Phenobarbital is used as an anticonvulsant for people suffering from seizure disorders such as febrile seizures, tonic-clonic seizures, status epilepticus, and eclampsia. Phenobarbital ( INN) or phenobarbitone (former BAN) is a Barbiturate, first marketed as Luminal by Friedr The anticonvulsants, also called antiepileptic drugs (abbreviated "AEDs" are a diverse group of pharmaceuticals used in the treatment of epileptic An epileptic seizure is caused by excessive and/or hypersynchronous electrical Neuronal activity and is usually self-limiting A febrile seizure, also known as a fever fit or febrile convulsion is a Convulsion triggered by a rise in Body temperature. Tonic-clonic seizures are a type of Generalized seizure affecting the entire brain Status epilepticus (SE refers to a life-threatening condition in which the Brain is in a state of persistent Seizure. Eclampsia is a serious complication of Pregnancy and is characterised by convulsions. [2]

Effects on the body

Barbiturates are classified as ultrashort-, short-, intermediate-, and long-acting, depending on how quickly they act and how long their effects last. [3] Ultrashort barbiturates such as thiopental (Pentothal) produce unconsciousness within about a minute of intravenous (IV) injection. The fictional truth drug Hyoscine-pentothal does not describe real pentothal accurately These drugs are used to prepare patients for surgery; other general anesthetics like nitrous oxide are then used to keep the patient from waking up before the surgery is complete. A general anaesthetic (or anesthetic, see Spelling differences) drug is an anaesthetic drug that brings about a reversible loss of Consciousness. Nitrous oxide, commonly known as " laughing gas," is a Chemical compound with the Chemical formula N 2 O. Because Pentothal and other ultrashort-acting barbiturates are typically used in hospital settings, they are not very likely to be abused, noted the DEA. [4]

Abusers tend to prefer short-acting and intermediate-acting barbiturates. [5] The most commonly abused are amobarbital (Amytal), pentobarbital (Nembutal), and secobarbital (Seconal). Amobarbital (formerly known as amylobarbitone is a drug that is a Barbiturate derivative Pentobarbital is a short-acting Barbiturate that is available as both a Free acid and a Sodium salt, the former of which is only slightly soluble in water Secobarbital (marketed by Eli Lilly and Company under the brand name Seconal) is a Barbiturate derivative drug A combination of amobarbital and secobarbital (called Tuinal) is also highly abused. Tuinal is the brand name of a combination Drug composed of two Barbiturate salts ( Secobarbital sodium and Amobarbital sodium in equal proportions Short-acting and intermediate-acting barbiturates are usually prescribed as sedatives and sleeping pills. These pills begin acting fifteen to forty minutes after they are swallowed, and their effects last from five to six hours. Veterinarians use pentobarbital to anesthetise animals before surgery; in large doses, it can be used to euthanise animals. Euthanasia (literally "good death" in Ancient Greek) refers to the practice of ending a life in a painless manner [4]

Long-acting barbiturates such as phenobarbital (Luminal) and mephobarbital (Mebaral) are prescribed for two main reasons. Phenobarbital ( INN) or phenobarbitone (former BAN) is a Barbiturate, first marketed as Luminal by Friedr Methylphenobarbital, also known as mephobarbital, (marketed in the US under the brand name Mebaral by Ovation) is a drug which is a Barbiturate When taken at bedtime, they help treat insomnia. Insomnia is a symptom of a sleeping disorder characterized by persistent difficulty falling asleep or staying asleep despite the opportunity When taken during the day, they have sedative effects that can aid in the treatment of tension and anxiety. These same effects have been found helpful in the treatment of convulsive conditions like epilepsy. Phenobarbital has also been used in the treatment of delirium tremens during alcohol detoxification, although benzodiazepines have a more favorable safety profile and are more often used. Delirium tremens (colloquially the DTs, " the horrors " " the fear "" the shakes "" jazz hands "" Alcohol detoxification, or detox, for individuals with Alcohol dependence, is the abrupt cessation of alcohol intake coupled with the substitution of alcohol with [6] Long-acting barbiturates take effect within one to two hours and last 12 hours or longer. [4]

Similarity to alcohol

Recreational users report that a barbiturate high makes them feel "relaxed, sociable, and good-humored", according to an independent article. Users typically describe feelings of decreased anxiety, a loss of inhibitions, and an increased sense of confidence. Physical effects include slowed breathing and a lowering of both blood pressure and heart rate.

Like ethanol, barbiturates are intoxicating. During the stage after mild intoxication, the user's speech may be slurred and a loss of coordination may become noticeable. Stumbling and staggering are common. Other symptoms include shallow breathing, fatigue, frequent yawning, and irritability.

When taken in high doses, barbiturates can cause serious side effects, including "unpredictable emotional reactions and mental confusion", noted the Independent. Judgment becomes severely impaired and the user may experience mood swings.

The mental effects of barbiturates generally depend on the amount of the drug taken and the strength of the dosage. Generally, a person falls asleep when taking a prescribed dosage at bedtime. But barbiturates remain in the system for a long time. "At normal doses", explained Cynthia Kuhn and her coauthors in Buzzed: The Straight Facts About the Most Used and Abused Drugs from Alcohol to Ecstasy, "the major concern is that they can have sedative effects that outlast their sleep-inducing properties. Driving, flying an airplane, or other activities requiring muscle coordination can be impaired for up to a day after a single dose. " Some barbiturates can be detected in a user's urine sample days or even weeks after the drug was consumed.

Truth serum

Thiopental is an ultra-short acting barbiturate that is marketed under the name Sodium Pentothal. The fictional truth drug Hyoscine-pentothal does not describe real pentothal accurately When dissolved in water, it can be swallowed or administered by intravenous injection. In large doses, it is one of three drugs used in the United States to execute prisoners on death row. In lower doses, it is sometimes used as a "truth serum". A truth drug (or truth serum) is a Psychoactive drug used to attempt to obtain information from an unwilling subject most often by a police intelligence or military

The drug does not itself force people to tell the truth, but is thought to decrease inhibitions, making subjects more likely to be caught off guard when questioned. [7]

Dependence, tolerance, and overdose

Barbiturate use can lead to both psychological and physical dependence. Psychological addiction can occur quickly. Signs of drug dependence include relying on a drug regularly for a desired effect. The addicted abuser believes he or she must take a barbiturate to sleep, relax, or just get through the day. Continued use of barbiturates leads to physical dependence. Particularly dangerous is the impact on short-term memory and judgement that can cause the user to re-dose because they do not remember how much they took.

As people develop a tolerance for barbiturates, they may need more of the drug or a higher dosage to get the desired effect. This can lead to an overdose, which results when a person takes a larger-than-prescribed dose of a drug. "People who get in the habit of taking sleeping pills every night to fall asleep", noted Andrew Weil and Winifred Rosen in From Chocolate to Morphine, "might start out with one a night, progress to two, then graduate to four to get the same effect. One night the dose they need to fall asleep might also be the dose that stops their breathing. " Generally, barbiturate overdoses "occur because the effective dose of the drug is not too far away from the lethal dose", explained Dr. Eric H. Chudler on the Neuroscience for Kids Web site.

Symptoms of an overdose typically include severe weakness, confusion, shortness of breath, extreme drowsiness, an unusually slow heartbeat, and darting eye movements. The amount of a fatal dosage of barbiturate varies from one individual to another. However, the lethal dose is usually ten to fifteen times as large as a usual dose. An overdose affects the heart and the respiratory system. The user then falls into a coma and dies.

Clayton pointed out that barbiturates "can have a 'multiplying' effect when taken with other depressants. For example, if someone drinks alcohol and takes a barbiturate, the effect may be ten times stronger than either one taken separately. " According to Weil, "many people have died because they were ignorant of this fact".

Older adults and pregnant women should consider the risks associated with barbiturate use. When a person ages, the body becomes less able to rid itself of barbiturates. As a result, people over the age of sixty-five are at higher risk of experiencing the harmful effects of barbiturates, including drug dependence and accidental overdose. When barbiturates are taken during pregnancy, the drug passes through the mother's bloodstream to her fetus. After the baby is born, it may experience withdrawal symptoms and have trouble breathing. In addition, nursing mothers who take barbiturates may transmit the drug to their babies through breast milk.

Slang terms for barbiturates include reds (Seconal), yellow jackets (Nembutal), Christmas Trees (Tuinal or barbiturate-amphetamine combinations), tuies (Tuinal), blue devils, red devils, dolls, and many others.

Other non-therapeutic use

Barbiturates in high doses are used for physician-assisted suicide (PAS), and in combination with a muscle relaxant for euthanasia and for capital punishment by lethal injection. Physician-assisted suicide: may refer to Euthanasia, in cases where the physician performs the action may refer to Assisted suicide, where This article refers to skeletal muscle relaxants For information on Smooth muscle relaxants see Antispasmodic. Euthanasia (literally "good death" in Ancient Greek) refers to the practice of ending a life in a painless manner Capital punishment, the death penalty or execution, is the Killing of a person by judicial process as Punishment.

Famous users


External links

References

  1. ^ a b Barbiturates. Retrieved on 2007-10-31. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 445 BC – Ezra reads the Book of the Law to the Israelites in Jerusalem (see Nehemiah 91 NLTse
  2. ^ a b Brunton, Laurence L. ; Lazo, John S. ; Parker, Keith L. ; Goodman, Louis Sanford; Gilman, Alfred Goodman. Goodman & Gilman's Pharmacological Basis of Therapeutics. McGraw-Hill. ISBN 0071422803.  
  3. ^ Barbiturates: How Is It Taken?. azdrugs. org (2005–2007). Retrieved on 2007-10-31. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 445 BC – Ezra reads the Book of the Law to the Israelites in Jerusalem (see Nehemiah 91 NLTse
  4. ^ a b c DEA Brief on Barbiturates
  5. ^ Coupey SM. "Barbiturates. " Pediatrics in Review. 1997 Aug;18(8):260-4. PMID 9255991
  6. ^ Kosten TR, O'Connor PG. "Management of drug and alcohol withdrawal. " New England Journal of Medicine. 2003 May 1;348(18):1786-95. PMID 12724485
  7. ^ Neuroscience for Kids - Barbiturates. Retrieved on 6-2-2008.

Dictionary

barbiturate

-noun

  1. (organic chemistry) Any salt or ester of barbituric acid.
  2. (pharmacology) Any of a class of drugs that act as depressants of the central nervous system and are used as sedatives or hypnotics.
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