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Brucine Wiki2Web Clarity Challenge

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Study Guide: Brucine: Properties, Applications, and Toxicology

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Brucine: Properties, Applications, and Toxicology Study Guide

Chemical Properties and Identification

Liquid chromatography-mass spectrometry (LC-MS) is a technique used for detecting and quantifying brucine.

Answer: True

Explanation: Liquid chromatography-mass spectrometry (LC-MS) is indeed a recognized analytical technique employed for the detection and quantification of brucine.

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A red color change occurs when formic acid is added to a mixture containing brucine and potassium nitrate, indicating the presence of nitrates.

Answer: True

Explanation: The reaction of brucine with potassium nitrate in the presence of formic acid produces an immediate red color, serving as a colorimetric test for nitrates.

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Brucine has a molar mass of approximately 394.471 grams per mole.

Answer: True

Explanation: The molar mass of brucine is accurately stated as approximately 394.471 g/mol.

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Brucine melts at a temperature significantly below freezing point of water.

Answer: False

Explanation: Brucine melts at 178 degrees Celsius, which is significantly above the freezing point of water (0 degrees Celsius).

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The CAS Registry Number for brucine is 357-57-3.

Answer: True

Explanation: The CAS Registry Number for brucine is indeed 357-57-3, serving as a unique identifier.

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Brucine is chemically identical to strychnine.

Answer: False

Explanation: While chemically related and convertible into the same molecule, brucine and strychnine are distinct compounds with different structures and properties.

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Brucine's chemical formula is C23H26N2O4.

Answer: True

Explanation: The chemical formula for brucine is correctly stated as C23H26N2O4.

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What is brucine primarily classified as?

Answer: A naturally occurring alkaloid that is poisonous

Explanation: Brucine is primarily classified as a poisonous, naturally occurring alkaloid.

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Which analytical technique is mentioned in the source for detecting and quantifying brucine?

Answer: Liquid Chromatography-Mass Spectrometry (LC-MS)

Explanation: Liquid Chromatography-Mass Spectrometry (LC-MS) is cited as a technique for detecting and quantifying brucine.

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What observable reaction indicates the presence of nitrates when brucine and potassium nitrate are mixed with formic acid?

Answer: The solution turns red instantly.

Explanation: The presence of nitrates is indicated by an immediate red color change when brucine and potassium nitrate are reacted with formic acid.

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The IUPAC name for brucine is given as:

Answer: 2,3-Dimethoxystrychnidin-10-one

Explanation: The official IUPAC name for brucine is 2,3-Dimethoxystrychnidin-10-one.

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Natural Sources and Discovery

Brucine is a synthetic alkaloid first isolated in the early 20th century.

Answer: False

Explanation: Brucine is a naturally occurring alkaloid, not a synthetic one. It was discovered in 1819, not the early 20th century.

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The primary natural source from which brucine is commonly extracted is the *Strychnos nux-vomica* tree.

Answer: True

Explanation: Brucine is indeed most commonly extracted from the *Strychnos nux-vomica* tree, also known as the poison nut tree.

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The name 'brucine' originates from the genus *Brucea*, which was named in honor of James Bruce, an explorer who introduced *Brucea antidysenterica* from Ethiopia.

Answer: True

Explanation: The nomenclature of brucine is derived from the genus *Brucea*, established in honor of James Bruce, who introduced the plant *Brucea antidysenterica* from Ethiopia.

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Brucine was first discovered in 1819 by the French chemists Pierre Joseph Pelletier and Joseph Bienaimé Caventou.

Answer: True

Explanation: The initial isolation and discovery of brucine were accomplished in 1819 by the French chemists Pierre Joseph Pelletier and Joseph Bienaimé Caventou.

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Brucine was initially isolated from the seeds of the *Strychnos nux-vomica* tree.

Answer: False

Explanation: Brucine was initially isolated from the bark of the *Strychnos nux-vomica* tree, not the seeds.

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In 1884, chemist Hanssen proved that brucine and strychnine could be converted into different, unrelated molecules.

Answer: False

Explanation: In 1884, Hanssen demonstrated that brucine and strychnine could be converted into the *same* molecule, establishing their close chemical relationship.

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Historically, brucine was distinguished from strychnine by its identical reaction patterns with chromic acid.

Answer: False

Explanation: Historically, brucine was distinguished from strychnine by their *different* reaction patterns when treated with chromic acid.

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In which plant is brucine most commonly found?

Answer: *Strychnos nux-vomica*

Explanation: Brucine is most commonly found in the *Strychnos nux-vomica* tree.

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The name 'brucine' originates from a genus named in honor of which historical figure?

Answer: James Bruce

Explanation: The genus *Brucea*, from which 'brucine' is derived, was named in honor of the explorer James Bruce.

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Who were the French scientists credited with the initial discovery of brucine?

Answer: Pelletier and Caventou

Explanation: Pierre Joseph Pelletier and Joseph Bienaimé Caventou, French chemists, are credited with the initial discovery of brucine in 1819.

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From which specific part of the *Strychnos nux-vomica* tree was brucine first isolated?

Answer: The bark

Explanation: Brucine was first isolated from the bark of the *Strychnos nux-vomica* tree.

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What did Hanssen demonstrate in 1884 regarding the chemical relationship between brucine and strychnine?

Answer: Both can be converted into the same molecule.

Explanation: Hanssen's 1884 work showed that both brucine and strychnine could be chemically converted into the same molecular structure, indicating a close relationship.

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How did chemists historically differentiate brucine from strychnine?

Answer: By their reaction patterns with chromic acid

Explanation: Historically, the differentiation between brucine and strychnine was achieved by observing their distinct reaction patterns when treated with chromic acid.

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The historical differentiation of brucine from strychnine using chromic acid relied on:

Answer: Different reaction patterns

Explanation: The historical method for distinguishing brucine from strychnine involved observing their different reaction patterns when treated with chromic acid.

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Chemical Applications and Synthesis

In chemical synthesis, brucine can be employed to facilitate the creation of molecules with a specific three-dimensional structure.

Answer: True

Explanation: Brucine's chiral nature makes it a valuable tool in stereospecific chemical syntheses, enabling the creation of molecules with precise three-dimensional arrangements.

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Due to its large chiral molecular structure, brucine is valuable for separating mirror-image forms of molecules.

Answer: True

Explanation: Brucine's significant chiral structure allows it to be used effectively in chiral resolution, a process critical for separating enantiomers (mirror-image isomers).

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Fisher first reported the use of brucine as a resolving agent in the year 1899.

Answer: True

Explanation: The use of brucine as a resolving agent was first documented by Fisher in 1899.

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Marckwald reported in 1904 that brucine was the first *synthetic* compound successfully used as an organocatalyst for enantiomeric enrichment.

Answer: False

Explanation: Marckwald reported in 1904 that brucine was the first *natural product* used as an organocatalyst for enantiomeric enrichment, not a synthetic compound.

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Brucine's bromide salt has been employed in High-Performance Liquid Chromatography (HPLC) as a component of the mobile phase.

Answer: False

Explanation: Brucine's bromide salt has been utilized as a *stationary phase* in HPLC columns, not as a component of the mobile phase.

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Brucine is used in fractional crystallization processes, specifically in acetone, to separate compounds like dihydroxy fatty acids.

Answer: True

Explanation: Brucine is indeed employed in fractional crystallization, often in acetone, for the separation of compounds such as dihydroxy fatty acids and diaryl carbinols.

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Brucine's chiral nature is irrelevant for its use in chemical resolution.

Answer: False

Explanation: Brucine's chiral nature is highly relevant and essential for its application in chemical resolution, enabling the separation of enantiomers.

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Which of the following is a practical application of brucine in chemical synthesis?

Answer: As a tool for stereospecific chemical syntheses

Explanation: Brucine's chiral structure makes it valuable for stereospecific syntheses, enabling the control of molecular three-dimensional arrangements.

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Brucine's utility in chiral resolution stems from which property?

Answer: Its large chiral molecular structure

Explanation: The effectiveness of brucine in chiral resolution is directly attributed to its large and complex chiral molecular structure.

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In what year did Fisher first document the use of brucine as a resolving agent?

Answer: 1899

Explanation: Fisher first reported the application of brucine as a resolving agent in the year 1899.

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What significant achievement in organocatalysis was reported by Marckwald in 1904 involving brucine?

Answer: It was the first natural product used to achieve enantiomeric enrichment.

Explanation: Marckwald's 1904 report highlighted brucine as the first natural product successfully employed as an organocatalyst to achieve enantiomeric enrichment.

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How has brucine's bromide salt been employed in HPLC?

Answer: As a stationary phase in columns for separating ionic enantiomers.

Explanation: Brucine's bromide salt has been utilized as a stationary phase in HPLC columns, facilitating the separation of ionic enantiomers.

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Brucine is used in fractional crystallization, often in acetone, for separating which types of compounds?

Answer: Dihydroxy fatty acids and diaryl carbinols

Explanation: Brucine is employed in fractional crystallization processes, particularly in acetone, for the separation of compounds such as dihydroxy fatty acids and diaryl carbinols.

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What is the significance of brucine being a chiral molecule in chemistry?

Answer: It allows it to be used in separating enantiomers.

Explanation: As a chiral molecule, brucine possesses a non-superimposable mirror image structure, which is fundamental to its utility in separating enantiomers (chiral resolution).

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Toxicology and Safety Information

Brucine poisoning is considered common because brucine is significantly more toxic than strychnine.

Answer: False

Explanation: Brucine poisoning is considered rare because brucine is significantly less toxic than strychnine. When ingested together, the more potent effects of strychnine are typically observed first.

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Common symptoms of brucine intoxication include muscle relaxation and euphoria.

Answer: False

Explanation: Symptoms of brucine intoxication typically include muscle spasms and convulsions, not muscle relaxation and euphoria.

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Brucine mimics strychnine's mechanism of action by acting as an antagonist at glycine receptors, thus paralyzing inhibitory neurons.

Answer: True

Explanation: Brucine functions similarly to strychnine by antagonizing glycine receptors, leading to the paralysis of inhibitory neurons.

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The estimated lethal dose of brucine for adult humans is approximately 10 grams.

Answer: False

Explanation: The probable lethal dose of brucine for adult humans is estimated to be 1 gram, significantly less than 10 grams.

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The GHS pictogram for brucine typically depicts a flame.

Answer: False

Explanation: The GHS pictogram associated with brucine's toxicity is typically a skull, not a flame.

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Brucine's GHS signal word is 'Warning'.

Answer: False

Explanation: Brucine's GHS signal word is 'Danger', indicating a higher level of hazard than 'Warning'.

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H300 is a GHS hazard statement indicating that brucine is fatal if swallowed.

Answer: True

Explanation: The GHS hazard statement H300 specifically denotes that the substance is fatal if swallowed.

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P270 is a precautionary statement advising users to wear respiratory protection when handling brucine.

Answer: False

Explanation: The precautionary statement P270 advises users 'Do not eat, drink or smoke when using this product.' Wearing respiratory protection is covered by P284.

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Brucine is assigned UN number 1570 for transportation.

Answer: True

Explanation: UN number 1570 is assigned to brucine for regulatory purposes during transportation.

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Brucine paralyzes inhibitory neurons by blocking glycine receptors.

Answer: True

Explanation: Brucine's mechanism of action involves blocking glycine receptors, which are crucial for inhibitory neurotransmission, leading to paralysis.

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Brucine acts as an agonist at glycine receptors.

Answer: False

Explanation: Brucine acts as an *antagonist* at glycine receptors, not an agonist.

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The LD50 for brucine in rabbits via oral administration is 4 mg/kg.

Answer: True

Explanation: The median lethal dose (LD50) for brucine in rabbits administered orally is documented as 4 mg/kg.

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Brucine's GHS hazard statement H412 means it is non-toxic to aquatic life.

Answer: False

Explanation: The GHS hazard statement H412 signifies that brucine is *harmful* to aquatic life with long-lasting effects, not non-toxic.

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Why is brucine poisoning relatively rare in clinical observations?

Answer: It is usually ingested alongside the much more toxic strychnine.

Explanation: Brucine poisoning is rare because it is often ingested with strychnine, which is considerably more toxic, leading to symptoms dominated by strychnine poisoning.

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Which of the following is a symptom associated with brucine intoxication?

Answer: Muscle spasms and convulsions

Explanation: Muscle spasms and convulsions are characteristic symptoms of brucine intoxication.

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Brucine's mechanism of action involves blocking which type of receptors in the nervous system?

Answer: Glycine receptors

Explanation: Brucine exerts its toxic effects by blocking glycine receptors in the nervous system.

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What is the estimated probable lethal dose of brucine for adult humans?

Answer: 1 gram

Explanation: The estimated probable lethal dose of brucine for adult humans is approximately 1 gram.

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Which of the following statements about brucine's toxicity is accurate according to the source?

Answer: It is less toxic than strychnine.

Explanation: Brucine is less toxic than strychnine. This difference in toxicity contributes to brucine poisoning being relatively rare when both are present.

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What is the GHS pictogram associated with brucine typically represented by?

Answer: A skull

Explanation: The GHS pictogram commonly associated with brucine, due to its toxicity, is the skull symbol.

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Historical and Traditional Uses

In traditional Chinese medicine, brucine is primarily utilized for its stimulant and energizing properties.

Answer: False

Explanation: In traditional Chinese medicine, brucine is primarily used for its anti-inflammatory and analgesic properties, not for stimulant or energizing effects.

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Brucine is used as a denaturant to make ethyl alcohol unfit for human consumption, allowing for tax-free industrial use.

Answer: True

Explanation: Brucine serves as a denaturant in industrial alcohol, rendering it unfit for consumption and thus eligible for tax-free industrial applications.

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Brucine is found in some traditional medicines used in Ayurveda and homeopathy.

Answer: True

Explanation: Brucine is documented as being present in certain traditional medicinal preparations within Ayurveda and homeopathy.

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Brucine is used to make industrial alcohol safe for drinking.

Answer: False

Explanation: Brucine is used as a denaturant to make industrial alcohol *unfit* for drinking, not safe for it.

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Which traditional medicine system uses brucine as an anti-inflammatory agent and analgesic?

Answer: Traditional Chinese Medicine

Explanation: Traditional Chinese Medicine utilizes brucine for its anti-inflammatory and analgesic properties.

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In the industrial processing of alcohol, brucine serves what purpose?

Answer: As a denaturant to make it unfit for consumption

Explanation: Brucine functions as a denaturant in industrial alcohol, rendering it unfit for human consumption.

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Brucine is found in drugs used in which traditional medicine systems, besides Traditional Chinese Medicine?

Answer: Ayurveda and Homeopathy

Explanation: In addition to Traditional Chinese Medicine, brucine is also found in some traditional medicines used in Ayurveda and homeopathy.

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Brucine's use as a denaturant for industrial alcohol means it is added to:

Answer: Render the alcohol unfit for human consumption

Explanation: When used as a denaturant, brucine is added to industrial alcohol to make it unfit for human consumption, thereby allowing for tax exemptions.

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Cultural and Fictional References

Brucine is famously referenced in Alexandre Dumas' classic novel *The Count of Monte Cristo*.

Answer: True

Explanation: The novel *The Count of Monte Cristo* by Alexandre Dumas features a notable reference to brucine.

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In *The Count of Monte Cristo*, brucine is discussed as a potential component in developing immunity to poisons through gradual dosing.

Answer: True

Explanation: Within *The Count of Monte Cristo*, brucine is mentioned in the context of mithridatism, the practice of developing immunity to poisons through gradual exposure.

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The film *The Mechanic*, released in 1972, depicts a character using brucine as a poison.

Answer: True

Explanation: The 1972 film *The Mechanic* includes a plot point where a character utilizes brucine as a poison.

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Fictional portrayals of brucine as a covert poison accurately reflect its extreme bitterness, making it easy to administer undetected.

Answer: False

Explanation: Fictional portrayals often fail to account for brucine's extreme bitterness, which would make covert administration difficult due to gag reflexes, despite its toxicity.

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The extreme bitterness of brucine makes it an ideal covert poison in real-world scenarios.

Answer: False

Explanation: The extreme bitterness of brucine makes it impractical as a covert poison, as even small amounts would likely cause gagging and detection, contrary to fictional portrayals.

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Brucine is famously referenced in which classic novel?

Answer: The Count of Monte Cristo

Explanation: Alexandre Dumas' novel, *The Count of Monte Cristo*, contains a notable reference to brucine.

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How is brucine's extreme bitterness relevant to its portrayal as a poison?

Answer: Its bitterness makes it difficult to administer covertly.

Explanation: The extreme bitterness of brucine poses a challenge for covert administration, as it would likely be detected by taste, contrasting with some fictional depictions.

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