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Questions and Answers
Which of the following plant families is NOT known for typically having high alkaloid levels?
Which of the following plant families is NOT known for typically having high alkaloid levels?
Which of the following alkaloids does NOT belong to the pyridine group?
Which of the following alkaloids does NOT belong to the pyridine group?
Which of the following represents the correct classification for reserpine?
Which of the following represents the correct classification for reserpine?
Vinblastine and vincristine, derived from Vinca alkaloids, are primarily used for what therapeutic purpose?
Vinblastine and vincristine, derived from Vinca alkaloids, are primarily used for what therapeutic purpose?
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Which characteristic is least likely to be associated with alkaloids?
Which characteristic is least likely to be associated with alkaloids?
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Which group of alkaloids includes compounds known for their effect on microtubule polymerization?
Which group of alkaloids includes compounds known for their effect on microtubule polymerization?
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An organic chemist isolates a compound from a plant extract. Initial tests reveal it contains nitrogen, is slightly alkaline, and produces a noticeable physiological effect on lab mice. Based on this information, the compound is most likely a(n):
An organic chemist isolates a compound from a plant extract. Initial tests reveal it contains nitrogen, is slightly alkaline, and produces a noticeable physiological effect on lab mice. Based on this information, the compound is most likely a(n):
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Which of the following alkaloids is derived from the isoquinoline group?
Which of the following alkaloids is derived from the isoquinoline group?
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Which of the following amino acids is least likely to be a precursor in the biosynthesis of an alkaloid?
Which of the following amino acids is least likely to be a precursor in the biosynthesis of an alkaloid?
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Identify the alkaloid that contains a steroidal structure.
Identify the alkaloid that contains a steroidal structure.
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Which of the following is a phenethylamine alkaloid?
Which of the following is a phenethylamine alkaloid?
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A researcher discovers a new indolizidine alkaloid with significant anti-inflammatory properties. Considering the known sources of these compounds, from which of the following sources could this alkaloid have been isolated?
A researcher discovers a new indolizidine alkaloid with significant anti-inflammatory properties. Considering the known sources of these compounds, from which of the following sources could this alkaloid have been isolated?
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A pharmaceutical company is developing a new pain reliever. Based on the examples provided, which naturally occurring alkaloid would be most likely to serve as a starting point or inspiration for their research?
A pharmaceutical company is developing a new pain reliever. Based on the examples provided, which naturally occurring alkaloid would be most likely to serve as a starting point or inspiration for their research?
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Which of these alkaloids is associated with anticancer drug development?
Which of these alkaloids is associated with anticancer drug development?
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A marine biologist is studying dinoflagellates. If they are investigating the source of saxitoxin, which genus should they focus on?
A marine biologist is studying dinoflagellates. If they are investigating the source of saxitoxin, which genus should they focus on?
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An investigator is analyzing a sample that may contain alkaloids. What is the most likely reason they would use an acid-base extraction technique during the purification process?
An investigator is analyzing a sample that may contain alkaloids. What is the most likely reason they would use an acid-base extraction technique during the purification process?
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The formation of a dark blue color is indicative of what result?
The formation of a dark blue color is indicative of what result?
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Which structural component is present in both psychoactive alkaloids and the neurotransmitter serotonin?
Which structural component is present in both psychoactive alkaloids and the neurotransmitter serotonin?
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How does synthetic LSD differ structurally from the ergine found in morning glories, and what is the consequence of this difference?
How does synthetic LSD differ structurally from the ergine found in morning glories, and what is the consequence of this difference?
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Native Indians of Mexico prize Ipomoea tricolor for its seeds, which they call 'tlitliltzin'. What is the primary psychoactive compound found in these seeds?
Native Indians of Mexico prize Ipomoea tricolor for its seeds, which they call 'tlitliltzin'. What is the primary psychoactive compound found in these seeds?
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Catharanthus roseus was studied after Jamaicans used it to treat diabetes. What discovery regarding its alkaloid content led to further research?
Catharanthus roseus was studied after Jamaicans used it to treat diabetes. What discovery regarding its alkaloid content led to further research?
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Vincristine and vinblastine, alkaloids derived from Catharanthus roseus, are primarily known for what therapeutic property?
Vincristine and vinblastine, alkaloids derived from Catharanthus roseus, are primarily known for what therapeutic property?
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Why is vincristine still primarily isolated from Catharanthus roseus rather than synthesized in a lab?
Why is vincristine still primarily isolated from Catharanthus roseus rather than synthesized in a lab?
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Which of the following best describes the action of ergine and psilocybin in the brain?
Which of the following best describes the action of ergine and psilocybin in the brain?
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Which of the following best describes a key difference in the typical sites of origin between Hodgkin's lymphoma and non-Hodgkin's lymphoma?
Which of the following best describes a key difference in the typical sites of origin between Hodgkin's lymphoma and non-Hodgkin's lymphoma?
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Vinblastine is contraindicated in patients with bacterial infections due to what primary concern?
Vinblastine is contraindicated in patients with bacterial infections due to what primary concern?
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Considering its mechanism of action, which metabolic process is most likely affected by vinblastine, leading to its anticancer effects?
Considering its mechanism of action, which metabolic process is most likely affected by vinblastine, leading to its anticancer effects?
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What is the primary rationale for not administering vinblastine to pregnant women?
What is the primary rationale for not administering vinblastine to pregnant women?
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A patient undergoing vinblastine treatment experiences a significant drop in their white blood cell count. What dose-limiting side effect is the patient experiencing?
A patient undergoing vinblastine treatment experiences a significant drop in their white blood cell count. What dose-limiting side effect is the patient experiencing?
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Why are synthetic alkaloids increasingly utilized as substitutes for quinine?
Why are synthetic alkaloids increasingly utilized as substitutes for quinine?
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A researcher aims to extract quinoline alkaloids from Cinchona bark. Which factor will LEAST influence the yield and composition of these alkaloids?
A researcher aims to extract quinoline alkaloids from Cinchona bark. Which factor will LEAST influence the yield and composition of these alkaloids?
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Which of the subsequent conditions is vincristine primarily used to manage?
Which of the subsequent conditions is vincristine primarily used to manage?
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Why has the use of Cinchona bark in malaria treatment declined?
Why has the use of Cinchona bark in malaria treatment declined?
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Which of the following alkaloids is NOT a primary constituent of Cinchona?
Which of the following alkaloids is NOT a primary constituent of Cinchona?
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What is the starting product for the biosynthesis of berberine, papaverine, and morphine?
What is the starting product for the biosynthesis of berberine, papaverine, and morphine?
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What characteristic defines alkaloids found in the opium poppy?
What characteristic defines alkaloids found in the opium poppy?
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Why can consuming poppy seeds lead to a positive result in drug tests?
Why can consuming poppy seeds lead to a positive result in drug tests?
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What process transforms morphine into heroin?
What process transforms morphine into heroin?
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Considering its historical and current applications, which statement best describes the use of chloroquine?
Considering its historical and current applications, which statement best describes the use of chloroquine?
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If a researcher is studying the biosynthesis of benzylisoquinolines, which starting material would be most appropriate based on the information provided?
If a researcher is studying the biosynthesis of benzylisoquinolines, which starting material would be most appropriate based on the information provided?
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Codeine is often combined with other medications. Which of the following is it commonly combined with?
Codeine is often combined with other medications. Which of the following is it commonly combined with?
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Heroin is derived from which other substance?
Heroin is derived from which other substance?
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What is the most common form of heroin?
What is the most common form of heroin?
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What physiological effect does Samandarin, an alkaloid secreted by salamanders, have on vertebrates?
What physiological effect does Samandarin, an alkaloid secreted by salamanders, have on vertebrates?
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Which defense mechanism do Salamandra salamandra adults employ when grasped by a predator?
Which defense mechanism do Salamandra salamandra adults employ when grasped by a predator?
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Compared to batrachotoxins, how would you describe pumiliotoxins?
Compared to batrachotoxins, how would you describe pumiliotoxins?
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Pumiliotoxins primarily interfere with which physiological process?
Pumiliotoxins primarily interfere with which physiological process?
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Within pumiliotoxins, the toxicity levels vary. Which of the following correctly orders pumiliotoxins A, B, and C from most to least toxic?
Within pumiliotoxins, the toxicity levels vary. Which of the following correctly orders pumiliotoxins A, B, and C from most to least toxic?
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Flashcards
Plant Families High in Alkaloids
Plant Families High in Alkaloids
Families like Papaveraceae, Solanaceae, and Rubiaceae contain high levels of alkaloids.
Epedrine
Epedrine
An alkaloid with exocyclic nitrogen found in the group of aliphatic amines.
Putresine, Spermidine, Spermine
Putresine, Spermidine, Spermine
Types of alkaloids that include Pausine and cadonocarpine.
Peptide Alkaloids
Peptide Alkaloids
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Pyridine Group Alkaloids
Pyridine Group Alkaloids
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Tropane Alkaloids
Tropane Alkaloids
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Vinca Alkaloids
Vinca Alkaloids
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Psychoactive Alkaloids
Psychoactive Alkaloids
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Alkaloids
Alkaloids
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Sources of Alkaloids
Sources of Alkaloids
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Pharmacological Effects
Pharmacological Effects
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Indolizidine Alkaloids
Indolizidine Alkaloids
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Biosynthesis Precursor
Biosynthesis Precursor
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Morphine
Morphine
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Venomous Alkaloids
Venomous Alkaloids
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Clinical Testing Alkaloids
Clinical Testing Alkaloids
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LSD
LSD
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Ergine
Ergine
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Indole structure
Indole structure
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Psilocybin
Psilocybin
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Vincristine
Vincristine
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Catharanthus roseus
Catharanthus roseus
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Psychedelic effects
Psychedelic effects
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Codeine
Codeine
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Heroin
Heroin
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Samandarin
Samandarin
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Dendrobates tinctorius
Dendrobates tinctorius
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Pumiliotoxins
Pumiliotoxins
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Batrachotoxin
Batrachotoxin
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Calcium channels
Calcium channels
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Tolerance to opioids
Tolerance to opioids
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Cinchona
Cinchona
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Quinine
Quinine
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Chloroquine
Chloroquine
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Mefloquine
Mefloquine
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Isoquinoline Alkaloids
Isoquinoline Alkaloids
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Opium Poppy
Opium Poppy
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Opium Alkaloids
Opium Alkaloids
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Vinblastine
Vinblastine
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Non-Hodgkin's Lymphoma
Non-Hodgkin's Lymphoma
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Hodgkin Lymphoma
Hodgkin Lymphoma
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Half-life of Vinblastine
Half-life of Vinblastine
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Quinoline Alkaloids
Quinoline Alkaloids
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Side effects of Vinblastine
Side effects of Vinblastine
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Study Notes
Alkaloids
- Alkaloids are naturally occurring amines produced by plants, animals, and fungi.
- Many alkaloids have pharmacological effects on humans and other animals.
- The term "alkaloid" originates from the word "alkaline," previously used to describe nitrogen-containing bases.
- Alkaloids are typically derivatives of amino acids and often have a bitter taste.
- They are found as secondary metabolites in plants (e.g., potatoes, tomatoes), animals (e.g., salamanders, frogs), and fungi.
- Many alkaloids are purified from crude extracts using acid-base extraction.
- While many are poisonous, some are used medicinally as analgesics (pain relievers) or anaesthetics (e.g., morphine, codeine).
Examples of Alkaloids and their Sources
- Morphine: Papaver somniferum (opium poppy) - analgesic
- Vinblastine: Catharanthus roseus (Madagascar periwinkle) - anticancer
- Lisergic acid: Claviceps purpurea (ergot fungus)
- Saxitoxin: Gonyaulax tamarensis (a dinoflagellate)
- Tetradotoxin: Spheroides rubripes (pufferfish), frogs, toads
- Various alkaloids are present in other plants and animals.
Indolizidine Alkaloids
- Indolizidine alkaloids are chemical constituents isolated from various marine and terrestrial plants and animals, including trees, fungi, ants, and frogs.
- They exhibit a wide array of important biological activities.
- Examples of well-known indolizidine alkaloids include:
- Swainsonine: from the fungus Rhizoctonia leguminicola. This is under clinical testing for anti-cancer applications.
- Pumilotoxin B: from Dendrobatid Amazonian frogs, which is a potent cardiovascular agent.
Alkaloid Characteristics
- Alkalinity: Alkaloids possess a basic character due to the nitrogen atoms in their molecules. They react with acids to form alkaloid salts.
- Solubility: Alkaloids are generally soluble in organic solvents like chloroform, but insoluable in water. Alkaloid salts, on the other hand, are soluble in water.
Alkaloid Detection and Stability
- Color reaction: Alkaloids can produce various colors when reacted with suitable reagents (e.g., Ehrlich reagent, Dragendorff reagent).
- Precipitation: Alkaloids in small quantities can precipitate when mixed with specific reagents (e.g., Mayer, Wagner, Dragendorff, Hager reagents provide white, brown, orange, and yellow precipitates, respectively).
- Stability to heat: Most alkaloids are unstable above 70°C, decomposing at high temperatures.
Alkaloid Activities
- Alkaloids exhibit a broad range of pharmacological activities, despite being present in minute quantities.
Classification of Alkaloids
- Alkaloids with exocyclic nitrogen and aliphatic amine: Example: Ephedrine
- Putrescine, spermidine, and spermine alkaloids: Examples: Pausine, cadonocarpine
- Peptide alkaloids: Example: Integerine
- Steroids and terpenoids alkaloids: Examples: Akonitine, salonidine
- Heterocyclic alkaloids: Various types of skeletons, including:
- Pyridine group: Piperine, coniine, trigonelline, etc.
- Pyrrolidine group: Hygrine, cuscohygrine, nicotine
- Tropane group: Atropine, cocaine, ecgonine, scopolamine
- Quinoline group: Quinine, quinidine, dihydroquinine, strychnine, brucine, veratrine, and cevadine
- Isoquinoline group: Morphine, codeine, thebaine, papaverine, narcotine, sanguinarine, narceine, hydrastine, berberine
- Phenethylamine group: Mescaline, ephedrine, dopamine, amphetamine
- Indole group: Tryptamines (DMT, N-methyltryptamine), psilocybin, serotonin, ergot alkaloids (ergine, ergotamine, lysergic acid), beta-carbolines (harmine, harmaline, yohimbine), reserpine, emetine
- Pyrrole group: Various pyrrole based alkaloids, also in Conocybe and Psilocybe fungi
- Purine group: Xanthines (caffeine, theobromine, theophylline)
- Terpenoid group: Aconite alkaloids (aconitine), steroids (solanine, samandaris, muscarine, choline, neurine) and Vinca alkaloids (Vinblastine, Vincristine)
- Steroidal: Solanum and Veratrum alkaloids
- Others: Further classification like those associated with the pyridine ring in tobacco.
Alkaloids from Plants and Animals
- Alkaloids occur in various plant species, and also in some animals (e.g., frogs, toads, and certain insects).
Alkaloid Biosynthesis
- Various amino acids (e.g., phenylalanine, tyrosine, lysine, ornithine, tryptophan) are involved in the synthesis of alkaloids.
- Biosynthetic pathways for specific alkaloids are detailed in the presentation.
Alkaloids in Natural Product Chemistry
- The accumulation of alkaloids is related to families of plants.
- Examples are given for plant families with high levels of alkaloids.
- There is historical use of alkaloids for medicinal, religious and other applications.
Additional Specific Alkaloid Information
- Details on specific alkaloids, including their structures, effects, sources, use in medications and isolation
Cinchona and its Alkaloids
- Cinchona bark is a source of quinine, quinidine, cinchonine, and cinchonidine.
- Quinine is a widely known antimalarial agent, with synthetic alternatives.
Vinca Alkaloids
- Vinca alkaloids (vincristine and vinblastine) are effective anti-cancer drugs.
Tropane Alkaloids
- Tropane alkaloids have applications in medicine and as drugs of abuse.
- Related to Solanaceae (e.g., Datura, nightshade) and Erythroxylaceae.
- Examples include atropine and scopolamine.
Other Alkaloids
- Information about other classes, sources, and properties of various alkaloids are included.
Alkaloids from Animals (additional details)
- Descriptions of the various toxins found, and animals.
- Details on the chemical structures of pumiliotoxins, tetrodotoxins, bufotoxins
- Information on their effects and defensive mechanisms in animals
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Description
Test your knowledge of alkaloids! This quiz covers plant families, alkaloid classifications (pyridine, isoquinoline), therapeutic uses (vinblastine, vincristine), biosynthesis, and key characteristics. Identify alkaloid precursors and effects.