Alkaloids: Chemistry and Pharmacology
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Questions and Answers

Which of the following plant families is NOT known for typically having high alkaloid levels?

  • Rutaceae
  • Solanaceae
  • Papaveraceae
  • Asteraceae (correct)
  • Which of the following alkaloids does NOT belong to the pyridine group?

  • Nicotine
  • Atropine (correct)
  • Pilocarpine
  • Coniine
  • Which of the following represents the correct classification for reserpine?

  • Terpenoid alkaloid
  • Indole alkaloid (correct)
  • Steroid alkaloid
  • Purine alkaloid
  • Vinblastine and vincristine, derived from Vinca alkaloids, are primarily used for what therapeutic purpose?

    <p>Antineoplastic agents (C)</p> Signup and view all the answers

    Which characteristic is least likely to be associated with alkaloids?

    <p>Found exclusively in terrestrial plants. (C)</p> Signup and view all the answers

    Which group of alkaloids includes compounds known for their effect on microtubule polymerization?

    <p>Vinca alkaloids (A)</p> Signup and view all the answers

    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):

    <p>Alkaloid. (C)</p> Signup and view all the answers

    Which of the following alkaloids is derived from the isoquinoline group?

    <p>Morphine (A)</p> Signup and view all the answers

    Which of the following amino acids is least likely to be a precursor in the biosynthesis of an alkaloid?

    <p>Alanine. (C)</p> Signup and view all the answers

    Identify the alkaloid that contains a steroidal structure.

    <p>Solanine (D)</p> Signup and view all the answers

    Which of the following is a phenethylamine alkaloid?

    <p>Ephedrine (A)</p> Signup and view all the answers

    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?

    <p>A newly identified species of Amazonian frog. (C)</p> Signup and view all the answers

    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?

    <p>Morphine. (C)</p> Signup and view all the answers

    Which of these alkaloids is associated with anticancer drug development?

    <p>Swainsonine. (B)</p> Signup and view all the answers

    A marine biologist is studying dinoflagellates. If they are investigating the source of saxitoxin, which genus should they focus on?

    <p>Gonyaulax. (A)</p> Signup and view all the answers

    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?

    <p>To selectively protonate and deprotonate the alkaloids. (B)</p> Signup and view all the answers

    The formation of a dark blue color is indicative of what result?

    <p>Positive results (D)</p> Signup and view all the answers

    Which structural component is present in both psychoactive alkaloids and the neurotransmitter serotonin?

    <p>Indole structure (B)</p> Signup and view all the answers

    How does synthetic LSD differ structurally from the ergine found in morning glories, and what is the consequence of this difference?

    <p>It has two additional ethyl groups, making it approximately 100 times more potent. (D)</p> Signup and view all the answers

    Native Indians of Mexico prize Ipomoea tricolor for its seeds, which they call 'tlitliltzin'. What is the primary psychoactive compound found in these seeds?

    <p>Ergine (d-lysergic acid amide) (A)</p> Signup and view all the answers

    Catharanthus roseus was studied after Jamaicans used it to treat diabetes. What discovery regarding its alkaloid content led to further research?

    <p>It contained a diverse range of alkaloids with various medicinal properties. (D)</p> Signup and view all the answers

    Vincristine and vinblastine, alkaloids derived from Catharanthus roseus, are primarily known for what therapeutic property?

    <p>Anticancer (B)</p> Signup and view all the answers

    Why is vincristine still primarily isolated from Catharanthus roseus rather than synthesized in a lab?

    <p>The structure is too complex to efficiently synthesize. (B)</p> Signup and view all the answers

    Which of the following best describes the action of ergine and psilocybin in the brain?

    <p>They interfere with the action of serotonin, potentially causing hallucinations. (D)</p> Signup and view all the answers

    Which of the following best describes a key difference in the typical sites of origin between Hodgkin's lymphoma and non-Hodgkin's lymphoma?

    <p>Hodgkin's lymphoma typically begins in the upper body, while non-Hodgkin's lymphoma can arise in lymph nodes throughout the body. (D)</p> Signup and view all the answers

    Vinblastine is contraindicated in patients with bacterial infections due to what primary concern?

    <p>Exacerbation of the bacterial infection by suppressing the immune system. (B)</p> Signup and view all the answers

    Considering its mechanism of action, which metabolic process is most likely affected by vinblastine, leading to its anticancer effects?

    <p>Glutamic acid metabolism (B)</p> Signup and view all the answers

    What is the primary rationale for not administering vinblastine to pregnant women?

    <p>It has been shown to cause severe birth defects in animal studies. (C)</p> Signup and view all the answers

    A patient undergoing vinblastine treatment experiences a significant drop in their white blood cell count. What dose-limiting side effect is the patient experiencing?

    <p>Bone marrow damage (C)</p> Signup and view all the answers

    Why are synthetic alkaloids increasingly utilized as substitutes for quinine?

    <p>Synthetic alkaloids are cheaper to produce and can overcome quinine supply limitations. (B)</p> Signup and view all the answers

    A researcher aims to extract quinoline alkaloids from Cinchona bark. Which factor will LEAST influence the yield and composition of these alkaloids?

    <p>The relative humidity during bark storage. (C)</p> Signup and view all the answers

    Which of the subsequent conditions is vincristine primarily used to manage?

    <p>Childhood leukemias (C)</p> Signup and view all the answers

    Why has the use of Cinchona bark in malaria treatment declined?

    <p>Synthetic drugs have been developed as alternatives. (C)</p> Signup and view all the answers

    Which of the following alkaloids is NOT a primary constituent of Cinchona?

    <p>Morphine (A)</p> Signup and view all the answers

    What is the starting product for the biosynthesis of berberine, papaverine, and morphine?

    <p>Dopamine (A)</p> Signup and view all the answers

    What characteristic defines alkaloids found in the opium poppy?

    <p>A double carbon ring with one nitrogen atom. (C)</p> Signup and view all the answers

    Why can consuming poppy seeds lead to a positive result in drug tests?

    <p>Poppy seeds may contain trace amounts of opium alkaloids. (C)</p> Signup and view all the answers

    What process transforms morphine into heroin?

    <p>Acetylation (C)</p> Signup and view all the answers

    Considering its historical and current applications, which statement best describes the use of chloroquine?

    <p>It was initially for malaria, then repurposed for other conditions. (A)</p> Signup and view all the answers

    If a researcher is studying the biosynthesis of benzylisoquinolines, which starting material would be most appropriate based on the information provided?

    <p>Two molecules of tyrosine (A)</p> Signup and view all the answers

    Codeine is often combined with other medications. Which of the following is it commonly combined with?

    <p>Acetaminophen or aspirin (B)</p> Signup and view all the answers

    Heroin is derived from which other substance?

    <p>Morphine (B)</p> Signup and view all the answers

    What is the most common form of heroin?

    <p>Hydrochloride salt (A)</p> Signup and view all the answers

    What physiological effect does Samandarin, an alkaloid secreted by salamanders, have on vertebrates?

    <p>Strong muscle convulsions, high-blood pressure, combined with hyperventilation (B)</p> Signup and view all the answers

    Which defense mechanism do Salamandra salamandra adults employ when grasped by a predator?

    <p>Extrusion of toxic skin secretions (A)</p> Signup and view all the answers

    Compared to batrachotoxins, how would you describe pumiliotoxins?

    <p>Much weaker (B)</p> Signup and view all the answers

    Pumiliotoxins primarily interfere with which physiological process?

    <p>Calcium channels affecting muscle contraction (C)</p> Signup and view all the answers

    Within pumiliotoxins, the toxicity levels vary. Which of the following correctly orders pumiliotoxins A, B, and C from most to least toxic?

    <p>A &gt; B &gt; C (A)</p> Signup and view all the answers

    Flashcards

    Plant Families High in Alkaloids

    Families like Papaveraceae, Solanaceae, and Rubiaceae contain high levels of alkaloids.

    Epedrine

    An alkaloid with exocyclic nitrogen found in the group of aliphatic amines.

    Putresine, Spermidine, Spermine

    Types of alkaloids that include Pausine and cadonocarpine.

    Peptide Alkaloids

    A class of alkaloids that includes compounds like Integerine.

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    Pyridine Group Alkaloids

    Includes compounds like nicotine and coniine, known for their psychoactive effects.

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    Tropane Alkaloids

    Alkaloids like atropine and cocaine; known for their pharmacological effects.

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    Vinca Alkaloids

    Class of antineoplastic agents including vinblastine and vincristine.

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    Psychoactive Alkaloids

    Includes groups like Indole (serotonin, DMT) and Phenethylamine (amphetamine), affecting mood.

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    Alkaloids

    Naturally occurring amines produced by plants, animals, and fungi with pharmacological effects.

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    Sources of Alkaloids

    Alkaloids are found in about 15% of plants and some animals and fungi.

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    Pharmacological Effects

    Many alkaloids have medicinal uses such as analgesics and are sometimes poisonous.

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    Indolizidine Alkaloids

    A type of alkaloid with important biological activities isolated from various organisms.

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    Biosynthesis Precursor

    Alkaloids are synthesized from amino acids like phenylalanine and tryptophan.

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    Morphine

    An alkaloid derived from Papaver somniferum used as a powerful analgesic.

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    Venomous Alkaloids

    Some alkaloids like saxitoxin are toxic and can cause harm.

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    Clinical Testing Alkaloids

    Some alkaloids, such as swainsonine, are being tested as anti-cancer drugs.

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    LSD

    A potent psychedelic compound also known as d-lysergic acid diethylamide.

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    Ergine

    A natural alkaloid also known as d-lysergic acid amide found in morning glories.

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    Indole structure

    A double carbon-nitrogen ring found in psychedelic alkaloids and serotonin.

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    Psilocybin

    A psychoactive compound found in specific mushrooms, causing hallucinations.

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    Vincristine

    A potent antileukemic drug derived from Vinca rosea, used in cancer treatment.

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    Catharanthus roseus

    A plant known for its alkaloids that treat diabetes and contain anticancer properties.

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    Psychedelic effects

    Hallucinations, delusions, and visions caused by substances like LSD and psilocybin.

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    Codeine

    An opioid used for pain relief, available alone or with acetaminophen/aspirin.

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    Heroin

    A semi-synthetic opioid derived from morphine, has high addiction potential.

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    Samandarin

    A neurotoxic alkaloid from salamanders that causes muscle convulsions.

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    Dendrobates tinctorius

    A species of poison dart frog known for its skin toxins, including pumiliotoxins.

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    Pumiliotoxins

    Toxins found in the skin of poison dart frogs, less toxic than batrachotoxins.

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    Batrachotoxin

    A highly toxic substance produced by Phyllobates frogs.

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    Calcium channels

    Cell structures that pumiliotoxins affect, leading to paralysis or death.

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    Tolerance to opioids

    A condition where the body becomes less responsive to opioids over time.

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    Cinchona

    A plant historically significant in malaria treatment.

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    Quinine

    Main quinoline alkaloid in Cinchona for malaria.

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    Chloroquine

    An aminoquinolone developed for malaria in the 1940s.

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    Mefloquine

    An antimalarial drug developed after Chloroquine.

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    Isoquinoline Alkaloids

    A class of alkaloids with a double carbon ring and nitrogen.

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    Opium Poppy

    Source of isoquinoline alkaloids like morphine.

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    Opium Alkaloids

    Alkaloids from opium that are narcotic.

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    Vinblastine

    A chemotherapy drug primarily used for treating Hodgkin's disease and some lymphomas.

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    Non-Hodgkin's Lymphoma

    Cancer that starts in the lymphatic system, causing abnormal growth of lymphocytes.

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    Hodgkin Lymphoma

    A type of cancer in the lymph system characterized by the presence of Reed-Sternberg cells.

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    Half-life of Vinblastine

    Vinblastine's half-life in the bloodstream is 24 hours, meaning it takes this long for half of the drug to be removed.

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    Quinoline Alkaloids

    Alkaloids obtained from Cinchona bark, including quinine, used for treating malaria.

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    Side effects of Vinblastine

    Common side effects include hair loss, nausea, lowered blood cell counts, and mouth sores.

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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.

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