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Questions and Answers
What percentage of pharmaceuticals is reported to contain nitrogen?
What percentage of pharmaceuticals is reported to contain nitrogen?
Which group of molecules contains amino groups?
Which group of molecules contains amino groups?
What is one characteristic of amino acids?
What is one characteristic of amino acids?
What mechanism does aspirin use to treat pain?
What mechanism does aspirin use to treat pain?
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Which of the following is NOT a type of base as characterized in the properties of amines?
Which of the following is NOT a type of base as characterized in the properties of amines?
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Which statement accurately describes morphine's action in pain relief?
Which statement accurately describes morphine's action in pain relief?
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What effect does morphine have on the body besides pain relief?
What effect does morphine have on the body besides pain relief?
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Which base is NOT included in the nucleobases of DNA?
Which base is NOT included in the nucleobases of DNA?
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Which feature contributes to the high boiling points of amines?
Which feature contributes to the high boiling points of amines?
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What is a potential risk associated with morphine use?
What is a potential risk associated with morphine use?
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How many essential amino acids must humans obtain from their diet?
How many essential amino acids must humans obtain from their diet?
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How do opioids like morphine affect the brain in relation to pleasure?
How do opioids like morphine affect the brain in relation to pleasure?
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What is an irreversible effect of taking non-steroidal anti-inflammatory drugs (NSAIDs) like aspirin?
What is an irreversible effect of taking non-steroidal anti-inflammatory drugs (NSAIDs) like aspirin?
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What type of molecules are alkaloids primarily classified as?
What type of molecules are alkaloids primarily classified as?
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Which component is primarily affected by the action of aspirin to relieve pain?
Which component is primarily affected by the action of aspirin to relieve pain?
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What role do endorphins play in relation to morphine's effects?
What role do endorphins play in relation to morphine's effects?
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What type of amine has one nitrogen atom bonded to only one alkyl or aryl group?
What type of amine has one nitrogen atom bonded to only one alkyl or aryl group?
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What distinguishes quaternary ammonium ions from other types of ammonia derivatives?
What distinguishes quaternary ammonium ions from other types of ammonia derivatives?
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What is the geometry around the nitrogen atom in an sp3-hybridized amine?
What is the geometry around the nitrogen atom in an sp3-hybridized amine?
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Why is pyramidal inversion not possible in quaternary ammonium ions?
Why is pyramidal inversion not possible in quaternary ammonium ions?
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Which type of bonding is primarily responsible for the solubility of amine salts in water?
Which type of bonding is primarily responsible for the solubility of amine salts in water?
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Which of the following statements about amines and hydrogen bonding is accurate?
Which of the following statements about amines and hydrogen bonding is accurate?
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What type of amine is represented by the structure where nitrogen is bonded to three different substituents?
What type of amine is represented by the structure where nitrogen is bonded to three different substituents?
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What is the primary characteristic of heterocyclic amines?
What is the primary characteristic of heterocyclic amines?
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What effect does the lone pair of electrons on nitrogen have on the basicity of amines?
What effect does the lone pair of electrons on nitrogen have on the basicity of amines?
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What compound is known as the hydrochloride salt form of cocaine?
What compound is known as the hydrochloride salt form of cocaine?
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Which type of interaction primarily determines the order of hydrogen bond strength between amines and alcohols?
Which type of interaction primarily determines the order of hydrogen bond strength between amines and alcohols?
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What is the typical melting point characteristic of amine salts?
What is the typical melting point characteristic of amine salts?
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What can be said about the stability of amine salts compared to their free amines?
What can be said about the stability of amine salts compared to their free amines?
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What distinguishes sulfa drugs like sulfanilamide and sulfamethoxazole in terms of their function?
What distinguishes sulfa drugs like sulfanilamide and sulfamethoxazole in terms of their function?
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Which statement accurately reflects the relationship between folic acid and sulfa drugs?
Which statement accurately reflects the relationship between folic acid and sulfa drugs?
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Which of the following statements about diuretic activity in sulfonamides is true?
Which of the following statements about diuretic activity in sulfonamides is true?
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What type of reaction is implied between acid chlorides and amines?
What type of reaction is implied between acid chlorides and amines?
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What is a key characteristic of sulfa drug selectivity?
What is a key characteristic of sulfa drug selectivity?
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What is true about the basicity of amines compared to alcohols?
What is true about the basicity of amines compared to alcohols?
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Which of the following statements about the equilibrium established by amines in water is correct?
Which of the following statements about the equilibrium established by amines in water is correct?
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How does the presence of alkyl groups affect the basicity of amines?
How does the presence of alkyl groups affect the basicity of amines?
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What does a higher pKa value indicate about an acid?
What does a higher pKa value indicate about an acid?
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What effect do three methyl groups have on the basicity of amines?
What effect do three methyl groups have on the basicity of amines?
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In the context of amines, what is the significance of the equilibrium constant (Kb)?
In the context of amines, what is the significance of the equilibrium constant (Kb)?
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What does a larger value of Kb imply about an amine's basicity?
What does a larger value of Kb imply about an amine's basicity?
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Which of the following statements about the inductive effect of alkyl groups is accurate?
Which of the following statements about the inductive effect of alkyl groups is accurate?
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What factor primarily enhances the basicity of guanidine compared to other organic compounds?
What factor primarily enhances the basicity of guanidine compared to other organic compounds?
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Why are arylamines significantly weaker bases than alkylamines?
Why are arylamines significantly weaker bases than alkylamines?
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Which characteristic of an amine indicates it is a stronger base?
Which characteristic of an amine indicates it is a stronger base?
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What type of amine is pyridine classified as?
What type of amine is pyridine classified as?
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How does the hybridization of nitrogen in amines affect their basicity?
How does the hybridization of nitrogen in amines affect their basicity?
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What role does resonance play in the basicity of aromatic amines?
What role does resonance play in the basicity of aromatic amines?
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What is the effect of delocalization of electrons in an amide's nitrogen regarding its basicity?
What is the effect of delocalization of electrons in an amide's nitrogen regarding its basicity?
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What is characteristic of amino acids when in a neutral solution?
What is characteristic of amino acids when in a neutral solution?
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Which reaction type is primarily used to synthesize arylamines from nitro compounds?
Which reaction type is primarily used to synthesize arylamines from nitro compounds?
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Which property distinguishes the basicity of heterocyclic aliphatic amines from heterocyclic aromatic amines?
Which property distinguishes the basicity of heterocyclic aliphatic amines from heterocyclic aromatic amines?
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What is a key factor contributing to the weak basicity of functional groups like amides?
What is a key factor contributing to the weak basicity of functional groups like amides?
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During the reductive amination of aldehydes or ketones, which statement about the reaction is correct?
During the reductive amination of aldehydes or ketones, which statement about the reaction is correct?
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Which of the following statements regarding the pKa values of amines is true?
Which of the following statements regarding the pKa values of amines is true?
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When amines react with carboxylic acid derivatives, what is a likely outcome?
When amines react with carboxylic acid derivatives, what is a likely outcome?
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Study Notes
MPharm Programme - PHA114 Amines
- This is a module on Amines for a Master of Pharmacy (MPharm) programme, PHA114.
- The course is delivered by Dr. Matt Smith.
Occurrence of Amines
- Many biologically significant molecules contain amino groups.
- Examples include: amino acids, vitamins, DNA bases (A, T, G, C), RNA bases (A, U, G, C), alkaloids (e.g., caffeine, nicotine), drug molecules, and physiological molecules.
- Approximately 70% of pharmaceuticals contain nitrogen.
Properties of Amines
- Amines contain a nitrogen atom with a lone pair of electrons.
- Nitrogen is electronegative (Group 5, 3.0).
- However, it's not as electronegative as oxygen (Group 6, 3.5).
- This results in N-H bonds being polar.
- Amines have hydrogen bonding, leading to higher boiling points.
- Amines exhibit drug-receptor interactions.
- Amines are organic bases, similar to ammonia.
- Amines are nucleophilic.
Amino Acids
- α-amino acids contain a basic amino group (-NH₂), an acidic carboxyl group (-COOH), and a side chain (R).
- There are twenty essential amino acids needed for protein synthesis.
- Humans can synthesize eleven non-essential amino acids.
- The other nine are essential amino acids obtained through diet.
- Amino acids differ in their side-chain characteristics (e.g., presence of H, alkyl groups, -OH, sulfur, non-basic nitrogen, -COOH, basic nitrogen).
Nucleosides
- Adenine (A), Guanine (G), Cytosine (C), and Thymine (T) are found in DNA.
- Adenine (A), Guanine (G), Cytosine (C), and Uracil (U) are found in RNA.
Alkaloids
- Alkaloids are natural products containing one or more nitrogen heteroatoms.
- Many are used as anesthetics, antidepressants, and stimulants.
- Examples include caffeine, nicotine, valium, serotonin.
Classifying Amines
- Alkylamines are alkyl-substituted.
- Arylamines are aryl-substituted.
- Amines are classified as primary (1°), secondary (2°), or tertiary (3°) based on the number of alkyl groups attached to the nitrogen atom.
Quaternary Ammonium Ions
- A nitrogen atom with four attached groups is positively charged.
- This forms quaternary ammonium salts when all substituents are alkyl or aryl compounds.
- Examples include acetylcholine, suxamethonium, tubocurarine.
Heterocyclic Amines
- If the nitrogen atom is part of a ring, the compound is a heterocyclic amine.
- Each ring system has its own unique parent name.
- Examples include pyridine, pyrrole, quinoline, imidazole, indole, pyrimidine, pyrrolidine, and piperidine.
Structure and Bonding in Amines
- Bonding in amines is similar to that in ammonia.
- Nitrogen is sp³-hybridized.
- The lone pair of electrons occupies an sp³ orbital.
- The amine molecule has a tetrahedral geometry.
Geometry at N
- The angle between the C-N bond and the bisector of the H-N-H angle varies depending on the hybridization of nitrogen.
- In methylamine (1° amine), nitrogen is sp³ hybridised and exhibits pyramidal geometry.
- In formamide (1° amide), the nitrogen is sp² hybridised and exhibits planar geometry.
Chirality Is Possible (But Not Observed)
- An amine with three different substituents on nitrogen is chiral in principle.
- However, most amines with three different substituents are not resolved due to pyramidal inversion.
Chirality of Amines - Exceptions
- Pyramidal inversion is not possible with quaternary ammonium ions, and their salts can be resolved.
Amines Form Hydrogen Bonds
- Amines can form hydrogen bonds, but the N-H bond is less polar than the O-H bond.
- This results in weaker hydrogen bonding compared to that involving oxygen.
Basicity of Amines
- Amines are basic and nucleophilic due to the lone pair of electrons on the nitrogen atom..
- They react with acids to form acid-base salts and with electrophiles.
- Amine salts are ionic, more soluble in water than parent amines.
Cocaine
- Cocaine is sold illegally as a hydrochloride salt or a free amine (commonly known as "crack cocaine").
Amine Salts
- Amine salts are ionic solids with high melting points.
- They are soluble in water.
- Generally, they are odourless and stable.
- Conversion between amine salts and free amines is reversible.
Purifying an Amine
- Methods using ether and water, HCL and NaOH are used to purify amines. Specific steps are detailed.
Pain Treatment
- Aspirin and morphine both treat pain.
- Aspirin works by inhibiting prostaglandin synthesis and pyrogen release, while morphine blocks nerve impulses associated with pain.
- Morphine has multiple binding sites, leading to sleepiness, well-being, and pleasurable sensations.
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Description
Test your knowledge on Amines as part of the MPharm PHA114 module. This quiz covers the significance of amines in biological molecules, their properties such as polarity and hydrogen bonding, and their role in pharmaceuticals. Prepare to challenge your understanding of amino acids and drug interactions.
