MPharm PHA114 Amines Quiz

Organic compounds containing a nitrogen atom with a lone pair of electrons. They are crucial in various biological molecules like amino acids, DNA, and RNA.

Molecules containing a basic amino group (-NH2), an acidic carboxyl group (-CO2H), and a side chain (R). There are twenty essential amino acids necessary for protein synthesis, and humans can synthesize eleven of them.

A type of amino acid where the amino group is attached to the alpha carbon, which is the carbon next to the carboxyl group.

A, G, C, T are found in DNA and A, G, C, U are found in RNA. They are composed of a sugar molecule, a nitrogenous base and a phosphate group.

Natural products containing one or more nitrogen heteroatoms. Many are used as anesthetics, antidepressants, and stimulants.

The property of amines that make them able to accept protons (H+) and form cations.

Amines can act as nucleophiles due to the presence of a lone pair of electrons on the nitrogen atom. This allows them to attack electron-deficient centers

The ability of amines to form hydrogen bonds with water, leading to higher boiling points than similar hydrocarbons

A type of drug that reduces pain by preventing the production of prostaglandins, which are chemicals involved in pain signaling.

A type of drug that prevents the body from producing prostaglandins, chemicals that contribute to pain, inflammation, and fever.

Chemicals that are released in response to injury or infection, contributing to pain, inflammation, and fever.

A powerful painkiller that belongs to the opioid class. It works by binding to opioid receptors in the central nervous system (CNS), blocking pain signals from being transmitted to the brain.

Specialized proteins in the body that bind to certain molecules, like neurotransmitters, triggering a response. Opioid receptors mediate pain perception.

Substances produced by the body that bind to opioid receptors. These natural painkillers produce euphoric feelings and contribute to the body's natural pain management.

The potential for a drug to be abused or misused, leading to addiction or dependence.

The ability of a drug to affect multiple areas of the body or nervous system, leading to various side effects. Morphine's effects go beyond pain relief, also affecting sleep and mood.

Amines are organic compounds containing nitrogen, with the general formula RNH2, R2NH, or R3N, where R can be alkyl or aryl groups.

Amines are classified based on the number of carbon atoms directly attached to the nitrogen atom. Primary amines have one carbon, secondary amines have two carbons, and tertiary amines have three carbons attached to the nitrogen.

Quaternary ammonium salts are positively charged ions formed when a nitrogen atom has four attached groups, all of which are alkyl or aryl compounds. It is a special type of amine with a positive charge.

Amines where the nitrogen atom is part of a ring structure are called heterocyclic amines. Each ring system has its own unique parent name.

Amines have similar bonding characteristics to ammonia. The nitrogen atom is sp3 hybridized, with a lone pair of electrons in an sp3 orbital. This hybridization leads to a tetrahedral geometry around the nitrogen. The shape of the amine is trigonal pyramidal if only the groups around the nitrogen are considered.

In methylamine (CH3NH2), the nitrogen atom is sp3 hybridized, resulting in a pyramidal geometry. The C-N bond angle is ~112°. In contrast, formamide (HC(=O)NH2), the nitrogen atom is sp2 hybridized, leading to a planar geometry. The C-N bond angle is ~125°.

Amines with three different substituents on the nitrogen atom are chiral because the lone pair of electrons acts as the fourth substituent. However, most of these amines are not resolved because they interconvert by pyramidal inversion.

Quaternary ammonium ions, unlike regular amines, cannot undergo pyramidal inversion. This makes them resolvable into enantiomers, exhibiting true chirality.

Amines can form hydrogen bonds due to the presence of the N-H bond, though they are weaker than O-H bonds. Their H-bonding abilities contribute to their physical properties.

The lone pair of electrons on nitrogen makes amines basic and nucleophilic. They react with acids to form salts, and with electrophiles.

Amine salts are ionic compounds that are more soluble in water than their parent amines. Many amine drugs are given as salts for better dissolution in body fluids.

Cocaine, an illegal drug, can be found as the hydrochloride salt or as the free amine, also known as ‘crack’ cocaine.

Amine salts are ionic solids with high melting points, water solubility, and are generally odorless and stable. They can be reversibly converted to the 'free' amine which may have a distinct odor and can be unstable to oxidation.

Amines are weak bases, meaning they can accept a proton (H+) to form a positively charged ion.

The basicity of an amine can be described by the acidity of its conjugate acid, the ammonium ion. A higher pKa of the ammonium ion indicates a stronger conjugate base (more basic amine).

Alkyl groups attached to the nitrogen atom increase electron density, making the amine more basic. However, steric hindrance can decrease basicity.

Amines, due to their lone pair, are good nucleophiles, readily reacting with electrophiles, especially when they are protonated.

Amine salts are formed when amines react with acids. They are often more soluble in water and used for drug delivery, aiding in dissolution in bodily fluids.

A class of antibacterial agents containing a sulfonamide group (-SO2NH2), which inhibits bacterial folate synthesis, a crucial metabolic pathway for growth. These drugs are effective against a wide range of bacterial infections.

Sulfanilamide and sulfamethoxazole are two examples of sulfa drugs. They have a similar structure with slight variations, but they have distinct biological effects. The key difference lies in the R-group attached to the sulfonamide group which influences activity.

Sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthase, which is vital for the synthesis of tetrahydrofolic acid (THF). The enzyme is essential for bacterial growth and is not present in humans, explaining the selective toxicity of sulfa drugs.

Folic acid is a crucial vitamin that is essential for human health. Bacteria synthesize their own folic acid but humans obtain it through diet. The selectivity of action of sulfonamides for bacterial enzymes is due to the difference in folic acid pathways between bacteria and humans.

Many sulfonamides display diuretic activity, leading to increased urine production, alongside their antibacterial action. This side effect is often beneficial in treating certain medical conditions, but it is important to monitor potential side effects.

The greater the availability of the lone pair electrons on nitrogen, the greater the base strength.

Arylamines are considerably weaker bases than aliphatic amines. The N lone-pair electrons in arylamines are delocalised by interaction with the aromatic ring  electron system.

Guanidine is the strongest base among neutral organic compounds. Enhanced basicity is due to the delocalisation of the positive charge over the three nitrogen atoms.

In neutral solution, amino acids exist as zwitterions, with a positive charge on the amino group and a negative charge on the carboxyl group.

Amino acids have pKa values for the carboxyl group, amino group, and in some cases their R-group. Charged R groups are extremely important in the structure and function of proteins.

Amides (RCONH2) are not proton acceptors because the C=O group is strongly electron-withdrawing, making the N a very weak base.

Amines are good nucleophiles and react with alkyl halides via SN2 reactions, but this results in a mixture of products due to further alkylation.

Amines react with carboxylic acid derivatives to form amides. This reaction involves nucleophilic attack on the carbonyl group and elimination of a leaving group.

Aldehydes and ketones react with amines in the presence of a reducing agent to form amines. This reaction is called reductive amination.

Primary or secondary amines react with sulfonyl chloride to produce sulfonamides.