Chp 18 - Amines Flashcards
are derivatives of ammonia, NH3, in which one or more hydrogen atoms are replaced with alkyl or aromatic groups.
Amines
contain N attached to one or more alkyl or aromatic groups.
Amines
In the IUPAC names for amines, the e in the corresponding alkane name is replaced with ____
-amine
Amines with a chain of ___(#) or more carbon atoms are numbered to show the position of the —NH2 group and any other substituents.
Three
If there is an alkyl group attached to the nitrogen atom, the prefix __ and ___ are placed in front of the amine name.
prefix N and the alkyl name
If there are two alkyl groups bonded to the N atom, the prefix N is used for each, and they are listed ____.
Alphabetically
Steps to write IUPAC name:
S1: name the longest carbon chain bonded to the N atom by replacing the e of its alkane name with AMINE
S2: Number the carbon chain to show the position of the amine group and other substituents.
S3: Any alkyl group attached to the nitrogen atom is indicated by the prefix N- and the alkyl name, which is placed in front of the amine name.
The amine of benzene is named ____ by IUPAC
Aniline
How are Amines classified:
Primary (1°)
Secondary (2°)
Tertiary (3°)
A _____ amine has one carbon group bonded to the nitrogen atom
Primary (1°)
A _____ amine has two carbon groups bonded to the nitrogen atom.
Secondary (2°)
A _____ amine has three carbon groups bonded to the nitrogen atom.
Tertiary (3°)
Primary and secondary amines can form ____ bonds with water molecules.
Hydrogen
Primary and secondary amines can form _____ bonds with each other.
Hydrogen
Tertiary amines can only form _____ bonds with water molecules
Hydrogen
Nitrogen is not as electronegative as oxygen, so hydrogen bonds in amines are _____ than the hydrogen bonds in alcohols
Weaker
Amines have boiling points that are ___ than those of alkanes but ____ than those of alcohols.
Higher
Lower
Primary (1°) amines can form more hydrogen bonds and have ____ boiling points than secondary (2°) amines of the same mass.
Higher
Tertiary (3°) amines cannot form hydrogen bonds with each other and have ____ boiling points than primary or secondary amines of the same mass.
Lower
Amines with one to ##? carbon atoms, including tertiary amines, are soluble in water.
Six
As the number of carbon atoms in an amine increases in the nonpolar alkyl portions, the effect of hydrogen bonding is ____
Diminished
A ___ ___ forms when amines such as those responsible for the odor in fish are neutralized by an acid
Amine Salt
A ___ ___ forms when amines react as a Brønsted–Lowry base in a neutralization reaction with citric acid.
Amine Salt
In a ___ ___ an amine acts as a base and reacts with an acid to form an ammonium salt.
Neutralization Reaction
In a neutralization reaction the lone pair of electrons on the nitrogen atom accepts H+ from an acid to give an ___ ___; no water is formed
Ammonium Salt
An ammonium salt is named by using its alkylammonium ion name followed by the name of the negative ion
cool
In a quaternary ammonium salt,
a nitrogen atom is bonded to four carbon groups, which classifies it as a ____ amine
Quaternary (4°)
In a quaternary ammonium salt, the nitrogen atom has a ____ charge and is not bonded to an H atom.
Postive
Ammonium salts are
___ at room temperature, odorless, and ____ in water and body fluids.
Solids
Soluble
Amines are therefore usually converted to their ___ ___ before being used as drugs.
Ammonium Salt
A heterocyclic amine is a cyclic organic compound that consists of a ring of five or six atoms, of which 1 or 2 are ____ atoms.
Nitrogen
Simplest heterocyclic, five-atom ring:
Pyrrolidine, which is a ring of four carbon atoms and one nitrogen atom, all with single bonds.
____ is a five-atom ring with one nitrogen atom and two double bonds.
Pyrrole
___ is a five-atom ring that contains two nitrogen atoms.
Imidazole
Of the six-atom rings, ____ is responsible for the pungent aroma and taste of black pepper, is a six-atom heterocyclic ring with a nitrogen atom.
Pipreridine
In ____, the structures of six-atom pyrimidine and five-atom imidazole are combined.
Purine
___ and ___ rings are found in DNA and RNA
Purine and Pyrimidine
___ are physiologically active compounds produced by plants that contain heterocyclic amines.
Used in anesthetics, in antidepressants, and as stimulants, and many are habit forming
Alkaloids
___ is an alkaloid found in coffee beans, tea, chocolate, and soft drinks.
is a stimulant of the central nervous system.
increases alertness but may cause insomnia
Caffeine
alkaloids obtained from the oriental poppy plant.
used as painkillers and in cough syrups
Morphine and Codeine
____, obtained by a chemical modification of morphine, is strongly addictive and is not used medically.
The prescription drug OxyContin (oxycodone) is used to relieve severe pain. Its structure is similar to that of ____
Heroin
A _____ is a chemical compound that transmits an impulse from a nerve cell to a target cell. Target cells may be another nerve cell, a muscle cell, or a gland cell
Neurotransmitter
Neurotransmitters can be removed from the receptors in different ways (3)
- The neurotransmitter diffuses away from the synapse.
- Enzymes in the receptors break down the neurotransmitter.
- Reuptake returns the neurotransmitter to the vesicles, where it is stored.
Neurotransmitters contain nitrogen atoms as ____ and ____;
they are synthesized from compounds such as amino acids obtained from our diets.
Amines and Alkylammonium Ions
Neurotransmitters contain nitrogen atoms as amines and alkylammonium ions;
they are usually ionized, forming ___ cations and ____ anions
Ammonium Cations and Carboxylate Anions
Acetylcholine is synthesized by forming an ____ between choline and acetate and is stored in the vesicles.
Ester
Nerve poisons such as Sarin, Soman, and Parathion
bind to the acetylcholinesterase enzyme and inhibit its action.
result in a buildup of acetylcholine in the ____, stopping nerve transmissions.
Because acetylcholine cannot be released, the muscles in the body cannot relax, and convulsions and respiratory failure soon occur
Synapse
Catecholimines are synthesized from the amino acid ____ found in meats, nuts, eggs, and cheese.
Tyrosine
Amphetamine and methamphetamine
are synthetic ___ ___ ___ stimulants.
increase excitatory catecholamine neurotransmitters, particularly dopamine and norepinephrine
Central Nervous System
Dopamine reuptake may be blocked by cocaine and amphetamines, leaving dopamine in the ____.
High levels of dopamine may contribute to addictive behavior and schizophrenia.
Synapes
____ is used to increase dopamine levels in the brain. Parkinson’s disease causes the midbrain nerve cells to lose their ability to produce dopamine.
L-Dopa
Epinephrine is synthesized from norepinephrine by the addition of a ___ ___ to the amine
Methyl Group
____ is synthesized from the amino acid tryptophan, which can cross the blood-brain barrier.
Serotonin
Histamine is
synthesized in nerve cells in the hypothalamus from the amino acid ____
Histidine
The most abundant neurotransmitter in the nervous system?
Glutamate
When glutamate binds to its receptor cells, it stimulates the synthesis of ___ ___, also a neurotransmitter in the brain
Nitrogen Oxide (NO)
Gamma(γ)-aminobutyric acid, or GABA,
is produced from ____
reduces anxiety by inhibiting the ability of nerve cells to send electrical signals to nearby nerve cells.
is involved in the regulation of muscle tone, sleep, and anxiety
Glutamate
The most common inhibitory neurotransmitter in the brain.
Gamma(γ)-aminobutyric acid, or GABA
Alcohol, sedatives, and tranquilizers increase the inhibitory effects of GABA. Caffeine decreases the GABA levels in the synapses, leading to conditions of anxiety and sleep problems.
Alrighty then
____ are derivatives of carboxylic acids in which a nitrogen group (—NH2) of a primary or secondary amine replaces the hydroxyl (—OH) group of carboxylic acids
Amides
Amides are produced
in a reaction called ___ or ___
Amidation or Condensation
Amides are produced when a carboxylic acid reacts with ammonia or a primary or secondary amine and ___.
Amide production is accompanied by the production of water.
Heat
In both the common and IUPAC names, amides are named by dropping the oic acid (IUPAC) or ic acid (common) from the carboxylic acid name and adding the suffix ____
-amide
Alkyl groups attached to the nitrogen of an amide are named with the prefix __ followed by the alkyl name.
N
Amides do not have the properties of bases seen in amines.
Only ____ is a liquid at room temperature, while other amides are solids
Methanamide
____ amides have the highest melting points because the —NH2 group can form the most hydrogen bonds.
Primary (1°)
Melting points of the secondary (2°) amides are ____ because they form fewer hydrogen bonds.
Lower
Tertiary (3°) amides cannot form hydrogen bonds; they have the ___ melting points
Lowest
Primary (1°) amides, can form
hydrogen bonds with water molecules making them soluble in water as long as they have less than ____ carbons
Five
Secondary (2°) amides
form hydrogen bonds with water molecules, making them soluble in water as long as they have fewer than ____ carbons.
Five
Tertiary (3°) amides can form ___ hydrogen bond with H2O
only one
The simplest natural amide:
Urea
The end product of protein metabolism in the body.
Excreted in the urine
Urea
If the kidneys malfunction, urea is not removed and builds to a toxic level, a condition called ____
Uremia
Aspirin substitutes
contain phenacetin and acetaminophen.
act to reduce fever and pain but have little anti-inflammatory effect
okey dokey
Many barbituates
are ___ ___ of barbituric acid.
act as sedatives in small doses or sleep inducers in large doses.
are habit forming
Cyclic Amides
Cocaine is…
a helluva drug
