unit 4 Flashcards
Hetero cyclic compounds are
cyclic organic compounds where other elements such as nitrogen and oxygen are also included in the rings along with carbon atoms
Hetero stands for more than one
element present in a single ring.
the largest and most varied family of organic compounds. They are compounds with 3,4,5,6 membered rings.
heterocyclic
The IUPAC rules allow three nomenclatures
I. The Hantzsch-Widman Nomenclature.
II. Common Names
III. The Replacement Nomenclature
Hantzsch-Widman nomenclature is based on the type
heteroatom; the ring size (n) and is it saturated or unsaturated.
are heterocyclic amines occurring naturally in plants
alkaloids
They show basic characteristics and therefore the name “alkali-like”. These are used as antidepressants, anesthetics and stimulants.
alkaloids
alkaloid examples
nicotine coniine morphine caffeine quinine atropine codeine
nicotine
structure and effect
pyrrolidine structure. It is addictive and increases the adrenaline level in blood.
Coniine is obtained from and what ring structure
obtained from hemlock, is extremely toxic with a piperidine ring.
Morphine is found and used as
found in opium, is an effective pain killer.
Caffeine is found, does and has what kind of ring
found in cocoa
stimulates the central nervous system
a purine ring
Quinine, is from and used to treat
from the bark of cinchona tree, has been used to treat malaria.
Atropine is from and used to
from belladonna
accelerate slow heart rate
and dilate the eyes
Codeine
is from and used for
from opium plant and used in perscription pain killers
oxycotin is from and used for
morphine and a pain killer
PYRROL
a five-membered ring with the formula C4H4NH. It is found in nicotine and other alkaloids.]
very low basic nature due to nitrogen pair
PORPHIN is the parent chemical for
porphyrins
C20H14N4. It is an aromatic heterocyclic solid substance. It consists of four pyrrole rings joined together by four methine (=CH—) groups to form a larger macrocycle ring.
porphin
Around the perimeter of the macrocycle ring, there is a cyclic chain of sp2 hybridized carbon atoms, all of which are part of a conjugated double bond system, giving the molecule its aromatic character
porphin
aromatic character of porphin stems both from its
conjugation as well as its flat or planar geometry, meaning that all the atoms lie in a single plane.
A porphyrin with an iron atom of the type found in myoglobin, hemoglobin, or certain cytochromes is called
heme
indole is what kind of compund
aromatic
bicyclic structure
6 member benzene ring, attached to a five member pyrole ring
first isolated by indigo dye with oleum
indole
is indole a base
no because of nitrogens lone pair
Even though it is used as a fixative in many perfumes, higher concentrations has a foul smell.
indole
Tryptamine
derivate of indole
Serotonin,
derivative of indole
pyrazole is what shape
5 membered heterocyclic ring
two nitrogen/hydrogen atoms
two derivatives of pyrazole
Antipyrine
analgin
Pyridine is
is a simple aromatic heterocyclic organic compound with the chemical formula C5H5N
is a benzene that has a nitrogen
is also used as a denaturant for antifreeze mixtures, for ethyl alcohol, for fungicides, and as a dyeing aid for textiles.
pyridine
Pyrimidine is a
aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring.
Three nucleobases found in nucleic acids (cytosine, thymine, and uracil) are
pyrimidine
it was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring, sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light.
uracil
three pyrimidine derivatives
cytosine
uracil
thymine
purine
consisting of a pyrimidine ring fused to an imidazole ring.
It is present in anti-cancer drugs.
PYRIMIDINE
PURINE
Modified alkaloids
Oxycontin – modification of morphine; pain killer
Procaine; Lidocaine – modification of cocaine
Meperidine – modification of morphine; pain killer
– purine ring; stimulant; pain killer
caffeine
pyrrolidine ring; adrenaline increase
nicotine
malaria treatment
Quinine
pain killer; cough syrup
codeine
pain killer
morphine
eye dilation; accelerate heart rate
atropine
piperidine ring
coniine
pyrrol
Pyrrolidine (another name) 5 membered ring Low basicity Nicotine Porphobilinogen (biosynthetic precursor )
porphin
solid
four pyrrole rings joined together by four methine (=CH—) groups
four central nitrogen atoms can act as ligands to bond to a metal ion in the center of the molecule.
myoglobin, hemoglobin (Fe)
Chlorophyll (Mg)
indole
six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring
used in many alkaloids and drugs
Not a base
Solid at room temperature
Tryptamine (monoamine alkaloid)
Serotonin (monoamine neurotransmitter)
pyrazole
5 membered hetero cyclic ring (three carbon atoms and two nitrogen atoms in adjacent positions)
Antipyrine
Analgin
pyrridine
found in several vitamins
colorless liquid with a distinctive, unpleasant fish-like odor
denaturant for antifreeze mixtures
pyridine is readily degraded by bacteria to ammonia and carbon dioxide.
Precursor to medicines
pyrimidine
present in anti-cancer drugs.
cytosine, thymine, and uracil are pyrimidine derivatives
Purine
pyrimidine ring fused to an imidazole ring
found in anti-cancer drugs
adenine & guanine has purine structure
caffeine
