Arguelles, Era F.

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Nitrogen Containing Organic Compounds

• By
• Arguelles, Era F.
• IV- BSCT
• NATURAL PRODUCTS

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The Amino Group

• Nitrogen - involves itself in organic chemistry
  as the amino group, -NH2 In this group, there are
  three normal bonds for N.
• Nitrogen can be attached to up to four carbon
  chains to make amines and ammonium ions, or can
  be substituted for OH in the carboxylic acids to
  make amides.

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Amines

• Amines - are basic compounds that show
  considerable physical and chemical similarities
  to ammonia and isolated from plants from a group
  of compounds called alkaloids

Ammonia
Amine
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• Amines however are classified as
• Primary amine (1)
• Secondary amine (2)
• Tertiary amine (3)

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Amines

• Naming amines is done similarly to the
  ethersname the carbon groups connected to the
  nitrogen
• If the amino group is not the only functional
  group present, it is not named as an amine, since
  it does not have priority. It is then named and
  numbered as a substitution, even if there are
  carbon chains attached to it.

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Examples

• propylamine
• methy ethyl amine
• dimethyl ethyl amine
• aniline
• N-methyl aniline
• N,N-dimethyl aniline

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Basic Properties of Amines

• Just like ammonia acts as a base due to its lone
  pair of electrons on the Nitrogen.
• The strength of amines as bases depends on the
  type and number of carbon groups attached to the
  N alkyl groups increase the strength, aromatic
  groups decrease the strength.

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Reactions of Amines

• With acids they form salts
• With alkyl halides, 3 amines can form quaternary
  ammonium salts
• With nitrites, nitrosamines can be formed
• These nitrosamines are highly carcinogenic, and
  are made from any amine with nitrites or
  nitrates in preserved foods within the stomach.

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• AMIDES

- are compounds which contain nitrogen directly
attached to a carbon in a carbonyl group and
nitrogen derivatives of carboxylic acids
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• Properties of Amides
• All amides can form hydrogen bond with water,
  so low molecular weight amides are water-soluble.
• unlike amines, amides are not basic.

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Examples of nitrogen- containing compounds
(Amines)
CAFFEINE
NICOTINE
QUININE
S E R O T O N I N
D O P A M I N E
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• Dopamine

• A catecholamine neurotransmitter present in a
  wide variety of animals, including both
  vertebrates and invertebrates.
• In the brain, this substituted phenethylamine
  functions as a neurotransmitter, activating the
  five known types of dopamine receptorsD1, D2,
  D3, D4, and D5and their variants

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• Dopamine

• Dopamine is produced in several areas of the
  brain, including the substantia nigra and the
  ventral tegmental area.
• It is also a neurohormone released by the
  hypothalamus.
• The main function as a hormone is to inhibit the
  release of prolactin from the anterior lobe of
  the pituitary.

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• Caffeine

• a bitter, white crystalline xanthine alkaloid
  that acts as a stimulant drug.
• Caffeine is found in varying quantities in the
  seeds, leaves, and fruit of some plants, where it
  acts as a natural pesticide that paralyzes and
  kills certain insects feeding on the plants.

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• Caffeine

• most commonly consumed by humans in infusions
  extracted from the bean of the coffee plant and
  the leaves of the tea bush, as well as from
  various foods and drinks containing products
  derived from the kola nut.

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• Nicotine

• Found in the nightshade family of plants
  (Solanaceae) that constitutes approximately
  0.63.0 of the dry weight of tobacco.
• Biosynthesis taking place in the roots and
  accumulation occurring in the leaves

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• Nicotine

• It functions as an antiherbivore chemical with
  particular specificity to insects nicotine was
  widely used as an insecticide in the past.
• Currently nicotine analogs such as imidacloprid
  continue to be widely used.

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• Nicotine

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• Quinine

• A natural white crystalline alkaloid having
  antipyretic (fever-reducing), antimalarial,
  analgesic (painkilling), anti-inflammatory
  properties and a bitter taste.
• A stereoisomer of quinidine which, unlike
  quinine, is an anti-arrhythmic.
• Quinine contains two major fused-ring systems
  the aromatic quinoline and the bicyclic
  quinuclidine.

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• Quinine

• occurs naturally in the bark of the cinchona tree.

(Plasmodium falciparum)

• Quinine was the first effective treatment for
  malaria caused by Plasmodium falciparum,
  appearing in therapeutics in the 17th century.

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• Serotonin

• A monoamine neurotransmitter.
• Biochemically derived from tryptophan, serotonin
  is primarily found in the gastrointestinal (GI)
  tract, platelets, and in the central nervous
  system (CNS) of animals including humans.
• It is a well-known contributor to feelings of
  well-being it is also known to contribute to
  happiness.

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• NITROGEN- CONTAINING PRIMARY METABOLITES

A. Purines and Pyrimidines
B. Nucleotides and Nucleosides
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A. Purines and Pyrimidines

• PYRIMIDINE
• A heterocyclic aromatic organic compound similar
  to benzene and pyridine, containing two nitrogen
  atoms at positions 1 and 3 of the six-member
  ring.
• It is isomeric with two other forms of diazine.

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1. Pyrimidine
Derived from the three nucleobases found in
nucleic acids, cytosine (C), thymine (T), and
uracil (U).
thymine
cytosine
uracil
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• 2. PURINE
• A heterocyclic aromatic organic compound,
  consisting of a pyrimidine ring fused to an
  imidazole ring.
• Purines, including substituted purines and their
  tautomers, are the most widely distributed kind
  of nitrogen-containing heterocycle in nature.

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• Other Notable Purines

isoguanine
caffeine
theobromine
Uric acid
hypoxanthine
xanthine
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• Functions of Purines

Aside from DNA and RNA, purines are
biochemically significant components in a number
of other important biomolecules, such as ATP,
GTP, cyclic AMP, NADH, and coenzyme A.
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A. Purines and Pyrimidines
DNA
Purine Pyrimidine
Adenine (A) Thymine (T)
Guanine (G) Cytosine (C)
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A. Purines and Pyrimidines
RNA
Purine Pyrimidine
Adenine (A) Uracil (U)
Guanine (G) Cytosine (C)
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B. Nucleotides and Nucleosides

• 1. Nucleosides
• Glycosylamines consisting of a nucleobase (often
  referred to as simply base) bound to a ribose or
  deoxyribose sugar via a beta-glycosidic linkage.
  Examples of nucleosides include cytidine,
  uridine, adenosine, guanosine, thymidine and
  inosine.

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1. Nucleosides
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B. Nucleotides and Nucleosides
2. Nucleotides

• Nucleotides are molecules that, when joined
  together, make up the structural units of RNA and
  DNA. In addition, nucleotides participate in
  cellular signaling (cyclic guanosine
  monophosphate and cyclic adenosine
  monophosphate).
• Incorporated into important cofactors of
  enzymatic reactions (coenzyme A, flavin adenine
  dinucleotide, flavin mononucleotide, and
  nicotinamide adenine dinucleotide phosphate).

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2. Nucleotides

• Nucleotide derivatives such as the nucleoside
  triphosphates play central roles in metabolism,
  in which capacity they serve as sources of
  chemical energy (adenosine triphosphate and
  guanosine triphosphate).

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2. Nucleotides