Republic of the Philippines

UNIVERSITY OF EASTERN PHILIPPINES

LAOANG CAMPUS
Laoang, Northern Samar

COLLEGE OF CRIMINAL JUSTICE EDUCATION

First Semester | A.Y. 2022-2023

GEROBEL R. VALENZUELA,LPT
Special Lecturer

1 | GENERAL CHEMISTRY (ORGANIC)

 MODULE 7
AMINES

OVERVIEW

Amines, organic compounds that contain nitrogen atoms. The amine

nitrogen atom can be bonded to one, two, or three alkyl groups, and many
amines have a nitrogen atom in a ring. All proteins contain amines, as do
many vitamins and hormones. Many common amines, such as caffeine in coffee
and the nicotine in tobacco, are naturally occurring.

Module Objectives:

1. Identify the characteristics of amines

2. Name of Amines
3. Give examples of common amines and alkaloids

WHAT IS A AMINES?

 Amines are carbon – hydrogen – nitrogen compounds.

OR R-NH2
 Amines are derivatives of ammonia (NH3)
 Amines occurs widely in living organisms.
 Many amines are naturally occurring compounds that are very active
physiologically.
 Numerous drugs used for the treatment of mental illness, hay fever,
heart problems ,and other physical disorders are amines.

BONDING CHARACTERISTICS OF NITROGEN ATOMS IN ORGANIC COMPOUNDS

In Organic Chemistry,

CARBON forms four bonds.

4 valence electron 4 covalent bond No nonbonding electron pair

2 | GENERAL CHEMISTRY (ORGANIC)

OXYGEN forms two bonds
6 valence electron 2 covalent bond 2 nonbonding electron pair

NITROGEN forms three bonds

5 valence electron 3 covalent bond 1 nonbonding electron pair

Understanding of the bonding characteristics of the Nitrogen atom

is a prerequisite to our study of amines.

Nitrogen is a member of Group VA of the periodic table; it has five

valence electrons and it will form three covalent bonds to complete its
octet of electrons.

3 | GENERAL CHEMISTRY (ORGANIC)

Structure and Classification of Amines

An Amine is an organic derivative of ammonia (NH3) in which one or more

alkyl, cycloalkyl, or aryl groups are attached to the nitrogen atom. Amines
are classified as primary, secondary, or tertiary on the basis of how many
hydrocarbon groups are bonded to the ammonia nitrogen atom.

Primary Amine
Is an amine in which the nitrogen atom is bonded to one hydrocarbon
group and two hydrogen atoms. The generalized formula for a primary
amine is RNH2.The functional group present in a primary amine, the NH2
group is called an Amino group. An Amino group is the -NH2 functional
group. CH3 – NH2

H
N
HR
Primary
Example:

Systematic name: Propanamine

Common name: propylamine

Secondary Amine
Is an amine in which the nitrogen atom is bonded to two hydrocarbon groups
and one hydrogen atom. The generalized formula for a secondary amine is
R2NH. CH3 – NH – CH3

4 | GENERAL CHEMISTRY (ORGANIC)

 R
N
H R
Secondary
Example:

Systematic name: N-Methylethanamine

Common name: ethylmethylamine

Tertiary Amine
Is an amine in which the nitrogen atom is bonded to three hydrocarbon
groups and no hydrogen atom. The generalized formula for a tertiary amine
is R3N.

R
N
RR
Tertiary
Example:

Systematic name: N,N-Dimethylmethanamine

Common name: trimethylamine

5 | GENERAL CHEMISTRY (ORGANIC)

NAMING OF AMINES

COMMON NAMES

Nomenclature of Amines Simple 1°, 2°, and 3° amines: common (trivial)

names are obtained by alphabetically arranging the names of the alkyl
substituents on the nitrogen and adding the suffix -amine (e.g.,
ethylmethylamine).

Explanation:
Ethyl- CH2CH3 (attach to nitrogen)
Methyl- CH3 (attach to nitrogen)
Amine- functional group of amines (secondary) is identify

IUPAC NAME/SYSTEMATIC NAME

Amines in the IUPAC system: the “e” ending of the alkane name for
the longest chain is replaced with –amine. The amine group is located by
the position number. Groups that are attached to the nitrogen atom are
located using “N” as the position number. More complex primary amines are
named with —NH2 as the amino substituent. Secondary and tertiary amines
having more than one kind of alkyl group are named as Nsubstituted.

EXAMPLE:

Common name: methylamine

Systematic name: methanamine

6 | GENERAL CHEMISTRY (ORGANIC)

Determine the classification of each of the following amines .

TERTIARY PRIMARY SECONDARY SECONDARY TERTIARY

FOCUS ON HEALTH

Caffeine and nicotine are widely used stimulants of the central nervous
system that contain amine heterocycles. Caffeine and nicotine, are
alkaloids, naturally occurring amines derived from plant sources.

Caffeine is a bitter-tasting amines found in coffee and tea. Caffeine is

also present in soft drinks and chocolate bars. Caffeine is a mild
stimulant, usually imparting feeling of alertness after consumption. It
also increases heart rate, dilates airways, and stimulates the secretion
of stomach acid. These effects are observed because caffeine increases
glucose production, making an individual feel energetic. Caffeins effects
are temporary, so an individual must consume it throughout the day to
maintain the same “high”.

Nicotine is a highly toxic amine isolated from tobacco. In small doses it

acts as a stimulant, but in larger doses causes depression, nausea, and
even death. Nicotine is synthesized in tobacco plants as a defense against
insect predators, and is used commercially as an insecticide.

Although inhaled tobacco smoke contains over 4,000 compounds, many of

which are toxic or cancer causing, nicotine is the compound that makes
smoking addictive. Nicotine imparts a sense of pleasure to the smoker,
and once a smoker is “hooked”, an individual needs to continue smoking to
avoid the extreme discomforts of withdrawal- restlessness, anxiety, and
craving.

Alkaloids - plant based amines

Morphine, quinine, and atropine are three alkaloids with useful medicinal
properties. All three compounds contain nitrogen heterocycles and have a
complex structure with several functional groups.

Morphine and Related Alkaloids

The psychological and analgesic effects of the opium poppy Papaver

somniferum have been known for probably 6,000 years, and it has been widely
used as a recreational drug and pain-killing remedy for centuries. The

7 | GENERAL CHEMISTRY (ORGANIC)

analgesic and narcotic effects of opium are largely due to morphine.
Codeine, an alkaloid of similar structure with a single methyl ether, is
also present, but in much smaller amounts.
Morphine is especially useful in relieving severe chronic pain, so it is
often prescribed for patients with terminal cancer. Morphine is also very
addictive, and with time, higher doses are needed to produce the same
effects.
Heroin, a widely used, very addictive illicit drug, is readily prepared
by converting the two hydroxyl groups of morphine to acetate esters. Heroin
is less polar than morphine, making it more soluble in fat cells in the
body. As a result, it is two to three times more potent than morphine in
producing euphoria and pain relief.
o Nicotine, caffeine, cocaine
o Chocolate
o Quinine, atropine
o Opium
o Codeine, Morphine (heroin)

Illegal drug
Methamphetamine (a.k.a Shabu) is one of many biological active amines.
Methamphetamine is a widely abused illegal drugs that has profound effects
on the body and mind. Methamphetamine imparts to the user a pleasurable
“high”. It is highly addictive, and has adverse effects on the heart,
lungs, blood vessels, and other organs. Prolonged used can lead to
sleepless, seizures, hallucinations, paranoia a serious heart disease.

8 | GENERAL CHEMISTRY (ORGANIC)

 MODULE ASSESSMENT
AMINES

1. What is Amines?
2. What are the characteristics of amines?
3. Compare primary amines, secondary amines and tertiary amines, in
terms of their functional group.
4. Give at least 3 examples of primary, secondary and tertiary
amines.
5. Complete the table:
 Give the name or structural formula
 Classify each amines as primary, secondary and tertiary.
Name(common name or Structural formula Primary/secondary/
systematic name) tertiary amine

propanamine
N-Methylethan-1-amine

CH3CH2CH2CH2CH2NH2
MDMA(ecstasy)
6. Discuss the effects to the human body of the following;
a. Nicotine
b. caffeine
c. cocaine
d. Chocolate (dark)
e. Quinine
f. atropine
g. Opium
h. Codeine,
i. Morphine (heroin)
j. MDMA
k. Methamphetamine

7. Give the chemical structure(structural or display formula) of the

following:
a. Nicotine, caffeine, cocaine
b. Chocolate (dark)
c. Quinine, atropine
d. Opium
e. Codeine, Morphine (heroin)
f. MDMA
g. Methamphetamine
*Locate the amine group in their chemical structure.

9 | GENERAL CHEMISTRY (ORGANIC)