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Analgesics
Chemistry Option D3.4
Discuss the advantages and disadvantages of using
morphine and its derivatives as strong analgesics
Classifying Morphine and its
derivatives (Narcotic Analgesics)
There are two types of narcotic analgesics: the opiates and the opioids
(derivatives of opiates). Opiates are the alkaloids found in opium (a
white liquid extract of unripe seeds of the poppy plant).
Opioids are any medication which bind to opioid receptors in the central
nervous system or gastointestinal tract.
There are four broad classes of opioids:
 Endogenous opioid peptides (produced in the body: endorphins,
dynorphins, enkephalins)
 Opium alkaloids (morphine, codeine, thebaine)
 Semi-synthetic opioids (heroin, oxycodone, hydrocodone,
dihydrocodeine, hydromorphone, oxymorphone, nicomorphine)
 Fully synthetic opioids (pethidine or Demerol, methadone, fentanyl,
propoxyphene, pentazocine, buprenorphine, butorphanol, tramadol, and
more)
Classification of Analgesics
Analgesics
Strong
Mild
Analgesics
Aspirin
Ibuprofen
Acetaminophen
Analgesics
Opium
Heroin
Codeine
What is a strong analgesic?
 Strong analgesics temporarily prevent the transmission of pain by binding with
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pain receptors in the brain and blocking the transmission of pain signals
between brain cells.
The human body contains “natural opiates” in the brain called endorphins
These are produced in the body during extreme conditions such as “running
high” and extreme injuries.
When these are absorbed by receptors in the brain, the body feels analgesia and
the pain is reduced.
Reduces suffering from pain by increasing one’s pain tolerance level.
Examples of these include heroin, codeine and morphine.
Most important naturally occurring are morphine and codeine; heroin and
Demerol(A.k.a, Meperidine—used for moderate to severe pain and to stop
muscle spasms and is usually injected or taken orally) are synthetically
produced.
Mechanism of Strong Analgesics
 Opiates derived from the poppy act in the same way as endorphins
but are not natural to the human body.
 The “high” is produced because of the absorption of opiates is
quicker than endorphins
 Drugs such as Naloxone act to fill the receptors in the brain but
are not analgesics and thus are used to prevent overdoses on
analgesics.
 Endorphins are not used as analgesics because the cannot be stored
and are unstable.
What is Morphine?
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Chemical formula: C17H19NO3
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Definition: an alkaloid narcotic drug extracted from opium; a powerful, habit-forming narcotic
used to relieve pain (Princeton)
Morphine (INN) is a highly potent opiate analgesic drug, is the principal active agent in opium, and
is considered to be the prototypical opioid (Wikipedia)
Naturally occurring in the poppy- Only needs to be isolated
Very strong pain reliever but also very addictive (2nd to Heroin)
Usually injected but can be smoked, sniffed or swallowed
Commonly used in hospitals
Large illegal street culture
Historical Background: Morphine was discovered as the first active alkaloid extracted from the
opium poppy plant in 1804 in Paderborn, Germany. The drug was first marketed to the general
public by Sertürner and Company in 1817 as an analgesic, and also as a treatment for opium and
alcohol addiction. Later it was found that morphine was more addictive than either alcohol or
opium, and its extensive use during the American Civil War allegedly resulted in over 400,000
sufferers from the "soldier's disease" of morphine addiction.
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What is it used for?
 Parenteral dosage forms of morphine are indicated to supplement general,
regional, or local anesthesia.
 During surgery, morphine is often used in conjunction with other agents, such
as a combination of an ultrashortacting barbiturate, a neuromuscular blocking
agent, and an inhalation anesthetic (usually nitrous oxide), for the maintenance
of "balanced" anesthesia.
 Parenteral dosage forms of most opioid analgesics are indicated to provide
analgesic, antianxiety, and sedative effects as presurgical medication.
 Morphine can be used as an analgesic to relieve:
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pain in myocardial infarction
pain in sickle cell crisis
pain associated with surgical conditions, pre- and postoperatively
pain associated with trauma
severe chronic pain, e.g., cancer
pain from kidney stones (renal colic, ureterolithiasis)
severe back pain
What is Codeine?
 Chemical formula: C18H21NO3
 Definition: An alkaloid of opium extracted from morphine. Codeine's
effects resemble those of morphine but with only one-sixth to one-tenth of the
analgesic action. Codeine is commonly found in cough medicine and minor
prescription pain relievers.
 Most commonly used strong analgesic
 Similar to Morphine except for the replacement of a (OH-)
group for (OCH3) group
 Commonly used with Tylenol as a more mild analgesic
 1/6 as strong as Morphine and less addictive
What is Heroin?
 Definition: a narcotic that is considered a hard drug; a highly addictive
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morphine derivative; intravenous injection provides the fastest and most intense
rush.
Heroin, or diacetylmorphine (INN), also known as diamorphine (BAN), It is
semi-synthetic opioid drug synthesized from morphine, a derivative of the
opium poppy. It is the 3,6-diacetyl ester of morphine (hence diacetylmorphine)
Originally sold as cough suppressant and pain killer
10 times stronger than Morphine
Incredibly addictive (many times, other strong analgesics are needed for
withdrawal)
Synthesized from morphine in a esterification reaction with acetyl chloride
It is absorbed by the brain very quickly resulting in a potent high
Many other problems are associated with heroin addiction, such as prostitution
and AIDS.
Morphine and its derivatives
 Morphine is the principal alkaloid and makes up about 10%
by mass of raw opium.
 Codeine makes up about 0.5% by mass of raw opium.
 Heroin is usually synthesized from morphine and thus is a
semi-synthetic drug. It is obtained by relatively simple
structural modification of morphine or codeine.
 Functional Groups:
- Morphine: benzine ring, ether (2), alkene, alcohol, tertiary
amine
- Codeine: benzene ring, ether, alkene, alcohol (2), tertiary
amine
- Diamorphine (heroin): benzene ring, ether, alkene, ester—
ethanoate (2), tertiary amine
Advantages and disadvantages
 For relief of pain due to acute myocardial infarction,
morphine is usually considered the drug of choice.
 Highly addictive substances
 Codeine is much less addictive than morphine and heroin.
 Morphine and Heroin are more useful for short-term
purposes, whereas codeine is more useful for long-term (less
risk).
Social and physiological effects (Shortterm use)
Short term
 Dulling of Pain
 Euphoria
 Slow Nervous system
 Slowed heart rate
 Loss of cough reflex
 Nausea
 Overdoses can lead to death
 Possibility of stroke
 Overall slowdown of biological systems
Social and physiological effects (Longterm use)
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Addiction to these drugs have lead to long-term use.
AIDS through injection
Mostly negative effects on mood and performance can lead to marital conflicts, joblessness
(inefficiency at work) and eventually homelessness.
Increased usage and addiction may become apparent to close relatives and family members and
cause others to feel emotional pain
Increased presence of prostitution
Higher debt (family)
Many drugs (e.g., heroin) can cross the placental barrier, resulting in addicted babies who
experience withdrawal symptoms soon after birth
Pregnant women who acquire HIV/AIDS through intravenous drug use have a high chance of
passing the virus onto their infant.
Drug-related crime can disrupt neighborhoods due to violence among drug dealers, threats to
residents, and the crimes of the addicts themselves.
In some neighborhoods, younger children are recruited as lookouts and helpers because of the
lighter sentences given to juvenile offenders, and guns have become commonplace among children
and adolescents.
The great majority of homeless people have either a drug or alcohol problem or a mental illnessmany have all three.
Cont.
 Addiction and very strong withdrawal effects
 Constipation
 Loss of libido
 Disruptions in menstruation
 “Cross-tolerance”
 Loss of appetite
 Problems associated with buying street drugs i.e. sharing
needles AIDS and prostitution.