Chemistry Option D3.4Discuss the advantages and disadvantages of using morphine and its derivatives as strong

analgesics

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

Aspirin Heroin

Codeine

OpiumIbuprofen

Acetaminophen

MildAnalgesics

StrongAnalgesics

Analgesics

What is a strong analgesic? Strong analgesics temporarily prevent the transmission of

pain by binding with 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? Chemical formula: C17H19NO3

 

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.

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:pain in myocardial infarctionpain in sickle cell crisispain associated with surgical conditions, pre- and

postoperativelypain associated with traumasevere chronic pain, e.g., cancerpain 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 analgesicSimilar 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 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 derivativesMorphine 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 disadvantagesFor relief of pain due to acute myocardial

infarction, morphine is usually considered the drug of choice.

Highly addictive substancesCodeine 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 (Short-term use)Short termDulling of PainEuphoriaSlow Nervous system Slowed heart rateLoss of cough reflexNauseaOverdoses can lead to deathPossibility of strokeOverall slowdown of biological systems

Social and physiological effects (Long-term use) 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 illness-many have all three.

Cont.Addiction and very strong withdrawal

effectsConstipationLoss of libidoDisruptions in menstruation“Cross-tolerance”Loss of appetiteProblems associated with buying street

drugs i.e. sharing needles AIDS and prostitution.