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Part One. MORPHINE. OPIUM ALKALOIDS. OPIUM. When the unripe seed capsule of the opium poppy ( Papaver somniferum ) is cut, a viscous milky liquid exudes. This is collected. On exposure to air the exudate dries and hardens, giving a hard but slightly sticky mass known as “opium”.

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MORPHINE

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Morphine

Part One

MORPHINE

OPIUM ALKALOIDS


Morphine

OPIUM

When the unripe seed capsule of the opium poppy

(Papaver somniferum) is cut, a viscous milky liquid exudes.

This is collected. On exposure to air the exudate dries and

hardens, giving a hard but slightly sticky mass known as

“opium”.

Many alkaloids (> 40) are present in opium; the major one is

morphine.

MAJOR OPIUM ALKALOIDS (% of total alkaloids)

morphine10-20%

noscapine4-8% (also called narcotine)

codeine0.2-0.8%

papaverine0.5-1.5%

thebaine0.2-1.0%

laudanosine< 0.1%


Morphine

WORLDWIDE DISTRIBUTION

Opium poppies are native to Asia Minor and SE Asia.

However, now they are cultivated in third world

countries worldwide and by drug cartels in

South America.

Before the war opium was a major income source for

for the Taliban, and still supports local tribal leaders

in Afghanistan.

It is a major item of illicit commerce, along with

cocaine, in Columbia.

Opium is converted to Heroin in drug labs. Heroin is

more potent than morphine.


Morphine

CALIFORNIA POPPIES

Papaver spp

Do not contain morphine or codeine,

but like all poppies have papaverine

(the “poppy alkaloid”).


Morphine

OPIUM POPPY

Papaver

somniferum


Morphine

Collecting Opium


Morphine

HARDENED OPIUM MASS

OPIUM, MORPHINE AND HEROIN


Morphine

MORPHINE PHARMACOLOGY

Powerful analgesic and sedative

- modifies the perception of pain rather than

eliminates it

- 10-15 mg of morphine take effect in 15 min

- produces sleep and analgesia lasting 6 hr

Unpleasant side effects

- physiolgically addicting

- constipating

- respiratory depresssant

overdoses cause death due to respiratory

failure and severe anaphylaxis (shock)

Lethal dose: 10 mg children, 0.5-2 g for adults,

addicts can tolerate up to 7 g per day


Morphine

MORPHINE - SOME HISTORY

Morphine was the first pure alkaloid (vegetable base)

to be isolated.

Serturner 1805 is usually credited with being first.

(with claims by Derosne 1803, Sequin 1804)

(codeine in 1833 by Robiquet)

He named it after Morpheus (Greek god of dreams)

It required more than 150 years (1805 - 1956) to

completely determine the structure of morphine.

Many research groups contributed to the effort.


Morphine

CLASSICAL TIMES

Homer (The Odyssey) called poppy juice “nepenthe”.

Poppy seeds and capsules have been found in neolithic

dwellings (3000 B.C.) in Switzerland.

Minoan cultures venerated the poppy and made goddess

figures with poppy seedpod crowns.

MIDDLE AGES

Opium was brought from Turkey, China and India along the

caravan routes in the middle ages.


Morphine

OPIUM WARS

British East India Company (starting in 1773) used it as an item

of trade for chinese silk and tea. They grew the opium in Bengal

and Burma. In China it was smoked in “opium dens”.

In the nineteenth century China recognized opium smoking was

becoming a serious societal problem.

In 1820 the Chinese outlawed importation of opium, which started

a vigorous black market, fueled by the British.

In 1839 the Chinese destroyed 20,000 cases of opium starting the

“Opium Wars” with England, which they lost in 1842, signing the

Treaty of Nanking, which opened several ports to the trade.

In 1858 opium was once again legalized by the Chinese.


Morphine

NINETEENTH CENTURY EUROPE AND AMERICA

In the nineteenth century, opium became a recreational drug

in Europe and the United States. Hector Berlioz is said to have

written his “Sinfonie fantastique” and Edgar Allen Poe is said to

have written stories and poems under its influence.

“Laudanum” and opium extracts were available in drugstores and

on the field of battle at the time of the Civil War. Many injured

soldiers became addicted.

Many tonics sold in stores and by travelling salesmen of the time

contained both alcoholANDopium.

PURE FOOD AND DRUG ACT

The Pure Food and Drug Act stopped all this in 1906.

This was truly a landmark piece of American legislation.


Morphine

OPIUM WARS

OPIUM DEN


Morphine

HEROIN

Morphine is easily acetylated to diacetylmorphine using acetic

anhydride.

morphine

HEROIN

diacetylmorphine

Originally introduced by drug companies as the “heroic” new drug,

with

“ all properties of morphine except the addiction tendency”

….. this was soon proved to be false!

Heroin is more potent than morphine (it takes less for the same

effect), lasts longer, and is more addicting.

Addiction to heroin is a serious social problem today.


Morphine

CODEINE

Codeine can be produced by methylation of morphine

morphine

CODEINE

OH-

monomethylmorphine

Codeine is a powerful antitussive - it blocks the cough reflex.


Morphine

ASSIGNMENTS

Read:

Hesse

Alkaloids - Nature’s Cure or Curse, Wiley-VCH (2000)

11.5 “Opium”, pp 338-350

Chapter 10 “Historical Aspects of Alkaloid Chemistry”

pp 313-323


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