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”.
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
Many alkaloids (> 40) are present in opium; the major one is
MAJOR OPIUM ALKALOIDS (% of total alkaloids)
noscapine 4-8% (also called narcotine)
laudanosine < 0.1%
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
Before the war opium was a major income source for
for the Taliban, and still supports local tribal leaders
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.
Do not contain morphine or codeine,
but like all poppies have papaverine
(the “poppy alkaloid”).
OPIUM, MORPHINE AND HEROIN
Powerful analgesic and sedative
- modifies the perception of pain rather than
- 10-15 mg of morphine take effect in 15 min
- produces sleep and analgesia lasting 6 hr
Unpleasant side effects
- physiolgically addicting
- 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 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.
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.
Opium was brought from Turkey, China and India along the
caravan routes in the middle ages.
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.
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 is easily acetylated to diacetylmorphine using acetic
Originally introduced by drug companies as the “heroic” new drug,
“ 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.
Codeine can be produced by methylation of morphine
Codeine is a powerful antitussive - it blocks the cough reflex.
Alkaloids - Nature’s Cure or Curse, Wiley-VCH (2000)
11.5 “Opium”, pp 338-350
Chapter 10 “Historical Aspects of Alkaloid Chemistry”