Strychnine

Strychnine (/strknin/; also US /strknan/ or

/strknn/) is a highly toxic, colorless, bitter crystalline alkaloid used as a pesticide, particularly for killing
small vertebrates such as birds and rodents. Strychnine,
when inhaled, swallowed, or absorbed through eyes or
mouth, causes a poisoning which results in muscular
convulsions and eventually death through asphyxia.[4]
While it has no known medicinal eects, in the past the
convulsant eect was believed to be benecial in small
doses. The most common source is from the seeds of the
Strychnos nux-vomica tree.

Joseph Bienaim Caventou and Pierre-Joseph Pelletier

in 1818 in the Saint-Ignatius bean.[5] In some Strychnos plants a 9,10-dimethoxy derivative of strychnine,
the alkaloid brucine, is also present. Brucine is not
as poisonous as strychnine. Historic records indicate
that preparations containing strychnine (presumably) had
been used to kill dogs, cats, and birds in Europe as far
back as 1640.[6] The structure of strychnine was rst determined in 1946 by Sir Robert Robinson and in 1954
this alkaloid was synthesized in a laboratory by Robert
B. Woodward. This is one of the most famous syntheses in the history of organic chemistry. Both chemists
won the Nobel prize (Robinson in 1947 and Woodward
in 1965).[6]

History

1.1 Performance enhancer

Strychnine was the rst alkaloid to be identied in plants

of the genus Strychnos, family Loganiaceae. Strychnos,
named by Carl Linnaeus in 1753, is a genus of trees and
climbing shrubs of the gentian order. The genus contains 196 various species and is distributed throughout the
warm regions of Asia (58 species), America (64 species),
and Africa (75 species). The seeds and bark of many
plants in this genus contain the powerful poison strychnine.

Strychnine was popularly used as an athletic performance

enhancer and recreational stimulant in the late 19th century and early 20th century, due to its convulsant eects.
It was thought to be similar to coee.[7][8] Its eects are
well-described in H. G. Wells novella The Invisible Man:
the title character states: " Strychnine is a grand tonic
... to take the abbiness out of a man. The protagoIts the devil, ... Its the palaeolithic in a
The toxic and medicinal eects of Strychnos nux-vomica nist replies:
[9]
bottle.
have been well known from the times of ancient India,
although the chemical compound itself was not identied
and characterized until the 19th century. The inhabitants
of these countries had historical knowledge of the species 2 Toxicity
Strychnos nux-vomica and Saint-Ignatius bean (Strychnos
ignatii). Strychnos nux-vomica is a tree native to the trop- Main article: Strychnine poisoning
ical forests on the Malabar Coast in Southern India, Sri
Lanka and Indonesia, which attains a height of about 12
m. The tree has a crooked, short, thick trunk and the In high doses, strychnine is very toxic to humans and
mg/kg in humans, 1
wood is close grained and very durable. The fruit has an many other animals (LD50 = 16
[10]
2
mg/kg
orally
in
rats
and
mice
),
and poisoning by inorange color and is about the size of a large apple with
halation,
swallowing,
or
absorption
through
eyes or mouth
a hard rind and contains ve seeds, which are covered
can
be
fatal.
S.
nux-vomica
seeds
are
generally
eective
with a soft wool-like substance. The ripe seeds look like
only
when
they
are
crushed
or
chewed
before
swallowing
attened disks, which are very hard. These seeds are the
chief commercial source of strychnine and were rst im- because the pericarp is quite hard and indigestible; poiported to and marketed in Europe as a poison to kill ro- soning symptoms may therefore not appear if the seeds
dents and small predators. Strychnos ignatii is a woody are ingested whole.
climbing shrub of the Philippines. The fruit of the plant,
known as Saint Ignatius bean, contains as many as 25
2.1 Animal toxicity
seeds embedded in the pulp. The seeds contain more
strychnine than other commercial alkaloids. The proper- Strychnine poisoning in animals usually occurs from inties of S. nux-vomica and S. ignatii are substantially those gestion of baits designed for use against gophers, moles,
of the alkaloid strychnine.
and coyotes. Strychnine is also used as a rodenticide, but
Strychnine was rst discovered by French chemists is not specic to such unwanted pests and may kill other
1

3 BIOSYNTHESIS

small animals.[11] In the United States, most baits containing strychnine have been replaced with zinc phosphide
baits since 1990. In the Netherlands, rodenticides with
strychnine are forbidden. Some animals are immune to
strychnine, usually these are species such as fruit bats that
have evolved resistance to poisonous alkaloids in the fruit
they eat. The drugstore beetle has a symbiotic gut yeast
that allows it to digest pure strychnine.
Strychnine toxicity in rats is dependent on sex. It is more
toxic to females than to males when administered via
subcutaneous injection or intraperitoneal injection. Differences are due to higher rates of metabolism by male
rat liver microsomes. Dogs and cats are more susceptible
among domestic animals, pigs are believed to be as susceptible as dogs, and horses are able to tolerate relatively
large amounts of strychnine. Birds aected by strychnine
poisoning exhibit wing droop, salivation, tremors, muscle tenseness, and convulsions. Death occurs as a result
of respiratory arrest. The clinical signs of strychnine poisoning relate to its eects on the central nervous system.
The rst clinical signs of poisoning include nervousness,
restlessness, twitching of the muscles, and stiness of the
neck. As the poisoning progresses, the muscular twitching becomes more pronounced and convulsions suddenly
appear in all the skeletal muscles. The limbs are extended and the neck is curved to opisthotonus. The pupils
are widely dilated. As death approaches, the convulsions
follow one another with increased rapidity, severity, and
duration. Death results from asphyxia due to prolonged
paralysis of the respiratory muscles. Following the ingestion of strychnine, symptoms of poisoning usually appear
within 15 to 60 min. The LD50 -values for strychnine in
animals are listed below in table 1.

2.2

Human toxicity

After injection, inhalation, or ingestion, the rst symptoms to appear are generalized muscle spasms. They appear very quickly after inhalation or injection within
as few as ve minutes and take somewhat longer to
manifest after ingestion, typically approximately 15 minutes. With a very high dose, the onset of respiratory failure and brain death can occur in 15 to 30 minutes. If a
lower dose is ingested, other symptoms begin to develop,
including seizures, cramping, stiness, hypervigilance,
and agitation. Seizures caused by strychnine poisoning can start as early as 15 minutes after exposure and
last 12 - 24 hours. They are often triggered by sights,
sounds, or touch and can cause other adverse symptoms,
including hyperthermia, rhabdomyolysis, myoglobinuric
kidney failure, metabolic acidosis, and respiratory acidosis. During seizures, mydriasis (abnormal dilation),
exophthalmos (protrusion of the eyes), and nystagmus
(involuntary eye movements) may occur.[11]
As strychnine poisoning progresses, tachycardia
(rapid heart beat), hypertension (high blood pressure),
tachypnea (rapid breathing), cyanosis (blue discoloration), diaphoresis (sweating), water-electrolyte
imbalance, leukocytosis (high number of white blood
cells), trismus (lockjaw), risus sardonicus (spasm of the
facial muscles), and opisthotonus (dramatic spasm of the
back muscles, causing arching of the back and neck) can
occur. In rare cases, the aected person may experience
nausea or vomiting.[11]
The proximate cause of death in strychnine poisoning can
be cardiac arrest, respiratory failure, multiple organ failure, or brain damage.[11]
The LD50 -values estimated from dierent cases of
strychnine poisoning are listed below in table 2.
For occupational exposures to strychnine, the
Occupational Safety and Health Administration and
the National Institute for Occupational Safety and Health
have set exposure limits at 0.15 mg/m3 over an 8-hour
work day.[31]
Because strychnine produces some of the most dramatic and painful symptoms of any known toxic reaction,
strychnine poisoning is often portrayed in literature and
lm including authors Agatha Christie and Arthur Conan
Doyle.[32]

3 Biosynthesis
An 1809 painting depicting opisthotonus

The symptoms of poisoning in humans are generally similar to those as in animals, because the mechanism of action is apparently similar across species. The toxicity of
strychnine in humans is not ethically studied, so most information known comes from cases of strychnine poisoning, both unintentional and deliberate.

Strychnine is a terpene indole alkaloid belonging to the

Strychnos family of Corynanthe alkaloids, and it is derived from tryptamine and secologanin.[33][34] The enzyme, strictosidine synthase, catalyzes the condensation
of tryptamine and secologanin, followed by a PictetSpengler reaction to form strictosidine.[35] While the enzymes that catalyze the following steps have not been
identied, the steps have been inferred by isolation of
intermediates from Strychnos nux-vomica.[36] The next

3
molecular size it is the most complex [organic] substance
known (attributed to Sir Robert Robinson).[39]
The rst total synthesis of strychnine was reported by the
research group of R. B. Woodward in 1954, and is considered a classic in this eld.[40][41] The Woodward account
published in 1954 was very brief (3 pp.),[42] but was followed by a 42-page report in 1963.[43] The molecule has
since received continuing wide attention in the years since
for the challenges to synthetic organic strategy and tactics
presented by its complexity; its synthesis has been targeted and its stereocontrolled preparation independently
achieved by more than a dozen research groups since the
rst success (see main strychnine total synthesis article).

5 Pharmacokinetics
strychnine biosynthesis

5.1 Absorption
step is hydrolysis of the acetal, which opens the ring by
elimination of glucose (O-Glu) and provides a reactive
aldehyde. The nascent aldehyde is then attacked by a
secondary amine to aord geissoschizine, a common intermediate of many related compounds in the Strychnos
family.[33]
A reverse Pictet-Spengler reaction cleaves the C2C3
bond, while a subsequent Mannich reaction forms the
C3C7 bond, and a Michael addition forms the C2
C16 bond to provide dehydropreakuammicine. Hydrolysis of the methyl ester and decarboxylation leads to
noruorocurarine. Stereospecic reduction of the endocyclic double bond by NADPH and hydroxylation
provides the Wieland-Gumlich aldehyde, which was
rst isolated by Heimberger and Scott in 1973, although previously synthesized by Wieland and Gumlich
in 1932.[36][37] To elongate the appendage by 2 carbons,
acetyl-CoA is added to the aldehyde in an aldol reaction
to aord prestrychnine. Strychnine is then formed by a
facile addition of the amine with the carboxylic acid or
its activated CoA thioester, followed by ring-closure via
displacement of an activated alcohol.

Chemical synthesis

Main article: Strychnine total synthesis

As early researchers have noted, the strychnine molecular structure, with its specic array of rings, stereocenters,
and nitrogen functional groups is a complex synthetic target, and has stimulated interest for that reason and for interest in the structure-activity relationships underlying its
pharmacologic activities.[38] An early synthetic chemist
targeting strychnine, R.B. Woodward, quoted the chemist
who determined its structure through chemical decomposition and related physical studies as saying that for its

Strychnine may be introduced into the body orally, by inhalation, or by injection. It is a potently bitter substance,
and in humans has been shown to activate bitter taste receptors TAS2R10 and TAS2R46.[44][45][46] Strychnine is
rapidly absorbed from the gastrointestinal tract.

5.2 Distribution
Strychnine is transported by plasma and erythrocytes.
Due to slight protein binding, strychnine leaves the bloodstream quickly and distributes to the tissues. Approximately 50% of the ingested dose can enter the tissues in
5 minutes. Also within a few minutes of ingestion, strychnine can be detected in the urine. Little dierence was
noted between oral and intramuscular administration of
strychnine. In persons killed by strychnine, the highest
concentrations are found in the blood, liver, kidney and
stomach wall. The usual fatal dose is 60100 mg strychnine and is fatal after a period of 12 hours, though lethal
doses vary depending on the individual.

5.3 Metabolism
Strychnine is rapidly metabolized by the liver microsomal
enzyme system requiring NADPH and O2 . Strychnine
competes with the inhibitory neurotransmitter glycine resulting in an excitatory state. However, the toxicokinetics
after overdose have not been well described. In most severe cases of strychnine poisoning, the patient dies before
reaching the hospital. The biological half-life of strychnine is about 10 hours. This half-life suggests that normal
hepatic function can eciently degrade strychnine even
when the quantity ingested is high enough to cause severe
poisoning.

5.4

Excretion

A few minutes after ingestion, strychnine is excreted unchanged in the urine, and accounts for about 5 to 15% of
a sublethal dose given over 6 hours. Approximately 10 to
20% of the dose will be excreted unchanged in the urine
in the rst 24 hours. The percentage excreted decreases
with the increasing dose. Of the amount excreted by the
kidneys, about 70% is excreted in the rst 6 hours, and
almost 90% in the rst 24 hours. Excretion is virtually
complete in 48 to 72 hours.[6]

Mechanism of action

REFERENCES

lavage with tannic acid or potassium permanganate solutions to oxidize strychnine. Seizures are controlled by
anticonvulsants, such as phenobarbital or diazepam,[11]
along with muscle relaxants such as dantrolene to combat
muscle rigidity. Chloroform or heavy doses of chloral,
bromide, urethane or amyl nitrate can also be used to restrain the convulsions. Because diazepam, as the anticonvulsant of choice, is not eective in all cases, a combination with midazolam, fentanyl, or pancuronium is recommended for controlling the convulsions. Strychnine
poisoning demands an aggressive management with early
intubation, control of muscle tremors, and prevention of
rhabdomyolysis and renal failure with dialysis. If a poisoned person is able to survive for 6 to 12 hours, they have
a good prognosis.[11]

Strychnine is a neurotoxin which acts as an antagonist of Also, George Harley (18291896) showed in 1850 that
glycine and acetylcholine receptors. It primarily aects Curare (wourali) was eective for the treatment of tetanus
the motor nerves in the spinal cord which control muscle and strychnine poisoning.
contraction. An impulse is triggered at one end of a nerve
by the binding of neurotransmitters to the receptors. In
the presence of a neuroinhibitor, such as glycine, a greater 8 See also
quantity of excitatory neurotransmitters must bind to receptors before there will be an action potential generated.
Avicide
Glycine acts primarily as an agonist of the glycine recep Denatonium
tor, which is a ligand-gated chloride channel in neurons
located in the spinal cord and in the brain. This chlo "Poisoning Pigeons in the Park"
ride channel will allow the negatively charged chloride
ions into the neuron, causing a hyperpolarization which
The Mysterious Aair at Styles
pushes the membrane potential further from threshold.
Strychnine is an antagonist of glycine, which means it
binds to the same receptor, preventing the inhibitory ef- 9 References
fects of glycine on the postsynaptic neuron. Therefore,
action potentials are triggered with lower levels of exci- [1] NIOSH Pocket Guide to Chemical Hazards #0570.
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National Institute for Occupational Safety and Health
prevented, the motor neurons are more easily activated
(NIOSH).
and the victim will have spastic muscle contractions, resulting in death by asphyxiation.[4][47] Structure of strych- [2] Everett, A. J.; Openshaw, H. T.; Smith, G. F. (1957).
221. The constitution of aspidospermine. Part III. Renine in complex with ACh binding protein (AChBP).[48]

Treatment

There is no specic antidote for strychnine but recovery

from strychnine exposure is possible with early hospital treatment. Treatment consists of removing the drug
from the body (decontamination) and administering supportive medical care in a hospital setting. Supportive care includes intravenous uids, medications against
convulsions and spasms, and cooling measures for high
temperature.[11] The patient should be kept in a quiet and
darkened room, because excessive manipulation and loud
noises may cause convulsions. Because these convulsions
are extremely painful, an appropriate painkiller should
be given. Treatment of strychnine poisoning involves an
oral administration of activated charcoal which adsorbs
any strychnine within the digestive tract. Unabsorbed
strychnine can be removed from the stomach by gastric

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REFERENCES

10
10.1

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Beetstra, Me2NiK, Gegnome, LSX, Lgolos, Meodipt, Kwilliamszaf, Ash73, Rieman 82, The snare, Christian75, Hallogallo, Headbomb,
AntiVandalBot, Martyn Smith, Figma, Deective, MegX, Savant13, WolfmanSF, Jancikotuc, ChemistHans, Froid, ChemNerd, Faazshift,
Leyo, Tgeairn, J.delanoy, Neolandes, Boghog, Zephyr78, Trumpet marietta 45750, HOUZI, LittleHow, Whiteandnerdy52, Tvbrichmond,
RockSolid44, VolkovBot, DSRH, SakotGrimshine, Dougie monty, TXiKiBoT, Oshwah, Technopat, Biswaskaushik, BotKung, Doc James,
PGWG, GirasoleDE, Prakash Nadkarni, Cwkmail, Calabraxthis, Keilana, Yerpo, Baseball Bugs, Android Mouse Bot 3, Gordonofcartoon, Chri$topher, Paulinho28, Chem-awb, Rjd0060, EoGuy, Jtomlin1uk, Soaringbear, PMDrive1061, Iohannes Animosus, The Red,
Versus22, DumZiBoT, EdChem, Chymra, Vanished 45kd09la13, Yum7977, Rummy666, Addbot, Ronhjones, Cuaxdon, NjardarBot,
Paulobrito, Zorrobot, Jarble, Luckas-bot, Yobot, CheMoBot, Backslash Forwardslash, AnomieBOT, Gtz, Missionmanmission, BWear2,
Citation bot, Clark89, JimVC3, , Anonymous from the 21st century, Polyphebus, FrescoBot, RicHard-59, TimonyCrickets,
Saehrimnir, Atlantia, Nirmos, Pinethicket, Jonesey95, Rodriguez d4 e5 r18, BogBot, SingingZombie, 777sms, Techhead7890, EmausBot,
Qdiderot, Dewritech, Dcirovic, Bamyers99, AManWithNoPlan, AlphaPikachu578, Ichgab, Flyhi152, Birlanady, Louisajb, ClueBot NG,
Pashihiko, Khakhalin, Ilse, Ilse, Judith, Vincent, Tox project, Jacopo188, Carlstak, Skpande, Patelbq, Pandoraten, NotWith, MisterMorton, Shisha-Tom, YoungLochinvar, BattyBot, Plutoniumjesus, K94u10, Xprofj, Dexbot, SantoshBot, Mogism, JZNIOSH, FDent, Leprof
7272, Arcane21, Flobbadob, ArmbrustBot, Gazapo, Monkbot, Medgirl131, Breedentials, Sometree, Coconutporkpie, MrProteinDNA,
Tilifa Ocaufa, Emily Temple-Wood (NIOSH), Cnishimu, KasparBot, HandsomeMrToad, Mrv3rsac3, Heaviside glow, CountryMusicMann,
Metaad0n3 and Anonymous: 237

10.2

Images

File:Opisthotonus_in_a_patient_suffering_from_tetanus_-_Painting_by_Sir_Charles_Bell_-_1809.jpg
Source:
https:
//upload.wikimedia.org/wikipedia/commons/d/d8/Opisthotonus_in_a_patient_suffering_from_tetanus_-_Painting_by_Sir_Charles_
Bell_-_1809.jpg License: Public domain Contributors: http://www.anatomyacts.co.uk/exhibition/object.asp?objectnum=62 Original
artist: Sir Charles Bell
File:Question_book-new.svg Source: https://upload.wikimedia.org/wikipedia/en/9/99/Question_book-new.svg License: Cc-by-sa-3.0
Contributors:
Created from scratch in Adobe Illustrator. Based on Image:Question book.png created by User:Equazcion Original artist:
Tkgd2007
File:Strychnine-from-xtal-3D-balls.png
Source:
https://upload.wikimedia.org/wikipedia/commons/f/fb/
Strychnine-from-xtal-3D-balls.png License: Public domain Contributors: Own work Original artist: Ben Mills
File:Strychnine2.svg Source: https://upload.wikimedia.org/wikipedia/commons/4/41/Strychnine2.svg License: Public domain Contributors: Selfmade with ChemDraw. Original artist: Calvero.
File:StrychnineIII.svg Source: https://upload.wikimedia.org/wikipedia/commons/1/1c/StrychnineIII.svg License: CC BY-SA 3.0 Contributors: Own work Original artist: Ipmccull
File:X_mark.svg Source: https://upload.wikimedia.org/wikipedia/commons/a/a2/X_mark.svg License: Public domain Contributors: Own
work Original artist: User:Gmaxwell
File:Yes_check.svg Source: https://upload.wikimedia.org/wikipedia/en/f/fb/Yes_check.svg License: PD Contributors: ? Original artist: ?

10.3

Content license

Creative Commons Attribution-Share Alike 3.0