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Case Study:

Cyanide and Almonds

Bailey Shawver

University of Idaho

FS 464: Food Toxicology

November 20, 2020

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Abstract

Bitter almonds a potential lethal phenotype of Prunus dulcis, contains the cyanogenic

glycosides, Amygdalin, which, once hydrolyzed, produces hydrogen cyanide. The amount of

bitter almonds needed to be lethal is less then two recommended servings of sweet almonds.

With the popularity of bitter almonds as a health food cases of cyanide toxicity through almonds

have increased.

Introduction

Almonds (Prunus dulcis), a popular seed consumed globally, while commonly praised

for its health benefits, can also be quite deadly (Barreca et al., 2020). Almonds depending on

whether they are the sweet or bitter variety can be lethal with less than a handful (Chaouali et al.,

2013). While not inherently toxic, all almonds contain cyanogenic glycosides which once

hydrolyzed during metabolization, breaks down into the bitter tasting compound, benzaldehyde,

and the known toxin, hydrogen cyanide (Boutbaoucht et al., 2013). When hydrogen cyanide is

released it causes oxygen deprivation of the cells which can cause irreversible damage and affect

the synthesis of adenosine triphosphate (ATP) (Chaouali et al., 2013).

Even with the known dangers of bitter or lethal almonds and the relative safety of sweet

almonds, almonds contain concerning levels of cyanogenic glycosides continue to make it into

the United States food supply (Toomey et al, 2012). In this case study we investigate the history

of almonds and hydrogen cyanide, the biological causes to the varying levels of cyanogenic

glycosides in different types of almonds, and the biological pathways of cyanogenic glycosides

and hydrogen cyanide.

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Background

In the early 1800’s chemists Robiquet and Bourton-Chalard identified cyanogenic

glucoside as the compound releasing hydrogen cyanide in bitter almonds (Thodberg et al, 2018).

The specific cyanogenic glucoside found in almonds is called Amygdalin. Amygdalin can also

be found in other members seeds, also known as pits, in the Prunus genus, including peaches,

apricots, and cherries. While the pits in these fruits can also cause cyanide toxicity, since the pits

are not typically consumed as a part of the human food supply, publications for these cases

appear to be less frequent then cyanide toxicity of other sources, but due to the lethality of the

plants found in the Prunus genus it was not uncommon for these plants to be used as poisons

with the first published description of poisoning due to almonds being in 1679 (Reade et al.,

2012).

When speaking of the types of almonds known there are two that are commonly

discussed, the sweet, non-lethal, almond and the bitter, lethal, almond. Both are the same species

of almond, but because of a mutation causing wild bitter almonds to become sweet, due to

having lesser amounts of Amygdalin, and humans cultivating the sweeter almonds for food, they

are by the public treated like two different species (Chaouali et al., 2013),( Sánchez-Pérez et al.,

2019). During production of almonds whether or not a tree will produce bitter or sweet almonds

is unknown until its first harvest, this is because of the genetic probability of the almonds

bitterness, which in case contributes to the high pricing of almonds compared to other nuts

because of the two to three years it takes almond trees to become harvestable (Thodberg et al,

2018),. When comparing the actual amounts of Amygdalin and, there forth, the hydrogen

cyanide that can be produced from these almonds, bitter almonds on average can produce about

40 times the amount of hydrogen cyanide then sweet almonds can (Chaouali et al., 2013).
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Discussion

When consuming almonds Amygdalin enzymatically hydrolysis into hydrogen cyanide

and other products of this hydrolysis in the mouth. As described by Lee, Zhang, Wood, Castillo,

and Mitchell (2013),

“The disruption of kernel tissue (e.g., chewing) enables amygdalin to come into contact

with hydrolytic enzymes to form hydrogen cyanide. This stepwise process involves the

initial hydrolysis of amygdalin into prunasin and glucose via the action of β-glucosidase

amygdalin hydrolase. The prunasin is subsequently hydrolyzed into mandelonitrile by

prunasin hydrolase and is finally converted into benzaldehyde and hydrogen cyanide by

β-mandelonitrile lyase.”

These set of reactions also create benzaldehyde, which is what causes the bitter tastes when

consuming bitter almonds (Boutbaoucht et al., 2013).

Once hydrogen cyanide has entered the body through an oral route it can take up to

twelve hours for symptoms to arise (United States Department of Health and Human Services,

1990). According to Graham and Traylor (2020), the hydrogen cyanide,

“absorbs quickly through… the gastrointestinal tract … providing fast diffusion into the

bloodstream. Cyanide reversibly binds to the ferric ions cytochrome oxidase three within

the mitochondria… halt(ing) cellular respiration by blocking the reduction of oxygen to

water. (This causes) cellular hypoxia and the depletion of ATP (to) occur, leading to

metabolic acidosis. The utilization of oxygen by the tissue occurs and is followed by the

impairment of vital functions”

Symptoms of cyanide toxicity include dizziness, headache, nausea and vomiting, rapid breathing,

rapid heart rate, restlessness, and weakness for small doses and convulsions, loss of
CASE STUDY: CYANIDE IN ALMONDS 5

consciousness, low blood pressure, lung injury, respiratory failure leading to death, and slow

heart rate for large doses. (CDC, 2011)

Due to the increase knowledge of Amygdalin being an alternative cancer treatment and

the apparent easy of getting bitter almonds and other Prunus genus seeds from heath food stores

and online realtors, the overall consumption of these protentional lethal seeds have gone up ().

These work arounds for laws prohibiting the growth and selling of bitter almonds continue to

endanger people daily.

While it takes around fifty almonds to be lethal to an adult it takes only five to ten to kill

a child (Chaouali et al., 2013). In 2013 a 5-year old boy was hospitalized for dizziness,

confusion, and vomiting after the ingestion of 10 bitter almonds (Boutbaoucht et al., 2013).

While he recovered with no permanent effects due to receiving medical attention quickly, the

dangers of being in position of such a product, especial with its similarities to sweet almonds, in

highly unadvised.

Conclusion

Hydrogen cyanide toxicity through bitter almonds is a real concern. With such a low

dosage needed to be lethal in both adults and children, the lack of public knowledge on how

dangerous they can be, and the accessibility to them, makes them dangerous to the general

public.

References

Barreca, D., Nabavi, S. M., Sureda, A., Rasekhian, M., Raciti, R., Silva, A. S., . . . Mandalari, G.

(2020). Almonds (Prunus Dulcis Mill. D. A. Webb): A Source of Nutrients and Health-

Promoting Compounds. Nutrients, 12(3), 672. doi:10.3390/nu12030672

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Boutbaoucht, M., Najib, M., Adib, A. E., Sbihi, M., Younous, S., Mouaffak, Y., & Zegzouti, F.

(2013). Cyanide poisoning after bitter almond ingestion. Annals of Tropical Medicine and

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Chaouali, N., Gana, I., Dorra, A., Khelifi, F., Nouioui, A., Masri, W., . . . Hedhili, A. (2013).

Potential Toxic Levels of Cyanide in Almonds (Prunus amygdalus), Apricot Kernels

(Prunus armeniaca), and Almond Syrup. ISRN Toxicology, 1-6. doi:10.1155/2013/610648

Graham, J., & Traylor, J. (2020). Cyanide Toxicity. In StatPearls. Treasure Island, Florida:

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Lee, J., Zhang, G., Wood, E., Castillo, C. R., & Mitchell, A. E. (2013). Quantification of

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(ESI)QqQ MS/MS. Journal of Agricultural and Food Chemistry, 61(32), 7754-7759.

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Reade, M. C., Davies, S. R., Morley, P. T., Dennett, J., & Jacobs, I. C. (2012). Review article:

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doi:10.1111/j.1742-6723.2012.01538.x
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Sánchez-Pérez, R., Pavan, S., Mazzeo, R., Moldovan, C., Cigliano, R. A., Cueto, J. D., . . .

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(2018). Elucidation of the Amygdalin Pathway Reveals the Metabolic Basis of Bitter and

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