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{{Short description|Class of chemical compounds}}
{{expand French|date=February 2019}}
{{expand French|date=February 2019}}

[[File:Bufotoxin.svg|thumb|right|250px|Chemical structure of one of the main components of bufotoxin, a conjugate of bufagin with suberylarginine. This component is itself sometimes called bufotoxin.]]
'''Bufotoxins''' are a family of toxic [[steroid]] [[lactones]] or substituted [[Substituted tryptamine|Tryptamines]] of which some may or may not be toxic. They occur in the [[parotoid gland]]s, skin and poison of many [[toad]]s ([[genus]] ''[[Bufo]]'') and other amphibians, and in some plants and mushrooms.<ref>{{cite journal |vauthors=Siperstein MD, Murray AW, Titus E |title=Biosynthesis of cardiotonic sterols from cholesterol in the toad, Bufo marinus |journal=Archives of Biochemistry and Biophysics |volume=67 |issue=1 |pages=154–60 |date=March 1957 |pmid=13412129 |doi=10.1016/0003-9861(57)90254-0}}</ref><ref>{{cite book |first1=Gary |last1=Lincoff |first2=Duane H. |last2=Mitchel |year=1977 |title=Toxic and Hallucinogenic Mushroom Poisoning: A Handbook for Physicians and Mushroom Hunters |url=https://archive.org/details/toxichallucinoge0000linc |url-access=registration |location=New York |publisher=Van Nostrand Reinhold |isbn=978-0-442-24580-1}}{{page needed|date=October 2014}}</ref><ref>{{cite journal |first1=B. |last1=Kißmer |first2=M. |last2=Wichtl |year=1986 |title=Bufadienolide aus Samen von Helleborus odorus |trans-title=Bufadienolides from the Seeds of Helleborus odorus |language=German |journal=Planta Medica |volume=52 |issue=2 |pages=152–3 |doi=10.1055/s-2007-969103}}</ref> The exact composition varies greatly with the specific source of the toxin. It can contain [[5-MeO-DMT]], [[bufagin]]s, [[bufalin]], [[bufotalin]], [[bufotenin]], [[bufothionine]], [[dehydrobufotenine]], [[epinephrine]], [[norepinephrine]], and [[serotonin]]. Some authors have also used the term ''bufotoxin'' to describe the conjugate of a [[bufagin]] with [[suberylarginine]].<ref>{{cite journal |vauthors=Chen KK, Kovaríková A |title=Pharmacology and toxicology of toad venom |journal=Journal of Pharmaceutical Sciences |volume=56 |issue=12 |pages=1535–41 |date=December 1967 |pmid=4871915 |doi=10.1002/jps.2600561202}}</ref>
'''Bufotoxins''' are a family of toxic [[steroid]] [[lactones]] or substituted [[Substituted tryptamine|tryptamines]] of which some are toxic. They occur in the [[parotoid gland]]s, skin, and poison of many [[toad]]s ([[True toad|Bufonidae]] family) and other amphibians, and in some plants and mushrooms.<ref>{{cite journal |vauthors=Siperstein MD, Murray AW, Titus E |title=Biosynthesis of cardiotonic sterols from cholesterol in the toad, Bufo marinus |journal=Archives of Biochemistry and Biophysics |volume=67 |issue=1 |pages=154–60 |date=March 1957 |pmid=13412129 |doi=10.1016/0003-9861(57)90254-0}}</ref><ref>{{cite book |first1=Gary |last1=Lincoff |first2=Duane H. |last2=Mitchel |year=1977 |title=Toxic and Hallucinogenic Mushroom Poisoning: A Handbook for Physicians and Mushroom Hunters |url=https://archive.org/details/toxichallucinoge0000linc |url-access=registration |location=New York |publisher=Van Nostrand Reinhold |isbn=978-0-442-24580-1}}{{page needed|date=October 2014}}</ref><ref>{{cite journal |first1=B. |last1=Kißmer |first2=M. |last2=Wichtl |year=1986 |title=Bufadienolide aus Samen von Helleborus odorus |trans-title=Bufadienolides from the Seeds of Helleborus odorus |language=German |journal=Planta Medica |volume=52 |issue=2 |pages=152–3 |doi=10.1055/s-2007-969103|s2cid=84240708 }}</ref> The exact composition varies greatly with the specific source of the toxin.
==Composition==
[[File:Bufotoxin.svg|thumb|right|300px|Chemical structure of one of the main components of bufotoxin, a conjugate of bufagin with suberylarginine. This component is itself sometimes called bufotoxin.]]
Bufotoxins can contain [[5-MeO-DMT]], [[bufagin]]s, [[bufalin]], [[bufotalin]], [[bufotenin]], [[bufothionine]], [[dehydrobufotenine]], [[epinephrine]], [[norepinephrine]], and [[serotonin]]. Some authors have also used the term ''bufotoxin'' to describe the conjugate of a [[bufagin]] with [[suberylarginine]].<ref>{{cite journal |vauthors=Chen KK, Kovaríková A |title=Pharmacology and toxicology of toad venom |journal=Journal of Pharmaceutical Sciences |volume=56 |issue=12 |pages=1535–41 |date=December 1967 |pmid=4871915 |doi=10.1002/jps.2600561202}}</ref>


The toxic substances found in toads can be divided by chemical structure in two groups:
The toxic substances found in toads can be divided by chemical structure in two groups:


#[[bufadienolide]]s, which are [[cardiac glycoside]]s (e.g., [[bufotalin]], [[bufogenin]])
#[[bufadienolide]]s, which are [[cardiac glycoside]]s (e.g., [[bufotalin]], [[bufogenin]]), are undesirable compounds that may be fatal if consumed.
#[[tryptamine]]-related substances (e.g., [[bufotenin]]), are sought after for [[entheogen]]ic and/or [[recreational drug|recreational]] purposes by some individuals. However, the practice of using these substances derived from animals for spiritual experiences or [[responsible drug use]] may raise [[ethics|ethical]] concerns about the potential suffering inflicted on the animal.
#[[tryptamine]]-related substances (e.g., [[bufotenin]])


==Species==
Toads known to secrete bufotoxin include the following:{{citation needed|date=March 2014}}
{{also|List of poisonous animals}}


Toads known to secrete bufotoxins.<ref name="5-Hydroxytryptamine and Related Indolealkylamines">{{cite book|title=5-Hydroxytryptamine and Related Indolealkylamines|date=2013|publisher=Springer Berlin|location=Berlin|isbn=978-3642854699}}</ref>
*''[[Colorado River toad|Bufo alvarius]]''

⚫
*''[[Bufo americanus]]''
===Toads frequently "milked"===
*''[[Bufo arenarum]]''
Despite being a frequent target for milking, these toads still carry cardio toxic bufotoxins which have been linked to deaths.
*''[[Bufo asper]]''

*''[[Bufo blombergi]]''
* [[5-HO-DMT]] (bufotenin)
*''[[Bufo boreas]]''
** ''[[Colorado River toad|Incilius alvarius]]'' (formerly ''Bufo alvarius'')<ref name="5-Hydroxytryptamine and Related Indolealkylamines" />
** ''[[Rhinella arenarum]]''<!-- "Bufo arenarum" in the reference --><ref name="5-Hydroxytryptamine and Related Indolealkylamines" />
** ''[[Rhinella diptycha]]''<!-- "Bufo paracnemis" in the reference --><ref name="5-Hydroxytryptamine and Related Indolealkylamines" />
** ''[[Nannophryne variegata]]''<!-- "Bufo variegatus" in the reference --><ref name="5-Hydroxytryptamine and Related Indolealkylamines" />
** ''[[Melanophryniscus moreirae]]''<!-- "Melanophryniscus moreiare" (typo) in the reference --><ref name="5-Hydroxytryptamine and Related Indolealkylamines" />
** ''[[Agile frog|Rana dalmativa]]''<ref name="5-Hydroxytryptamine and Related Indolealkylamines" />
* [[5-MeO-DMT]]
** ''[[Colorado River toad|Incilius alvarius]]'' (formerly ''Bufo alvarius'')<!-- "Bufo alvarius" in the reference --><ref name="5-Hydroxytryptamine and Related Indolealkylamines" />

===Other toads===
The effects of the bufotoxins in these toads are not well understood.

⚫
*''[[American toad|Anaxyrus americanus]]''
*''[[Bufo bufo]]''
*''[[Bufo bufo]]''
*''[[Asiatic toad|Bufo bufo gargarizans]]''
*''[[Guttural toad|Sclerophrys gutturalis]]'' (syn. ''Bufo gutturalis'')
*''[[Bufo formosus]]''
*''[[Bufo fowleri]]''
⚫
*''[[Cane toad|Rhinella marina]]'' (formerly ''Bufo marinus'')
*''[[Bufo melanostictus]]''
*''[[Bufo melanostictus]]''
⚫
*''[[Cane toad|Rhinella marina]]'' (formerly ''Bufo marinus'')
*''[[Bufo peltocephalus]]''
*''[[Bufo quercicus]]''
*''[[Bufo regularis]]''
*''[[Bufo valliceps]]''
*''[[Bufo viridis]]''
*''[[Bufo vulgaris]]''


==Extraction==
==Extraction==
Extract from the skin of certain Asian toads, such as ''Bufo bufo gargarizans'' and ''Bufo melanostictus'', is often found in certain Chinese folk remedies. The [[Pharmacopoeia of the People's Republic of China]] (ChP) considers the two species valid sources of toad venom ({{zh|s=蟾酥|p=Chánsū}}; {{lang-la|bufonis venenum}}), and requires the dry product to contain at least 6% of [[cinobufagin]] and [[resibufogenin]] combined by weight. The extract is obtained by squeezing the [[parotoid gland]]s of caught, washed toads for a white venom and drying; the final dried venom is usually brown, with a chunk or flake form.<ref>{{cite book |author1=国家药典委员会 |title=中华人民共和国药典|trans-title=Pharmacopoeia of the People's Republic of China|volume=1 |date=2015 |publisher=中国医药科技出版社 |isbn=9787506773379 |page=333 |edition=10 |language=zh}} entries: [http://db.ouryao.com/yd2015/view.php?id=616 蟾酥 bufonis venenum]</ref>
Extract from the skin of certain Asian toads, such as ''Bufo bufo gargarizans'' and ''Bufo melanostictus'', is often found in certain Chinese folk remedies. The [[Pharmacopoeia of the People's Republic of China]] (ChP) considers the two species valid sources of toad poison ({{zh|s=蟾酥|p=Chánsū}}; {{langx|la|bufonis venenum}}), and requires the dry product to contain at least 6% of [[cinobufagin]] and [[resibufogenin]] combined by weight. The extract is obtained by squeezing the [[parotoid gland]]s of caught, washed toads for a white venom and drying; the final dried poison is usually brown, with a chunk or flake form.<ref>{{cite book |author1=国家药典委员会 |title=中华人民共和国药典|trans-title=Pharmacopoeia of the People's Republic of China|volume=1 |date=2015 |publisher=中国医药科技出版社 |isbn=9787506773379 |page=333 |edition=10 |language=zh}} entries: [http://db.ouryao.com/yd2015/view.php?id=616 蟾酥 bufonis venenum]</ref>


==Human poisoning==
==Human poisoning==
Toad‐venom poisoning is rare but can kill.{{R|withreview}} It can occur when someone drinks toad soup, eats toad meat or toad eggs, or swallows live toads on a bet.{{R|withreview}}{{R|slate}} It can also happen when someone deliberately takes commercial substances made with toad toxins.{{R|slate}} These go under names including "Kyushin", "Chan Su" (marketed as a painkiller,{{R|slate}} topical anesthetic or cardiac treatment{{R|Forensic2009}}), "Rockhard" and "Love Stone" (marketed as aphrodisiacs).{{R|slate}}
Poisoning from toad toxin is rare but can kill.{{R|withreview}} It can occur when someone drinks toad soup, eats toad meat or toad eggs, or swallows live toads on a bet.{{R|withreview}}{{R|slate}} It can also happen when someone deliberately takes commercial substances made with toad toxins.{{R|slate}} These go under names including "Kyushin", "Chan Su" (marketed as a painkiller,{{R|slate}} topical anesthetic or cardiac treatment{{R|Forensic2009}}), "Rockhard" and "Love Stone" (marketed as aphrodisiacs).{{R|slate}}


"Chan Su" (literally "toad venom") is often adulterated with standard painkillers, such as [[paracetamol]], [[promethazine]] and [[diclofenac]]. It may be ingested or injected.{{R|poisoning}}
"Chan Su" (literally "toad venom") is often adulterated with standard painkillers, such as [[paracetamol]], [[promethazine]] and [[diclofenac]]. It may be ingested or injected.{{R|poisoning}}


<!--Potentially toxic compounds include [[bufagin]]s, [[catecholamine]]s and [[indolealkylamine]]s.{{R|withreview}} Venom may also contain [[Bufotenin|bufotenine]], a [[tryptamine]] derivative [[alkaloid]] found in various toads' secretions, and the [[bufadienolide]]s [[resibufogenin]], [[cinobufagin]] and [[bufalin]].{{R|Forensic2009}}-->
<!--Potentially toxic compounds include [[bufagin]]s, [[catecholamine]]s and [[indolealkylamine]]s.{{R|withreview}} Venom may also contain [[Bufotenin|bufotenine]], a [[tryptamine]] derivative [[alkaloid]] found in various toads' secretions, and the [[bufadienolide]]s [[resibufogenin]], [[cinobufagin]] and [[bufalin]].{{R|Forensic2009}}-->
=== Symptoms of Intoxication ===

Symptoms may vary depending on certain factors such as the size and age of the victim. Other than the first, more benign symptoms (such as a tingling or burning sensation in the eyes, mucous membranes, or in exposed wounds), the most frequently described symptoms in the medical literature are :
* [[Pallor|paleness]]
* [[bradycardia]]
* [[cardiac arrhythmia]] (including [[ventricular fibrillation|ventricular]] and [[atrial fibrillation]])
* [[bundle branch block]]
* [[hypotension]]
* [[dyspnea]]
* [[tachypnea]]
* [[hallucination]]
* [[Blurred Vision]]
* [[paralysis]] (starting at extremities)
* [[hypersalivation]]
* [[diarrhea]]
* [[vomiting]]
* [[anaphylactic shock]]
* [[loss of consciousness]]
* [[respiratory arrest]]
* [[cardiac arrest]]

One epileptic episode caused by Bufotoxins was observed in a 5-year old child, minutes after they had placed a Bufo alvarius in their mouth. The child was successfully treated with diazepam and phenobarbital. <ref>Hitt M, Ettinger DD. Toad toxicity. N Engl J Med ; 1986 ; 314:1517</ref>

In extreme cases following ingestion of mucus or skin of the toad, death generally occurs within 6 and 24 hours. Victims surviving past 24 hours generally will recover.

== References ==
== References ==


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{{Toxins}}
{{Toxins}}


[[Category:Vertebrate toxins]]
[[Category:Alpha-Amino acids]]
[[Category:Amphibian toxins]]
[[Category:Causes of death]]

Latest revision as of 06:07, 25 October 2024

Bufotoxins are a family of toxic steroid lactones or substituted tryptamines of which some are toxic. They occur in the parotoid glands, skin, and poison of many toads (Bufonidae family) and other amphibians, and in some plants and mushrooms.[1][2][3] The exact composition varies greatly with the specific source of the toxin.

Composition

[edit]
Chemical structure of one of the main components of bufotoxin, a conjugate of bufagin with suberylarginine. This component is itself sometimes called bufotoxin.

Bufotoxins can contain 5-MeO-DMT, bufagins, bufalin, bufotalin, bufotenin, bufothionine, dehydrobufotenine, epinephrine, norepinephrine, and serotonin. Some authors have also used the term bufotoxin to describe the conjugate of a bufagin with suberylarginine.[4]

The toxic substances found in toads can be divided by chemical structure in two groups:

  1. bufadienolides, which are cardiac glycosides (e.g., bufotalin, bufogenin), are undesirable compounds that may be fatal if consumed.
  2. tryptamine-related substances (e.g., bufotenin), are sought after for entheogenic and/or recreational purposes by some individuals. However, the practice of using these substances derived from animals for spiritual experiences or responsible drug use may raise ethical concerns about the potential suffering inflicted on the animal.

Species

[edit]
See also: List of poisonous animals

Toads known to secrete bufotoxins.[5]

Toads frequently "milked"

[edit]

Despite being a frequent target for milking, these toads still carry cardio toxic bufotoxins which have been linked to deaths.

Other toads

[edit]

The effects of the bufotoxins in these toads are not well understood.

Extraction

[edit]

Extract from the skin of certain Asian toads, such as Bufo bufo gargarizans and Bufo melanostictus, is often found in certain Chinese folk remedies. The Pharmacopoeia of the People's Republic of China (ChP) considers the two species valid sources of toad poison (Chinese: 蟾酥; pinyin: Chánsū; Latin: bufonis venenum), and requires the dry product to contain at least 6% of cinobufagin and resibufogenin combined by weight. The extract is obtained by squeezing the parotoid glands of caught, washed toads for a white venom and drying; the final dried poison is usually brown, with a chunk or flake form.[6]

Human poisoning

[edit]

Poisoning from toad toxin is rare but can kill.[7] It can occur when someone drinks toad soup, eats toad meat or toad eggs, or swallows live toads on a bet.[7][8] It can also happen when someone deliberately takes commercial substances made with toad toxins.[8] These go under names including "Kyushin", "Chan Su" (marketed as a painkiller,[8] topical anesthetic or cardiac treatment[9]), "Rockhard" and "Love Stone" (marketed as aphrodisiacs).[8]

"Chan Su" (literally "toad venom") is often adulterated with standard painkillers, such as paracetamol, promethazine and diclofenac. It may be ingested or injected.[10]

Symptoms of Intoxication

[edit]

Symptoms may vary depending on certain factors such as the size and age of the victim. Other than the first, more benign symptoms (such as a tingling or burning sensation in the eyes, mucous membranes, or in exposed wounds), the most frequently described symptoms in the medical literature are :

One epileptic episode caused by Bufotoxins was observed in a 5-year old child, minutes after they had placed a Bufo alvarius in their mouth. The child was successfully treated with diazepam and phenobarbital. [11]

In extreme cases following ingestion of mucus or skin of the toad, death generally occurs within 6 and 24 hours. Victims surviving past 24 hours generally will recover.

References

[edit]
  1. ^ Siperstein MD, Murray AW, Titus E (March 1957). "Biosynthesis of cardiotonic sterols from cholesterol in the toad, Bufo marinus". Archives of Biochemistry and Biophysics. 67 (1): 154–60. doi:10.1016/0003-9861(57)90254-0. PMID 13412129.
  2. ^ Lincoff, Gary; Mitchel, Duane H. (1977). Toxic and Hallucinogenic Mushroom Poisoning: A Handbook for Physicians and Mushroom Hunters. New York: Van Nostrand Reinhold. ISBN 978-0-442-24580-1.[page needed]
  3. ^ Kißmer, B.; Wichtl, M. (1986). "Bufadienolide aus Samen von Helleborus odorus" [Bufadienolides from the Seeds of Helleborus odorus]. Planta Medica (in German). 52 (2): 152–3. doi:10.1055/s-2007-969103. S2CID 84240708.
  4. ^ Chen KK, Kovaríková A (December 1967). "Pharmacology and toxicology of toad venom". Journal of Pharmaceutical Sciences. 56 (12): 1535–41. doi:10.1002/jps.2600561202. PMID 4871915.
  5. ^ 国家药典委员会 (2015). 中华人民共和国药典 [Pharmacopoeia of the People's Republic of China] (in Chinese). Vol. 1 (10 ed.). 中国医药科技出版社. p. 333. ISBN 9787506773379. entries: 蟾酥 bufonis venenum
  6. ^ a b Kuo, HY; Hsu, CW; Chen, JH; Wu, YL; Shen, YS (March 2007). "Life-threatening episode after ingestion of toad eggs: a case report with literature review". Emergency Medicine Journal. 24 (3): 215–6. doi:10.1136/emj.2006.044602. PMC 2660035. PMID 17351232.
  7. ^ a b c d Cartwright, Megan (29 June 2015). "These Men Died Trying to Achieve Epic Erections". Slate Magazine. Retrieved 22 April 2021.
  8. ^ Kostakis, Chris; Byard, Roger W. (2009-07-01). "Sudden death associated with intravenous injection of toad extract". Forensic Science International. 188 (1): e1–e5. doi:10.1016/j.forsciint.2009.02.006. ISSN 0379-0738. PMID 19303230.
  9. ^ Trakulsrichai, S; Chumvanichaya, K; Sriapha, C; Tongpoo, A; Wananukul, W (2020). "Toad Poisoning: Clinical Characteristics and Outcomes". Therapeutics and Clinical Risk Management. 16: 1235–1241. doi:10.2147/TCRM.S272863. PMC 7752649. PMID 33363378.
  10. ^ Hitt M, Ettinger DD. Toad toxicity. N Engl J Med ; 1986 ; 314:1517
[edit]
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