Bufotoxin

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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.

Contents

Composition

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

Toads known to secrete bufotoxins. [5]

Toads frequently "milked"

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

Other toads

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

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 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

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

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, mucus 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.

Related Research Articles

<span class="mw-page-title-main">Cane toad</span> Worlds largest true toad

The cane toad, also known as the giant neotropical toad or marine toad, is a large, terrestrial true toad native to South and mainland Central America, but which has been introduced to various islands throughout Oceania and the Caribbean, as well as Northern Australia. It is a member of the genus Rhinella, which includes many true toad species found throughout Central and South America, but it was formerly assigned to the genus Bufo.

<span class="mw-page-title-main">Cardiac glycoside</span> Class of organic compounds

Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses include treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants and milkweed plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.

<i>Bufo</i> Genus of amphibians

Bufo is a genus of true toads in the amphibian family Bufonidae. As traditionally defined, it was a wastebasket genus containing a large number of toads from much of the world but following taxonomic reviews most of these have been moved to other genera, leaving only seventeen extant species from Europe, northern Africa and Asia in this genus, including the well-known common toad. Some of the genera that contain species formerly placed in Bufo are Anaxyrus, Bufotes, Duttaphrynus, Epidalea and Rhinella.

<span class="mw-page-title-main">5-MeO-DMT</span> Chemical compound

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, the power, bufo, and toad venom.

<span class="mw-page-title-main">Common toad</span> Species of amphibian

The common toad, European toad, or in Anglophone parts of Europe, simply the toad, is a frog found throughout most of Europe, in the western part of North Asia, and in a small portion of Northwest Africa. It is one of a group of closely related animals that are descended from a common ancestral line of toads and which form a species complex. The toad is an inconspicuous animal as it usually lies hidden during the day. It becomes active at dusk and spends the night hunting for the invertebrates on which it feeds. It moves with a slow, ungainly walk or short jumps, and has greyish-brown skin covered with wart-like lumps.

<span class="mw-page-title-main">Bufotenin</span> Psychedelic drug found in toads, mushrooms and plants

Bufotenin is a tryptamine derivative, more specifically, a DMT analog, related to the neurotransmitter serotonin. It is an alkaloid found in some species of mushrooms, plants and toads, especially the skin.

Bufagin is a toxic steroid C24H34O5 obtained from toad's milk, the poisonous secretion of a skin gland on the back of the neck of a large toad (Rhinella marina, synonym Bufo marinus, the cane toad). The toad produces this secretion when it is injured, scared or provoked. Bufagin resembles chemical substances from digitalis in physiological activity and chemical structure.

<span class="mw-page-title-main">Bufotalin</span> Chemical compound

Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species. Bufotalin can be extracted from the skin parotoid glands of several types of toad.

<span class="mw-page-title-main">Colorado River toad</span> Species of amphibian

The Colorado River toad, also known as the Sonoran Desert toad, is a toad species found in northwestern Mexico and the southwestern United States. It is well known for its ability to exude toxins from glands within its skin that have psychoactive properties.

<span class="mw-page-title-main">American toad</span> Species of amphibian

The American toad is a common species of toad found throughout Canada and the eastern United States. It is divided into three subspecies: the eastern American toad, the dwarf American toad and the rare Hudson Bay toad. Recent taxonomic treatments place this species in the genus Anaxyrus instead of Bufo.

<i>Duttaphrynus melanostictus</i> Species of amphibian

Duttaphrynus melanostictus is commonly called Asian common toad, Asian black-spined toad, Asian toad, black-spectacled toad, common Sunda toad, and Javanese toad. It is probably a complex of more than one true toad species that is widely distributed in South and Southeast Asia.

<span class="mw-page-title-main">True toad</span> Family of amphibians

A true toad is any member of the family Bufonidae, in the order Anura. This is the only family of anurans in which all members are known as toads, although some may be called frogs. The bufonids now comprise more than 35 genera, Bufo being the best known.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

<span class="mw-page-title-main">Parotoid gland</span> External skin gland on the back, neck, and shoulder of toads, some frogs, and salamanders

The parotoid gland is an external skin gland on the back, neck, and shoulder of some frogs, and salamanders. It can secrete a number of milky alkaloid substances known collectively as bufotoxins, which act as neurotoxins to deter predation. These cutaneous glands are called parotoid as they are somewhat similarly positioned to mammalian parotid gland, although the latter have a different function, excreting saliva within the mouth rather than externally excreted defensive chemicals.

<i>Rhinella icterica</i> Species of amphibian

Rhinella icterica is a species of toad in the family Bufonidae that is found in northeastern Argentina, southern Brazil, and eastern Paraguay. "Cururu" is its indigenous name and refers to the male advertisement call that is a melodious tremolo. "Cururu toad", without the specifier "yellow", is a common name used for a few other closely related species.

<span class="mw-page-title-main">Arenobufagin</span> Chemical compound

Arenobufagin is a cardiotoxic bufanolide steroid secreted by the Argentine toad Bufo arenarum. It has effects similar to digitalis, blocking the Na+/K+ pump in heart tissue.

<span class="mw-page-title-main">Poisonous amphibian</span> Amphibians that produce poison

Poisonous amphibians are amphibians that produce toxins to defend themselves from predators.

HuaChanSu is a traditional Chinese medicine extracted from the skin of toads from the genus Bufo that is believed by some to slow the spread of cancerous cells. The parotoid gland of toads of the Bufo genus secrete a venom, which is dried and dissolved in water. This solution, HuaChanSu, is injected into a cancerous area and targets specific cancer cells. HuaChanSu is undergoing further trials, and its effect is not completely understood.

Native to both South and Central America, Cane toads were introduced to Australia in the 1930s and have since become an invasive species and a threat to the continent's native predators and scavengers.

References

  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. 1 2 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. 1 2 3 4 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