Bufotenin
Encyclopedia
Bufotenin or 5-hydroxy-dimethyltryptamine (5-HO-DMT or 5-OH-DMT), is a tryptamine
related to the neurotransmitter
serotonin
. It is an alkaloid
found in the skin of some species of toad
s; in mushrooms, higher plants, and mammals.
The name bufotenin originates from the Bufo
genus of toads, which includes several species of psychoactive toad
s, most notably Bufo alvarius, that secrete bufotoxin
s from their parotoid gland
s. Bufotenin is similar in chemical structure to the psychedelic
s psilocin (4-HO-DMT)
, 5-MeO-DMT
, and DMT
, chemicals which also occur in some of the same fungus, plant, and animal species as bufotenin. Psychedelic effects of bufotenin in humans have been observed in some studies.
during World War I
. The structure of bufotenine was first confirmed in 1934 by Heinrich Wieland’s laboratory in Munich, and the first reported synthesis of bufotenine was by Toshio Hoshino in 1936.
(Bufo alvarius) as it is the only toad species in which bufotenin is present in large enough quantities for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines such as ch’an su (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China.
The toad was "recurrently depicted in Mesoamerican art," which some authors have interpreted as indicating that the effects of ingesting Bufo secretions have been known in Mesoamerica for many years; however, others doubt that this art provides sufficient "ethnohistorical evidence" to support the claim.
In addition to bufotenine, Bufo venoms also contain digoxin
-like cardiac glycoside
s, and ingestion of the venom can be fatal. Ingestion of Bufo toad venom and eggs by humans has resulted in several reported cases of poisoning, some of which resulted in death.
Contemporary reports indicate that bufotenine-containing toad venom has been used as a street drug; that is, as an aphrodisiac
, ingested orally in the form of ch’an su, and as a psychedelic, by smoking or orally ingesting Bufo toad venom or dried Bufo skins. The use of chan'su and love stone (a related toad venom preparation used as an aphrodisiac in the West Indies) has resulted in several cases of poisoning and at least one death. The practice of orally ingesting toad venom has been referred to in popular culture and in the scientific literature as toad licking and has drawn media attention. Albert Most, founder of the Church of the Toad of Light and a proponent of recreational use of Bufo alvarius
venom, published a booklet titled Bufo alvarius: The Psychedelic Toad of the Sonoran Desert in 1983 which explained how to extract and smoke the secretions.
Bufotenin is also present in the skin secretion of three arboreal amphibian species of the Osteocephalus genus (Osteocephalus taurinus, Osteocephalus oophagus
, and Osteocephalus langsdorffii) from the Amazon
and Atlantic rain forests.
of Anadenanthera colubrina and Anadenanthera peregrina trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff
preparations by indigenous cultures of Central and South America.
mushrooms, including Amanita muscaria
, Amanita citrina, and Amanita porphyria
, though this is widely disputed and likely untrue.
acutifolium) tree, which is used as a psychedelic by South American shamans, and in the seeds of Mucuna pruriens
, and blood
, and to a much lesser extent, the brain
(hypothalamus
, brain stem
, striatum
, and cerebral cortex
) and liver
. It reaches peak concentrations at 1 hour and is nearly completely eliminated within 8 hours. In humans, intravenous administration of bufotenin results in excretion
of (70%) of injected drug in the form of 5-HIAA, an endogenous
metabolite
of serotonin, while roughly 4% is eliminated unmetabolized in the urine. Orally administered bufotenine undergoes extensive first-pass metabolism by the enzyme monoamine oxidase
.
A subject given 1 mg reported “a tight feeling in the chest” and prickling “as if he had been jabbed by needles.” This was accompanied by a “fleeting sensation of pain in both thighs and a mild nausea.”
Another subject given 2 mg reported “tightness in his throat”. He had tightness in the stomach, tingling in pretibial areas, and developed a purplish hue in the face indicating blood circulation problems. He vomited after 3 minutes.
Another subject given 4 mg complained of “chest oppression” and that “a load is pressing down from above and my body feels heavy.” The subject also reported “numbness of the entire body” and “a pleasant Martini feeling-my body is taking charge of my mind”. The subject reported he saw red spots passing before his eyes and red-purple spots on the floor, and the floor seemed very close to his face. Within 2 minutes these visual effects were gone, and replaced by a yellow haze, as if he were looking through a lens filter.
Fabing and Hawkins commented that bufotenin’s psychedelic effects were "reminiscent of LSD
and mescaline
but develop and disappear more quickly, indicating rapid central action and rapid degradation of the drug".
experimented with bufotenine as a snuff. He reported “no subjective or objective effects were observed after spraying with as much as 40 mg bufotenine”; however subjects who received 10–12 mg injected intramuscularly reported “elements of visual hallucinations consisting of a play of colors, lights, and patterns”.
After pushing doses to the morally admissible limit without producing visuals, Turner and Merlis conservatively concluded: “We must reject bufotenine…as capable of producing the acute phase of Cohoba
intoxication”.
at a dose of 1–16 mg had no effect, other than intense local irritation. When given intravenously at low doses (2–4 mg), bufotenine oxalate
caused anxiety but no other effects; however, a dose of 8 mg resulted in profound emotional and perceptual changes, involving extreme anxiety
, a sense of imminent death, and visual disturbance associated with color reversal and distortion, and intense flushing of the cheeks and forehead.
published the results of a study in which he self-administered free base bufotenine via insufflation
(5–100 mg), sublingual
ly (50 mg), intrarectally (30 mg), orally
(100 mg) and via vaporization
(2–8 mg). Ott reported “visionary effects" of intranasal bufotenine and that the "visionary threshold dose" by this route was 40 mg, with smaller doses eliciting perceptibly psychoactive effects. He reported that "intranasal bufotenine is throughout quite physically relaxing; in no case was there facial rubescence, nor any discomfort nor disesteeming side effects".
At 100 mg, effects began within 5 minutes, peaked at 35–40 minutes, and lasted up to 90 minutes. Higher doses produced effects that were described as psychedelic, such as "swirling, colored patterns typical of tryptamines, tending toward the arabesque".
Free base bufotenin taken sublingually was found to be identical to intranasal use. The potency, duration, and psychedelic action was the same. Ott found vaporized free base bufotenin active from 2–8 mg with 8 mg producing "ring-like, swirling, colored patterns with eyes closed". He noted that the visionary effects of insufflated bufotenine were verified by one colleague, and those of vaporized bufotenine by several volunteers.
Ott concluded that free base bufotenin taken intranasally and sublingually produced effects similar to those of Yopo
without the toxic peripheral symptoms, such as facial flushing, observed in other studies in which the drug was administered intravenously.
Studies have detected endogenous bufotenin in urine specimens from individuals with other psychiatric disorders, such as infant autistic patients. Another study indicated that paranoid violent offenders or those who committed violent behaviour towards family members have higher bufotenin levels in their urine than other violent offenders.
A 2010 study utilized a mass spectrometry
approach to detect levels of bufotenin in the urine of individuals with severe autism spectrum disorder (ASD), schizophrenia, and asymptomatic subjects. Their results indicate significantly higher levels of bufotenin in the urine of the ASD and schizophrenic groups when compared to asymptomatic individuals.
In the UK, the substance is a Class A drug under the 1971 Misuse of Drugs Act, although numerous shops sell Amanita muscaria across the Internet. Although some people claim that they may contain the substance, it is often considered an area of dispute and based on unverified claims.
Tryptamine
Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
related to the neurotransmitter
Neurotransmitter
Neurotransmitters are endogenous chemicals that transmit signals from a neuron to a target cell across a synapse. Neurotransmitters are packaged into synaptic vesicles clustered beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to...
serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
. It is an alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
found in the skin of some species of toad
Toad
A toad is any of a number of species of amphibians in the order Anura characterized by dry, leathery skin , short legs, and snoat-like parotoid glands...
s; in mushrooms, higher plants, and mammals.
The name bufotenin originates from the Bufo
Bufo
Bufo is a large genus of about 150 species of true toads in the amphibian family Bufonidae. Bufo is a Latin word for toad.- Description :...
genus of toads, which includes several species of psychoactive toad
Psychoactive toad
Psychoactive toad is a name used for toads from which psychoactive substances from the family of bufotoxins can be derived. The skin and poison of Bufo alvarius contain 5-MeO-DMT and bufotenin. Other species contain only bufotenin. 5-MeO-DMT and bufotenin both belong to the family of...
s, most notably Bufo alvarius, that secrete bufotoxin
Bufotoxin
Bufotoxins are a family of toxic substances found in the parotoid glands, skin and venom of many toads ; other amphibians; and some plants and mushrooms. The exact composition varies greatly with the specific source of the toxin. It can contain: 5-MeO-DMT, bufagins, bufotalin, bufotenine,...
s from their parotoid gland
Parotoid gland
The parotoid gland is an external skin gland on the back, neck, and shoulder of toads and some frogs and salamanders. It secretes a milky alkaloid substance to deter predators...
s. Bufotenin is similar in chemical structure to the psychedelic
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
s psilocin (4-HO-DMT)
Psilocin
Psilocin , an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin...
, 5-MeO-DMT
5-MeO-DMT
5-MeO-DMT is a powerful psychedelic tryptamine. It is found in a wide variety of plant and psychoactive toad species and, like its close relatives DMT and bufotenin , it has been used as an entheogen by South American shamans for thousands of years.-Chemistry:5-MeO-DMT was first synthesized in...
, and DMT
Dimethyltryptamine
N,N-Dimethyltryptamine is a naturally occurring psychedelic compound of the tryptamine family. DMT is found in several plants, and also in trace amounts in humans and other mammals, where it is originally derived from the essential amino acid tryptophan, and ultimately produced by the enzyme INMT...
, chemicals which also occur in some of the same fungus, plant, and animal species as bufotenin. Psychedelic effects of bufotenin in humans have been observed in some studies.
Nomenclature
Bufotenin (bufotenine) is also known by the chemical names 5-hydroxy-dimethyltryptamine (5-HO-DMT), N,N-dimethyl-5-hydroxytryptamine, dimethyl serotonin, and mappine.History
Bufotenin was first isolated, from toad skin, and named by the Austrian chemist Handovsky at the University of PragueCzech Technical University in Prague
Czech Technical University in Prague is one of the largest universities in the Czech Republic, and the oldest institute of technology in Central Europe....
during World War I
World War I
World War I , which was predominantly called the World War or the Great War from its occurrence until 1939, and the First World War or World War I thereafter, was a major war centred in Europe that began on 28 July 1914 and lasted until 11 November 1918...
. The structure of bufotenine was first confirmed in 1934 by Heinrich Wieland’s laboratory in Munich, and the first reported synthesis of bufotenine was by Toshio Hoshino in 1936.
Toads
Bufotenin is a chemical constituent in the venom and eggs of several species of toads belonging to the Bufo genus, but most notably in the Colorado River toadColorado River Toad
The Colorado River toad, Bufo alvarius, also known as the Sonoran Desert toad, is a psychoactive toad found in northern Mexico and the southwestern United States...
(Bufo alvarius) as it is the only toad species in which bufotenin is present in large enough quantities for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines such as ch’an su (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China.
The toad was "recurrently depicted in Mesoamerican art," which some authors have interpreted as indicating that the effects of ingesting Bufo secretions have been known in Mesoamerica for many years; however, others doubt that this art provides sufficient "ethnohistorical evidence" to support the claim.
In addition to bufotenine, Bufo venoms also contain digoxin
Digoxin
Digoxin INN , also known as digitalis, is a purified cardiac glycoside and extracted from the foxglove plant, Digitalis lanata. Its corresponding aglycone is digoxigenin, and its acetyl derivative is acetyldigoxin...
-like cardiac glycoside
Cardiac glycoside
Cardiac glycosides are drugs used in the treatment of congestive heart failure and cardiac arrhythmia. These glycosides are found as secondary metabolites in several plants, but also in some animals, such as the milkweed butterflies. -Function:...
s, and ingestion of the venom can be fatal. Ingestion of Bufo toad venom and eggs by humans has resulted in several reported cases of poisoning, some of which resulted in death.
Contemporary reports indicate that bufotenine-containing toad venom has been used as a street drug; that is, as an aphrodisiac
Aphrodisiac
An aphrodisiac is a substance that increases sexual desire. The name comes from Aphrodite, the Greek goddess of sexuality and love. Throughout history, many foods, drinks, and behaviors have had a reputation for making sex more attainable and/or pleasurable...
, ingested orally in the form of ch’an su, and as a psychedelic, by smoking or orally ingesting Bufo toad venom or dried Bufo skins. The use of chan'su and love stone (a related toad venom preparation used as an aphrodisiac in the West Indies) has resulted in several cases of poisoning and at least one death. The practice of orally ingesting toad venom has been referred to in popular culture and in the scientific literature as toad licking and has drawn media attention. Albert Most, founder of the Church of the Toad of Light and a proponent of recreational use of Bufo alvarius
Colorado River Toad
The Colorado River toad, Bufo alvarius, also known as the Sonoran Desert toad, is a psychoactive toad found in northern Mexico and the southwestern United States...
venom, published a booklet titled Bufo alvarius: The Psychedelic Toad of the Sonoran Desert in 1983 which explained how to extract and smoke the secretions.
Bufotenin is also present in the skin secretion of three arboreal amphibian species of the Osteocephalus genus (Osteocephalus taurinus, Osteocephalus oophagus
Osteocephalus oophagus
Osteocephalus oophagus is a species of frog in the Hyperoliidae family.It is found in Brazil, Colombia, French Guiana, and possibly Suriname.Its natural habitat is subtropical or tropical moist lowland forests. It is also reported to produce Bufotenin....
, and Osteocephalus langsdorffii) from the Amazon
Amazon Rainforest
The Amazon Rainforest , also known in English as Amazonia or the Amazon Jungle, is a moist broadleaf forest that covers most of the Amazon Basin of South America...
and Atlantic rain forests.
Anadenanthera seeds
Bufotenin is a constituent of the seedsSEEDS
SEEDS is a voluntary organisation registered under the Societies Act of India....
of Anadenanthera colubrina and Anadenanthera peregrina trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff
Snuff
Snuff is a product made from ground or pulverised tobacco leaves. It is an example of smokeless tobacco. It originated in the Americas and was in common use in Europe by the 17th century...
preparations by indigenous cultures of Central and South America.
Mushrooms
Bufotenin is also allegedly found in several species of AmanitaAmanita
The genus Amanita contains about 600 species of agarics including some of the most toxic known mushrooms found worldwide. This genus is responsible for approximately 95% of the fatalities resulting from mushroom poisoning, with the death cap accounting for about 50% on its own...
mushrooms, including Amanita muscaria
Amanita muscaria
Amanita muscaria, commonly known as the fly agaric or fly amanita , is a poisonous and psychoactive basidiomycete fungus, one of many in the genus Amanita...
, Amanita citrina, and Amanita porphyria
Amanita porphyria
Amanita porphyria, also known as the Grey Veiled Amanita, is a fairly common, inedible basidiomycete mushroom of the genus Amanita found in Europe and North America.-Description:...
, though this is widely disputed and likely untrue.
Other sources
Bufotenin has been identified as a component in the latex of the takini (BrosimumBrosimum
Brosimum is a genus of plants in the mulberry family, Moraceae, native to tropical regions of the Americas.The Breadnut was used by the Maya civilization for its edible nut. The dense vividly colored scarlet wood of Satine Bloodwood is used for decorative woodworking...
acutifolium) tree, which is used as a psychedelic by South American shamans, and in the seeds of Mucuna pruriens
Mucuna pruriens
Mucuna pruriens is a tropical legume known as velvet bean or cowitch and by other common names , found in Africa, India and the Caribbean. The plant is infamous for its extreme itchiness produced on contact, particularly with the young foliage and the seed pods...
Uptake and elimination
In rats, subcutaneously administered bufotenin (1–100 μg/kg) distributes mainly to the lungs, heartHeart
The heart is a myogenic muscular organ found in all animals with a circulatory system , that is responsible for pumping blood throughout the blood vessels by repeated, rhythmic contractions...
, and blood
Blood
Blood is a specialized bodily fluid in animals that delivers necessary substances such as nutrients and oxygen to the cells and transports metabolic waste products away from those same cells....
, and to a much lesser extent, the brain
Brain
The brain is the center of the nervous system in all vertebrate and most invertebrate animals—only a few primitive invertebrates such as sponges, jellyfish, sea squirts and starfishes do not have one. It is located in the head, usually close to primary sensory apparatus such as vision, hearing,...
(hypothalamus
Hypothalamus
The Hypothalamus is a portion of the brain that contains a number of small nuclei with a variety of functions...
, brain stem
Brain stem
In vertebrate anatomy the brainstem is the posterior part of the brain, adjoining and structurally continuous with the spinal cord. The brain stem provides the main motor and sensory innervation to the face and neck via the cranial nerves...
, striatum
Striatum
The striatum, also known as the neostriatum or striate nucleus, is a subcortical part of the forebrain. It is the major input station of the basal ganglia system. The striatum, in turn, gets input from the cerebral cortex...
, and cerebral cortex
Cerebral cortex
The cerebral cortex is a sheet of neural tissue that is outermost to the cerebrum of the mammalian brain. It plays a key role in memory, attention, perceptual awareness, thought, language, and consciousness. It is constituted of up to six horizontal layers, each of which has a different...
) and liver
Liver
The liver is a vital organ present in vertebrates and some other animals. It has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...
. It reaches peak concentrations at 1 hour and is nearly completely eliminated within 8 hours. In humans, intravenous administration of bufotenin results in excretion
Excretion
Excretion is the process by which waste products of metabolism and other non-useful materials are eliminated from an organism. This is primarily carried out by the lungs, kidneys and skin. This is in contrast with secretion, where the substance may have specific tasks after leaving the cell...
of (70%) of injected drug in the form of 5-HIAA, an endogenous
Endogenous
Endogenous substances are those that originate from within an organism, tissue, or cell. Endogenous retroviruses are caused by ancient infections of germ cells in humans, mammals and other vertebrates...
metabolite
Metabolite
Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
of serotonin, while roughly 4% is eliminated unmetabolized in the urine. Orally administered bufotenine undergoes extensive first-pass metabolism by the enzyme monoamine oxidase
Monoamine oxidase
L-Monoamine oxidases are a family of enzymes that catalyze the oxidation of monoamines. They are found bound to the outer membrane of mitochondria in most cell types in the body. The enzyme was originally discovered by Mary Bernheim in the liver and was named tyramine oxidase...
.
Lethal dose
The acute toxicity of bufotenin in rodents has been estimated at 200 to 300 mg/kg. Death occurs by respiratory arrest.Fabing & Hawkins (1955)
In 1955, Fabing and Hawkins administered bufotenin intravenously at doses of up to 16 mg to prison inmates at Ohio State Penitentiary. A troubling toxic blood circulation effect causing a purpling of the face was seen in these tests.A subject given 1 mg reported “a tight feeling in the chest” and prickling “as if he had been jabbed by needles.” This was accompanied by a “fleeting sensation of pain in both thighs and a mild nausea.”
Another subject given 2 mg reported “tightness in his throat”. He had tightness in the stomach, tingling in pretibial areas, and developed a purplish hue in the face indicating blood circulation problems. He vomited after 3 minutes.
Another subject given 4 mg complained of “chest oppression” and that “a load is pressing down from above and my body feels heavy.” The subject also reported “numbness of the entire body” and “a pleasant Martini feeling-my body is taking charge of my mind”. The subject reported he saw red spots passing before his eyes and red-purple spots on the floor, and the floor seemed very close to his face. Within 2 minutes these visual effects were gone, and replaced by a yellow haze, as if he were looking through a lens filter.
Fabing and Hawkins commented that bufotenin’s psychedelic effects were "reminiscent of LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...
and mescaline
Mescaline
Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally occurring psychedelic alkaloid of the phenethylamine class used mainly as an entheogen....
but develop and disappear more quickly, indicating rapid central action and rapid degradation of the drug".
Isbell (1956)
In 1956, Dr. Harris S. Isbell at the Public Health Service Hospital in Lexington, KentuckyLexington, Kentucky
Lexington is the second-largest city in Kentucky and the 63rd largest in the US. Known as the "Thoroughbred City" and the "Horse Capital of the World", it is located in the heart of Kentucky's Bluegrass region...
experimented with bufotenine as a snuff. He reported “no subjective or objective effects were observed after spraying with as much as 40 mg bufotenine”; however subjects who received 10–12 mg injected intramuscularly reported “elements of visual hallucinations consisting of a play of colors, lights, and patterns”.
Turner & Merlis (1959)
Turner and Merlis (1959) experimented with intravenous administration of bufotenine (as the water soluble creatinine sulfate salt) to schizophrenics at a New York state hospital. They reported that when one subject received 10 mg during a 50-second interval, “the peripheral nervous system effects were extreme: at 17 seconds, flushing of the face, at 22 seconds, maximal inhalation, followed by maximal hyperventilation for about 2 minutes, during which the patient was unresponsive to stimuli; her face was plum-colored". Finally, Turner and Merlis reported that:- “on one occasion, which essentially terminated our study, a patient who received 40 mg intramuscularly, suddenly developed an extremely rapid heart rate; no pulse could be obtained; no blood pressure measured. There seemed to have been an onset of auricular fibrillation…extreme cyanosisCyanosisCyanosis is the appearance of a blue or purple coloration of the skin or mucous membranes due to the tissues near the skin surface being low on oxygen. The onset of cyanosis is 2.5 g/dL of deoxyhemoglobin. The bluish color is more readily apparent in those with high hemoglobin counts than it is...
developed. Massage over the heart was vigorously executed and the pulse returned to normal…shortly thereafter the patient, still cyanotic, sat up saying: ‘Take that away. I don’t like them’.”
After pushing doses to the morally admissible limit without producing visuals, Turner and Merlis conservatively concluded: “We must reject bufotenine…as capable of producing the acute phase of Cohoba
Cohoba
Cohoba is an old Taino Indian transliteration for a ceremony in which psychedelic ground seed of the cojóbana tree was snufed in twin nasal Y-shaped pipe also called Cohoba...
intoxication”.
McLeod and Sitaram (1985)
A 1985 study by McLeod and Sitaram in humans reported that bufotenine administered intranasallyInsufflation (medicine)
Insufflation is the practice of inhaling a substance. Insufflation has limited medical use, but is a common route of administration with many respiratory drugs used to treat conditions in the lungs and paranasal sinus .The technique is common for many recreational drugs and is also used for some...
at a dose of 1–16 mg had no effect, other than intense local irritation. When given intravenously at low doses (2–4 mg), bufotenine oxalate
Oxalate
Oxalate , is the dianion with formula C2O42− also written 22−. Either name is often used for derivatives, such as disodium oxalate, 2C2O42−, or an ester of oxalic acid Oxalate (IUPAC: ethanedioate), is the dianion with formula C2O42− also written (COO)22−. Either...
caused anxiety but no other effects; however, a dose of 8 mg resulted in profound emotional and perceptual changes, involving extreme anxiety
Anxiety
Anxiety is a psychological and physiological state characterized by somatic, emotional, cognitive, and behavioral components. The root meaning of the word anxiety is 'to vex or trouble'; in either presence or absence of psychological stress, anxiety can create feelings of fear, worry, uneasiness,...
, a sense of imminent death, and visual disturbance associated with color reversal and distortion, and intense flushing of the cheeks and forehead.
Ott (2001)
In 2001, ethnobotanist Jonathan OttJonathan Ott
Jonathan Ott is an ethnobotanist, writer, translator, publisher, natural products chemist and botanical researcher in the area of entheogens and their cultural and historical uses, and helped coin the term "entheogen".-Writings:...
published the results of a study in which he self-administered free base bufotenine via insufflation
Insufflation (medicine)
Insufflation is the practice of inhaling a substance. Insufflation has limited medical use, but is a common route of administration with many respiratory drugs used to treat conditions in the lungs and paranasal sinus .The technique is common for many recreational drugs and is also used for some...
(5–100 mg), sublingual
Sublingual
Sublingual, literally 'under the tongue', from Latin, refers to the pharmacological route of administration by which drugs diffuse into the blood through tissues under the tongue...
ly (50 mg), intrarectally (30 mg), orally
Mouth
The mouth is the first portion of the alimentary canal that receives food andsaliva. The oral mucosa is the mucous membrane epithelium lining the inside of the mouth....
(100 mg) and via vaporization
Smoking
Smoking is a practice in which a substance, most commonly tobacco or cannabis, is burned and the smoke is tasted or inhaled. This is primarily practised as a route of administration for recreational drug use, as combustion releases the active substances in drugs such as nicotine and makes them...
(2–8 mg). Ott reported “visionary effects" of intranasal bufotenine and that the "visionary threshold dose" by this route was 40 mg, with smaller doses eliciting perceptibly psychoactive effects. He reported that "intranasal bufotenine is throughout quite physically relaxing; in no case was there facial rubescence, nor any discomfort nor disesteeming side effects".
At 100 mg, effects began within 5 minutes, peaked at 35–40 minutes, and lasted up to 90 minutes. Higher doses produced effects that were described as psychedelic, such as "swirling, colored patterns typical of tryptamines, tending toward the arabesque".
Free base bufotenin taken sublingually was found to be identical to intranasal use. The potency, duration, and psychedelic action was the same. Ott found vaporized free base bufotenin active from 2–8 mg with 8 mg producing "ring-like, swirling, colored patterns with eyes closed". He noted that the visionary effects of insufflated bufotenine were verified by one colleague, and those of vaporized bufotenine by several volunteers.
Ott concluded that free base bufotenin taken intranasally and sublingually produced effects similar to those of Yopo
Yopo
"Ebene" redirects here. For the city in Mauritius, see Ebene City.Anadenanthera peregrina, also known as Yopo, Jopo, Cohoba, Mopo, Nopo, Parica or Calcium Tree, is a perennial tree of the Anadenanthera genus native to the Caribbean and South America. It grows up to 20 m tall, having a thorny bark...
without the toxic peripheral symptoms, such as facial flushing, observed in other studies in which the drug was administered intravenously.
Association with schizophrenia and other mental disorders
A study conducted in the late 1960s reported the detection of bufotenin in the urine of schizophrenic subjects; however, subsequent research has failed to confirm these findings.Studies have detected endogenous bufotenin in urine specimens from individuals with other psychiatric disorders, such as infant autistic patients. Another study indicated that paranoid violent offenders or those who committed violent behaviour towards family members have higher bufotenin levels in their urine than other violent offenders.
A 2010 study utilized a mass spectrometry
Mass spectrometry
Mass spectrometry is an analytical technique that measures the mass-to-charge ratio of charged particles.It is used for determining masses of particles, for determining the elemental composition of a sample or molecule, and for elucidating the chemical structures of molecules, such as peptides and...
approach to detect levels of bufotenin in the urine of individuals with severe autism spectrum disorder (ASD), schizophrenia, and asymptomatic subjects. Their results indicate significantly higher levels of bufotenin in the urine of the ASD and schizophrenic groups when compared to asymptomatic individuals.
Legal status
Bufotenine is regulated as a Schedule I drug (ID number 7403) by the U.S. Drug Enforcement Agency. It is classified as a Schedule I controlled substance according to the Criminal Code Regulations of the Government of the Commonwealth of Australia.In the UK, the substance is a Class A drug under the 1971 Misuse of Drugs Act, although numerous shops sell Amanita muscaria across the Internet. Although some people claim that they may contain the substance, it is often considered an area of dispute and based on unverified claims.
See also
- List of entheogens
- TryptamineTryptamineTryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
s - Psychoactive toadPsychoactive toadPsychoactive toad is a name used for toads from which psychoactive substances from the family of bufotoxins can be derived. The skin and poison of Bufo alvarius contain 5-MeO-DMT and bufotenin. Other species contain only bufotenin. 5-MeO-DMT and bufotenin both belong to the family of...
- Bufo alvarius
- Anadenanthera colubrina
- Anadenanthera peregrina