Bufotenin

Bufotenin, 5-HO-DMT or 5-hydroxy-N,N-dimethyltryptamine is a ring-substituted indole alkaloid molecule of the tryptamine class. Tryptamines share a core structure comprised of a bicylic indole heterocycle attached at R₃ to a terminal amine group via an ethyl side chain. Bufotenin is substituted at R₅ of its indole heterocycle with a hydroxy (OH) functional group; it also contains two methyl groups CH₃- bound to the terminal amine R_N of its tryptamine backbone (DMT).

In rats, subcutaneously administered bufotenin (1–100 μg/kg) distributes mainly to the lungs, heart, and blood, and to a much lesser extent, the brain (hypothalamus, brain stem, striatum, and cerebral cortex), and liver. It reaches peak concentrations at one hour and is nearly completely eliminated within 8 hours.^[1] 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 bufotenin undergoes extensive first-pass metabolism by the enzyme monoamine oxidase.

Bufotenin's psychedelic effects are primarily believed to come from its efficacy at the 5-HT_2A receptor as a partial agonist. Specifically, this molecule shows high binding affinity for the 5-HT_2A and 5-HT_1A subtypes.^[2] However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

Additional mechanisms of action such as reuptake inhibition of neurotransmitters such as serotonin, noradrenaline and dopamine are also thought to be involved to an extent.^[3] This can result in bufotenin becoming dangerously toxic when combined with MAOIs, RIMAs, SSRIs, stimulants or any substance which acts as a releasing agent or reuptake inhibitor of monoamine neurotransmitters.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

• Erowid Experience Vaults: Bufotenin

Colorado River toad

The Colorado River toad (Incilius alvarius), also known as the Sonoran Desert toad, is a psychoactive toad found in northern Mexico and the southwestern United States. Its skin and venom contain 5-MeO-DMT and bufotenin.

The toad's primary defense system are glands that produce a poison that may be potent enough to kill a grown dog.^[4] These parotoid glands also produce the 5-MeO-DMT^[5] and bufotenin for which the toad is known. Fresh venom can easily be collected from these glands without harm to the toad. To do this, obtain a flat glass plate or any other smooth, nonporous surface of at least 12-inches square and hold the toad in front of the plate (which is fixed in a vertical position). When the desert toad is stroked near the parotid glands in the neck region, there is a squirting out of this venom. When it is allowed to dry on a hard surface it takes on the texture of rubber cement. It contains up to 15% 5-MeO-DMT, as well as N-methyl-5-methoxytryptamine, 5-MeO-NMT and Bufotenin, which have their own entries. In this manner, the venom can be collected on the glass plate, free of dirt and liquid released when the toad is handled.

The toxicity and long-term health effects of recreational bufotenin do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because bufotenin is a research chemical with very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried bufotenin suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

It is strongly recommended that one use harm reduction practices when using this drug.

Tolerance and addiction potential

Bufotenin is not habit-forming and the desire to use it can actually decrease with use. It is most often self-regulating.

Tolerance to the effects of bufotenin is built almost immediately after ingestion. After that, it takes about 1 hour for the tolerance to be reduced to half and 2 hours to be back at baseline (in the absence of further consumption). Bufotenin does not have a cross-tolerance with other psychedelics, meaning that after the consumption of bufotenin psychedelics will not have a reduced effect.

Dangerous Interactions

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

• Lithium - Lithium is commonly prescribed for the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
• Cannabis - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of Bufotenin. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid unintentional overdose.
• Stimulants - Stimulants like amphetamine, cocaine or methylphenidate affect many parts of the brain and alter dopaminergic function. This combination can increase the risk of anxiety, paranoia, panic attacks, and thought loops. This interaction may also result in an elevated risk of mania and psychosis.^{[citation needed]}
• Tramadol - Tramadol is well-documented to lower the seizure threshold^[6] and psychedelics may act to trigger seizures in susceptible individuals.^{[citation needed]}

Deaths from bufotenin are rare but, as a powerful monoamine reuptake inhibitor (MRI), injury can occur when excessive doses are taken or when taken with drugs such as MAOIs, RIMAs, stimulants and any substance which act as a releasing agent or reuptake inhibitor of neurotransmitters such as serotonin and dopamine. This has resulted in well documented deaths^[7][8] that are easily avoidable and could have been otherwise prevented.

• Germany: Bufotenin is controlled under the NpSG^[9] (New Psychoactive Substances Act) as of July 18, 2019.^[10] Production and import with the aim to place it on the market, administration to another person, placing it on the market and trading is punishable. Possession is illegal but not punishable.^[11][12] The legislator considers it possible that orders of Bufotenin are punishable as an incitement to place it on the market.^[13]
• Switzerland: Bufotenin is not controlled under Buchstabe A, B, C and D. It could be considered legal.^[14]
• United Kingdom: Bufotenin is a Class A drug.^[15]
• United States: Bufotenin is a Schedule I substance.^{[citation needed]}

• Responsible use
• Psychoactive substance index
• Psychedelics
• DMT
• 5-MeO-DMT

• Bufotenin (Wikipedia)
• Bufotenin (Erowid Vault)
• Bufotenin (TiHKAL / Isomer Design)
• Bufotenin (DrugBank)