Absorption, Distribution and Excretion
Rapidly absorbed after intravenous injection. Metabolism/Metabolites After oral administration, bufotenine is primarily metabolized by monoamine oxidases. Bufotenine is a known human metabolite of N,N-dimethyl-5-methoxytryptamine.

Toxicity Summary
Bufotenine is a neurotoxin similar to the mushroom toxin psilocybin. Therefore, it may act as a partial agonist of the 5-HT2A serotonin receptor in the brain, mimicking the effects of serotonin (5-HT). It may also be an agonist of both 5-HT1A and 5-HT2A/2C receptors. (L1081, L1673)

: Peng C, Yang ZD. [Chemical Constituents of the Endophytic Fungus Rhinocladiella sp. lgt-3 from Tripterygium wilfordii]. Zhong Yao Cai. 2016 Aug;39(8):1775-8. Chinese. PubMed PMID: 30204382.

Bufotenine is a tertiary amine composed of N,N-dimethyltryptamine with a hydroxyl substituent at the 5-position. It is a hallucinogen and a metabolite of coral. It is a tryptamine alkaloid and tertiary amine functionally related to N,N-dimethyltryptamine. Bufotenine is a Category 1 controlled substance under the U.S. Drug Enforcement Administration (DEA). DEA Category 1 controlled substances currently have no recognized medical use in the United States, lack safety under medical supervision, and have a high potential for abuse. It is a hallucinogenic substance. Bufotenine is a hallucinogenic serotonin analog found in the skin of frogs or toads, mushrooms, higher plants, and mammals, particularly in the brain, plasma, and urine of patients with schizophrenia. Bufotenine has been used as a tool in central nervous system research and has also been abused as a hallucinogen. Bufotenine has been reported in African toads (Bufo gargarizans), citrus (Citrus reticulata), and other organisms with relevant data. Bufotenine (5-OH-DMT) is a tryptamine associated with the neurotransmitter serotonin. It is an alkaloid found in the skin of certain toads, mushrooms, higher plants, and mammals. Bufotenine is a chemical component of the venom and eggs of several Bufo species, most notably the Colorado River toad (Bufo alvarius), as it is the only toad species with sufficient bufotenine to produce psychoactive effects. Toad venom extracts, containing bufotenine and other bioactive compounds, have been used in some traditional medicines (possibly derived from the Chinese toad, Bufo gargarizans), which has been used medicinally in China for centuries. Bufotenine is also a component of the seeds of the coral tree (Anadenanthera colubrina) and the wandering coral tree (Anadenanthera peregrina). Indigenous cultures in the Caribbean, Central America, and South America used coral tree seeds as an ingredient in psychedelic snuff preparations. The acute toxicity (LD50) of bufotenine in rodents is estimated to be 200 to 300 mg/kg. The cause of death is respiratory arrest. Bufotenine is a hallucinogenic serotonin analog found in the skin of frogs or toads, mushrooms, higher plants, and mammals, particularly in high concentrations in the brain, plasma, and urine of patients with schizophrenia. Bufotenine has been used as a tool in central nervous system research and has also been abused as a hallucinogen. Pharmacodynamics: Bufotenine is a tryptamine substance associated with the neurotransmitter serotonin.

C12H16N2O

204.2682

204.126

487-93-4

10257

Typically exists as solid at room temperature

1.178g/cm3

392.8ºC at 760 mmHg

62-64ºC

191.3ºC

9.89E-07mmHg at 25°C

1.646

1.977

2

2

3

15

208

0

VTTONGPRPXSUTJ-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

1H-Indol-5-ol, 3-(2-(dimethylamino)ethyl)-

Bufotenine Cinobufotenine Cohoba Mappin Mappine

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)