Dehydrobufotenine is a phenolic quaternary amine indole. Unlike bufotenine, dehydrobufotenine is not truly a tryptamine. It lacks the typical tryptamine side chain. However, both bufotenine and dehydrobufotenine are indoles. Dehydrobufotenine contains the same 5-Hydroxyindole structure contained in bufotenine. Instead of the tryptamine side chain as bufotenine has, dehydrobufotenine contains a piperidine structure similar to 1,1-dimethylpiperidinium. This gives dehydrobufotenine some structural similarity to the indole side of LSD's chemical structure.
The human metabolism of dehydrobufotenine is currently unknown. It's metabolism appears not to have been studied in either humans or animals.
THE REST OF THIS SECTION IS PURE CONJECTURE
Quaternary amines are typically not substrates of Monoamine Oxidase A or Monoamine Oxidase B. Bufotenine, which dehydrobufotenine is derived from, and the related psilocin are minor substrates of Monoamine Oxidase A. Dehydrobufotenine is likely not affected by either enzyme.
The related psilocin is a major substrate of Glucuronosyltransferases UGT1A9 and UGT1A10. Bufotenine is also a major substrate of Glucuronosyltransferase in rats, and is likely to also be so in humans. Dehydrobufotenine is potentially also a substrate of Glucuronosyltransferase. Because it should not be a substrate of either Monoamine Oxidase A or Monoamine Oxidase B, Glucuronosyltransferase is likely to be a major enzyme involved in dehydrobufotenine metabolism. If correct, then the major metabolite of dehydrobufotenine should be dehydrobufotenine glucuronide.
The psychoactivity of dehydrobufotenine remains unstudied in humans. Anonymous reports give the low dose range as 2-10 mg orally, producing stimulation, euphoria, and mild psychoactive effects. Effects begin within about 30 minutes after ingestion. Peak after about 3 hours. Total effects last approximately 12-16 hours. Larger doses are reported to have full blown psychedelic effects similar to LSD and mescaline, and unlike those of bufotenine or psilocin. The long duration of effects is likely attributed to it being a quaternary amine. Quaternary amines are typically not substrates of Monoamine Oxidase A or Monoamine Oxidase B.
THE REST OF THIS SECTION IS PURE CONJECTURE
The XLogP3 of dehydrobufotenine at 1.6 is higher than that of 5-MeO-DMT at 1.5, and much higher than bufotenine at 1.2. If accurate, the predicted XLogP3 gives it much greater ability to cross the blood-brain barrier. However, there is some conflict concerning the lipid solubility of dehydrobufotenine. Some older logP prediction software gives high water solubility for dehydrobufotenine. ACD/Labs gives a prediction of -3.71 for it's lipid solubility. If ACD/Labs logP is correct, dehydrobufotenine should have extreme difficulty entering the brain. Without actual lipid solubility data, and such a huge conflict between these two different algorithms, it's uncertain what it's lipid solubility actually is. The XLogP3 algorithm is generally more accurate than the older logP algorithms used by ACD/Labs. Until actual real lipid solubility data is available, even the highly accurate XLogP3 predicted values should be treated as potentially flawed.
Anecdotal reports indicate that the skin of Bufo marinus is hallucinogenic when smoked. The toad Bufo marinus contains substantial quantities of dehydrobufotenine as the major indole alkaloid, as well as other toxins.
Bufo marinus is believed by some to have once been used as a sacred hallucinogen by the Olmec, Mayan and Aztec people. Bufo marinus is a prominent symbol in Olmec, Mayan and Aztec iconography, cultures very well known to use hallucinogens for divination, and other spiritual purposes. In Olmec and Mayan sites Bufo marinus bones have been found in great quantity often in a ritual context.
There is also a theory that authentic yopo snuff contains dehydrobufotenine as a major hallucinogenic indole alkaloid, but only when prepared correctly using natural sources of calcium carbonate (such as limestone) and water, and allowed to react for 1 day. Prior to proper preparation, it contains no dehydrobufotenine. See The Yopo Transformation Theory for more information.
Dehydrobufotenine has been isolated from the roots of Arundo donax at 0.06 %.
Dehydrobufotenine occurs in various toads including Bufo marinus, Bufo valliceps, Bufo arenarum, Bufo regularis, Bufo chilensis, Bufo crucifer, Bufo paracnemis, and Bufo spinulosus..
It's important to note that the toxicity of dehydrobufotenine has not been thoroughly investigated.
No reports of toxicity exist for man, or any animals other than mice.
A single report from 1967 gives the LDLo in mice subcutaneously as 6mg/kg (6000 ug/kg), which is apparently based off of a single dose of 120 micrograms producing convulsions and death in 1 mouse. This single lab test is referenced in countless articles. The test could have been contaminated with other alkaloids such as bufotenidine, which are normally present in the materiel dehydrobufotenine is often extracted from. No additional reports verifying this lab test could be found in the literature. For that reason, this information should be considered potentially flawed until other researchers verify this finding. If other references from other lab tests exist please leave a comment on this page.
- Pyrrolo(4,3,2-de)quinolinium, 1,3,4,5-tetrahydro-6-hydroxy-5,5-dimethyl-
IUPAC Name: 6-Hydroxy-5,5-dimethyl-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinolin-5-ium
Molecular Formula: C12H15N2O+
Molecular Weight: 203.2603 g/mol
Melting Point: 218 C, 199 C, 198 C, 202 C, 217 C
Boiling Point: Unknown, predicted to be 515.55 C by EPISuite.
ACD/Labs Predicted LogP: -3.711
ChemAxon Predicted LogP: -2.132
InChI Key: XRZDSPVDZKCARG-UHFFFAOYSA-O
Canonical SMILES: C[N+]1(CCC2=CNC3=C2C1=C(C=C3)O)C
CAS No: 17232-69-8
PubChem CID: 205042
Solubility: soluble in acetone, methanol
UV: λmax 218-220 (4.55), 285 nm (3.98)
Appearance: Needles from ethanol; Long colorless needles from concentration in hydrochloric acid
Melting Point: 242 C, 237-238, 240-241, 243 C, 244 C
Solubility: Insoluble in ethyl acetate. Soluble in dilute hydrochloric acid.
Crystallization: Crystallized from dilute hydrochloric acid via desiccator concentration.