Bufotenine Glucuronide


Bufotenine glucuronide is the conjugated form of bufotenine and glucuronic acid.

Bufotenine glucuronide has been positively identified as the major metabolite of bufotenine in rat urine.[1]

The closely related hallucinogen psilocin also follows a very similar pathway in rats with psilocin glucuronide being the main route of elimination for psilocin created via glucuronosyltransferase.[3] Human glucuronosyltransferase was shown to only convert psilocin into psilocin glucuronide.[3]

Glucuronidation of bufotenine is likely catalyzed by glucuronosyltransferase as it is with psilocin glucuronide.

Test showed that 59.9 - 69.0% of bufotenine was excreted in conjugated form in human urine. The conjugated form of bufotenine was tentatively identified as bufotenine glucuronide.[2]

Conjugation of bufotenine and the related psilocin is possible because of the acidic phenolic hydroxyl group on these molecules.

Glucuronidation of bufotenine brings it's XLogP3 from 1.2 down to -1.8. Greatly reducing it's ability to cross the blood-brain barrier.

The activity of bufotenine glucuronide is unknown. Bufotenine glucuronide is unlikely to have hallucinogenic effects because of its very low XLogP value of -1.8 which should greatly reduce it's ability to cross the blood brain barrier. However, because it's still a tryptamine alkaloid, its likely to have somatic effects, possibly producing nausea or other side effects. It's possible that bufotenine glucuronide might be responsible for a good portion of the side effects reported from oral bufotenine use.

Chemical Properties

IUPAC Name: (2S,3S,4S,5R,6S)-6-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

  • Glucopyranosiduronicacid, 3-[2-(dimethylamino)ethyl]indol-5-yl, b-D- (8CI)
  • Indol-5-ol, 3-[2-(dimethylamino)ethyl]-, 3-b-D-glucopyranuronoside (8CI)
  • Bufotenin glucuronide
  • b-D-Glucopyranosiduronic acid,3-[2-(dimethylamino)ethyl]-1H-indol-5-yl
  • Dmguht
  • N,N-dimethyl-O-glucopyranuronosyl-5-hydroxytryptamine

Molecular Formula: C18H24 N2 O7
Molecular Weight: 380.3924
CAS No: 24703-15-9
PubChem CID: 3082119
Canonical SMILES: CN(C)CCC1=CNC2=C1C=C(C=C2)OC3C(C(C(C(O3)C(=O)O)O)O)O
Isomeric SMILES: CN(C)CCC1=CNC2=C1C=C(C=C2)O[C@H]3[CH]([C@H]([CH]([C@H](O3)C(=O)O)O)O)O
XLogP3: -1.8

1. Anadenanthera: Visionary Plant of Ancient South America
Constantino M Torres, David B Repke; Routledge, 2014; ISBN 1317955161, 9781317955160
2. The presence of free and conjugated bufotenin in normal human urine.
Life Sci. 1984 May 21;34(21):2041-5.; Räisänen MJ.; PMID: 6374347
3. Studies in Natural Products Chemistry, Volume 46
Atta-ur-Rahman; Elsevier, 2015; ISBN 044463469X, 9780444634696
Unless otherwise stated, the content of this page is licensed under Creative Commons Attribution-ShareAlike 3.0 License