Bufotenine glucuronide is the conjugated form of bufotenine and glucuronic acid.
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. Human glucuronosyltransferase was shown to only convert psilocin into psilocin glucuronide.
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.
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
Molecular Formula: C18H24 N2 O7
Molecular Weight: 380.3924
CAS No: 24703-15-9
PubChem CID: 3082119
InChI Key: WWCGYOHFQQBADT-RNGZQALNSA-N
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