
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
Synonyms:
- 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
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
XLogP3: -1.8