Bufotenidine (5-HTQ) is the trimethyl version of bufotenine. It's chemical structure is often shown with the 5-hydroxy group replaced by a negatively charged oxygen atom. Bufotenidine acts as a selective 5-HT3 receptor agonist.[1] 5-HT3 agonists produce intense nausea when ingested.
The closely related aeruginascin is found in the mushroom Inocybe aeruginascens.
Natural Sources
Bufotenidine is found in several toads including Bufo americanus, B. calamita, B. gargarizans, B. paracnemis, and B. viridis.[2]
Toxicity
Reported to have curariform activity on isolated muscles and to block acetylcholine induced spasms. Neither death nor ataxia was noted in mice at 2 mg/kg ip.[5]
Lethal dose from respiratory failure has been given as 10 mg/kg ip in mice.[5]
The LD50 in mice is recorded as 1.3 mg/kg intravenously.[3][4] Subcutaneously the LD50 is 90 mg/kg in mice.[4]
Chemical Properties
Bufotenidine Freebase
PubChem CID: 3083591
Chemical Names: Bufotenidine; 5-HTQ; 5-Hydroxy-N,N,N-trimethyltryptammonium; 3-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate; 487-91-2; Bufotenidin; AC1MJ0WJ; AGN-PC-0KP03Q;
Molecular Formula: C13H18N2O
Molecular Weight: 218.29482 g/mol
CAS No: 487-91-2
XLogP3: 1.9
Solubility: soluble in acetone, methanol[5]
UV: λmax 218-220 (4.55), 284-288 nm (3.98)[5]
Bufotenidine Iodide
Melting Point: 216-217 C[2]
Bufotenidine Oxalate
Melting Point: 96.5 C[2]
Bufotenidine Picrate
Appearance: Red crystals from aqueous ethanol; reddish-yellow crystals from crude from EtOH; orange needles when recrystallized from aqueous alcohol[5]
Melting Point: 198 C[2]
Bufotenidine Flavianate
Melting Point: 195-200 C[2]
Bufotenidine Picronolate
Appearance: Yellow prisms; Fine yellow needles from 50% Ethanol[5]
Melting Point: 255 C[2]