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]


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]

See Also


1. The Serotonin Receptors: From Molecular Pharmacology to Human Therapeutics
Bryan L. Roth; Springer Science & Business Media, 2008; ISBN 1597450804, 9781597450805
2. Venomous Animals and Their Venoms: Venomous Vertebrates, Volume 2
Wolfgang Bücherl, El eanor E. Buckley; Elsevier, 2013; ISBN 148326288X, 9781483262888
3. Alkaloids: Biochemistry, Ecology,and Medicinal Applications
Margaret F. Roberts, Michael Wink; Springer Science & Business Media, 1998; ISBN 0306454653, 9780306454653
4. 5-Hydroxytryptamine and Related Indolealkylamines
Volume 19 of Handbook of Experimental Pharmacology; Vittorio Erspamer; Springer Science & Business Media, 2012; ISBN 3642854672, 9783642854675
5. Some Simple Tryptamines
Friends, Keeper of the Trout &: Mydriatic Productions, 2007; ISBN 0977087654, 9780977087655
Unless otherwise stated, the content of this page is licensed under Creative Commons Attribution-ShareAlike 3.0 License