Bufoviridine, also known as bufotenine ''O''-sulfate, dihydrobufothionine, or 5-sulfooxy-''N'',''N''-dimethyltryptamine (5-sulfooxy-DMT or 5-SO-DMT), is a
naturally occurring
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical ...
tryptamine
Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the firs ...
found in ''
Bufo
''Bufo'' is a genus of true toads in the amphibian family Bufonidae. As traditionally defined, it was a wastebasket genus containing a large number of toads from much of the world but following taxonomic reviews most of these have been moved to ...
'' species such as ''
Bufo viridis
The European green toad (''Bufotes viridis'') is a species of true toad found in steppes, mountainous areas, semi-deserts, urban areas and other habitats in mainland Europe, ranging from far eastern France and Denmark to the Balkans, Western Ru ...
'' and ''
Bufo calamita
The natterjack toad (''Epidalea calamita'') is a toad native to sandy and heathland areas of Europe and the United Kingdom. Adults are in length, and are distinguished from common toads by a yellow line down the middle of the back and parallel ...
''.
It is the ''O''-
sulfate
The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
of
bufotenin
Bufotenin, also known as dimethylserotonin or as 5-hydroxy-''N'',''N''-dimethyltryptamine (5-HO-DMT), is a serotonergic psychedelic of the tryptamine family. It is a derivative of the psychedelic dimethyltryptamine (DMT) and of the neurotransmi ...
(5-HO-DMT).
The compound shows very weak
serotonergic
A serotonergic substance, medication, or receptor protein is one that affects neurotransmission pathways that involve serotonin, as follows:
* Serotonergic drugs
** Serotonin receptor agonists
** Serotonin receptor antagonists
** Serotonin reupta ...
activity.
Bufoviridine is not known to have been evaluated in humans, but is suggested to be inactive based on
animal studies
Animal studies is a recently recognised field in which animals are studied in a variety of cross-disciplinary ways. Scholars who engage in animal studies may be formally trained in a number of diverse fields, including art history, anthropology ...
.
The 4-''O''-
acetate
An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic, or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...
, 4-''O''-
phosphate
Phosphates are the naturally occurring form of the element phosphorus.
In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthop ...
, and 4-''O''-
benzoate
Benzoic acid () is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which ...
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s of
psilocin
Psilocin, also known as 4-hydroxy-''N'',''N''-dimethyltryptamine (4-HO-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocy ...
(4-HO-DMT) are all active, but the 4-''O''-sulfate ester is inactive, suggesting that bufoviridine may be inactive as well.
It was first described in the 1950s.
See also
*
Substituted tryptamine
Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all trypt ...
*
Bufotenin
Bufotenin, also known as dimethylserotonin or as 5-hydroxy-''N'',''N''-dimethyltryptamine (5-HO-DMT), is a serotonergic psychedelic of the tryptamine family. It is a derivative of the psychedelic dimethyltryptamine (DMT) and of the neurotransmi ...
*
Bufotenidine
Bufotenidine, also known as 5-hydroxy-''N'',''N'',''N''-trimethyltryptammonium (5-HTQ), is an indole toxin related to bufotenin, serotonin, and other tryptamines which is found in the venom of a variety of toads. It acts as a selective serotonin ...
*
Bufothionine
Bufothionine is a sulfur-containing compound which is present in the bufotoxins secreted by the parotoid gland of certain toads of the genera ''Bufo'' and '' Chaunus''. This specific compound can be found in the skin of certain species of toad su ...
*
''O''-Acetylbufotenine
*
''O''-Pivalylbufotenine
References
External links
Bufoviridine - Isomer DesignBufoviridine - Trout's Notes
Amphibian toxins
N,N-Dialkyltryptamines
5-Hydroxytryptamines
Serotonin receptor modulators
Substances discovered in the 1950s
Sulfate esters
Dimethylamino compounds
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