Dendrobine is an

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

found in ''

Dendrobium nobile ''Dendrobium nobile'', commonly known as the noble dendrobium, is a member of the family Orchidaceae. It has become a popular cultivated decorative house plant, because it produces colourful blooms in winter and spring, at a time when little el ...

'' at an average of 0.5% by weight.Kreis, L. M., ''Consice textbook of forensic medicine & toxicology'', Elsevier, 2008 It is a colorless solid at room temperature. It is related to the

picrotoxin Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound. It was first isolated by the French pharmacist and chemist Pierre François Guillaume Boullay (1777–1869) in 1812. The name "picrotoxin" is a combination of the Gree ...

family of natural products. When given a fatal dose, death is usually caused by convulsions. It possesses a molecular structure that attracted interest in its

total synthesis Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes i ...

organic chemist Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J. ...

Synthesis

There have been 3 successful enantioselective syntheses of dendrobine reported with yields ranging from 0.2-4.0%. The structure of dendrobine is intriguing due to its tetracyclic ring system with seven contiguous stereocenters. Most recently, a full synthesis of (-)-dendrobine was carried out by Kreis ''et al''. with a yield of 4.0%. The novelty of Kreis' synthesis is the key reaction cascade with an amine functioning as the linchpin that initiates the sequence of reactions while embedding itself in the target structure. This reaction cascade occurs stereoselectively only when it is carried out without isolation of intermediates. The cascade successfully installs a key quaternary center while simultaneously designating a stereosymetric carbon center.

Effects

While dendrobine's effects on humans have not been studied extensively, studies of its pharmacological effects on various small animals were conducted in 1935 by Chen and Chen. It was concluded that dendrobine exhibited a weak analgesic effect when administered to mice (5–15 mg/kg), and an

antipyretic An antipyretic (, from ''anti-'' 'against' and ' 'feverish') is a substance that reduces fever. Antipyretics cause the hypothalamus to override a prostaglandin-induced increase in temperature. The body then works to lower the temperature, which r ...

effect when administered to rabbits (8.5 mg/kg).

Hypotensive Hypotension is low blood pressure. Blood pressure is the force of blood pushing against the walls of the arteries as the heart pumps out blood. Blood pressure is indicated by two numbers, the systolic blood pressure (the top number) and the dia ...

effects were reported in experiments with frogs, cats, and a dog.

Toxicity

The minimum lethal doses by intravenous injection are 20 mg/kg for mice and rats, 22 mg/kg in guinea pigs, and 17 mg/kg in rabbits. Dendrobine is a strongly selective competitive antagonist of β-alanine,

taurine Taurine (), or 2-aminoethanesulfonic acid, is an organic compound that is widely distributed in animal tissues. It is a major constituent of bile and can be found in the large intestine, and accounts for up to 0.1% of total human body weight. I ...

, and

glycine Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid ( carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinog ...

. While structurally related to

in, dendrobine is not an antagonist of GABA.

References

{{Neurotoxins Antipyretics Glycine receptor antagonists Alkaloids Plant toxins Isopropyl compounds Lactones Convulsants Neurotoxins