ANABASEINE

Molecular Weight (Sarcodictyin A): 160.216 g/mol
Molecular Formula (Sarcodictyin A): C₁₀H₁₂N₂

Source: Various nemertine worms, esp. Paranemertes peregrina (NEMERTEA)
Activity: Anti-Alzheimer agent
Status: Phase I clinical trials

Pioneering marine pharmacological work carried out by Bacq in the 1930s examined the toxic activity of extracts prepared from predatory marine nemertines. The worms use the substance as a venom to paralyze prey and it may also play a role in deterring predators. The state of the science was not yet advanced enough to permit purification and complete chemical characterization of the suspected toxin Kem dubbed "amphiporine."

Later, in the early 1970s, William Kem extracted and successfully purified a hoplonemertine toxin with similar activity from the nemertine Paranemertes peregrina collected at Friday Harbor WA. Chemical characterization revealed that hoplonemertine toxin was structurally identical to the compound anabaseine, first synthesized in the laboratory in the 1930s and structurally related to a compound isolated from tobacco. The same compound has more recently been found as a venom component in two different ant species (Aphaenogaster spp.).

Anabaseine is a nicotinoid alkaloid. It is capable of stimulating vertebrate neuromuscular nicotinic receptors and increasing cholinergenic transmission. As such it has potential as a treatment of cognitive function loss. A synthetic analog, DMXBA (GTS-21) has exhibited memory enhancing effects in recipients. The compound is currently under license by the Japanese pharmaceutical company Taiho and is in Phase I trials for treating Alzheimer's disease.

NCBI PubChem compound summary page - [ LINK ]

NCBI PubMed biomedical literature citations and abstracts - [ LINK ]

References

Kem WR. 1985. Structure and action of nemertine toxins. Amer. Zool. 25:99-111.

Newman DJ, and GM Cragg. 2004. Advanced Preclinical and Clinical trials of natural Products and Related Compounds from marine Sources. Current Medicinal Chemistry 11:1693-1713.

United States Patent: 6,630,491 (Summary)