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Relative Toxicities and Neuromuscular Nicotinic Receptor Agonistic Potencies of Anabasine Enantiomers and Anabaseine

Relative Toxicities and Neuromuscular Nicotinic Receptor Agonistic Potencies of Anabasine Enantiomers and Anabaseine

Stephen T Lee, Kristin Wildeboer, Kip E Panter, William R Kem, Dale R Gardner, Russell J Molyneux, Cheng-Wei Tom Chang, Ferenc Soti, James A Pfister

Neurotoxicol Teratol. Mar-Apr 2006;28(2):220-8.

PMID: 16488116

Abstract:

Anabasine occurring in wild tree tobacco (Nicotiana glauca) and anabaseine occurring in certain animal venoms are nicotinic receptor agonist toxins. Anabasine lacks the imine double bond of anabaseine; the two possible enantiomers of anabasine occur in N. glauca. A comparision of the relative potencies of S- and R-anabasine has not been previously reported. We separated the enantiomers of anabasine by reaction of the racemic N. glauca natural product with 9-fluorenylmethoxycarbonyl-L-alanine (Fmoc-L-Ala-OH) to give diastereomers, which were separated by preparative reversed phase HPLC. The S- and R-anabasine enantiomer fractions were then obtained by Edman degradation. A mouse bioassay was used to determine the relative lethalities of S- and R-enriched anabasine enantiomers. The intravenous LD50 of the (+)-R-anabasine rich fraction was 11 +/- 1.0 mg/kg and that of the (-)-S-anabasine-rich fraction was 16 +/- 1.0 mg/kg. The LD50 of anabaseine was 0.58 +/- 0.05 mg/kg. Anabaseine was significantly more toxic in the mouse bioassay than S-anabasine (27-fold) and R-anabasine (18-fold). The relative agonistic potencies of these three alkaloids on human fetal nicotinic neuromuscular receptors were of the same rank order: anabaseine>>R-anabasine>S-anabasine.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13078041	Anabasine		13078-04-1	Price

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