Lupanine  (Synonyms: D-Lupanine)

Lupanine (D-Lupanine) is a natural ketonic derivative of Sparteine ((+)-Sparteine (HY-W008350)) with a ganglioplegic activity. Lupanine shows binding affinity for nicotinic receptor (nAChR) with a K_i value of 500 nM^[1].

Ki: 500 nM (Nicotinic receptor) and 11000 nM (Muscarinic receptor)^[1]

Lupanine shows binding affinity for nicotinic receptor with a K_i value of 500 nM. While, Lupanine shows a very weak affinity for the muscarinic receptor with a K_i value of 11000 nM^[1].
Lupanine (0-100 μM) is a weak agonist and desensitizer in SH-SY5Y cells, with EC₅₀ and DC₅₀ of 10.7 μM and 28.2 μM, respectively^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Lupanine (100-300 mg/kg for i.p.; 175-700 mg/kg for p.o.) is much less toxic in one single injection in EOPS male Swiss mice (20-22 g) and Hartley guinea-pigs (400-500 g)^[1].
Lupanine (1-7.5 mg/kg; i.v.) is more efficient than Sparteine for antagonizing secondary reflex hypertension in carotid occlusion and hypotension resulting from the stimulation of the pneumogastric nerve in both the cat and the dog^[1].
Lupanine has an inhibitory action on nicotinic type hypertension produced by injection of Acetylcholine (500 p.g/kg i.v.) in the Atropine-treated dog^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

248.36

C₁₅H₂₄N₂O

550-90-3

Liquid

Colorless to light yellow

O=C1N2[C@]([C@](C3)([H])CN(CCCC4)[C@]4([H])[C@]3([H])C2)([H])CCC1

Room temperature in continental US; may vary elsewhere.

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

• [1]. K Yovo, et al. Comparative pharmacological study of sparteine and its ketonic derivative lupanine from seeds of Lupinus albus. Planta Med. 1984 Oct;50(5):420-4.  [Content Brief]

  [2]. Green BT, et al. Anagyrine desensitization of peripheral nicotinic acetylcholine receptors. A potential biomarker of quinolizidine alkaloid teratogenesis in cattle. Res Vet Sci. 2017 Dec;115:195-200.  [Content Brief]