An alkaloid with diverse biological activities
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(–)-Lobelin (hydrochloride)

Item No. 29526

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-ethanone, monohydrochloride
CAS Number
134-63-4
Synonyms
  • (–)-α-Lobeline
  • VUF 10751
Molecular Formula
C22H27NO2 • HCl
Formula Weight
373.9
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.3 mg/mlEthanol: 2 mg/ml
λmax
245 nm
SMILES
CN1[C@@H](CC(C2=CC=CC=C2)=O)CCC[C@H]1C[C@H](O)C3=CC=CC=C3.Cl
InChi Code
InChI=1S/C22H27NO2.ClH/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18;/h2-7,9-12,19-21,24H,8,13-16H2,1H3;1H/t19-,20+,21-;/m0./s1
InChi Key
MKMYPTLXLWOUSO-NFQNBQCWSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $63

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    500 mg

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    1 g

    $158

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    Product Description

    (–)-Lobeline is an alkaloid that has been found in Lobelia and has diverse biological activities.1,2,3 It binds to nicotinic acetylcholine receptors (nAChRs) in rat brain homogenates (Ki = 4 nM) and has antinociceptive effects in the tail-flick assay in mice.1 (–)-Lobeline (0.3 and 0.9 mg/kg) reduces the number of errors in a repeated acquisition procedure in the radial arm maze in rats.2 It also decreases immobility time in the forced swim test and feeding latency in the novelty suppressed feeding test, indicating antidepressant-like activity, in mice when administered at doses of 1 and 4 mg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Flammia, D., Dukat, M., Damaj, M.I., et al. Lobeline: Structure-affinity investigation of nicotinic acetylcholinergic receptor binding. J. Med. Chem. 42(18), 3726-3731 (1999).

    2. Levin, E.D., and Christopher, C.N. Lobeline-induced learning improvement of rats in the radial-arm maze. Pharmacol. Biochem. Behav. 76(1), 133-139 (2003).

    3. Roni, M.A., and Rahman, S. Antidepressant-like effects of lobeline in mice: Behavioral, neurochemical, and neuroendocrine evidence. Prog. Neuropsychopharmacol. Biol. Psychiatry 41, 44-51 (2013).