Lobeline
2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
Molecular Identity
Lobeline
2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
PubChem CID: 101616
(-)-lobeline is an optically active piperidine alkaloid having a 2-oxo-2-phenylethyl substituent at the 2-position and a 2-hydroxy-2-phenylethyl group at the 6-position. It has a role as a nicotinic acetylcholine receptor agonist. It is a piperidine alkaloid, a tertiary amine and an aromatic ketone.
2D Structure
Properties
C22H27NO2
Molecular Formula
337.50
Molecular Weight
g/mol
337.2042
Exact Mass
Da
3.8
XLogP
Drug-like (Lipinski: < 5)
40.5
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
3
H-Bond Acceptors
412
Complexity
SMILES
Canonical SMILES
SMILES: CN1C(CCCC1CC(=O)C2=CC=CC=C2)CC(C3=CC=CC=C3)OIsomeric SMILES
SMILES: CN1[C@@H](CCC[C@@H]1CC(=O)C2=CC=CC=C2)C[C@@H](C3=CC=CC=C3)OSynonyms(20)
lobeline(-)-LobelineInflatinealpha-LobelineLobnicoLobelinumLobelin90-69-7Lobelina8,10-DiphenyllobelionolDTXSID30232192-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanoneD0P25S3P812-(6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Lobeline
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