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| ECHA InfoCard | 100.001.830 |
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| Formula | C22H27NO2 |
| Molar mass | 337.463 g·mol−1 |
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| Melting point | 130 to 131 °C (266 to 268 °F) |
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Lobeline is a piperidinealkaloid found in a variety of plants, particularly those in the genusLobelia, including Indian tobacco (Lobelia inflata), Devil's tobacco (Lobelia tupa), great lobelia (Lobelia siphilitica),Lobelia chinensis, andHippobroma longiflora. In its pure form, it is a white amorphous powder which is freely soluble in water.
Lobeline has been sold, in tablet form, for use as asmoking cessation aid, but scientific research has not provided supporting evidence for this use.[1][2][3] Lobeline has also been studied for the treatment of other drug addictions such as addiction to amphetamines,[4][5] cocaine,[6] or alcohol;[7] however, there is limited clinical evidence of anyefficacy.[1][8]
Ingestion of lobeline may cause nausea, vomiting, diarrhea, coughing, dizziness, visual disturbances, hearing disturbances, mental confusion, weakness, slowed heart rate, increased blood pressure, increased breathing rate, tremors, and seizures.[9][10] Lobeline has a narrowtherapeutic index: the potentially beneficial dose of lobeline is very close to the toxic dose.[9]
Lobeline has multiple mechanisms of action, acting as aVMAT2 ligand,[11][12][13] which stimulatesdopamine release to a moderate extent when administered alone, but reduces the dopamine release caused bymethamphetamine.[14][15] It also inhibits thereuptake of dopamine andserotonin,[16] and acts as a mixedagonist–antagonist atnicotinic acetylcholine receptors[17][18] to which it binds at the subunit interfaces of the extracellular domain.[19] It is also anantagonist atμ-opioid receptors.[20] It seems to be aP-glycoprotein inhibitor, according to at least one study.[21] It has been hypothesized that P-glycoprotein inhibition reduces chemotherapeutic resistance in cancer,[22] presumably affecting any substrates of P-gp.
Analogous compounds, such aslobelane (a minor alkaloid found in the same plants) and its synthetic derivatives have similar biological effects with somewhat different relative affinities to VMAT and other proteins.[23] A related alkaloidsedamine,[24] with only one 2-phenylethyl group on thepiperidine ring and found in plants of genussedum, is known to be an inhibitor of pea seedlings amine oxidase,[25] but its affinity to proteins such as the dopamine transporter has apparently not been tested.
On the basis of the trials which have been published in the past sixty years there is no evidence that lobeline has any long term effect on smoking cessation.