Lobeline

Source: Wikipedia, the free encyclopedia.
Lobeline
Clinical data
AHFS/Drugs.comInternational Drug Names
ATCvet code
Identifiers
  • 2-((2R,6S)-6-((S)-2-Hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone
JSmol)
Melting point130 to 131 °C (266 to 268 °F)
  • O=C(C[C@@H]1N([C@@H](CCC1)C[C@@H](C2=CC=CC=C2)O)C)C3=CC=CC=C3
  • InChI=1S/C22H27NO2/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/t19-,20+,21-/m0/s1 ☒N
  • Key:MXYUKLILVYORSK-HBMCJLEFSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Lobeline is a piperidine

Hippobroma longiflora
. In its pure form, it is a white amorphous powder which is freely soluble in water.

Potential uses

Lobeline has been sold, in tablet form, for use as a smoking 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 any efficacy.[1][8]

Toxicity

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 narrow therapeutic index: the potentially beneficial dose of lobeline is very close to the toxic dose.[9]

Pharmacology

Lobeline has multiple mechanisms of action, acting as a

μ-opioid receptors.[20] It seems to be a P-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 as lobelane (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 alkaloid sedamine,[24] with only one 2-phenylethyl group on the piperidine ring and found in plants of genus sedum, 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.

See also

References

  1. ^
    PMID 22336780
    . 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.
  2. PMID 14651764
    .
  3. S2CID 46875770
    .
  4. PMID 17612524
    .
  5. S2CID 19787823
    .
  6. PMID 16765386
    .
  7. S2CID 23762679
    .
  8. ^ "Lobelia". drugs.com.
  9. ^ a b "Lobelia". drugs.com.
  10. ^ "Symptoms of Plant poisoning -- Lobeline".
  11. PMID 17233532
    .
  12. PMID 17331733
    .
  13. PMID 16107155
    .
  14. PMID 18191815
    .
  15. S2CID 1315645
    .
  16. PMID 16905316
    .
  17. PMID 9223582
    .
  18. S2CID 20510311
    .
  19. PMID 16193063
    .
  20. PMID 17368966
    .
  21. PMID 18222670
    .
  22. PMID 25685543
    .
  23. S2CID 438066
    .
  24. ^ "(-)-Sedamine, CID=442657". PubChem Database. National Center for Biotechnology Information. Retrieved July 7, 2019.
  25. PMID 11916142
    .
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