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Chemical Compound Review

lobeline     2-[(2R,6S)-6-[(2S)-2-hydroxy- 2-phenyl...

Synonyms: Lobelina, Inflatine, Lobelinum, Lobron, alpha-Lobeline, ...
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Disease relevance of lobeline


Psychiatry related information on lobeline

  • Lobeline, an alkaloid from Indian tobacco (Lobelia inflata), is classified as a nicotinic agonist and is currently used as a smoking cessation agent [5].
  • Cytisine and lobeline failed to increase locomotor activity at any dose tested [6].
  • The deficit in the acquisition of a trace eyeblink classical conditioning was reverted by the systemic administration of carbachol, a nonselective cholinergic muscarinic agonist, but not by lobeline, a nicotinic agonist [7].
  • In saline challenge groups, the doses of lobeline examined did not affect spontaneous locomotion nor induced any stereotyped behaviors [8].
  • The comparison was made between 6 right handers and 9 left handers (all males) for (i) the dose of lobeline required to produce sensory threshold (viz., first appearance of respiratory sensations) and cough threshold (first appearance of cough); and (ii) latency and duration of sensations for sensory and cough threshold [9].

High impact information on lobeline

  • The brainstem and spinal cord were examined in cats administered multiple emetic drugs (cisplatin, lobeline, protoveratrine, naloxone, apomorphine) or control saline injections [10].
  • However, some of the nAChR agonists at higher concentrations (1, 1-dimethyl-4-phenylpiperazinium (DMPP) and lobeline), besides their effects on presynaptic nAChRs, are able to inhibit the uptake of NE and 5-HT into nerve terminals, thereby their transmitter releasing effects are extended in time and space [11].
  • Generally, all of these analogues had lower affinities at alpha4beta2 and alpha7 nAChRs compared to lobeline, thereby increasing selectivity for VMAT2 [12].
  • Lobeline inhibited [3H]DTBZ binding with an IC50 of 0.90 microM, consistent with its previously reported IC50 of 0.88 microM for inhibition of [3H]DA uptake into vesicles [5].
  • These results suggest that lobeline specifically interacts with DTBZ sites on VMAT2 to inhibit DA uptake into synaptic vesicles [5].

Chemical compound and disease context of lobeline


Biological context of lobeline

  • An increase in [3H]nicotine binding was observed in all regions except cerebellum following chronic infusion with nicotine and anabasine, whereas lobeline did not alter the number or affinity of these binding sites [15].
  • Such presumed increased activity in the RARs of man produced by forced expiration to residual volume at the time lobeline-induced sensations were expected did not enhance the sensations in any subject [16].
  • 3. Injections of lobeline at doses sufficient to evoke respiratory discomfort lasting 25-32 s (37-73 microgram kg-1) increased the size of the H reflex in soleus with an onset latency of about 10 s and lasting about 20 s [17].
  • Lobeline, at the time of maximal effect, dose-dependently produced motor impairment and decreased locomotor activity and body temperature in mice after s.c. treatment [18].
  • Lobeline administration (142+/-6 microg/kg) produced either apnea (n=7, latency -2.0+/-0.3 s) or excitation of breathing (n=8, latency -3.5+/-0.3 s) and no change in heart rate [19].

Anatomical context of lobeline


Associations of lobeline with other chemical compounds


Gene context of lobeline

  • The reaction was sensitive to inhibition by the CYP2D6-selective inhibitors quinidine, quinine, lobeline and norfluoxetine, whereas chemical inhibitors selective for other CYP isoforms failed to affect the reaction [27].
  • Lobelane and ketoalkene were 5-fold more potent (Ki = 0.92 and 1.35 microM, respectively) than lobeline (Ki = 5.46 microM) in inhibiting [3H]methoxytetrabenazine binding to VMAT2 in vesicle preparations [28].
  • Mesotransdiene and (-)-trans-transdiene competitively inhibited DAT function, whereas lobelane and lobeline acted noncompetitively [28].
  • In the present study, lobeline and two structurally simplified analogs were evaluated for activity in muscarinic and nicotinic binding assays, a functional assay for nicotinic receptor activation (86Rb+ efflux from striatal synaptosomes) and an acetylcholinesterase (AChE) assay [29].
  • The biosynthesis of lobelia alkaloids. Part III. Intermediates in the biosynthesis of lobeline; biosynthesis of 8, 10-diethyl-lobelidione [30].

Analytical, diagnostic and therapeutic context of lobeline

  • Changes in respiratory sensations induced by lobeline after human bilateral lung transplantation [1].
  • Chiral separation of lobeline analogs using high performance capillary electrophoresis and derivatized cyclodextrins as chiral additives [2].
  • 1. Intravenous injections of lobeline HCl into twenty-six normal young male human volunteers produced sensations of choking, pressure or fumes in the throat and upper chest at a mean threshold dose of 12 micrograms kg-1 [16].
  • 5. For transplant subjects studied more than a year after transplantation, there was some evidence that the noxious respiratory sensations evoked by lobeline had returned [1].
  • In three out of four cats lobeline had no excitatory effect on the RARs in the absence of normal activity (i.e. when it was injected while artificial respiration was suspended), but on restarting the respiration the activity increased greatly [16].


  1. Changes in respiratory sensations induced by lobeline after human bilateral lung transplantation. Butler, J.E., Anand, A., Crawford, M.R., Glanville, A.R., McKenzie, D.K., Paintal, A.S., Taylor, J.L., Gandevia, S.C. J. Physiol. (Lond.) (2001) [Pubmed]
  2. Chiral separation of lobeline analogs using high performance capillary electrophoresis and derivatized cyclodextrins as chiral additives. McCurdy, C.R., Venkateshwaran, T.G., Beach, J.W., Stewart, J.T. Electrophoresis (1999) [Pubmed]
  3. Lobeline attenuates methamphetamine-induced changes in vesicular monoamine transporter 2 immunoreactivity and monoamine depletions in the striatum. Eyerman, D.J., Yamamoto, B.K. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
  4. Analysis of postinspiratory activity of phrenic motoneurons with chemical and vagal reflexes. Prabhakar, N.R., Mitra, J., Overholt, J.L., Cherniack, N.S. J. Appl. Physiol. (1986) [Pubmed]
  5. Lobeline displaces [3H]dihydrotetrabenazine binding and releases [3H]dopamine from rat striatal synaptic vesicles: comparison with d-amphetamine. Teng, L., Crooks, P.A., Dwoskin, L.P. J. Neurochem. (1998) [Pubmed]
  6. Dissociations between the locomotor stimulant and depressant effects of nicotinic agonists in rats. Stolerman, I.P., Garcha, H.S., Mirza, N.R. Psychopharmacology (Berl.) (1995) [Pubmed]
  7. Cholinergic septo-hippocampal innervation is required for trace eyeblink classical conditioning. Fontán-Lozano, A., Troncoso, J., Múnera, A., Carrión, A.M., Delgado-García, J.M. Learn. Mem. (2005) [Pubmed]
  8. Lobeline Attenuates Methamphetamine-induced Stereotypy in Adolescent Mice. Tatsuta, T., Kitanaka, N., Kitanaka, J., Morita, Y., Takemura, M. Neurochem. Res. (2006) [Pubmed]
  9. Comparison of respiratory sensations induced by J receptor stimulation with lobeline in left handers & right handers. Jaju, D.S., Dikshit, M.B., Agrawal, M.J., Gupte, N.A. Indian J. Med. Res. (1998) [Pubmed]
  10. Emetic reflex arc revealed by expression of the immediate-early gene c-fos in the cat. Miller, A.D., Ruggiero, D.A. J. Neurosci. (1994) [Pubmed]
  11. Modulatory role of presynaptic nicotinic receptors in synaptic and non-synaptic chemical communication in the central nervous system. Vizi, E.S., Lendvai, B. Brain Res. Brain Res. Rev. (1999) [Pubmed]
  12. Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter. Zheng, G., Dwoskin, L.P., Deaciuc, A.G., Norrholm, S.D., Crooks, P.A. J. Med. Chem. (2005) [Pubmed]
  13. Effects of SKF 525-A, phenobarbital and 3-methylcholanthrene on the toxicity of lobeline sulfate. Kim, H.L. Veterinary and human toxicology. (1985) [Pubmed]
  14. Smoking cessation. Marlow, S.P., Stoller, J.K. Respiratory care. (2003) [Pubmed]
  15. Regulation of brain nicotinic receptors by chronic agonist infusion. Bhat, R.V., Turner, S.L., Selvaag, S.R., Marks, M.J., Collins, A.C. J. Neurochem. (1991) [Pubmed]
  16. Sensory origin of lobeline-induced sensations: a correlative study in man and cat. Raj, H., Singh, V.K., Anand, A., Paintal, A.S. J. Physiol. (Lond.) (1995) [Pubmed]
  17. Absence of viscerosomatic inhibition with injections of lobeline designed to activate human pulmonary C fibres. Gandevia, S.C., Butler, J.E., Taylor, J.L., Crawford, M.R. J. Physiol. (Lond.) (1998) [Pubmed]
  18. Pharmacology of lobeline, a nicotinic receptor ligand. Damaj, M.I., Patrick, G.S., Creasy, K.R., Martin, B.R. J. Pharmacol. Exp. Ther. (1997) [Pubmed]
  19. Role of vagal afferents in the reflex effects of capsaicin and lobeline in monkeys. Deep, V., Singh, M., Ravi, K. Respiration physiology. (2001) [Pubmed]
  20. Nicotinic cholinergic agonists inhibit androgen biosynthesis by cultured rat testicular cells. Kasson, B.G., Hsueh, A.J. Endocrinology (1985) [Pubmed]
  21. Lobeline does not serve as a reinforcer in rats. Harrod, S.B., Dwoskin, L.P., Green, T.A., Gehrke, B.J., Bardo, M.T. Psychopharmacology (Berl.) (2003) [Pubmed]
  22. Multiple cellular mechanisms mediate the effect of lobeline on the release of norepinephrine. Sántha, E., Sperlágh, B., Zelles, T., Zsilla, G., Tóth, P.T., Lendvai, B., Baranyi, M., Vizi, E.S. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  23. Differential mechanisms involved in the effect of nicotinic agonists DMPP and lobeline to release [3H]5-HT from rat hippocampal slices. Lendvai, B., Sershen, H., Lajtha, A., Santha, E., Baranyi, M., Vizi, E.S. Neuropharmacology (1996) [Pubmed]
  24. A novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse. Dwoskin, L.P., Crooks, P.A. Biochem. Pharmacol. (2002) [Pubmed]
  25. Human hepatic cytochrome P450 2D6-like activity in nonhuman primates: catalytic characterization in vitro. Wu, D., Otton, S.V., Morrow, P., Inaba, T., Kalow, W., Sellers, E.M. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
  26. Lobeline inhibits nicotine-evoked [(3)H]dopamine overflow from rat striatal slices and nicotine-evoked (86)Rb(+) efflux from thalamic synaptosomes. Miller, D.K., Crooks, P.A., Dwoskin, L.P. Neuropharmacology (2000) [Pubmed]
  27. Evidence for the catalysis of dextromethorphan O-demethylation by a CYP2D6-like enzyme in pig liver. Jurima-Romet, M., Casley, W.L., Leblanc, C.A., Nowakowska, M. Toxicology in vitro : an international journal published in association with BIBRA. (2000) [Pubmed]
  28. Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters. Miller, D.K., Crooks, P.A., Zheng, G., Grinevich, V.P., Norrholm, S.D., Dwoskin, L.P. J. Pharmacol. Exp. Ther. (2004) [Pubmed]
  29. Lobeline and structurally simplified analogs exhibit differential agonist activity and sensitivity to antagonist blockade when compared to nicotine. Terry, A.V., Williamson, R., Gattu, M., Beach, J.W., McCurdy, C.R., Sparks, J.A., Pauly, J.R. Neuropharmacology (1998) [Pubmed]
  30. The biosynthesis of lobelia alkaloids. Part III. Intermediates in the biosynthesis of lobeline; biosynthesis of 8, 10-diethyl-lobelidione. O'Donovan, D.G., Long, D.J., Forde, E., Geary, P. J. Chem. Soc. Perkin Trans. I (1975) [Pubmed]
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