Lobelina
Lobelina es el nombre de un alcaloide que se encuentra en varias plantas, entre ellas la Lobelia inflata, la Lobelia tupa, la Lobelia cardinalis, la Lobelia siphilitica y la Hippobroma longiflora. En su forma pura se presenta como un polvo que se disuelve fácilmente en agua.
| Lobelina | ||
|---|---|---|
 | ||
| Nombre (IUPAC) sistemático | ||
| 2-[6- (2-hidroxi- 2-fenil- etil)- 1-metil- 2-piperidil]- 1-fenil- etanona | ||
| Identificadores | ||
| Número CAS | 90-69-7 | |
| Código ATC | No adjudicado | |
| Código ATCvet | No adjudicado | |
| Datos químicos | ||
| Fórmula | C22H27NO2 | |
| Peso mol. | 337.455 g/mol | |
| Datos físicos | ||
| P. de fusión | 130–131 °C | |
La lobelina se ha usado como sustitutivo de la nicotina en tratamientos para abandonar esa adicción,[1][2][3] y se ha aplicado también en tratamientos para la adicción o abuso de otras drogas, como la anfetamina,[4][5] la cocaína[6] o el alcohol.[7]
La lobelina actúa a través de diferentes mecanismos, como el ligando del transportador vesicular de monoamina (VMAT2),[8][9][10] reduciendo la liberación de dopamina causada por la metanfetamina.[11][12] También es un inhibidor de la recaptación de la dopamina y la serotonina,[13] actuando de manera mixta como agonista-antagonista en los receptores nicotínicos[14][15] y como antagonista en receptores μ-opioides.[16]
Referencias
editar- ↑ Stead L, Hughes J (2000). «Lobeline for smoking cessation». Cochrane Database Syst Rev (2): CD000124. PMID 10796490. doi:10.1002/14651858.CD000124.
- ↑ Marlow SP, Stoller JK. Smoking cessation. Respiratory Care. 2003 Dec;48(12):1238-56. PMID 14651764
- ↑ Buchhalter AR, Fant RV, Henningfield JE. Novel pharmacological approaches for treating tobacco dependence and withdrawal : current status. Drugs. 2008;68(8):1067-88. PMID 18484799
- ↑ Neugebauer NM, Harrod SB, Stairs DJ, Crooks PA, Dwoskin LP, Bardo MT. Lobelane decreases methamphetamine self-administration in rats. European Journal of Pharmacology. 2007 Sep 24;571(1):33-8. PMID 17612524
- ↑ Eyerman DJ, Yamamoto BK. Lobeline attenuates methamphetamine-induced changes in vesicular monoamine transporter 2 immunoreactivity and monoamine depletions in the striatum. Journal of Pharmacology and Experimental Therapeutics. 2005 Jan;312(1):160-9. PMID 15331654
- ↑ Polston JE, Cunningham CS, Rodvelt KR, Miller DK. Lobeline augments and inhibits cocaine-induced hyperactivity in rats. Life Sciences. 2006 Aug 1;79(10):981-90. PMID 16765386
- ↑ Farook JM, Lewis B, Gaddis JG, Littleton JM, Barron S. Lobeline, a nicotinic partial agonist attenuates alcohol consumption and preference in male C57BL/6J mice. Physiology and Behavior. 2009 Jun 22;97(3-4):503-6. PMID 19268674
- ↑ Zheng G, Dwoskin LP, Crooks PA. Vesicular monoamine transporter 2: role as a novel target for drug development. AAPS Journal. 2006 Nov 10;8(4):E682-92. PMID 17233532
- ↑ Zheng F, Zheng G, Deaciuc AG, Zhan CG, Dwoskin LP, Crooks PA. Computational neural network analysis of the affinity of lobeline and tetrabenazine analogs for the vesicular monoamine transporter-2. Bioorganic and Medicinal Chemistry. 2007 Apr 15;15(8):2975-92. PMID 17331733
- ↑ Zheng G, Dwoskin LP, Deaciuc AG, Norrholm SD, Crooks PA. Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter. Journal of Medicinal Chemistry. 2005 Aug 25;48(17):5551-60. PMID 16107155
- ↑ Wilhelm CJ, Johnson RA, Eshleman AJ, Janowsky A. Lobeline effects on tonic and methamphetamine-induced dopamine release. Biochemical Pharmacology. 2008 Mar 15;75(6):1411-5. PMID 18191815
- ↑ Wilhelm CJ, Johnson RA, Lysko PG, Eshleman AJ, Janowsky A. Effects of methamphetamine and lobeline on vesicular monoamine and dopamine transporter-mediated dopamine release in a cotransfected model system. Journal of Pharmacology and Experimental Therapeutics. 2004 Sep;310(3):1142-51. PMID 15102929
- ↑ Zheng G, Horton DB, Deaciuc AG, Dwoskin LP, Crooks PA. Des-keto lobeline analogs with increased potency and selectivity at dopamine and serotonin transporters. Bioorganic and Medicinal Chemistry Letters. 2006 Oct 1;16(19):5018-21. PMID 16905316
- ↑ Damaj MI, Patrick GS, Creasy KR, Martin BR. Pharmacology of lobeline, a nicotinic receptor ligand. Journal of Pharmacology and Experimental Therapeutics. 1997 Jul;282(1):410-9. PMID 9223582
- ↑ Miller DK, Harrod SB, Green TA, Wong MY, Bardo MT, Dwoskin LP. Lobeline attenuates locomotor stimulation induced by repeated nicotine administration in rats. Pharmacology, Biochemistry and Behaviour. 2003 Jan;74(2):279-86. PMID 12479946
- ↑ Miller DK, Lever JR, Rodvelt KR, Baskett JA, Will MJ, Kracke GR. Lobeline, a potential pharmacotherapy for drug addiction, binds to mu opioid receptors and diminishes the effects of opioid receptor agonists. Drug and Alcohol Dependence. 2007 Jul 10;89(2-3):282-91. PMID 17368966
