Lobeline, (+)- | CAS#246018-80-4 | alkaloid

MedKoo Cat#: 599130 | Name: Lobeline, (+)-

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lobeline, (+)- is an alkaloid that has actions similar to nicotine on nicotinic cholinergic receptors but is less potent. It has been proposed for a variety of therapeutic uses including in respiratory disorders, peripheral vascular disorders, insomnia, and smoking cessation.

Chemical Structure

Lobeline, (+)-

CAS#246018-80-4

Theoretical Analysis

MedKoo Cat#: 599130

Name: Lobeline, (+)-

CAS#: 246018-80-4

Chemical Formula: C22H27NO2

Exact Mass: 337.2042

Molecular Weight: 337.46

Elemental Analysis: C, 78.30; H, 8.06; N, 4.15; O, 9.48

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Lobeline, (+)-; (+)-Lobeline;

IUPAC/Chemical Name

2-((2S,6R)-6-((R)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethan-1-one

InChi Key

MXYUKLILVYORSK-QHAWAJNXSA-N

InChi Code

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-/m1/s1

SMILES Code

CN1[C@H](CC(C2=CC=CC=C2)=O)CCC[C@@H]1C[C@@H](O)C3=CC=CC=C3

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 337.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Dwoskin LP, Crooks PA. A novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse. Biochem Pharmacol. 2002 Jan 15;63(2):89-98. Review. PubMed PMID: 11841781. 2: Miller DK, Crooks PA, Zheng G, Grinevich VP, Norrholm SD, Dwoskin LP. Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters. J Pharmacol Exp Ther. 2004 Sep;310(3):1035-45. Epub 2004 Apr 30. PubMed PMID: 15121762. 3: Reavill C, Walther B, Stolerman IP, Testa B. Behavioural and pharmacokinetic studies on nicotine, cytisine and lobeline. Neuropharmacology. 1990 Jul;29(7):619-24. PubMed PMID: 2385332. 4: Raj H, Singh VK, Anand A, Paintal AS. Sensory origin of lobeline-induced sensations: a correlative study in man and cat. J Physiol. 1995 Jan 1;482 ( Pt 1):235-46. PubMed PMID: 7730986; PubMed Central PMCID: PMC1157767. 5: Zheng G, Dwoskin LP, Deaciuc AG, Norrholm SD, Crooks PA. Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter. J Med Chem. 2005 Aug 25;48(17):5551-60. PubMed PMID: 16107155; PubMed Central PMCID: PMC3617589. 6: Marlin DJ, Roberts CA, Schroter RC, Lekeux P. Respiratory responses of mature horses to intravenous lobeline bolus. Equine Vet J. 2000 May;32(3):200-7. PubMed PMID: 10836474. 7: Eyerman DJ, Yamamoto BK. Lobeline attenuates methamphetamine-induced changes in vesicular monoamine transporter 2 immunoreactivity and monoamine depletions in the striatum. J Pharmacol Exp Ther. 2005 Jan;312(1):160-9. Epub 2004 Aug 26. PubMed PMID: 15331654. 8: Lim DY, Kim YS, Miwa S. Influence of lobeline on catecholamine release from the isolated perfused rat adrenal gland. Auton Neurosci. 2004 Jan 30;110(1):27-35. PubMed PMID: 14766322. 9: Wang JJ, Liu SM, Chen R, Li L, Guo XS, Xue B, Hu WC. A novel effect of lobeline on vascular smooth muscle cell: inhibition of proliferation induced by endothelin-1. Pharmazie. 2007 Aug;62(8):620-4. PubMed PMID: 17867559. 10: Ma Y, Wink M. Lobeline, a piperidine alkaloid from Lobelia can reverse P-gp dependent multidrug resistance in tumor cells. Phytomedicine. 2008 Sep;15(9):754-8. doi: 10.1016/j.phymed.2007.11.028. Epub 2008 Jan 28. PubMed PMID: 18222670. 11: Wellman PJ, Elliott AE, Barbee S, Hollas CN, Clifford PS, Nation JR. Lobeline attenuates progressive ratio breakpoint scores for intracranial self-stimulation in rats. Physiol Behav. 2008 Mar 18;93(4-5):952-7. doi: 10.1016/j.physbeh.2007.12.018. Epub 2007 Dec 31. PubMed PMID: 18272188; PubMed Central PMCID: PMC2740660. 12: Wilhelm CJ, Johnson RA, Eshleman AJ, Janowsky A. Lobeline effects on tonic and methamphetamine-induced dopamine release. Biochem Pharmacol. 2008 Mar 15;75(6):1411-5. doi: 10.1016/j.bcp.2007.11.019. Epub 2007 Dec 4. PubMed PMID: 18191815; PubMed Central PMCID: PMC2435375. 13: Teng L, Crooks PA, Dwoskin LP. Lobeline displaces [3H]dihydrotetrabenazine binding and releases [3H]dopamine from rat striatal synaptic vesicles: comparison with d-amphetamine. J Neurochem. 1998 Jul;71(1):258-65. PubMed PMID: 9648873. 14: Butler JE, Anand A, Crawford MR, Glanville AR, McKenzie DK, Paintal AS, Taylor JL, Gandevia SC. Changes in respiratory sensations induced by lobeline after human bilateral lung transplantation. J Physiol. 2001 Jul 15;534(Pt. 2):583-93. PubMed PMID: 11454974; PubMed Central PMCID: PMC2278721. 15: Harrod SB, Dwoskin LP, Green TA, Gehrke BJ, Bardo MT. Lobeline does not serve as a reinforcer in rats. Psychopharmacology (Berl). 2003 Feb;165(4):397-404. Epub 2002 Nov 30. PubMed PMID: 12459929. 16: Raj H, Bakshi GS, Tiwari RR, Anand A, Paintal AS. How does lobeline injected intravenously produce a cough? Respir Physiol Neurobiol. 2005 Jan 15;145(1):79-90. PubMed PMID: 15652790. 17: Miller DK, Harrod SB, Green TA, Wong MY, Bardo MT, Dwoskin LP. Lobeline attenuates locomotor stimulation induced by repeated nicotine administration in rats. Pharmacol Biochem Behav. 2003 Jan;74(2):279-86. PubMed PMID: 12479946. 18: Sántha E, Sperlágh B, Zelles T, Zsilla G, Tóth PT, Lendvai B, Baranyi M, Vizi ES. Multiple cellular mechanisms mediate the effect of lobeline on the release of norepinephrine. J Pharmacol Exp Ther. 2000 Jul;294(1):302-7. PubMed PMID: 10871326. 19: Terry AV Jr, Williamson R, Gattu M, Beach JW, McCurdy CR, Sparks JA, Pauly JR. Lobeline and structurally simplified analogs exhibit differential agonist activity and sensitivity to antagonist blockade when compared to nicotine. Neuropharmacology. 1998;37(1):93-102. PubMed PMID: 9680262. 20: Tatsuta T, Kitanaka N, Kitanaka J, Morita Y, Takemura M. Lobeline attenuates methamphetamine-induced stereotypy in adolescent mice. Neurochem Res. 2006 Nov;31(11):1359-69. Epub 2006 Oct 20. PubMed PMID: 17053968.