Lobeline hydrochloride | CAS#134-63-4

MedKoo Cat#: 527026 | Name: Lobeline hydrochloride

Description:

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

Lobeline hydrochloride is a VMAT2 ligand, stimulating dopamine release, inhibiting the reuptake of dopamine and serotonin, acting as a mixed agonist-antagonist at nicotinic acetylcholine receptors and antagonist at µ-opioid receptors.

Chemical Structure

Lobeline hydrochloride

CAS#134-63-4

Theoretical Analysis

MedKoo Cat#: 527026

Name: Lobeline hydrochloride

CAS#: 134-63-4

Chemical Formula: C22H28ClNO2

Exact Mass: 373.1809

Molecular Weight: 373.92

Elemental Analysis: C, 70.67; H, 7.55; Cl, 9.48; N, 3.75; O, 8.56

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 hydrochloride

IUPAC/Chemical Name

2-[(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone hydrochloride

InChi Key

MKMYPTLXLWOUSO-NFQNBQCWSA-N

InChi Code

InChI=1S/C22H27NO2.ClH/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;1H/t19-,20+,21-;/m0./s1

SMILES Code

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

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

>2 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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 373.92 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: Nickell JR, Siripurapu KB, Horton DB, Zheng G, Crooks PA, Dwoskin LP. GZ-793A inhibits the neurochemical effects of methamphetamine via a selective interaction with the vesicular monoamine transporter-2. Eur J Pharmacol. 2017 Jan 15;795:143-149. doi: 10.1016/j.ejphar.2016.12.016. Epub 2016 Dec 13. PubMed PMID: 27986625. 2: Buoli M, Serati M, Cahn W. Alternative pharmacological strategies for adult ADHD treatment: a systematic review. Expert Rev Neurother. 2016;16(2):131-44. doi: 10.1586/14737175.2016.1135735. Epub 2016 Jan 14. Review. PubMed PMID: 26693882. 3: da Costa E Silva LD, Rodrigues LC, Dos Santos VR, da Costa Allgayer M, de Barros Falcão Ferraz A, Rolla HC, Pereira P, Picada JN. Evaluation of mutagenic and genotoxic activities of lobeline and its modulation on genomic instability induced by ethanol. Life Sci. 2014 May 17;103(2):73-8. doi: 10.1016/j.lfs.2014.03.034. Epub 2014 Apr 12. PubMed PMID: 24727238. 4: Elrashidi MY, Ebbert JO. Emerging drugs for the treatment of tobacco dependence: 2014 update. Expert Opin Emerg Drugs. 2014 Jun;19(2):243-60. doi: 10.1517/14728214.2014.899580. Epub 2014 Mar 22. Review. PubMed PMID: 24654737. 5: Meyer AC, Neugebauer NM, Zheng G, Crooks PA, Dwoskin LP, Bardo MT. Effects of VMAT2 inhibitors lobeline and GZ-793A on methamphetamine-induced changes in dopamine release, metabolism and synthesis in vivo. J Neurochem. 2013 Oct;127(2):187-98. doi: 10.1111/jnc.12373. Epub 2013 Aug 20. PubMed PMID: 23875705; PubMed Central PMCID: PMC3795981. 6: Kraziński BE, Radecki J, Radecka H. Surface plasmon resonance based biosensors for exploring the influence of alkaloids on aggregation of amyloid-β peptide. Sensors (Basel). 2011;11(4):4030-42. doi: 10.3390/s110404030. Epub 2011 Apr 6. PubMed PMID: 22163834; PubMed Central PMCID: PMC3231330. 7: Nickell JR, Zheng G, Deaciuc AG, Crooks PA, Dwoskin LP. Phenyl ring-substituted lobelane analogs: inhibition of [³H]dopamine uptake at the vesicular monoamine transporter-2. J Pharmacol Exp Ther. 2011 Mar;336(3):724-33. doi: 10.1124/jpet.110.172882. Epub 2010 Sep 28. PubMed PMID: 20876747; PubMed Central PMCID: PMC3061534. 8: Beckmann JS, Siripurapu KB, Nickell JR, Horton DB, Denehy ED, Vartak A, Crooks PA, Dwoskin LP, Bardo MT. The novel pyrrolidine nor-lobelane analog UKCP-110 [cis-2,5-di-(2-phenethyl)-pyrrolidine hydrochloride] inhibits VMAT2 function, methamphetamine-evoked dopamine release, and methamphetamine self-administration in rats. J Pharmacol Exp Ther. 2010 Dec;335(3):841-51. doi: 10.1124/jpet.110.172742. Epub 2010 Aug 30. PubMed PMID: 20805303; PubMed Central PMCID: PMC2993560. 9: Locati A, Berthelot M, Evain M, Lebreton J, Le Questel JY, Mathé-Allainmat M, Planchat A, Renault E, Graton J. The exceptional hydrogen-bond properties of neutral and protonated lobeline. J Phys Chem A. 2007 Jul 19;111(28):6397-405. Epub 2007 Jun 23. PubMed PMID: 17585846. 10: Koch C, Straub R, Ramseyer A, Widmer A, Robinson NE, Gerber V. Endoscopic scoring of the tracheal septum in horses and its clinical relevance for the evaluation of lower airway health in horses. Equine Vet J. 2007 Mar;39(2):107-12. PubMed PMID: 17378438. 11: Hoffman AM, Swanson LG, Bruns SJ, Kuehn H, Bedenice D. Effects of tension of the girth strap on respiratory system mechanics in horses at rest and during hyperpnea induced by administration of lobeline hydrochloride. Am J Vet Res. 2005 Jul;66(7):1167-74. PubMed PMID: 16111154. 12: Van Erck E, Votion D, Kirschvink N, Genicot B, Lindsey J, Art T, Lekeux P. Influence of breathing pattern and lung inflation on impulse oscillometry measurements in horses. Vet J. 2004 Nov;168(3):259-69. PubMed PMID: 15501143. 13: Herholz C, Straub R, Busato A. The variability and repeatability of indices derived from the single-breath diagram for CO2 in horses with chronic obstructive pulmonary disease and the effect of lobelin hydrochloride on these indices. Vet Res Commun. 2001 Jul;25(5):401-12. PubMed PMID: 11469511. 14: Herholz C, Tschudi P, Gerber H, Moens Y, Straub R. Ultrasound spirometry in the horse: a preliminary report on the method and the effects of xylazine and lobeline hydrochloride medication. Schweiz Arch Tierheilkd. 1997;139(12):558-63. PubMed PMID: 9451919. 15: Barlow RB, Johnson O. Relations between structure and nicotine-like activity: X-ray crystal structure analysis of (-)-cytisine and (-)-lobeline hydrochloride and a comparison with (-)-nicotine and other nicotine-like compounds. Br J Pharmacol. 1989 Nov;98(3):799-808. PubMed PMID: 2590771; PubMed Central PMCID: PMC1854759. 16: Kim HL. Effects of SKF 525-A, phenobarbital and 3-methylcholanthrene on the toxicity of lobeline sulfate. Vet Hum Toxicol. 1985 Feb;27(1):1-2. PubMed PMID: 3976162. 17: Koldaev VN. [Effect of various analeptics on the outcome of acute microwave lesion in mice]. Farmakol Toksikol. 1976 Sep-Oct;39(5):543-4. Russian. PubMed PMID: 18366. 18: Yalçindağ ON. [Stability of injectable lobeline hydrochloride to sterilization with steam and lobeline hydrochloride assay in solutions]. Turk Hij Tecr Biyol Derg. 1966;26(1):93-8. Turkish. PubMed PMID: 5931243. 19: KATO H, BUCKLEY JP. POSSIBLE SITES OF ACTION OF THE RESPIRATORY STIMULANT EFFECT OF DOXAPRAM HYDROCHLORIDE. J Pharmacol Exp Ther. 1964 May;144:260-4. PubMed PMID: 14183438. 20: DONZELOT E, MILOVANOVICH JB. [Effects of lobeline hydrochloride on the heart of the frog in situ]. C R Seances Soc Biol Fil. 1954 Jul;148(13-14):1167-70. French. PubMed PMID: 13231377.