alpha-Lobeline hydrochloride

alpha-Lobeline hydrochloride Basic information
Product Name:alpha-Lobeline hydrochloride
Synonyms:2-[6-(2-HYDROXY-2-PHENETHYL)-1-METHYL-2-PIPERIDYL]ACETOPHENONE HCL;2-(6-[2-HYDROXY-2-PHENYLETHYL]-1-METHYL-2-PIPERIDINYL)-1-PHENYLETHANONE HYDROCHLORIDE;2-[(2r,6s)-6-[(2s)-2-hydroxy-2-phenyl-ethyl]-1-methyl-2-piperidyl]-1-phenyl-ethanone hydrochloride;[2-[(2R,6S)-6-[(2S)-2-HYDROXYPHENETHYL]]-1-METHYL-2-PIPERIDYL]ACETOPHENONE HYDROCHLORIDE;(-)-LOBELINE HCL;LOBELINE HCL, A-;(-)-LOBELINE HYDROCHLORIDE;L-LOBELINE HYDROCHLORIDE
CAS:134-63-4
MF:C22H28ClNO2
MW:373.92
EINECS:205-150-2
Product Categories:Acetylcholine receptor;Other APIs;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Alkaloids;Heterocyclic Compounds;Biochemistry;Pyridine Alkaloids;Neurochemicals;134-63-4
Mol File:134-63-4.mol
alpha-Lobeline hydrochloride Structure
alpha-Lobeline hydrochloride Chemical Properties
Melting point 183-185 °C (dec.)(lit.)
alpha D20 -43° (c = 2)
refractive index -57.5 ° (C=1, H2O)
storage temp. Inert atmosphere,Room Temperature
solubility H2O: 25 mg/mL
form powder
color white to off-white
optical activity[α]20/D 56.8°, c = 2 in H2O
Merck 14,5551
BRN 3920196
LogP3.610 (est)
CAS DataBase Reference134-63-4(CAS DataBase Reference)
Safety Information
Hazard Codes T
Risk Statements 23/25
Safety Statements 36/37/39-45
RIDADR UN 1544 6.1/PG 3
WGK Germany 3
RTECS OJ8490100
8
HazardClass 6.1(b)
PackingGroup III
MSDS Information
ProviderLanguage
SigmaAldrich English
alpha-Lobeline hydrochloride Usage And Synthesis
Description(–)-Lobeline is an alkaloid that has been found in Lobelia and has diverse biological activities. It binds to nicotinic acetylcholine receptors (nAChRs) in rat brain homogenates (Ki = 4 nM) and has antinociceptive effects in the tail-flick assay in mice. (–)-Lobeline (0.3 and 0.9 mg/kg) reduces the number of errors in a repeated acquisition procedure in the radial arm maze in rats. It also decreases immobility time in the forced swim test and feeding latency in the novelty suppressed feeding test, indicating antidepressant-like activity, in mice when administered at doses of 1 and 4 mg/kg.
Chemical PropertiesWhite to Off-White Solid
UsesA neuronal nicotinic acetylcholine receptor agonist. A CNS stimulant.
UsesA neuronal nicotinic acetylcholine receptor agonist. A respiratory stimulant
Biological ActivityHigh affinity nicotinic receptor ligand, with a K i value of 4.4 nM in rat brain.
in vitroclastogenicity of lobeline and possible interactions between lobeline and ethyl alcohol were investigated in a mutagen-sensitivity assay on cultures of human lymphoblastoid cell lines. lobeline alone was not clastogenic, but there was a marked increase in genetic damage resulting from a coclastogenic interaction between lobeline and ethyl alcohol. [5]
in vivomale c57bl/6j mice were individually housed and acclimatized to 10% alcohol. lobeline is a partial nicotinic agonist that attenuates alcohol consumption and preference in male c57bl/6j mice. [3] cf-1 male mice received an intraperitoneal injection of lobeline (5 or 10mg/kg). lobeline did not show genotoxic or mutagenic effects and did not increase the ethanol-induced genotoxic effects in blood. lobeline also protected blood cells against oxidative damage induced by hydrogen peroxide. [4]
Methyl 3'-Hydroxyacetophenone Lobeline Topotecan hydrochloride Sibutramine hydrochloride 1-[(2-Chlorophenyl)-N-(methylimino)methyl]cyclopentanol hydrochloride N-Ethylmethylamine 1-Hydroxyethylidene-1,1-diphosphonic acid 3-(DIMETHYLAMINO)-1-PHENYLPROPAN-1-ONE Kresoxim-methyl PHENYL VALERATE 3,4-Dihydroxyacetophenone 1-AdaMantanethylaMine Thiophanate-methyl 4-Ethyl-5-fluoro-6-hydroxypyrimidine CHLOROPHOSPHONAZO III METSULFURON METHYL alpha-Lobeline hydrochloride

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