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alpha-Lobeline hydrochloride

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alpha-Lobeline hydrochloride Basic information

Product Name:
alpha-Lobeline hydrochloride
Synonyms:
  • (-)-id
  • 2-(6-(beta-hydroxyphenethyl)-1-methyl-2-piperidyl)-acetophenonhydrochlor
  • 2-[6-(.beta.-hydroxyphenethyl)-1-methyl-2-piperidyl]-,hydrochloride,(-)-Acetophenone
  • Lobelinhydrochloride
  • 2-((2R,6S)-6-((S)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone
  • Lobelin Hydrochlorde
  • 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
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
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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
LogP
3.610 (est)
CAS DataBase Reference
134-63-4(CAS DataBase Reference)
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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

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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 Properties

White to Off-White Solid

Uses

A neuronal nicotinic acetylcholine receptor agonist. A respiratory stimulant

Uses

A neuronal nicotinic acetylcholine receptor agonist. A CNS stimulant.

Biological Activity

High affinity nicotinic receptor ligand, with a K i value of 4.4 nM in rat brain.

in vitro

clastogenicity 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 vivo

male 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]

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