alpha-Lobeline hydrochloride
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
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)
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
- F
- 8
- HazardClass
- 6.1(b)
- PackingGroup
- III
MSDS
- Language:English Provider:SigmaAldrich
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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