Products Categories
CAS No.: | 90-69-7 |
---|---|
Name: | Lobeline |
Article Data: | 13 |
Molecular Structure: | |
Formula: | C22H27 N O2 |
Molecular Weight: | 337.462 |
Synonyms: | Ethanone,2-[6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl]-1-phenyl-, [2R-[2a,6a(S*)]]-; Lobeline (8CI); a-Lobeline (7CI); (-)-Lobeline; (-)-a-Lobeline; 2-[6-(b-Hydroxyphenethyl)-1-methyl-2-piperidyl]acetophenone;8,10-Diphenyllobelionol; Inflatine; L-Lobeline; Lobelin; Lobnico; NIH 11034;l-Lobeline |
Density: | 1.085g/cm3 |
Melting Point: | 130-131° |
Boiling Point: | 485.6oC at 760 mmHg |
Flash Point: | 247.5oC |
Hazard Symbols: | T |
Risk Codes: | 23/24/25 |
Safety: | Poison by intraperitoneal and intravenous routes. Causes stimulation which leads to convulsions in severe cases. Nausea and vomiting are frequent. When heated to decomposition it emits toxic fumes of NOx. |
PSA: | 40.54000 |
LogP: | 4.17390 |
Conditions | Yield |
---|---|
With ammonium formate In 1,2-dichloro-ethane at 75℃; for 1h; Inert atmosphere; | 91% |
lobeline
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at 60℃; for 12h; | 90% |
lobeline
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water for 0.5h; Large scale; | 88% |
lobeline
Conditions | Yield |
---|---|
Stage #1: (+/-)-Lobelanine hydrochloride With hydrogen; triethylamine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (2R,4R)-4-(dicyclohexylphosphino)-2-(diphenylphosphino-methyl)-N-methyl-aminocarbonyl-pyrrolidine In methanol at 47 - 53℃; under 525.053 - 97584.8 Torr; Industry scale; Stage #2: With hydrogenchloride In water; toluene at 35 - 40℃; for 0.333333h; pH=0.5 - 1.5; Stage #3: With sodium hydroxide In water; toluene at 35 - 40℃; for 0.333333h; pH=12 - 13; | 29% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water for 48h; |
(2S,6S,2R)-2-<6-(2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl>-1-phenylethan-<1,3>-dioxolane
B
lobeline
Conditions | Yield |
---|---|
With hydrogenchloride Heating; Yield given; Yields of byproduct given; |
(1S)-2-((S)-oxiranyl)-1-phenylethanol
lobeline
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 3 h / 20 °C 2.1: CuI / diethyl ether / 0.25 h / -30 °C 2.2: 92 percent / diethyl ether / 0.5 h / -40 °C 3.1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 4.1: 88 percent / dimethylformamide; H2O / 20 h / 50 °C 5.1: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C 6.1: tetrahydrofuran / 0 - 20 °C 7.1: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C 8.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 9.1: 82 percent / tetrahydrofuran / 13 h / 65 °C 10.1: HCl / propan-2-ol / 3 h / 60 °C View Scheme |
(1S,3S)-tert-butyldimethyl(2-oxiranyl-1-phenylethoxy)silane
lobeline
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: CuI / diethyl ether / 0.25 h / -30 °C 1.2: 92 percent / diethyl ether / 0.5 h / -40 °C 2.1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 3.1: 88 percent / dimethylformamide; H2O / 20 h / 50 °C 4.1: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C 5.1: tetrahydrofuran / 0 - 20 °C 6.1: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C 7.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 8.1: 82 percent / tetrahydrofuran / 13 h / 65 °C 9.1: HCl / propan-2-ol / 3 h / 60 °C View Scheme |
(1S,3S)-4-nitrobenzoic acid 2-oxiranyl-1-phenylethyl ester
lobeline
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: 77 percent / K2CO3; methanol / H2O / 2 h / 20 °C 2.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 3 h / 20 °C 3.1: CuI / diethyl ether / 0.25 h / -30 °C 3.2: 92 percent / diethyl ether / 0.5 h / -40 °C 4.1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 5.1: 88 percent / dimethylformamide; H2O / 20 h / 50 °C 6.1: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C 7.1: tetrahydrofuran / 0 - 20 °C 8.1: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C 9.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 10.1: 82 percent / tetrahydrofuran / 13 h / 65 °C 11.1: HCl / propan-2-ol / 3 h / 60 °C View Scheme |
(1S,3R)-1-(tert-butyldimethylsilanoxy)-1-phenylhept-6-en-3-ol
lobeline
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 2: 88 percent / dimethylformamide; H2O / 20 h / 50 °C 3: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C 4: tetrahydrofuran / 0 - 20 °C 5: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C 6: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 7: 82 percent / tetrahydrofuran / 13 h / 65 °C 8: HCl / propan-2-ol / 3 h / 60 °C View Scheme |
Molecular Structure of Lobeline (CAS NO.90-69-7):
IUPAC Name: 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
Empirical Formula: C22H27NO2
Molecular Weight: 337.4553
Index of Refraction: 1.562
Surface Tension: 41.8 dyne/cm
Density: 1.085 g/cm3
Flash Point: 247.5 °C
Enthalpy of Vaporization: 79.11 kJ/mol
Boiling Point: 485.6 °C at 760 mmHg
Vapour Pressure: 3.05E-10 mmHg at 25°C
Synonyms of Lobeline (CAS NO.90-69-7): L-lobeline free base ; Lobeline;LOBELIDINE95%,98% ; LOBELINE HCl, a-(P) ; Lobeline (base and/or unspecified salts) ; (-)-α-[(2R,6S)-6-[(S)-β-hydroxyphenethyl]-1-methyl-2-piperidinyl] ; acetophenone ; Inflatine ; Lobelin
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 43500ug/kg (43.5mg/kg) | Strahlentherapie. Vol. 127, Pg. 245, 1965. | |
mouse | LD50 | intravenous | 6300ug/kg (6.3mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 103, Pg. 146, 1955. | |
mouse | LDLo | subcutaneous | 100mg/kg (100mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 132, Pg. 63, 1928. |
rabbit | LD50 | subcutaneous | 35mg/kg (35mg/kg) | Farmakologiya i Toksikologiya Vol. 4(1), Pg. 34, 1941. | |
rabbit | LDLo | intravenous | 10mg/kg (10mg/kg) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Journal of Pharmacology and Experimental Therapeutics. Vol. 31, Pg. 43, 1927. |
rat | LDLo | subcutaneous | 80mg/kg (80mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 132, Pg. 63, 1928. |
Poison by intraperitoneal and intravenous routes. Causes stimulation which leads to convulsions in severe cases. Nausea and vomiting are frequent. When heated to decomposition it emits toxic fumes of NOx.
Lobeline (CAS NO.90-69-7) is a highly-toxic material,Iis pure form is a white amorphous powder which is freely soluble in water.burning will produce nitrogen oxides emitted toxic fumes.Besides should be stored and transported in low-temperature,drying environment. separately with oxidizing agents.Fire extinguishing agents water, carbon dioxide, dry powder, foam would be used if emergency.
Lobeline (CAS NO.90-69-7) has been used as a smoking cessation aid, and may have application in the treatment of other drug addictions such as addiction to amphetamines, cocaine or alcohol..Lobeline has multiple mechanisms of action, acting as a VMAT2 ligand, which stimulates dopamine release to a moderate extent when administered alone, but reduces the dopamine release caused by methamphetamine. It also inhibits the reuptake of dopamine and serotonin, and acts as a mixed agonist-antagonist at nicotinic acetylcholine receptors and an antagonist at μ-opioid receptors.