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Name	Lobeline	EINECS	N/A
CAS No.	90-69-7	Density	1.085g/cm3
PSA	40.54000	LogP	4.17390
Solubility	N/A	Melting Point	130-131°
Formula	C22H27 N O2	Boiling Point	485.6oC at 760 mmHg
Molecular Weight	337.462	Flash Point	247.5oC
Transport Information	N/A	Appearance	N/A
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 NO_x.	Risk Codes	23/24/25
Molecular Structure		Hazard Symbols	T
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	Article Data	13

Lobeline Synthetic route

: 579-21-5
Lobelanine

: 90-69-7
lobeline

Conditions

Conditions	Yield
With ammonium formate In 1,2-dichloro-ethane at 75℃; for 1h; Inert atmosphere;	91%

: 2-{(6S)-6-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-1-methylpiperidin-(2R)-2-yl}-1-phenylethanone

: 90-69-7
lobeline

Conditions

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 60℃; for 12h;	90%

: C32H49NO3SSi

: 90-69-7
lobeline

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water for 0.5h; Large scale;	88%

: (+/-)-Lobelanine hydrochloride

: 90-69-7
lobeline

Conditions

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%

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%

: 134-63-4
Lobeline hydrochloride

A: (2S)-Lobeline

B: 90-69-7
lobeline

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water for 48h;

: 237059-21-1
(2S,6S,2R)-2-<6-(2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl>-1-phenylethan-<1,3>-dioxolane

A: (2S)-Lobeline

B: 90-69-7
lobeline

Conditions

Conditions	Yield
With hydrogenchloride Heating; Yield given; Yields of byproduct given;

: 491837-37-7
(1S)-2-((S)-oxiranyl)-1-phenylethanol

: 90-69-7
lobeline

Conditions

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

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

: 491837-39-9
(1S,3S)-tert-butyldimethyl(2-oxiranyl-1-phenylethoxy)silane

: 90-69-7
lobeline

Conditions

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

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

: 491837-38-8
(1S,3S)-4-nitrobenzoic acid 2-oxiranyl-1-phenylethyl ester

: 90-69-7
lobeline

Conditions

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

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

: 491837-40-2
(1S,3R)-1-(tert-butyldimethylsilanoxy)-1-phenylhept-6-en-3-ol

: 90-69-7
lobeline

Conditions

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

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

Lobeline Chemical Properties

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

Lobeline Toxicity Data With Reference

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.

Lobeline Safety Profile

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 NO_x.

Lobeline Specification

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.

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