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alpha-Lobeline hydrochloride
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Name

alpha-Lobeline hydrochloride

 EINECS 205-150-2
CAS No. 134-63-4 Density N/A
PSA 40.54000 LogP 4.97590
Solubility N/A Melting Point 183-185 °C (dec.)(lit.)
Formula C22H28ClNO2 Boiling Point 485.6 °C at 760 mmHg
Molecular Weight 373.923 Flash Point 247.5 °C
Transport Information UN 1544 6.1/PG 3 Appearance White to off-white solid
Safety 36/37/39-45 Risk Codes 23/25
Molecular Structure Molecular Structure of 134-63-4 (alpha-Lobeline hydrochloride) Hazard Symbols ToxicT
Synonyms

Ethanone,2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-,hydrochloride (9CI);Ethanone,2-[6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl]-1-phenyl-,hydrochloride, [2R-[2a,6a(S*)]]-;Lobeline, hydrochloride(8CI);(-)-Lobeline hydrochloride;(-)-a-Lobeline hydrochloride;Lobelin hydrochloride;Lobron;Zoolobelin;

Article Data 3

alpha-Lobeline hydrochloride Synthetic route

950194-40-8

(S)-2-[(2R,6S)-6-(2-propionyloxy-2-phenylethyl)-1-methylpiperidin-2-yl]-1-phenylethanone

134-63-4

Lobeline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;
950194-38-4

C25H33NO3

134-63-4

Lobeline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CrO3; H2SO4 / acetone / 1 h / 20 °C
2: aq. HCl / methanol / Heating
View Scheme
6168-88-3

2,2′-((2,6)-1-methylpiperidine-2,6-diyl)bis(1-phenylethanone) hydrochloride

134-63-4

Lobeline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 65 percent / NaBH4 / methanol / 20 °C
2: 92 percent / (S)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; Na2SO4 / CDCl3 / 48 h / 20 °C
3: CrO3; H2SO4 / acetone / 1 h / 20 °C
4: aq. HCl / methanol / Heating
View Scheme
552-72-7

NSC 95097

134-63-4

Lobeline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / (S)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; Na2SO4 / CDCl3 / 48 h / 20 °C
2: CrO3; H2SO4 / acetone / 1 h / 20 °C
3: aq. HCl / methanol / Heating
View Scheme
1070913-26-6

(cis:trans)-(-)-lobeline

134-63-4

Lobeline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 60℃; for 8h; Inert atmosphere;
134-63-4

Lobeline hydrochloride

(-)cis-N-methyl-2-(2-chloro-2-phenylethyl)-6-(2-oxo-2-phenylethyl)piperidine hydrochloride

Conditions
ConditionsYield
With thionyl chloride In chloroform at 20℃; for 24h; Chlorination;80%
134-63-4

Lobeline hydrochloride

324078-36-6

cis-2S,6R-N-methyl-6-phenacyl-2-trans-styrylpiperidine

Conditions
ConditionsYield
With phosphonic Acid at 45 - 50℃; for 22h; Dehydration;75%
134-63-4

Lobeline hydrochloride

818377-08-1

(S)-2-[(2S,6R)-1-Methyl-6-((E)-styryl)-piperidin-2-yl]-1-phenyl-ethanol

Conditions
ConditionsYield
With hydrogenchloride; mercury; zinc for 0.25h; Dehydration; reduction; Heating;46%
134-63-4

Lobeline hydrochloride

A

(2S)-Lobeline

B

90-69-7

lobeline

Conditions
ConditionsYield
With sodium hydrogencarbonate In water for 48h;
134-63-4

Lobeline hydrochloride

2-((2R,6S)-1-Methyl-6-phenethyl-piperidin-2-yl)-1-phenyl-ethanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 75 percent / 85 percent aq. H3PO3 / 22 h / 45 - 50 °C
2: H2 / 5 percent Pd/C / methanol / 1.5 h / 2585.74 Torr
3: pyridinium dichromate / CH2Cl2 / 3 h / 20 °C
View Scheme

alpha-Lobeline hydrochloride Chemical Properties

Chemical Name: alpha-Lobeline hydrochloride          
IUPAC NAME: 2-[(2R,6S)-6-[(2R)-2-Hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone hydrochloride    
CAS No.: 134-63-4
EINECS: 205-150-2
RTECS: OJ8490100
Molecular Formula: C22H28ClNO2
Molecular Weight: 373.92 g/mol
Melting Point: 183-185 °C (dec.)(lit.)
Flash Point: 247.5 °C
Boiling Point: 485.6 °C at 760 mmHg
Following is the structure of Lobeline hydrochloride (134-63-4):


Product Categories are Alkaloids ; Heterocyclic Compounds ; Biochemistry ; Pyridine Alkaloids ; Neurochemicals ; Acetylcholine receptor                       
The chemical synonyms of Lobeline hydrochloride (CAS NO.134-63-4) are 2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)-acetophenonhydrochlor ; 2-[6-(.beta.-Hydroxyphenethyl)-1-methyl-2-piperidyl]-,hydrochloride,(-)-acetophenone ; lobelinhydrochloride ;  ; lobeline Hcl, a- ; (-)-lobeline hydrochloride              

alpha-Lobeline hydrochloride Uses

  Lobeline hydrochloride (CAS NO.134-63-4) is used as a neuronal nicotinic acetylcholine receptor agonist and also used as a respiratory stimulant.

alpha-Lobeline hydrochloride Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo parenteral 150mg/kg (150mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 163, Pg. 279, 1931.
mouse LD50 intraperitoneal 39900ug/kg (39.9mg/kg)   Drugs in Japan Vol. 6, Pg. 913, 1982.
mouse LD50 intravenous 7800ug/kg (7.8mg/kg)   Drugs in Japan Vol. 6, Pg. 913, 1982.
mouse LD50 subcutaneous 87500ug/kg (87.5mg/kg)   Drugs in Japan Vol. 6, Pg. 913, 1982.

alpha-Lobeline hydrochloride Safety Profile

Poison by subcutaneous, intravenous, and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx and HCl. See also LOBELINE and CARDINAL FLOWER.
Hazard Codes:
T: Toxic
Risk Statements about Lobeline hydrochloride (CAS NO.134-63-4):
R23/25: Toxic by inhalation and if swallowed.
Safety Statements:
S45 In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.

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