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| CAS No.: | 134-63-4 |
|---|---|
| Name: | alpha-Lobeline hydrochloride |
| Molecular Structure: | |
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|
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| Formula: | C22H28ClNO2 |
| Molecular Weight: | 373.923 |
| 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; |
| EINECS: | 205-150-2 |
| Melting Point: | 183-185 °C (dec.)(lit.) |
| Boiling Point: | 485.6 °C at 760 mmHg |
| Flash Point: | 247.5 °C |
| Appearance: | White to off-white solid |
| Hazard Symbols: |
 T
|
| Risk Codes: | 23/25 |
| Safety: | 36/37/39-45 |
| Transport Information: | UN 1544 6.1/PG 3 |
| PSA: | 40.54000 |
| LogP: | 4.97590 |
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- 950194-40-8
(S)-2-[(2R,6S)-6-(2-propionyloxy-2-phenylethyl)-1-methylpiperidin-2-yl]-1-phenylethanone
- 134-63-4
Lobeline hydrochloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol Heating; |
- 950194-38-4
C25H33NO3
- 134-63-4
Lobeline hydrochloride
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With hydrogenchloride In water; isopropyl alcohol at 60℃; for 8h; Inert atmosphere; |
- 134-63-4
Lobeline hydrochloride
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With hydrogenchloride; mercury; zinc for 0.25h; Dehydration; reduction; Heating; | 46% |
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In water for 48h; |
- 134-63-4
Lobeline hydrochloride
| Conditions | Yield |
|---|---|
| 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 |
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Chemistry
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
Uses
Lobeline hydrochloride (CAS NO.134-63-4) is used as a neuronal nicotinic acetylcholine receptor agonist and also used as a respiratory stimulant.
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. |
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:
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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.