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| CAS No.: | 300-08-3 |
|---|---|
| Name: | Arecoline hydrobromide |
| Article Data: | 1 |
| Molecular Structure: | |
|
|
|
| Formula: | C8H14BrNO2 |
| Molecular Weight: | 236.109 |
| Synonyms: | 3-Pyridinecarboxylicacid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester, hydrobromide (9CI);Nicotinicacid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester, hydrobromide (8CI);Arecolinebromide; |
| EINECS: | 206-087-3 |
| Melting Point: | 171-175 °C |
| Boiling Point: | 209 °C at 760 mmHg |
| Flash Point: | 81.1 °C |
| Solubility: | 0.1 g/mL in water |
| Appearance: | white fine powder |
| Hazard Symbols: |
 Xn,  T
|
| Risk Codes: | 22-23/24/25 |
| Safety: | 45-38-36/37/39-28A |
| PSA: | 29.54000 |
| LogP: | 1.31730 |
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| Conditions | Yield |
|---|---|
| With potassium carbonate In dichloromethane; water at 20℃; for 0.5h; | 100% |
| With sodium carbonate pH=10 - 11; deprotonation; | |
| With water; sodium carbonate for 0.5h; | |
| With sodium hydroxide; water In ethyl acetate | |
| With sodium carbonate In water pH=13 - 14; |
| Conditions | Yield |
|---|---|
| In diethyl ether | 96% |
- 300-08-3
arecoline hydrobromide
- 98-09-9
benzenesulfonyl chloride
- 929803-75-8
methyl 1-benzenesulfonyl-1,2,5,6-tetrahydropyridine-3-carboxylate
| Conditions | Yield |
|---|---|
| Multistep reaction; | 90% |
| Conditions | Yield |
|---|---|
| Stage #1: arecoline hydrobromide With sodium carbonate In water pH=10 - 11; Stage #2: With water Reflux; | 89% |
| With barium dihydroxide at 40℃; for 0.5h; | |
| Multi-step reaction with 2 steps 1: aq. Na2CO3 / pH 10 - 11 2: 8.2 g / water / 24 h / Heating View Scheme | |
| With hydrogenchloride; water Heating / reflux; |
- 300-08-3
arecoline hydrobromide
- 100-58-3
phenylmagnesium bromide
- 53757-41-8
1-Methyl-4-phenyl-piperidine-3-carboxylic acid methyl ester
| Conditions | Yield |
|---|---|
| Stage #1: arecoline hydrobromide With sodium hydride In toluene at -10℃; for 0.25h; Stage #2: phenylmagnesium bromide In diethyl ether; toluene at -10℃; for 1h; | 83% |
| Conditions | Yield |
|---|---|
| In nitromethane | 77% |
- 300-08-3
arecoline hydrobromide
- 1885-14-9
phenyl chloroformate
- 323201-17-8
3-methoxycarbonyl-1-phenoxycarbonyl-1,2,5,6-tetrahydropyridine
| Conditions | Yield |
|---|---|
| Stage #1: arecoline hydrobromide With sodium hydrogencarbonate Stage #2: phenyl chloroformate In dichloromethane at 0 - 20℃; for 24h; | 76% |
| With sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 24h; |
| Conditions | Yield |
|---|---|
| In nitromethane | 47% |
| Conditions | Yield |
|---|---|
| Stage #1: arecoline hydrobromide With sodium carbonate In water Stage #2: (S,S)-hydrobenzoin With potassium tert-butylate In toluene for 16h; Reflux; Molecular sieve; stereoselective reaction; | 22% |
- 6345-29-5
hydroxyguanidine hemisulfate hemihydrate
- 300-08-3
arecoline hydrobromide
- 114724-86-6
3-(3-amino-1,2,4-oxadiazol-5-yl)-1-methyl-1,2,5,6-tetrahydropyridine
| Conditions | Yield |
|---|---|
| With 4 A molecular sieve; sodium In ethanol 1.) 20 deg C, 0.5 h, 2.) reflux, 0.5 h; | 17% |
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- 7778-80-5Potassium sulfate
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- 7772-98-7Sodium thiosulfate
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Chemistry
IUPAC NAME: Methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate hydrobromide
EINECS: 206-087-3
Molecular Formula: C8H14BrNO2
Molecular Weight: 236.11 g/mol
Melting Point: 171-175 °C
Flash Point: 81.1 °C
Boiling Point: 209 °C at 760 mmHg
Molecule structure of Arecoline hydrobromide (CAS NO.300-08-3):
Solubility H2O: 0.1 g/mL, clear, colorless
H-Bond Acceptor: 3
Rotatable Bond Count: 2
Exact Mass: 235.020791
MonoIsotopic Mass: 235.020791
Topological Polar Surface Area: 29.5
Canonical SMILES: CN1CCC=C(C1)C(=O)OC.Br
InChI: InChI=1S/C8H13NO2.BrH/c1-9-5-3-4-7(6-9)8(10)11-2;/h4H,3,5-6H2,1-2H3;1H
InChIKey: AXOJRQLKMVSHHZ-UHFFFAOYSA-N
EINECS: 206-087-3
Product Categories: Heterocyclic Compounds; Pyridine Alkaloids; Alkaloids; Biochemistry;Esters; Pyridines
Toxicity Data With Reference
| frog | LD50 | parenteral | 160mg/kg (160mg/kg) | Acta Biologica et Medica Germanica. Vol. 28, Pg. 681, 1972. | |
| mouse | LD50 | intravenous | 18mg/kg (18mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#11778, | |
| mouse | LD50 | oral | 600mg/kg (600mg/kg) | United States Patent Document. Vol. #4921868, | |
| mouse | LDLo | subcutaneous | 65mg/kg (65mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 35, Pg. 75, 1929. | |
| rat | LD50 | parenteral | 270mg/kg (270mg/kg) | Acta Biologica et Medica Germanica. Vol. 28, Pg. 681, 1972. |
Safety Profile
Hazard Codes: 
Xn, 
T
Risk Statements: 22-23/24/25
R22:Harmful if swallowed.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 45-38-36/37/39-28A
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S38:In case of insufficient ventilation, wear suitable respiratory equipment.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S28:After contact with skin, wash immediately with plenty of soap-suds.
WGK Germany: 3
RTECS: QT2275000
F: 8
HS Code: 29399990
Poison by parenteral, subcutaneous, and intravenous routes. When heated to decomposition it emits very toxic fumes of HBr and NOx.
Specification
Arecoline hydrobromide (CAS NO.300-08-3) is also named as Arecoline bromide ; Arekolinhydrobromid ; Arekolinhydrobromid [German] ; Methyl 1,2,5,6-tetrahydro-1-methylnicotinate, hydrobromide ; Methyl N-methyl-1,2,5,6-tetrahydronicotinate hydrobromide ; N-Methyltetrahydronicotinic acid methyl ester hydrobromide ; NSC 31750 ; Taeniolin ; UNII-24S79B9CX7 . It is white fine powder. Arecoline hydrobromide (CAS NO.300-08-3) is highly toxic. It is flammable. It will produce toxic nitrogen oxide and hydrogen bromide fumes when buring. So the storage environment should be ventilate, low-temperature and dry. Keep Arecoline hydrobromide (CAS NO.300-08-3) separate from raw materials of food.