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300-08-3

Basic Information
CAS No.: 300-08-3
Name: Arecoline hydrobromide
Article Data: 1
Cas Database
Molecular Structure:
Molecular Structure of 300-08-3 (Arecoline hydrobromide)
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: HarmfulXn, ToxicT
Risk Codes: 22-23/24/25
Safety: 45-38-36/37/39-28A
PSA: 29.54000
LogP: 1.31730
Synthetic route
300-08-3

arecoline hydrobromide

63-75-2

arecoline

Conditions
ConditionsYield
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;
300-08-3

arecoline hydrobromide

74-88-4

methyl iodide

4554-30-7

N-Methylarecolinium iodide

Conditions
ConditionsYield
In diethyl ether96%
300-08-3

arecoline hydrobromide

98-09-9

benzenesulfonyl chloride

929803-75-8

methyl 1-benzenesulfonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions
ConditionsYield
Multistep reaction;90%
300-08-3

arecoline hydrobromide

499-04-7

1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid

Conditions
ConditionsYield
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
ConditionsYield
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%
100-39-0

benzyl bromide

300-08-3

arecoline hydrobromide

1-Benzyl-5-methoxycarbonyl-1-methyl-1,2,3,6-tetrahydro-pyridinium; bromide

Conditions
ConditionsYield
In nitromethane77%
300-08-3

arecoline hydrobromide

1885-14-9

phenyl chloroformate

323201-17-8

3-methoxycarbonyl-1-phenoxycarbonyl-1,2,5,6-tetrahydropyridine

Conditions
ConditionsYield
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;
300-08-3

arecoline hydrobromide

106-94-5

propyl bromide

5-Methoxycarbonyl-1-methyl-1-propyl-1,2,3,6-tetrahydro-pyridinium; bromide

Conditions
ConditionsYield
In nitromethane47%
2325-10-2

(S,S)-hydrobenzoin

300-08-3

arecoline hydrobromide

(1S,2S)-(-)-2-hydroxy-1,2-diphenylethyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions
ConditionsYield
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
ConditionsYield
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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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: HarmfulXn, ToxicT
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.