Arecoline hydrobromide supplier

Name
Arecoline hydrobromide
EINECS 206-087-3
CAS No. 300-08-3
Article Data1
CAS DataBase
Density
Solubility 0.1 g/mL in water
Melting Point 171-175 °C
Formula C₈H₁₄BrNO₂
Boiling Point 209 °C at 760 mmHg
Molecular Weight 236.109
Flash Point 81.1 °C
Transport Information
Appearance white fine powder
Safety 45-38-36/37/39-28A
Risk Codes 22-23/24/25
Molecular Structure
Hazard Symbols Xn, T
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;
PSA 29.54000
LogP 1.31730

Synthetic route

: 300-08-3
arecoline hydrobromide

: 63-75-2
arecoline

Conditions

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;

: 300-08-3
arecoline hydrobromide

: 74-88-4
methyl iodide

: 4554-30-7
N-Methylarecolinium iodide

Conditions

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

Conditions	Yield
Multistep reaction;	90%

: 300-08-3
arecoline hydrobromide

: 499-04-7
1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid

Conditions

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

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%

: 100-39-0
benzyl bromide

: 300-08-3
arecoline hydrobromide

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

Conditions

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

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;

: 300-08-3
arecoline hydrobromide

: 106-94-5
propyl bromide

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

Conditions

Conditions	Yield
In nitromethane	47%

: 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

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

Conditions	Yield
With 4 A molecular sieve; sodium In ethanol 1.) 20 deg C, 0.5 h, 2.) reflux, 0.5 h;	17%

: 579-43-1
(1S,2R)-1,2-diphenylethane-1,2-diol

: 300-08-3
arecoline hydrobromide

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

Conditions

Conditions	Yield
Stage #1: arecoline hydrobromide With sodium carbonate In water Stage #2: (1S,2R)-1,2-diphenylethane-1,2-diol With potassium tert-butylate In toluene for 16h; Reflux; Molecular sieve; stereoselective reaction;	16%

: 75-44-5
phosgene

: 300-08-3
arecoline hydrobromide

: 121661-86-7
(N-chlorocarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester)

Conditions

Conditions	Yield
In toluene

: 42956-75-2
N'-hydroxypivalimidamide

: 300-08-3
arecoline hydrobromide

: 131865-05-9
5-(3-tert-Butyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 77072-12-9
3-methoxypropionamide oxime

: 300-08-3
arecoline hydrobromide

: 123686-54-4
5-[3-(2-Methoxy-ethyl)-[1,2,4]oxadiazol-5-yl]-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 108724-16-9
hexanamide oxime

: 300-08-3
arecoline hydrobromide

: 114905-01-0
1-Methyl-5-(3-pentyl-[1,2,4]oxadiazol-5-yl)-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 67015-06-9
N'-hydroxypentanimidamide

: 300-08-3
arecoline hydrobromide

: 114904-63-1
1-methyl-3-(3-butyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydropyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 35613-84-4
isobutyramide oxime

: 300-08-3
arecoline hydrobromide

: 114904-61-9
5-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 51285-13-3
cyclopropanecarboxamide oxime

: 300-08-3
arecoline hydrobromide

: 114904-31-3
5-(3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 95298-88-7
N'-hydroxy-2-methoxyethanimidamide

: 114904-32-4
5-(3-Methoxymethyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 3-Ethoxy-N'-hydroxypropanimid amide

: 123686-56-6
5-[3-(2-Ethoxy-ethyl)-[1,2,4]oxadiazol-5-yl]-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 152821-00-6
2-cyclopropyl-N'-hydroxyethanimidamide

: 131865-07-1
5-(3-Cyclopropylmethyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 114878-45-4
octanamide oxime

: 114905-03-2
5-(3-Heptyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 103499-15-6
n-nonanamidoxime

: 114904-99-3
1-Methyl-5-(3-octyl-[1,2,4]oxadiazol-5-yl)-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 99623-08-2
N-hydroxycyclobutanecarboxamidine

: 123686-50-0
5-(3-Cyclobutyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 99623-12-8
N-hydroxycyclopentanecarboxamidine

: 123686-52-2
5-(3-Cyclopentyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: N-hydroxy-cycloheptanecarboximidamide

: 131865-06-0
5-(3-Cycloheptyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 118493-85-9, 117771-39-8, 1141922-26-0
acetamide oxime

: 114724-56-0
3-methyl-5-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2,4-oxadiazole

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 29335-36-2
N-hydroxypropanimidamide

: 114904-48-2
5-(3-Ethyl-[1,2,4]oxadiazol-5-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

: 300-08-3
arecoline hydrobromide

: 27620-10-6
butyramide oxime

: 114904-46-0
1-Methyl-5-(3-propyl-[1,2,4]oxadiazol-5-yl)-1,2,3,6-tetrahydro-pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve; sodium 1.) ethanol, RT, 10 min, 2.) ethanol, 80 deg C, 12 h; Multistep reaction;

Arecoline hydrobromide Chemical Properties

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

Arecoline hydrobromide 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.

Arecoline hydrobromide Safety Profile

Hazard Codes: Harmful Xn, Toxic 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 NO_x.

Arecoline hydrobromide 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.

Product Name

Arecoline hydrobromide

Synthetic route

Arecoline hydrobromide Chemical Properties

Arecoline hydrobromide Toxicity Data With Reference

Arecoline hydrobromide Safety Profile

Arecoline hydrobromide Specification

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