Arecaidine supplier | CasNO.499-04-7

Name
ARECAIDINE BUT-2-YNYL ESTER TOSYLATE
EINECS
CAS No. 499-04-7
Article Data18
CAS DataBase
Density 1.166g/cm3
Solubility
Melting Point 232oC (dec.)
Formula C₇H₁₁NO₂
Boiling Point 266.7oC at 760 mmHg
Molecular Weight 141.17
Flash Point 115.1oC
Transport Information
Appearance
Safety Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid;3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-;
PSA 40.54000
LogP 0.27080

Synthetic route

: 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;

: 5657-66-9
3-cyano-1-methyl-1,2,5,6-tetrahydropyridine

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

Conditions

Conditions	Yield
With hydrogenchloride Erwaermen des Rueckstands mit Barytwasser;

: 63-75-2
arecoline

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

Conditions

Conditions	Yield
With hydrogen bromide
With water for 24h; Hydrolysis; Heating;	8.2 g

: 63-75-2
arecoline

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

B: 5809-87-0
1-methyl-1,2,5,6-tetrahydropyridine-3-carboxamide

Conditions

Conditions	Yield
With ammonium hydroxide

: 13221-89-1, 56026-45-0
1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester

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

Conditions

Conditions	Yield
With aluminum nickel; ethanol Hydrogenation.Behandeln des Reaktionsprodukts mit HCl in Essigsaeure;

: 37673-66-8
4-hydroxy-1-methyl-piperidine-3-carboxylic acid ethyl ester

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

Conditions

Conditions	Yield
With hydrogenchloride

: 6138-42-7
3-Carboxy-1-methylpyridiniumiodid

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

Conditions

Conditions	Yield
With potassium borohydride; alkaline aqueous solution

: 535-83-1
Trigonelline

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

Conditions

Conditions	Yield
With sulfuric acid Electrolysis;

1-methyl-4-oxy-piperidine-carboxylic acid-(3)-ethyl ester: 1-methyl-4-oxy-piperidine-carboxylic acid-(3)-ethyl ester

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

Conditions

Conditions	Yield
With hydrogenchloride; potassium iodide
With hydrogen bromide

4t-chloro-1-methyl-piperidine-3r-carboxylic acid methyl ester: 4t-chloro-1-methyl-piperidine-3r-carboxylic acid methyl ester

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

Conditions

Conditions	Yield
With sodium hydroxide

arecoline: arecoline

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

: 50-00-0
formaldehyd

guvacine: guvacine

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

Conditions

Conditions	Yield
With formic acid at 155 - 160℃; im Rohr;

: 562-54-9
potassium methyl sulfate

guvacine: guvacine

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

Conditions

Conditions	Yield
With sodium methylate at 140 - 150℃;

nicotinic acid methyl ester chloromethylate: nicotinic acid methyl ester chloromethylate

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

Conditions

Conditions	Yield
With hydrogenchloride; tin

trigonellin: trigonellin

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

Conditions

Conditions	Yield
With hydrogenchloride; tin

: 535-83-1
Trigonelline

lead-cathodes: lead-cathodes

aqueous H2SO4: aqueous H2SO4

A: 695-36-3
1,5-dimethyl-1,2,3,6-tetrahydro-pyridine

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

C: 695-35-2
1,3-dimethylpiperidine

Conditions

Conditions	Yield
Electrolysis;

...Expand

: 25012-72-0
ethyl 1-methyl-4-oxo-piperidin-3-carboxylate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lead-cathode; aqueous H2SO4 / elektrochemischen Reduktion 2: aqueous HCl View Scheme

: 6315-60-2
3,3'-methylimino-di-propionic acid diethyl ester

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaNH2; xylene 2: lead-cathode; aqueous H2SO4 / elektrochemischen Reduktion 3: aqueous HCl View Scheme

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

: (+)-1-methylpiperidine-3-carboxylic acid

Conditions

Conditions	Yield
With C63H78IrNOP(2+)*C32H12BF24(1-); hydrogen In methanol at 60℃; under 4560.31 Torr; for 12h; Autoclave; enantioselective reaction;	98%

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

: 538-75-0
dicyclohexyl-carbodiimide

: N-cyclohexyl-N-(cyclohexylcarbamoyl)-1-methyl-1,2,5,6-tetrahydropyridine-3-carboxamide

Conditions

Conditions	Yield
With dmap; 1,1-Diphenylmethanol In dichloromethane; N,N-dimethyl-formamide at 0 - 70℃; for 1.5h;	69%

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

: sodium (4-bromophenyl)(4-fluorophenyl)methanolate

: (4-bromophenyl)(4-fluorophenyl)methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 0.5h; Stage #2: sodium (4-bromophenyl)(4-fluorophenyl)methanolate In N,N-dimethyl-formamide at 20℃; for 336h;	25%

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

: benzhydryl 4-methylmorpholine-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 0.5h; Stage #2: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid In N,N-dimethyl-formamide at 20℃; for 18h;	24%

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

: 1204-50-8
benzhydrol sodium salt

: benzhydryl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 0.25h; Stage #2: benzhydrol sodium salt In N,N-dimethyl-formamide at 20℃; for 18h;	19%

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

: 112-35-6
triethylene glucol monomethyl ether

: 2-[2-(2-methoxyethoxy)ethoxy]ethyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide Stage #2: triethylene glucol monomethyl ether In N,N-dimethyl-formamide at 20℃; for 60h;	18%

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

: sodium furan-2-yl(phenyl)methanolate

: furan-2-yl(phenyl)methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 0.333333h; Stage #2: sodium furan-2-yl(phenyl)methanolate In N,N-dimethyl-formamide at 20℃; for 60h;	15%

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

: 28797-48-0
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

: 2-oxo-2-(6-oxo-5,6-dihydro-11H-benzo[e]pyrido[3,2-b][1,4]diazepin-11-yl)ethyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With sodium hydride In N,N-dimethyl-formamide for 0.0166667h; Stage #2: 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one With sodium iodide In N,N-dimethyl-formamide at 70℃; for 1h;	13%

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

: 52340-78-0
(R,R)-hydroxybenzoin

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

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1h; Stage #2: (R,R)-hydroxybenzoin In N,N-dimethyl-formamide at 20℃; for 168h; stereoselective reaction;	13%

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

: 91-00-9
Benzhydrylamine

: N-benzhydryl-1-methyl-1,2,5,6-tetrahydropyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1h; Stage #2: Benzhydrylamine In N,N-dimethyl-formamide at 20℃; for 18h;	12%

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

: sodium 4,4'-difluordiphenylmethanolate

: bis(4-fluorophenyl)methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1h; Stage #2: sodium 4,4'-difluordiphenylmethanolate In N,N-dimethyl-formamide at 20℃; for 60h;	9%

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

: sodium 4,4'-dimethoxydiphenylmethanolate

: bis(4-methoxyphenyl)methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1h; Stage #2: sodium 4,4'-dimethoxydiphenylmethanolate In N,N-dimethyl-formamide at 20℃; for 24h;	4%

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

: sodium bis(6-fluoropyridin-3-yl)methanolate

: bis(6-fluoropyridin-3-yl)methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1h; Stage #2: sodium bis(6-fluoropyridin-3-yl)methanolate In N,N-dimethyl-formamide at 20℃; for 24h;	3%

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

: 119-53-9
2-hydroxy-2-phenylacetophenone

: 2-oxo-1,2-diphenylethyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1h; Stage #2: 2-hydroxy-2-phenylacetophenone In N,N-dimethyl-formamide at 20℃; for 120h;	3%

: 71-23-8
propan-1-ol

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

: 5497-44-9
1-methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid propyl ester

Conditions

Conditions	Yield
With hydrogenchloride

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

: 67-63-0
isopropyl alcohol

: 10558-56-2
1-methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid isopropyl ester

Conditions

Conditions	Yield
With hydrogenchloride

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

: 71-36-3
butan-1-ol

: 5497-45-0
1-methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid butyl ester

Conditions

Conditions	Yield
With hydrogenchloride

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

: 63-75-2
arecoline

Conditions

Conditions	Yield
With hydrogenchloride

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

: 28125-84-0
Homoarecoline

Conditions

Conditions	Yield
With hydrogenchloride

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

: 74024-49-0
N-methyl-1,2,5,6-tetrahydronicotinoyl chloride hydrochloride

Conditions

Conditions	Yield
With thionyl chloride

: 110-91-8
morpholine

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

: 4-(1-methyl-1,2,5,6-tetrahydro-pyridine-3-carbonyl)-morpholine

Conditions

Conditions	Yield
(i) SOCl2, benzene, (ii) /BRN= 102549/; Multistep reaction;

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

: 107-19-7
propargyl alcohol

: 35516-99-5
Arecaidine propargyl ester hydrobromide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Heating; Yield given;

Arecaidine Chemical Properties

IUPAC name: 1-Methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid
Molecular Formula: C₇H₁₁NO₂
Molecular Weight: 141.167740 g/mol
Index of Refraction: 1.524
Surface Tension: 44.7 dyne/cm
Density: 1.166 g/cm³
Flash Point: 115.1 °C
Melting point: 232°C (dec.)
Appearance: Crystalline Solid
Enthalpy of Vaporization: 55.56 kJ/mol
Boiling Point: 266.7 °C at 760 mmHg
Vapour Pressure: 0.00245 mmHg at 25 °C
Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Neurochemicals;Pharmaceuticals;Acetylcholine receptor
Following is the structure of Arecaidine (CAS NO.499-04-7):

Arecaidine Uses

Arecaidine (CAS NO.499-04-7) can be used as a metabolite of Arecoline, a cholinergic agonist.

Arecaidine Toxicity Data With Reference

1.	sce-mus-ipr 1 g/kg/5 D-I	CALEDQ Cancer Letters (Shannon, Ireland). 23 (1984),189.
2.	otr-ham:kdy 2500 µg/L	LANCAO Lancet. 1 (1979),112.
3.	msc-ham:lng 10 mg/L	CRNGDP Carcinogenesis. 5 (1984),501.

Arecaidine Safety Profile

Mutation data reported. When heated to decomposition, Arecaidine (CAS NO.499-04-7) emits toxic fumes of NO_x.

Arecaidine Specification

Arecaidine , its cas register number is 499-04-7. It also can be called 1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid ; Arecaine ; Methylguvacine ; and N-Methylguvacine . And its classification code is Mutation data.

Product Name

ARECAIDINE BUT-2-YNYL ESTER TOSYLATE

Synthetic route

Arecaidine Chemical Properties

Arecaidine Uses

Arecaidine Toxicity Data With Reference

Arecaidine Safety Profile

Arecaidine Specification

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