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

• ChemBase ID: 85808
• Molecular Formular: C8H14BrNO2
• Molecular Mass: 236.10626
• Monoisotopic Mass: 235.02079069
• SMILES: N1(CC(=CCC1)C(=O)OC)C.Br
• Canonical SMILES: COC(=O)C1=CCCN(C1)C.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

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrobromide
• IUPAC Traditional name: arecoline hydrobromide
• Synonyms: 1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic Acid Methyl Ester Hydrobromide; 1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic Acid Methyl Ester Hydrobromide; Arecolin Hydrobromide; Methylarecaidine Hydrobromide; Arecoline hydrobromide; Methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrobromide; ARECOLINE HYDROBROMIDE; 1-Methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester hydrobromide; Arecaidine methyl ester hydrobromide; Methyl 1,2,5,6-tetrahydro-1-methyl-3-pyridinecarboxylate hydrobromide; Methyl 1-methyl-1,2,5,6-tetrahydronicotinate hydrobromide; Arecoline hydrobromide; Arecoline; 1,2,5,6-四氢-1-甲基-3-吡啶羧酸甲酯 氢溴酸盐; 1-甲基-1,2,5,6-四氢-3-吡啶羧酸甲酯 氢溴酸盐; 1-甲基-1,2,5,6-四氢烟酸甲酯 氢溴酸盐; 槟榔碇甲酯 氢溴酸盐; 槟榔碱 氢溴酸盐

Database IDs

• CAS Number: 300-08-3
• EC Number: 206-087-3
• MDL Number: MFCD00039041
• Beilstein Number: 3914826
• PubChem SID: 162072924; 24846938; 24869721
• PubChem CID: 9301

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.0103986
• LogD (pH = 7.4): -0.23643036
• Log P: 0.64880264
• Molar Refractivity: 43.861 cm^3
• Polarizability: 16.78932 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; H2O: soluble0.1 g/mL, clear, colorless; Methanol
• Apperance: Beigh Solid
• Melting Point: 162-163°C; 170-175 °C; 171-176°C; 172-176 °C(lit.)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Toxic/Light Sensitive/Store under Argon
• RTECS: QT2275000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H301; H302
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: AChR

Product Information

• Purity: ≥99.0% (NT)
• Grade: VETRANAL™, analytical standard
• Salt Data: HBr
• Empirical Formula (Hill Notation): C8H13NO2 · HBr

DETAILS

MP Biomedicals - 05207965

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 10980

Other Notes
Alkaloid from seeds of betel nut palm. Effect on human learning1

Sigma Aldrich - 31593

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A767500

A cholinergic alkaloid from seeds of the betel nut palm Areca catechu. Anthelmintic (Cestodes); cathartic.

REFERENCES

• Sitaram, N., et al.: Science, 201, 274 (1978)
• Soncrant, T.T., et al.: Psychopharmacology, 112, 421 (1978)