methyl[2-(pyridin-2-yl)ethyl]amine

• ChemBase ID: 4436
• Molecular Formular: C8H12N2
• Molecular Mass: 136.19428
• Monoisotopic Mass: 136.10004839
• SMILES: CNCCc1ccccn1
• Canonical SMILES: CNCCc1ccccn1
• InChI: InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3
• InChIKey: UUQMNUMQCIQDMZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl[2-(pyridin-2-yl)ethyl]amine
• IUPAC Traditional name: betahistine; methyl[2-(pyridin-2-yl)ethyl]amine
• Brand Name: Serc
• Synonyms: Betahistine; N-Methyl-N-[2-(2-pyridyl)ethyl]amine; 2-[2-(Methylamino)ethyl]pyridine; N-methyl-N-[2-(2-pyridyl)ethyl]amine; 2-(2-Methylaminoethyl)pyridine; N-Methyl-2-pyridineethanamine Dihydrochloride; 2-[2-(Methylamino)ethyl]pyridine Dihydrochloride; Betaserc; PT 9; Serc; Sinmenier; Vasomotal; Betahistine Dihydrochloride; N-Methyl-2-(pyridin-2-yl)ethanamine; 2-(2-METHYLAMINOETHYL)PYRIDINE; N-Methyl-2-pyridineethanamine; Betahistine; Beta-Histine; Betahistine; 2-(2-甲基氨基乙基)吡啶

Database IDs

• CAS Number: 5579-84-0; 5638-76-6
• EC Number: 227-086-4
• MDL Number: MFCD00006362
• PubChem SID: 99443252; 160967868; 24896774
• PubChem CID: 2366
• CHEBI ID: 35677
• ATC CODE: N07CA01
• CHEMBL: 24441
• Chemspider ID: 2276
• DrugBank ID: DB06698
• KEGG ID: D07522
• Unique Ingredient Identifier: X32KK4201D
• Wikipedia Title: Betahistine

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -2.5812378
• LogD (pH = 7.4): -1.6845183
• Log P: 0.63240683
• Molar Refractivity: 41.3263 cm^3
• Polarizability: 16.420544 Å^3
• Polar Surface Area: 24.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.59
• LOG S: -0.44
• Solubility (Water): 4.93e+01 g/l

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 152-155°C
• Boiling Point: 113-114 °C/30 mmHg(lit.); 113-114°C/30mm
• Flash Point: 206.6 °F; 97 °C
• Density: 0.984 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.518(lit.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Corrosive
• RTECS: UT5552000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Half Life: 3–4 hours
• Metabolism: To 2-(2-aminoethyl)pyridine and 2-pyridylacetic acid
• Protein Bound: Very low
• Legal Status: Rx-only (US)
• Mechanism of Action: Diamine oxidase inhibitor

Product Information

• Purity: 95+%; 97%
• Application(s): Antihistamine; Has been used to treat the symptoms of Meacuteniegravere's disease; Used in treatment of circulatory diseases
• Empirical Formula (Hill Notation): C8H12N2

DETAILS

MP Biomedicals - 05206493

MP Biomedicals Rare Chemical collection

DrugBank - DB06698

• Drug Groups: approved
• Description: Betahistine is an antivertigo drug first used for treating vertigo assosicated with Ménière's disease. It is also commonly used for patients with balance disorders.
• Indication: For the reduction of episodes of vertigo association with Ménière's disease.
• Pharmacology: Betahistine primarily acts as a histamine H1-agonist with 0.07 times the activity of histamine. Stimulating the H1-receptors in the inner ear causes a vasodilatory effect and increased permeability in the blood vessels which results in reduced endolymphatic pressure. Betahistine is believed to act by reducing the asymmetrical functioning of sensory vestibular organs as well as by increasing vestibulocochlear blood flow. Doing so aids in decreasing symptoms of vertigo and balance disorders.; Betahistine also acts as a histamine H3-receptor antagonist which causes an increased output of histamine from histaminergic nerve endings which can further increase the direct H1-agonist activity. Furthermore, H3-receptor antagonism increases the levels of neurotransmitters such as serotonin in the brainstem, which inhibits the activity of vestibular nuclei, helping to restore proper balance and decrease in vertigo symptoms.
• Toxicity: Symptoms of overdose (< 640 mg) include mild to moderate nausea, dry mouth, dyspepsia, abdominal pain and somnolence. More serious complications such as convulsions, pulmonary or cardiac complications, may occur with higher intentional overdoses (> 640 mg).
• Affected Organisms: Humans and other mammals
• Biotransformation: Betahistine is metabolized primarily into 2-pyridylacetic acid and is subsequently excreted in the urine.
• Absorption: When given orally, betahistine is rapidly absorbed from the gastrointestinal tract.
• Half Life: 3-4 hours
• Protein Binding: Very low.
• Elimination: Renal
• References: [Health Canada]
• External Links: Wikipedia

Sigma Aldrich - M28804

Packaging
5, 25 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M28804.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - B324001

Betahistine is most commonly used to treat the symptoms of Ménière's disease and vertigo. Vasodilator.

REFERENCES

• Health Canada
• Gilligan, P., et al.: J. Med. Chem., 43, 1641 (2000)
• Keller, P., et al.: Bioorg. Med. Chem., 8, 1213 (2000)
• Hauger, R., et al.: Pharmacol. Rev., 55, 21 (2000)
• Han, X., et al.: Bioorg. Med. Chem. Lett., 15, 3870 (2000)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 290A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 764D; 765A, (ir)
• Aldrich Library of FT-IR Spectra: Vapor Phase, 1989, 3, 1535D, (ir)
• Lffler, K., Ber., 1904, 37, 161, (synth)
• Walter, L.A. et al., J.A.C.S., 1941, 63, 2771, (synth)
• Hunt, W.H. et al., J. Pharmacol., 1942, 75, 299, (pharmacol)
• Sternson, L. et al., Drug Metab. Dispos., 1974, 2, 123, (metab)
• Ger. Pat., 1974, 2 359 107; CA, 82, 57570, (synth, use)
• Sakamoto, T. et al., Chem. Pharm. Bull., 1984, 32, 4866, (synth)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1341