Arecaidine

Names

[ CAS No. ]:
499-04-7

[ Name ]:
Arecaidine

[Synonym ]:
1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid
1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid
Arecaidine
1-Methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylic acid
3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-

Biological Activity

[Description]:

Arecaidine, a pyridine alkaloid, is a potent GABA uptake inhibitor. Arecaidine is a substrate of H+-coupled amino acid transporter 1 (PAT1, SLC36A1) and competitively inhibits L-proline uptake[1][2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[References]

[1]. D Lodge, et al. Effects of the Areca nut constituents arecaidine and guvacine on the action of GABA in the cat central nervous system. Brain Res. 1977 Nov 18;136(3):513-22.

[2]. Valerie Voigt, et al. Transport of the areca nut alkaloid arecaidine by the human proton-coupled amino acid transporter 1 (hPAT1). J Pharm Pharmacol. 2013 Apr;65(4):582-90.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
266.7±35.0 °C at 760 mmHg

[ Melting Point ]:
232ºC (dec.)

[ Molecular Formula ]:
C₇H₁₁NO₂

[ Molecular Weight ]:
141.168

[ Flash Point ]:
115.1±25.9 °C

[ Exact Mass ]:
141.078979

[ PSA ]:
40.54000

[ LogP ]:
0.77

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.524

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QT2070800

CHEMICAL NAME :: Nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-

CAS REGISTRY NUMBER :: 499-04-7

BEILSTEIN REFERENCE NO. :: 0112366

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C7-H11-N-O2

MOLECULAR WEIGHT :: 141.19

WISWESSER LINE NOTATION :: T6N CUTJ A1 CVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Sister chromatid exchange

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 10 mg/L

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 5,501,1984

Safety Information

[ HS Code ]:
2933399090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%