Arecoline hydrobromide

Modify Date: 2024-01-03 19:34:25

Arecoline hydrobromide Structure
Arecoline hydrobromide structure
Common Name Arecoline hydrobromide
CAS Number 300-08-3 Molecular Weight 236.106
Density N/A Boiling Point 209ºC at 760mmHg
Molecular Formula C8H14BrNO2 Melting Point 171-175 °C
MSDS Chinese USA Flash Point 81.1ºC
Symbol GHS07
GHS07
Signal Word Warning

 Use of Arecoline hydrobromide


Arecoline Hydrobromide is a muscarinic acetylcholine receptor agonist. Target: mAChRArecoline is an alkaloid found in the areca nut. Arecoline. a drug obtained from the Areca Catechu L., induced a dose-dependent antinociception (0.3-1 mg kg(-1) i.p.) which was prevented by the muscarinic antagonists pirenzepine (0.1 microg per mouse i.c.v.) and S-(-)-ET-126 (0.01 microg per mouse i.c.v.) [1]. Arecoline exerts its excitatory actions by binding to M2-muscarinic receptors on the cell membrane of neurons of the locus coeruleus [2]. Arecoline (1 nM - 1 microM) produced a concentration-dependent contraction in both the longitudinal and the circular smooth muscle of rabbit colon. Atropine (10 microM) abolished the arecoline (80 nM)--induced contraction. M3 receptor antagonist, 4 - DAMP (0.4 microM), abolished the arecoline (80 nM)--related response, whereas M2 receptor antagonist, gallamine (0.4 microM), did not affect the effect of arecoline. These results suggest that arecoline excites the colonic motility via M3 receptor in rabbits [3].

 Names

Name methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate,hydrobromide
Synonym More Synonyms

 Arecoline hydrobromide Biological Activity

Description Arecoline Hydrobromide is a muscarinic acetylcholine receptor agonist. Target: mAChRArecoline is an alkaloid found in the areca nut. Arecoline. a drug obtained from the Areca Catechu L., induced a dose-dependent antinociception (0.3-1 mg kg(-1) i.p.) which was prevented by the muscarinic antagonists pirenzepine (0.1 microg per mouse i.c.v.) and S-(-)-ET-126 (0.01 microg per mouse i.c.v.) [1]. Arecoline exerts its excitatory actions by binding to M2-muscarinic receptors on the cell membrane of neurons of the locus coeruleus [2]. Arecoline (1 nM - 1 microM) produced a concentration-dependent contraction in both the longitudinal and the circular smooth muscle of rabbit colon. Atropine (10 microM) abolished the arecoline (80 nM)--induced contraction. M3 receptor antagonist, 4 - DAMP (0.4 microM), abolished the arecoline (80 nM)--related response, whereas M2 receptor antagonist, gallamine (0.4 microM), did not affect the effect of arecoline. These results suggest that arecoline excites the colonic motility via M3 receptor in rabbits [3].
Related Catalog
References

[1]. Ghelardini, C., et al., M1 receptor activation is a requirement for arecoline analgesia. Farmaco, 2001. 56(5-7): p. 383-5.

[2]. Yang, Y.R., et al., Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor. Chin J Physiol, 2000. 43(1): p. 23-8.

[3]. Xie, D.P., et al., Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits. Chin J Physiol, 2004. 47(2): p. 89-94.

 Chemical & Physical Properties

Boiling Point 209ºC at 760mmHg
Melting Point 171-175 °C
Molecular Formula C8H14BrNO2
Molecular Weight 236.106
Flash Point 81.1ºC
Exact Mass 235.020782
PSA 29.54000
LogP 1.31730
Storage condition Refrigerator
Water Solubility H2O: 0.1 g/mL, clear, colorless

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QT2275000
CHEMICAL NAME :
Nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester, hydrobromide
CAS REGISTRY NUMBER :
300-08-3
LAST UPDATED :
199012
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C8-H13-N-O2.Br-H
MOLECULAR WEIGHT :
236.14
WISWESSER LINE NOTATION :
T6N CUTJ A1 CVO1 &EH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
270 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 28,681,1972
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
65 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 35,75,1929
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
18 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#11778
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
160 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 28,681,1972

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful;
Risk Phrases R22
Safety Phrases S45-S38-S36/37/39-S28A
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS QT2275000
HS Code 29399990

 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%

 Articles2

More Articles
Determination and pharmacokinetic studies of arecoline in dog plasma by liquid chromatography-tandem mass spectrometry.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 969 , 12-8, (2014)

A rapid and sensitive high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) method was developed and validated for the determination of arecoline concentration in dog plasma. Plas...

Arecoline is cytotoxic for human endothelial cells.

J. Oral. Pathol. Med. 43(10) , 761-9, (2014)

Oral submucous fibrosis is a pre-malignant fibrotic condition caused by areca nut use and involves reduced mucosal vascularity. Arecoline is the principal areca nut alkaloid and is cytotoxic for epith...

 Synonyms

1-Methyl-1,2,5,6-tetrahydro-pyridin-3-carbonsaeure-methylester,Hydrobromid
MFCD00039041
Methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrobromide (1:1)
EINECS 206-087-3
Arecaidine methyl ester hydrobromide
methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrobromide
3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester, hydrobromide (1:1)
Arecoline
Methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate hydrobromide
ARECOLINE HBr
Methyl 1,2,5,6-Tetrahydro-1-methylnicotinate Hydrobromide
Methyl-1-methyl-1,2,5,6-tetrahydro-3-pyridincarboxylathydrobromid
1-methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester,hydrobromide
arecolinium bromide
Methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate hydrobromide (1:1)
Arecoline hydrobromide
Taeniolin
Arecoline bromide
1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic Acid Methyl Ester Hydrobromide
3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester, hydrobromide (9CI)
1-Méthyl-1,2,5,6-tétrahydro-3-pyridinecarboxylate de méthyle bromhydrate
Arecoline (hydrobromide)
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