CAS 300-08-3|Arecoline hydrobromide

Introduction：Basic information about CAS 300-08-3|Arecoline hydrobromide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Arecoline hydrobromide BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles2
8. Synonyms

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

Names

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

Arecoline hydrobromide BiologicalActivity

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	Signaling Pathways >>GPCR/G Protein >>mAChRSignaling Pathways >>Neuronal Signaling >>mAChRResearch Areas >>Neurological Disease
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.

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

Signaling Pathways >>GPCR/G Protein >>mAChRSignaling Pathways >>Neuronal Signaling >>mAChRResearch Areas >>Neurological Disease

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
InChIKey	AXOJRQLKMVSHHZ-UHFFFAOYSA-N
SMILES	Br.COC(=O)C1=CCCN(C)C1
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
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

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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