Arecoline hydrobromide - analytical standard , CAS No.300-08-3

CAS: 300-08-3 Cat. No.: A107392 Molecular Weight: 236.11 Beilstein Registry Number: 3914826 EC Number: 206-087-3

GRADE & PURITY Analytical standard

Synonyms

Areciline Hydrochloride,(S) | Nicotinic acid,2,5,6-tetrahydro-1-methyl-, methyl ester, hydrobromide | s2614 | SR-01000075307-1 | NCGC00093563-04 | UNII-24S79B9CX7 | BCP02923 | BCP9000314 | Q27253878 | NCGC00093563-03 | NICOTINIC ACID, 1,2,5,6-TETRAHYDRO-1

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

Areciline Hydrochloride, (S) | Nicotinic acid, 2, 5, 6-tetrahydro-1-methyl-, methyl ester, hydrobromide | s2614 | SR-01000075307-1 | NCGC00093563-04 | UNII-24S79B9CX7 | BCP02923 | BCP9000314 | Q27253878 | NCGC00093563-03 | NICOTINIC ACID, 1, 2, 5, 6-TETRAHYDRO-1

Specifications & Purity

analytical standard

Storage

Room temperature

Shipped In

Normal

Grade

Analytical standard

Names and Identifiers

• Canonical Smiles: CN1CCC=C(C1)C(=O)OC.Br
• IUPAC Name: methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate;hydrobromide
• InChIKey: AXOJRQLKMVSHHZ-UHFFFAOYSA-N
• INCHI: 1S/C8H13NO2.BrH/c1-9-5-3-4-7(6-9)8(10)11-2;/h4H,3,5-6H2,1-2H3;1H
• Isomeric SMILES: CN1CCC=C(C1)C(=O)OC.Br
• WGK Germany: 3
• RTECS: QT2275000
• Molecular Weight: 236.11
• Beilstein: 3914826
• Reaxy-Rn: 3914826
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3914826&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Not available
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Alkaloids and derivatives
• Alternative Parents: Hydropyridines Methyl esters Enoate esters Trialkylamines Amino acids and derivatives Monocarboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Hydrobromides Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Alkaloid or derivatives - Hydropyridine - Methyl ester - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Carboxylic acid ester - Amino acid or derivatives - Tertiary amine - Tertiary aliphatic amine - Azacycle - Carboxylic acid derivative - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Amine - Organic nitrogen compound - Hydrobromide - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (0 Activities)

Discover Target: CHRM3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM4 Tclin Muscarinic acetylcholine receptor M4 (0 Activities)

Discover Target: CHRM4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (0 Activities)

Discover Target: CHRM1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EDNRA Tclin Endothelin receptor ET-A (5008 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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BLM Tchem Bloom syndrome protein (4248 Activities)

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MCOLN3 Tchem MCOLN3 protein (319 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GMNN Tbio Geminin (128009 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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BCHE Cholinesterase (8742 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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nompc Ion channel NompC (277 Activities)

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Trpc4 Short transient receptor potential channel 4 (1615 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 171-175°C
• Molecular Weight: 236.110 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 235.021 Da
• Monoisotopic Mass: 235.021 Da
• Topological Polar Surface Area: 29.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 187.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Xiao Run-mei, Wang Jun-jun, Chen Jing-ya, Sun Li-juan, Chen Yong.  (2014)  Effects of arecoline on hepatic cytochrome P450 activity and oxidative stress.  JOURNAL OF TOXICOLOGICAL SCIENCES,  39  (4): (609-614).  [PMID:25056785] [10.2131/jts.39.609]

2. Jin Liu, Li Ma, Senwen Deng, Xinzhi Chen, Qi Li, Aiqing Xu, Ting Tong, Shuhua Tan, Mingkang Wang, Jiangtao Cai, Haihua Wang.  (2024)  Deep Eutectic Solvents for Efficient and Selective Extraction of α-Glucosidase Inhibitors from Waste Seeds of Refined Betel Nuts.  Foods,  13  (7): (1070).  [PMID:38611374] [10.3390/foods13071070]