3-Bromocytisine - Moligand™,≥98% , CAS No.207390-14-5

CAS: 207390-14-5 Cat. No.: B288330 Molecular Weight: 269.14

GRADE & PURITY Moligand™, ≥98%

Synonyms

(1R,5S)-9-Bromo-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one | (-)-3-Bromocytisine | (1R,5S)-9-Bromo-1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one | UNII-PL64C996QA | BDBM50329578 | SCHEMBL20164035 | 1,5-Metha

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

(1R, 5S)-9-Bromo-1, 2, 3, 4, 5, 6-hexahydro-1, 5-methano-pyrido[1, 2-a][1, 5]diazocin-8-one | (-)-3-Bromocytisine | (1R, 5S)-9-Bromo-1, 2, 3, 4, 5, 6-hexahydro-1, 5-methano-8H-pyrido[1, 2-a][1, 5]diazocin-8-one | UNII-PL64C996QA | BDBM50329578 | SCHEMBL20164035 | 1, 5-Metha

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Potent agonist ofα4β4, α4β2 andα7 nACh receptors (IC50values are 0.28, 0.30 and 31.6 nM respectively). Displays different effects on high (HS) and low (LS) ACh sensitivityα4β2 nAChRs (EC50values are 0.008 and 0.05μM respectively).

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1C2CNCC1C3=CC=C(C(=O)N3C2)Br
• IUPAC Name: (1R,9S)-5-bromo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• InChIKey: DWDCLEHDNICBMI-JGVFFNPUSA-N
• INCHI: 1S/C11H13BrN2O/c12-9-1-2-10-8-3-7(4-13-5-8)6-14(10)11(9)15/h1-2,7-8,13H,3-6H2/t7-,8+/m0/s1
• Isomeric SMILES: C1[C@H]2CNC[C@@H]1C3=CC=C(C(=O)N3C2)Br
• Molecular Weight: 269.14
• Reaxy-Rn: 13603832
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=13603832&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Lupin alkaloids
      • Subclass Cytisine and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Lupin alkaloids
• Subclass: Cytisine and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Cytisine and derivatives
• Alternative Parents: Pyridinones Aralkylamines Piperidines Aryl bromides Heteroaromatic compounds Lactams Dialkylamines Azacyclic compounds Organooxygen compounds Organobromides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cytisine - Pyridinone - Aralkylamine - Aryl bromide - Aryl halide - Piperidine - Pyridine - Heteroaromatic compound - Lactam - Organoheterocyclic compound - Secondary amine - Secondary aliphatic amine - Azacycle - Organic oxygen compound - Amine - Organooxygen compound - Organonitrogen compound - Organobromide - Organohalogen compound - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one.
• 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)

CHRNA3 Tclin Neuronal acetylcholine receptor subunit alpha-3 (1 Activities)

Discover Target: CHRNA3

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

CHRNA7 Tchem Neuronal acetylcholine receptor protein alpha-7 subunit (3524 Activities)

Discover Target: CHRNA7

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

CHRNA3 Tclin Neuronal acetylcholine receptor subunit alpha-3 (93 Activities)

Discover Target: CHRNA3

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

U2OS (164939 Activities)

Explore this target

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

CHRNB2 Tclin Neuronal acetylcholine receptor; alpha4/beta2 (3972 Activities)

Discover Target: CHRNB2

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

CHRNB4 Tclin Neuronal acetylcholine receptor; alpha4/beta4 (276 Activities)

Discover Target: CHRNB4

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

Associated Targets(non-human)

Chrna3 Neuronal acetylcholine receptor; alpha3/beta4 (1368 Activities)

Discover Target: Chrna3

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:water, Max Conc. mg/mL: 26.91, Max Conc. mM: 100; Solvent:DMSO, Max Conc. mg/mL: 26.91, Max Conc. mM: 100
• Sensitivity: Light sensitive
• Molecular Weight: 269.140 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 268.021 Da
• Monoisotopic Mass: 268.021 Da
• Topological Polar Surface Area: 32.299 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 375.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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: 1