(1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

• ChemBase ID: 126840
• Molecular Formular: C11H14N2O
• Molecular Mass: 190.24166
• Monoisotopic Mass: 190.11061308
• SMILES: O=c1cccc2n1C[C@@H]1CNC[C@H]2C1
• Canonical SMILES: O=c1cccc2n1C[C@@H]1CNC[C@H]2C1
• InChI: InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1
• InChIKey: ANJTVLIZGCUXLD-DTWKUNHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S)-7,11-diazatricyclo[7.3.1.0^2,^7]trideca-2,4-dien-6-one
• IUPAC Traditional name: cytisine
• Synonyms: Cytisine; Baptitoxine; Sophorine; Cytisine; (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one; Baptitoxin; Cytisin; Cytiton; Cytitone; Laburnin; Sophorin; Tabex; Tsitafat; Ulexin; Ulexine; (-)-Cytisine; (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one; (1S,9S)-3,11-Diazatricyclo[7.3.1.03,8]trideca-5,7-dien-4-one; Cytisine; (-)-金雀花碱; (1S,9S)-3,11-二氮杂三环[7.3.1.03,8]三癸-5,7-二烯-4-酮; 野靛碱; 金雀花碱

Database IDs

• CAS Number: 485-35-8
• EC Number: 207-616-0
• MDL Number: MFCD00136048
• PubChem SID: 162221167
• PubChem CID: 10235
• CHEMBL: 497939
• Chemspider ID: 9818
• Unique Ingredient Identifier: 53S5U404NU
• Wikipedia Title: Cytisine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -3.4873016
• LogD (pH = 7.4): -2.6434913
• Log P: -0.2798536
• Molar Refractivity: 56.9283 cm^3
• Polarizability: 21.054716 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: Off-White to Tan Solid
• Melting Point: 152-153 °C; 154-155°C; 154-156 °C(lit.)
• Boiling Point: 218 °C at 2 mmHg; 218 °C/2 mmHg(lit.)
• Optical Rotation: [α]/D -108±3°, c = 1% in ethanol; [α]25/D -115°, c = 0.1 in H2O

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: HA4025000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥99%; ≥99.0% (HPLC); 98%
• Empirical Formula (Hill Notation): C11H14N2O

DETAILS

Sigma Aldrich - 712264

Biochem/physiol Actions
Potent agonist at α3β4 and α7 nicotinic acetylcholine receptors and partial agonist at α4β2 nicotinic acetylcholine receptors.
Packaging
100, 500 mg in glass bottle

Sigma Aldrich - 335126

Biochem/physiol Actions
Potent agonist at α3β4 and α7 nicotinic acetylcholine receptors and partial agonist at α4β2 nicotinic acetylcholine receptors.

Toronto Research Chemicals - C998500

Toxic priniciple in seed of Laburnum anagyroides and other Leguminosae. A neuronal nicotinic acetylcholine agonist.

REFERENCES

• Barlow, R.D., et al.: Brit. J. Pharmacol., 35, 161 (1969)
• Jensen, A.A., et al.: J. Med. Chem., 48, 15, 4705(1969)