(1R,2S,5S,6S,9R,12S,13R,16S)-N,N,6,7,13-pentamethyl-7-azapentacyclo[10.8.0.02,9.05,9.013,18]icos-18-en-16-amine

• ChemBase ID: 153271
• Molecular Formular: C24H40N2
• Molecular Mass: 356.5878
• Monoisotopic Mass: 356.31914929
• SMILES: C[C@H]1[C@H]2CC[C@@H]3[C@@]2(CC[C@H]2[C@H]3CC=C3[C@@]2(CC[C@@H](C3)N(C)C)C)CN1C
• Canonical SMILES: CN([C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]24[C@H]3CC[C@@H]4[C@@H](N(C2)C)C)C1)C)C
• InChI: InChI=1S/C24H40N2/c1-16-20-8-9-22-19-7-6-17-14-18(25(3)4)10-12-23(17,2)21(19)11-13-24(20,22)15-26(16)5/h6,16,18-22H,7-15H2,1-5H3/t16-,18-,19+,20+,21-,22-,23-,24-/m0/s1
• InChIKey: GPLGAQQQNWMVMM-MYAJQUOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5S,6S,9R,12S,13R,16S)-N,N,6,7,13-pentamethyl-7-azapentacyclo[10.8.0.0^2,^9.0^5,^9.0^1^3,^1^8]icos-18-en-16-amine
• IUPAC Traditional name: conessine
• Synonyms: (3β)-N,N-dimethyl-con-5-enin-3-amine; Conessin; NSC 119994; Neriine; Roquessine; Wrightine; Conessine

Database IDs

• CAS Number: 546-06-5
• EC Number: 208-897-2
• MDL Number: MFCD00016752
• PubChem SID: 162247410
• PubChem CID: 441082

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.9220407
• LogD (pH = 7.4): -1.4459958
• Log P: 4.0291567
• Molar Refractivity: 111.7518 cm^3
• Polarizability: 44.160336 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: ≥2 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C24H40N2

DETAILS

Sigma Aldrich - SML0095

Biochem/physiol Actions
Conessine is a plant steroid alkaloid that acts as a potent and specific antagonist of histamine H3 receptors (Ki = 5.37 and 24.5 nM for human and rat receptors, respectively). Conessine is 1860-fold selective for H3 over H4 and does not bind to H1 or H2 receptors. The molecule also binds to the human α2C4 adrenergic receptor (pKi = 7.98).