Deramciclane

Title: Deramciclane
CAS Registry Number: 120444-71-5
CAS Name: N,N-Dimethyl-2-[[(1R,2S,4R)-1,7,7-trimethyl-2-phenylbicyclo[2.2.1]hept-2-yl]oxy]ethanamine
Additional Names: (-)-[1R,2S,4R]-2-(2-dimethylaminoethoxy)-2-phenyl-1,7,7-trimethylbicyclo[2.2.1]heptane
Molecular Formula: C20H31NO
Molecular Weight: 301.47
Percent Composition: C 79.68%, H 10.36%, N 4.65%, O 5.31%
Literature References: Serotonin (5-HT2)-receptor antagonist. Prepn: BE 886579; Z. Budai et al., US 4342762 (1981, 1982 both to Egyt); L. Ladanyi et al., Chirality 11, 689 (1999). LC/MS/MS determn in plasma: A. Tolokán et al., J. Chromatogr. A 896, 279 (2000). Receptor binding profile and pharmacology: I. Gacsalyi et al., Drug Dev. Res. 40, 333 (1997). Clinical pharmacokinetics and tolerability: H. Kanerva et al., Int. J. Clin. Pharmacol. Ther. 37, 589 (1999). Clinical evaluation in generalized anxiety disorder: H. Naukkarinen et al., Eur. Neuropsychopharmcol. 15, 617 (2005). Review: S. Koks, E. Vasar, Curr. Opin. Invest. Drugs 3, 289-294 (2002).
Properties: Colorless oil. Log P (octanol/water): 5.9. Soly in water (25°): 0.0088 g/100 ml.
Log P: Log P (octanol/water): 5.9
Derivative Type: Fumarate
CAS Registry Number: 120444-72-6
Manufacturers' Codes: EGIS-3886
Molecular Formula: C20H31NO.C4H4O4
Molecular Weight: 417.54
Percent Composition: C 69.04%, H 8.45%, N 3.35%, O 19.16%
Properties: Crystals from DMF, mp 210-213°. [a]43620 -88.0° ± 1 (c = 0.4 in DMSO). Log P (octanol/water): 1.41. pKa 9.61.
Melting point: mp 210-213°
pKa: pKa 9.61
Optical Rotation: [a]43620 -88.0° ± 1 (c = 0.4 in DMSO)
Log P: Log P (octanol/water): 1.41
Therap-Cat: Anxiolytic.
Keywords: Anxiolytic; Serotonin Receptor Antagonist.
Dermostatin Derris Root D-Erythrose D-Erythrose 4-Phosphate Desaspidin BB

Deramciclane
Deramciclane.svg
Systematic (IUPAC) name
N,N-dimethyl-2-([(1R,4R,6S)-1,7,7-trimethyl-6-phenyl-6-bicyclo[2.2.1]heptanyl]oxy)ethanamine
Clinical data
Legal status  ?
Identifiers
CAS number 120444-72-6 YesY
ATC code None
PubChem CID 119590
ChemSpider 23498865 N
UNII O5KFK61E74 YesY
ChEMBL CHEMBL2104698 N
Synonyms Deramciclane
Chemical data
Formula C20H31NO 
Mol. mass 301.466 g/mol
 N (what is this?)  (verify)

Deramciclane (EGIS-3886) is a drug which acts as an antagonist at the 5-HT2A receptor,[1] as an inverse agonist at the 5-HT2C receptor,[2] and as a GABA reuptake inhibitor.[3]

In 2003 Orion Pharma of Finland and partner Pharmacia discontinued the development of deramciclane for generalized anxiety disorder, owing to a lack of efficacy in the combined results of the Phase III trials of the agent.