5774. Mecamylamine
Nomenclature
CAS number: 60-40-2
N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine; N,2,3,3-tetramethyl-2-norbornanamine; N,2,3,3-tetramethyl-2-norcamphanamine; 3-methylaminoisocamphane; 2-methylaminoisocamphane; 2-methylamino-2,3,3-trimethylnorbornane; N-methyl-2-isocamphanamine; 3β-methylamino-2,2,3-trimethylbicyclo[2.2.1]heptane; mecamine. C11H21N; mol wt 167.29.
C 78.98%, H 12.65%, N 8.37%.
Description and references
Nicotinic receptor antagonist; orally active ganglionic blocker. Prepn: G. A. Stein et al., J. Am. Chem. Soc. 78, 1514 (1956); K. Pfister, III, G. A. Stein, US 2831027 (1958 to Merck & Co.). Structure activity study: C. A. Stone et al., J. Med. Pharm. Chem. 5, 665 (1962). GC-MS determn in plasma: P. Jacob, III et al., J. Pharm. Biomed. Anal. 23, 653 (2000). Receptor binding study of isomers: R. L. Papke et al., J. Pharmacol. Exp. Ther. 297, 646 (2001). Review of pharmacology and clinical experience: J. M. Young et al., Clin. Ther. 23, 532-565 (2001).
Properties
Oily liquid. bp4.0 72°. nD25 1.4881. Slightly sol in water.Derivative
Hydrochloride.Nomenclature
CAS number: 826-39-1
Inversine (Targacept). C11H21N.HCl; mol wt 203.75.
C 64.84%, H 10.88%, N 6.87%, Cl 17.40%.
Properties
Crystals, dec 245.5-246.5°. Bittersweet. Soly (g/100 ml): water 21.2; ethanol 8.2; glycerol 10.4; isopropanol 2.1. pH of 1% aq soln 6.0-7.5.Therapeutic Category
Antihypertensive.
Keywords
Antihypertensive