Stereochemical characteristics of dopamine agonists: molecular structure of bromocriptine and structural comparisons with apomorphine
Camerman, N.; Chan, L.Y.; Camerman, A.
Molecular Pharmacology 16(3): 729-736
1979
ISSN/ISBN: 0026-895X PMID: 530256 Document Number: 146782
Crystals of bromocriptine methanesulfonate.cntdot.0.5 isopropanol are monoclinic with cell dimensions a = 13.991, b = 8.296, c = 17.596 .ANG., .beta. = 97.09.degree., space group P21 with 2 formula units per cell. The structure was determined by direct phasing and Fourier methods and refined to a residual of R = 0.08. The molecule of bromocriptine consists of 2 different similarly-oriented substituted-polycyclic systems connected by an amide linkage whose plane is roughly perpendicular to them. The absolute configuration has been verified crystallographically. The dopamine-like portion of the molecule has been compared conformationally with the active and inactive forms of apomorphine; conclusions regarding the stereochemistry of the agonist-receptor interaction have been drawn.