Direct chromatographic resolution and isolation of the four stereoisomers of meta-hydroxyphenylpropanolamine

Chirality

Volumn 11, Issue 9, 1999, Pages 684-688

  Van Dort, Marcian E ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

Cardiac imaging; Chiral resolution; Metaraminol; Positron emission tomography; Preparative chromatography; Sympathomimetic amines

Indexed keywords

FUMARIC ACID DERIVATIVE; METARAMINOL; PROPANOLAMINE DERIVATIVE; TARTARIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; CHROMATOGRAPHY; CRYSTALLIZATION; DRUG ISOLATION; DRUG STRUCTURE; ENANTIOMER; OPTICAL RESOLUTION; PRIORITY JOURNAL; SPECTRAL SENSITIVITY; STEREOISOMERISM;

CHROMATOGRAPHY, ION EXCHANGE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; PROPANOLAMINES; STEREOISOMERISM;

EID: 0032729013     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:9<684::AID-CHIR3>3.0.CO;2-4     Document Type: Article

References (19)

1. 18F]fluorodopamine for positron emission tomography studies of sympathetic nervous tissue. J Med Chem 1991;34:861-863.
2. 18F]fluoronorepinephrine via the nucleophilic aromatic substitution reaction. J Med Chem 1991;34:767-771.
3. 18F]fluorodopamine: initial findings in humans. J Am Coll Cardiol 1993;22:1961-1971.
4. 11C]Metaraminol, a false neurotransmitter preparation, metabolite studies and positron emission tomography examination in monkey. Nucl Med Biol 1996;23:221-227.
5. 11C]epinephrine for routine PET studies in humans. Nucl Med Biol 1993;20:939-944.
6. Crout JR, Alpers HS, Tatum EL, Shore PA. Release of metaraminol (Aramine) from the heart by sympathetic nerve stimulation. Science 1964;145:828-829.
7. Giachetti A, Shore PA. Intracellular distribution of metaraminol and related compounds in rat heart. Life Sci 1965;4:1455-1460.
8. Rosenspire KC, Haka MS, Van Dort ME, Jewett DM, Gildersleeve DL, Schwaiger M, Wieland DM. Synthesis and preliminary evaluation of carbon-11-meta-hydroxyephedrine: a false transmitter agent for heart neuronal imaging. J Nucl Med 1990;31:1328-1334.
9. Allman KC, Stevens MJ, Wieland DM, Hutchins GD, Wolfe ER, Greene DA, Schwaiger M. Noninvasive assessment of cardiac diabetic neuropathy by carbon-11 hydroxyephedrine and positron emission tomography. J Am Coll Cardiol 1993;22:1425-1432.
10. Allman KC, Wieland DM, Muzik O, DeGrado TR, Wolfe ER, Schwaiger M. Carbon-11 hydroxyephedrine with positron emission tomography for serial assessment of cardiac adrenergic neuronal function after acute myocardial infarction in humans. J Am Coll Cardiol 1993;22:368-375.
11. Schwaiger M, Hutchins GD, Kalff V, Rosenspire K, Haka MS, Mallette S, Deeb GM, Abrams GD, Wieland DM. Evidence for regional catecholamine uptake and storage sites in the transplanted human heart by positron emission tomography. J Clin Invest 1991;87:1681-1690.
12. Di Carli MF, Tobes MC, Mangner T, Levine AB, Muzik O, Chakraborty P, Levine TB. Effects of cardiac sympathetic innervation on coronary blood flow. N Engl J Med 1997;336:1208-1215.
13. Saari WS, Raab AW, Engelhardt EL. The stereoisomers of α-(1-aminoethyl)-m-hydroxybenzyl alcohol. J Med Chem 1968;11:1115-1117.
14. Snyder LR, Kirkland JJ. Introduction to modern liquid chromatography. New York: John Wiley & Sons; 1979. p 22-37.
15. Bockmuhl M, Ehrhart G, Stein L Process of preparing compounds of the 1-phenyl-2-aminoalcohols-1 series hydroxylated in the phenyl nucleus. U.S. Patent 1,948,162 (1934): Chem Abstr 1934;28:2849.
16. I. G. Farbenindustrie Aktiengesellschaft. Manufacture of 1-phenyl-2-amino-alcohols-1 containing hydroxyl in the phenyl residue. Br. Patent 368,613 (1932); Chem Abstr 1933;27:2158.
17. I. G. Farbenindustrie Aktiengesellschaft. Manufacture of optically active 1-monohydroxy-phenyl-2-aminopropanols (1). Br. Patent 396,951 (1933); Chem Abstr 1934;28:482.
18. Albertson NF, McKay FC, Lape HE, Hoppe JO, Selberis WH, Arnold A The optical isomers of metaraminol, synthesis and biological activity. J Med Chem 1970;13:132-134.
19. Shinbo T, Yamagushi T, Nishimura K, Sugiura M. Chromatographic separation of racemic amino acids by use of chiral crown ether-coated reversed-phase packings. J Chromatogr 1987;405:145-153.