The synthesis of (R)- and (S)-[N-methyl-11C]β, β- difluoromethamphetamine for the investigation of the binding mechanism of biogenic amines in vivo

Applied Radiation and Isotopes

Volumn 50, Issue 4, 1999, Pages 707-714

  Gillings, N M ^a   Gee, A D ^a   Inoue, O ^b  

^a AARHUS UNIVERSITY HOSPITAL   (Denmark)

^b OSAKA UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BRAIN; CARBON; FLUORINE COMPOUNDS; HALOGENATION; NITROGEN; POSITRON EMISSION TOMOGRAPHY; RADIATION CHEMISTRY; RADIOACTIVITY; RADIOISOTOPES; SYNTHESIS (CHEMICAL);

BROMINATION; DIFLUOROMETHAMPHETAMINE; FLUORINATION; METHYLATION;

DRUG PRODUCTS;

AZIRINE DERIVATIVE; BETA DIFLUOROMETHAMPHETAMINE; CARBON 11; CARBON DIOXIDE; METHYL IODIDE; N METHYL BETA,BETA DIFLUOROMETHAMPHETAMINE; UNCLASSIFIED DRUG;

AMINE TRANSPORT; ARTICLE; BROMINATION; CHIRALITY; ENANTIOMER; NITROGEN BALANCE; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOACTIVITY; RADIOCHEMISTRY; SYNTHESIS;

BINDING SITES; BIOGENIC AMINES; BRAIN; CARBON RADIOISOTOPES; ISOTOPE LABELING; KINETICS; METHAMPHETAMINE; RADIOPHARMACEUTICALS; STEREOISOMERISM;

EID: 0033120375     PISSN: 09698043     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8043(98)00137-7     Document Type: Article

References (25)

1. Albert, A., Serjeant, E.P., 1984. The Determination of Ionization Constants, chapter 2, 3rd ed. Chapman and Hall, New York.
2. Alvernhe G., Lacombe S., Laurent A. Action de l'acide fluorhydrique sur les azirines: synthèse d'α-fluorocétones et de difluoroamines - étude de l'orientation de la réaction. Tetrahedron Lett. 21:1980;1437-1440.
3. Bjurling, P., Reineck, R., Westerberg, G., Schultz, J., Gee, A.D., Sutcliffe, J., Långström, B., 1995. SYNTHIA, a compact radiochemistry system for automated production of radiopharmaceuticals. In: Proceedings of the 6th Workshop on Targetry and Target Chemistry. Vancouver.
4. Cho, A.K., Segal, D.S. (1994) Amphetamine and its Analogs: Psychopharmacology, Toxicology and Abuse. Academic Press, California.
5. 11C -methyl iodide Int. J. Appl. Radiat. Isot. 38:1987;601-603.
6. Fuller R.W., Shaw W.N., Molloy B.B. Dissociation of the lipid mobilizing and hyperthermic effects of amphetamine by beta-fluoro substitution. Arch. Int. Pharmacodyn. 199:1972;266-271.
7. a on the transport and binding of amphetamine analogues in the pig brain. In: Quantification of Brain Function Using PET. Academic Press, California, pp. 42-46.
8. Hassner A., Fowler F.W. A general synthesis of vinyl azides from olefins. Stereochemistry of elimination from β-iodo azides. J. Org. Chem. 33:1968;2686-2691.
9. Hortmann G., Robertson D.A., Gillard B.K. A convenient procedure for the preparation of 2-arylazirines. J. Org. Chem. 37:1972;322-324.
10. Inoue O., Axelsson S., Lundqvist H., Oreland L., Långström B. Effect of reserpine on the brain uptake of carbon-11 methamphetamine and its N-propargyl derivative, deprenyl. Eur. J. Nucl. Med. 17:1990;121-126.
11. 11C ]methionine J. Nucl. Med. 28:1987;1037-1040.
12. Melega W.P., Williams A.E., Schmitz D., Stefano E.D., Cho A.K. Pharmacokinetic/pharmacodynamic analysis of D-amphetamine and D-methamphetamine. Soc. Neurosci. Abstr. 18:1992;363.
13. Mitsuo K., Ichijima S., Ohshiro Y., Agawa T. Catalysis of tertiary amines in the thermolysis of vinyl azides to 1-azirines. J. Org. Chem. 38:1973;4341-4342.
14. Mizugaki M., Hishinuma T., Nakamura H., Yamashita M., Shimomura K., Itoh K., Hirose A., Tomioka Y., Aso H., Edo K., Takahashi T., Ido T. Distribution of carbon-11 labeled methamphetamine and the effect of its chronic administration in mice. Nucl. Med. Biol. 20:1993;487-492.
15. Nair V. The reaction of azirines with diazomethane to produce allylic azides. J. Org. Chem. 33:1968;2121-2123.
16. Robinson T.E., Becker J.B. Enduring changes in brain and behaviour by chronic amphetamine administration: a review and evaluation of animal models of amphetamine. Brain Res. 396:1986;157-198.
17. Rolston J.H., Yates K. Polar additions to the styrene and 2-butene systems. I. Distribution and stereochemistry of bromination products in acetic acid. J. Am. Chem. Soc. 91:1968;1469-1476.
18. Sato S. Azirines. III. The preparation of azirine derivatives by the base-catalyzed rearrangement of quaternary hydrazones. Bull. Chem. Soc. Jpn. 41:1968;1440-1444.
19. Shiue C., Shiue G., Rysavy J., Pleus R., Huang H., Bai L., Cornish K., Sunderland J.J., Frick M.P. Fluorine-18 and carbon-11 labeled amphetamine analogs: synthesis, distribution, binding characteristics in mice and rats and a PET study in monkey. Nucl. Med. Biol. 20:1993;973-981.
20. Stewart J.J. MOPAC: a semiempirical molecular orbital program. J. Comput. Aided Mol. Des. 4:1990;1-105.
21. 3H -labelled sympathomimetic amines for neuronal mapping J. Label. Compd. Radiopharm. 28:1990;831-840.
22. Van Dort M.E., Yong-Woon Y., Sherman P.S., Kilbourn M.R., Wieland D.M. Fluorine for hydroxy substitution in biogenic amines: asymmetric synthesis and biological evaluation of fluorine-18-labelled β-fluorophenylalkylamines as model systems. J. Med. Chem. 38:1995;810-815.
23. Vree T.B., Muskens A.Th.J.M., van Rossum J.M. Some physico-chemical properties of amphetamine and related drugs. J. Pharm. Pharmac. 21:1969;774-775.
24. Wade T.N., Kheribet R. New convenient synthesis of β,β-difluoro amines and β,β-difluoro-α-amino acid alkyl esters by the addition of hydrogen fluoride to 1-azirines. J. Org. Chem. 45:1980;5333-5335.
25. Atkinson and Kelly, 1989. Author please provide details.