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Title: A mild, rapid synthesis of freebase [ 11C]nicotine from [ 11C]methyl triflate

Here a rapid, mild radiosynthesis of freebase [ 11C]nicotine was developed by the methylation of freebase nornicotine with [ 11C]methyl triflate in acetone (5 min, 45 ºC). A basic (pH 10.5-11.0) HPLC system reproducibly yielded freebase [ 11C]nicotine as a well-defined single peak. The freebase [ 11C]nicotine was concentrated by solid phase extraction and formulated in 50 μL ethanol (370 MBq/50 μL) without evaporative loss suitable for a cigarette spiking study. A radiochemical yield of 60.4 ± 4.7 % (n = 3), radiochemical purity ≥ 99.9 % and specific activity of 648 GBq/μmol at EOB for 5 min beams were achieved.
Authors:
 [1] ;  [1] ;  [1] ;  [1] ;  [1] ;  [1]
  1. Brookhaven National Lab. (BNL), Upton, NY (United States). Biology Dept.
Publication Date:
Report Number(s):
BNL-112719-2016-JA
Journal ID: ISSN 0969-8043; TRN: US1701687
Grant/Contract Number:
SC00112704; AC02-98CH10886
Type:
Accepted Manuscript
Journal Name:
Applied Radiation and Isotopes
Additional Journal Information:
Journal Volume: 118; Journal Issue: C; Journal ID: ISSN 0969-8043
Publisher:
Elsevier
Research Org:
Brookhaven National Laboratory (BNL), Upton, NY (United States)
Sponsoring Org:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; Freebase [(11)C]nicotine; [(11)C]methyl triflate
OSTI Identifier:
1340399
Alternate Identifier(s):
OSTI ID: 1397558

Xu, Youwen, Kim, Sung Won, Kim, Dohyun, Alexoff, David, Schueller, Michael J., and Fowler, Joanna S.. A mild, rapid synthesis of freebase [11C]nicotine from [11C]methyl triflate. United States: N. p., Web. doi:10.1016/j.apradiso.2016.08.020.
Xu, Youwen, Kim, Sung Won, Kim, Dohyun, Alexoff, David, Schueller, Michael J., & Fowler, Joanna S.. A mild, rapid synthesis of freebase [11C]nicotine from [11C]methyl triflate. United States. doi:10.1016/j.apradiso.2016.08.020.
Xu, Youwen, Kim, Sung Won, Kim, Dohyun, Alexoff, David, Schueller, Michael J., and Fowler, Joanna S.. 2016. "A mild, rapid synthesis of freebase [11C]nicotine from [11C]methyl triflate". United States. doi:10.1016/j.apradiso.2016.08.020. https://www.osti.gov/servlets/purl/1340399.
@article{osti_1340399,
title = {A mild, rapid synthesis of freebase [11C]nicotine from [11C]methyl triflate},
author = {Xu, Youwen and Kim, Sung Won and Kim, Dohyun and Alexoff, David and Schueller, Michael J. and Fowler, Joanna S.},
abstractNote = {Here a rapid, mild radiosynthesis of freebase [11C]nicotine was developed by the methylation of freebase nornicotine with [11C]methyl triflate in acetone (5 min, 45 ºC). A basic (pH 10.5-11.0) HPLC system reproducibly yielded freebase [11C]nicotine as a well-defined single peak. The freebase [11C]nicotine was concentrated by solid phase extraction and formulated in 50 μL ethanol (370 MBq/50 μL) without evaporative loss suitable for a cigarette spiking study. A radiochemical yield of 60.4 ± 4.7 % (n = 3), radiochemical purity ≥ 99.9 % and specific activity of 648 GBq/μmol at EOB for 5 min beams were achieved.},
doi = {10.1016/j.apradiso.2016.08.020},
journal = {Applied Radiation and Isotopes},
number = C,
volume = 118,
place = {United States},
year = {2016},
month = {8}
}