Dopamine: Approaches to its side chain labeling with tritium

Tritium NMR: A compilation of data and a practical guide

“…In continuation of the earlier studies [ 86 ] discussed above, Ahern et al [ 87 ] reported the synthesis of the high specific activity [ 3 H]‐dopamine with tritium incorporated in the side chain. The location of tritium for each particular product was determined by means of tritium NMR.…”

“…Reproduced with minor editing privilege from Vogt et al [83] with the permission of John Wiley and Sons F I G U R E 5 8 Proton decoupled tritium NMR of [2,3,4-3H] γ-hydroxybutyric acid in CD 3 OD. Reproduced with minor editing privilege from Egan et al [85] with the permission of Springer Nature F I G U R E 5 9 Proton decoupled tritium NMR spectra of tritiated derivatives of melatonin (shown in figure) in D 2 O. Reproduced with minor editing privilege from Ahern et al [86] with the permission of Springer Nature Reproduced with minor editing privilege from Ahern et al [87] with the permission of Elsevier S C H E M E 1 Selective tritiation of complex pharmaceuticals containing diverse functional groups. Reproduced from Kopf et al [89] under the CC BY 4.0 International Public License with the permission of the American Chemical Society activity of 28.9 Ci/mmol, which was almost equal to theoretical value.…”

“…Proton decoupled tritium NMR spectra of [ 3 H]‐dopamine in D 2 O, obtained using different precursors (shown in figure). Reproduced with minor editing privilege from Ahern et al [ 87 ] with the permission of Elsevier…”

Tritiation and characterization of several polyamine natural products

“…We then turned to the identification of a suitable precursor which could be tritiated in one step to give [ 3 H] spermine and our search uncovered dinitrile 7 whose straightforward one step synthesis from putrescine was well described by workers preparing [ 13 C] spermine (Ha et al, 1998). We had earlier employed a similar nitrile tritiation strategy to successfully radiolabel other natural products such as dopamine (Ahern et al, 2014) and melatonin (Ahern et al, 2009). It was anticipated that the incorporation of two tritium reducible nitriles on precursor 7 would also facilitate an elevated product specific activity.…”

Tritium-labelled alkaloids: Synthesis and applications

“…Examples of the latter are purine and steroid alkaloids. This discussion will not include the rather simple nitrogen‐containing natural products like dopamine and tyramine whose tritiations have already been described, nor will it address the natural polyamine substances like putrescine, spermine, and spermidine. However, [ 3 H]putrescine is mentioned in the context of a pyrrolizidine alkaloid precursor.…”