Synthesis of deuterium labeled phenethylamine derivatives

Synthesis of deuterium‐labelled standards of (±)‐DOM and (±)‐MMDA

“…Many researchers are interested in the preparation of deuterium-labelled control drugs as internal standards for GC-MS analysis. [4][5][6] This work describes synthetic routes to DOM-d 6 and MMDA-d 3 , and presents relevant characteristic analytical data. The compounds investigated in this study have not been examined before.…”

Determination of dimethoxyphenethylamine derivatives in urine by deuterium labeled internal standards

“…[29][30][31][32][33][34][35][36][37][38][39] The synthetic routes to 2C-C-d 6 , 2C-B-d 6 , 2C-I-d 6 , 2C-T-2-d 6 and 2C-T-7-d 6 have been described elsewhere. 31 The present investigation explores the applications of 2C-C-d 6 , 2C-B-d 6 , 2C-I-d 6 , 2C-T-2-d 6 and 2C-T-7-d 6 as internal standards.…”

Synthesis of deuterium‐labeled zaleplon‐d5 as an internal standard

“…The use of deuterium-labeled controlled drugs as internal standards for use in GC-MS analysis is well documented. [5][6][7][8][9] This work describes a synthesis of zaleplon-d 5 , which can serve as an internal standard for the identification of zaleplon by GC-MS analysis.…”

“…31 In the following step, compounds 4 and 2 underwent cyclization under mild acidic condition at reflux to yield 7-(3-nitro-phenyl)-pyrazolo[1,5-a]-pyrimidine-3-carbonitrile (5). 29 An efficient reduction of 5 using 10% Pd/C catalyst at an H 2 pressure of 60 psi gave 7-(3-amino-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carbonitrile (6).…”

“…3 0 -Nitroacetophenone 1 was reduced to 3 0 -aminoacetophenone 9 35 and subsequent acylation yielded the acetamide 10, which in turn was treated with N,N-dimethylformamide dimethylacetal to produce enamide 11. Enamide 11 was alkylated using ethyl iodide-d 5 and sodium hydride as base at room temperature to yield the N-ethylated enamide 12. 34 In the final step, N-ethylenamide 12 was coupled with 5-aminopyrazole 4 in aqueous acid at 501C to produce zaleplon-d 5 8 in 85% yield.…”