Diptamine — A new alkaloid from the epigeal part ofDipthychocarpus strictus

Chemistry of Natural Compounds
1983.0

Abstract

Continuing the preparation of the total alkaloids of the epigeal part of Dipthychocarpus strictus (Fisch.) Trautv. (family Cruciferae) collected in the Chimkent province, column chromatography of the mixture of bases on silica gel (1:25) yielded a crystalline substance with mp 87-89°C, which was a new alkaloid named diptamine. Diptamine is an optically active substance ([α]₂₀ -42° in MeOH), readily soluble in chloroform, methanol, and water and sparingly soluble in benzene, ether, and acetone. Its IR spectrum shows absorption bands at (cm⁻¹) 3320-3370 (active hydrogen), 1630 (amide carbonyl), and 1035 (sulfoxide group). The mass spectrum contains the molecular ion peak at m/z 262 (M⁺) and key fragments including m/z 58 (indicating it is a N-alkyl derivative of isopropylurea). The PHR spectrum (CDCl₃) showed proton signals of groups such as C(CH₃)₂, (CH₂)₅, CH₃S(O), O=S-CH₂-, -CH₂-N-, -CH-N-, and two NH groups. Comparative study with diptocarpamine (differing in molecular ion m/z by 14) revealed diptamine is a homolog with one more methylene group. Thus, based on spectral characteristics and comparative analysis, diptamine has the structure of N-isopropyl-N'-(7-methylsulfinyl-n-heptyl)urea.

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