1446-61-3

clear yellow viscous liquid

Dehydroabiethylamine is a primary amine with high molecular weight; shows a strong antibiotic effect with a broad spectrum of activity against Staphylococcus p.a. (sic), Escherichia coli, Mycobacterium tuberculosis, and Candida albicans.

ChEBI: [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine is a diterpenoid.

CB 1 agonist. Displaces binding of [ 3 H]-SR141716A with an IC 50 value of 2.86 μ M.

The general procedure for the synthesis of dehydroabietic amine from dehydroabietic amine acetate was as follows: crude 60% (+)-dehydroabietic amine (42.0 g) was dissolved in toluene (70.0 cm3) and a toluene (30.0 cm3) solution of acetic acid (9.65 g) was slowly added. The mixture was crystallized in a refrigerator. The product was collected by filtration and washed with hexane (30.0 cm3). The (+)-dehydrofiramine ethanol compound was recrystallized from methanol. (+)-Dehydrofiramine acetate (21.0 g) was dissolved in hot water and 10% NaOH aqueous solution (28.0 cm3) was added. The (+)-dehydrofiramine was extracted with diethyl ether (50.0 cm3) and the organic phase was washed with water to neutrality and subsequently dried over anhydrous sodium sulfate. The solvent was evaporated and the (+)-dehydrofiramine obtained was dried in vacuum to give a white solid; yield 37.0 g, 88.2%; melting point 44.28 °C (literature value 44-45 °C [16]). [α]22D +44.3480 (c, 10.0 mg/cm3, CHCl?).1H NMR (500 MHz, CDCl?) δ 0.89 (s, 3H, CH?), 1.22 (s, 3H, CH?), 1.22 (d, J=7.0 Hz, 6H, 2 × CH?), 1.33 (m, 2H, CH?), 1.39 ( m, 1H, CHH), 1.52 (dd, J=11.8,3.3Hz, 1H, CH), 1.69 (m, 2H, CH?), 1.74 (m, 2H, CH?), 2.30 (dt, J=13.1,1.7Hz, 1H, CHH), 2.40 (d, J=13.5Hz, 1H, CHH), 2.61 (d, J= 13.5 Hz, 1H, CHH), 2.82 (sep, J=7.0 Hz, CH), 2.88 (m, 2H, CH?), 6.89 (d, J=1.9 Hz, 1H, CHAr), 7.00 (dd, J=8.1,1.9 Hz, 1H, CHAr), 7.18 (d, J=8.1 Hz, 1H, CHAr). 13C NMR (500 MHz, CDCl?) δ 18.78 (CH?), 18.90 (CH?), 18.90 (CH?), 24.11 (CH?), 24.13 (CH?), 25.37 (CH?), 30.31 (CH?), 33.58 (CH), 35.36 (CH?), 37.36 (C). 37.53 (C), 38.70 (CH?), 45.00 (CH), 53.99 (CH?), 123.96 (CHAr), 124.38 (CHAr), 126.94 (CHAr), 134.84 (CAr), 145.67 (CAr), 147.63 (CAr).HRMS-ESI m/z 286.2540; C??H??N [M+H]? Calculated value 286.2529.

Store at -20°C

The crude base is purified by converting 2g of base in toluene (3.3mL) into the acetate salt by heating at 65-70o with 0.46g of AcOH, and the crystals are collected and dried (0.96g from two crops, m 141-143o). The acetate salt is dissolved in warm H2O, basified with aqueous NaOH and extracted with *C6H6. The dried extract (MgSO4) is evaporated in vacuum leaving a viscous oil which crystallises and can be distilled. [Gottstein & Cheney J Org Chem 30 2072 1965.] The picrate has m 234-236o (from aqueous MeOH), and the formate has m 147-148o (from heptane). [Beilstein 12 IV 3005.]

[1] Australian Journal of Chemistry, 2017, vol. 70, # 7, p. 845 - 856