3423. Dopastin

Nomenclature

CAS number: 37134-80-8
(2E)-N-[(2S)-2-(Hydroxynitrosoamino)-3-methylbutyl]-2-butenamide; N-(2-nitrosohydroxylamino-3-methylbutyl)crotonamide.
C9H17N3O3; mol wt 215.25.
C 50.22%, H 7.96%, N 19.52%, O 22.30%.

Description and references

Dopamine β-hydroxylase inhibitor isolated from a culture filtrate of a bacterium of the Pseudomonas genus. Prodn, isoln and characterization: Iinuma et al., Agric. Biol. Chem. 38, 2093 (1974). Structure and synthesis: Iinuma et al., ibid. 2099. Biochemical and biological studies: Iinuma et al., ibid. 2107.

Chemical structure

Properties

Crystals from acetone + n-hexane or from ethyl ether, mp 116-119°. Monobasic acid, pKa 5.1. [α]D21 -246° (c = 0.5 in alcohol). uv max (0.01N HCl): 215 nm (ε 20900).

Derivative

Copper salt.
C9H16N3O3. 1/2 Cu; mol wt 246.01.
C 43.94%, H 6.56%, N 17.08%, O 19.51%, Cu 12.92%.

Properties

Dark blue needles from ethanol, mp 142-144°.