10. Abrine
Nomenclature
CAS number: 526-31-8
N-Methyl-l-tryptophan; (S)-3-(1H-indol-3-yl)-2-methylaminopropionic
acid. C12H14N2O2; mol wt 218.25.
C 66.04%, H 6.47%, N 12.84%, O 14.66%.
Description and references
Not to be confused with the albuminous substance abrin, q.v. Obtained from the seeds of Abrus precatorius L., Leguminosae (jequirity): Hoshino, Ann. 520, 31 (1935) DOI. Synthesis: Miller, Robson, J. Chem. Soc. 1938, 1910 DOI. Configuration: Cahill, Jackson, J. Biol. Chem. 126, 29 (1938).
Properties
Prisms from water, dec 295°. [α]D21 +44° (0.28 g in 10 ml 0.5N HCl). One gram dissolves in about 100 ml methanol, slightly sol in water, insol in ether. Sol in dil acids, alkalies.Derivative
Hydrochloride.C12H14N2O2.HCl; mol wt 254.71.
C 56.59%, H 5.94%, N 11.00%, O 12.56%, Cl 13.92%.
Properties
Needles, mp 222°, soluble in water.Derivative
Nitrate.C12H14N2O2.HNO3; mol wt 281.26.
C 51.24%, H 5.38%, N 14.94%, O 28.44%.
Properties
Needles, dec 143°.Derivative
Acetyl derivative.C14H16N2O3; mol wt 260.29.
C 64.60%, H 6.20%, N 10.76%, O 18.44%.