1113. Benzoylecgonine

Nomenclature

CAS number: 519-09-5
3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid; 3β-hydroxy-1αH,5αH-tropane-2β-carboxylic acid benzoate; ecgonine benzoate.
C16H19NO4; mol wt 289.33.
C 66.42%, H 6.62%, N 4.84%, O 22.12%.

Description and references

Cocaine metabolite. Isoln from coca leaves: De Jong, Rec. Trav. Chim. 42, 980 (1923). Prepn from l-ecgonine and benzoic anhydride: idem, ibid. 66, 544 (1947).

Chemical structure

Derivative

Tetrahydrate.

Properties

Orthorhombic prisms or needles from water, mp 86-92° (dec 195°, dry). [α]D15 -45° (c = 3 in abs alc). Soluble in alc, hot H2O.