3492. Ecgonidine

Nomenclature

CAS number: 484-93-5
(1R)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid; 2-tropidinecarboxylic acid; anhydroecgonin.
C9H13NO2; mol wt 167.21.
C 64.65%, H 7.84%, N 8.38%, O 19.14%.

Description and references

Prepn from ecgonine and structure: Findlay, J. Am. Chem. Soc. 75, 1033 (1953). Prepn and formation of l-form: de Jong, Rec. Trav. Chim. 42, 980 (1923), 66, 99 (1947). Synthesis of dl-form: Grundmann, Ottmann, Ann. 605, 24 (1957); US 2783235 (1957 to Olin Mathieson).

Chemical structure

Derivative

dl-Form.

Properties

Crystals from alcohol + ether, dec 235-236°. Soluble in water; sparingly sol in alcohol.

Derivative

l-Form.

Properties

Crystals from abs alcohol, mp 235°. [α]D14 -84.6° (c = 1.7).

Therapeutic Category

Anesthetic (topical).

Keywords

Anesthetic (Local)