Ecgonine
Title: Ecgonine
CAS Registry Number: 481-37-8
CAS Name: [1R-(exo,exo)]-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Additional Names: 3b-hydroxy-1aH,5aH-tropane-2b-carboxylic acid
Molecular Formula: C9H15NO3
Molecular Weight: 185.22
Percent Composition: C 58.36%, H 8.16%, N 7.56%, O 25.91%
Literature References: The principal part of the cocaine molecule; naturally occurring as the l-form. Obtained by hydrolysis of cocaine: Willstätter et al., Ann. 434, 111 (1923); Bell, Archer, J. Am. Chem. Soc. 82, 4642 (1960). From coca leaves: de Jong, Rec. Trav. Chim. 59, 687 (1940). Structure: Gadamer, John, Arch. Pharm. 259, 227 (1921). Stereochemistry: Fodor, Nature 170, 278 (1952); Fodor, Kovács, J. Chem. Soc. 1953, 724. Synthesis: Willstätter, Bommer, Ann. 422, 15 (1920). Review: Stoll, Jucker, Angew. Chem. 66, 376 (1954).
 
Derivative Type: l-Form monohydrate
CAS Registry Number: 5796-30-5
Properties: Triboluminescent, monoclinic prisms from alc, mp 198° (anhydr, dec 205°). [a]D15 -45° (c = 5). Neutral to litmus. pKa 11.11; pKb 11.22. One gram dissolves in 5 ml water, 67 ml alc, 20 ml methanol, 75 ml ethyl acetate. Sparingly sol in acetone, ether, benzene, chloroform, petr ether.
Melting point: mp 198° (anhydr, dec 205°)
pKa: pKa 11.11; pKb 11.22
Optical Rotation: [a]D15 -45° (c = 5)
 
Derivative Type: Hydrochloride
CAS Registry Number: 5796-31-6
Molecular Formula: C9H15NO3.HCl
Molecular Weight: 221.68
Percent Composition: C 48.76%, H 7.27%, N 6.32%, O 21.65%, Cl 15.99%
Properties: Triclinic plates from water, mp 246°. [a]D15 -59° (c = 10). Sol in water; slightly in alc.
Melting point: mp 246°
Optical Rotation: [a]D15 -59° (c = 10)
 
Derivative Type: dl-Form trihydrate
Properties: Plates from 90% alcohol, mp 93-118° (anhydr dec 212°).
Melting point: mp 93-118° (anhydr dec 212°)
 
NOTE: This is a controlled substance: 21 CFR, 1308.12.
Therap-Cat: Anesthetic (topical).
Keywords: Anesthetic (Local).

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