Benzoylecgonine

Title: Benzoylecgonine
CAS Registry Number: 519-09-5
CAS Name: 3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Additional Names: 3b-hydroxy-1aH,5aH-tropane-2b-carboxylic acid benzoate; ecgonine benzoate
Molecular Formula: C16H19NO4
Molecular Weight: 289.33
Percent Composition: C 66.42%, H 6.62%, N 4.84%, O 22.12%
Literature 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).
Derivative Type: Tetrahydrate
Properties: Orthorhombic prisms or needles from water, mp 86-92° (dec 195°, dry). [a]D15 -45° (c = 3 in abs alc). Soluble in alc, hot H2O.
Melting point: mp 86-92° (dec 195°, dry)
Optical Rotation: [a]D15 -45° (c = 3 in abs alc)
Benzoylpas Benzphetamine Benzpiperylon Benzpyrinium Bromide Benzquinamide

Benzoylecgonine
Benzoylecgonine-2D-skeletal.png
Benzoylecgonine-3D-balls.png
Identifiers
CAS number 519-09-5 YesY
ChemSpider 395095 YesY
UNII 5353I8I6YS YesY
DrugBank DB01515
KEGG C10847 YesY
ChEBI CHEBI:41001 YesY
Jmol-3D images Image 1
Properties
Molecular formula C16H19NO4
Molar mass 289.33 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Benzoylecgonine is a topical analgesic and the main metabolite of cocaine.