Ecgonidine

Title: Ecgonidine
CAS Registry Number: 484-93-5
CAS Name: (1R)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid
Additional Names: 2-tropidinecarboxylic acid; anhydroecgonin
Molecular Formula: C9H13NO2
Molecular Weight: 167.21
Percent Composition: C 64.65%, H 7.84%, N 8.38%, O 19.14%
Literature 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).
Derivative Type: dl-Form
Properties: Crystals from alcohol + ether, dec 235-236°. Soluble in water; sparingly sol in alcohol.
Derivative Type: l-Form
Properties: Crystals from abs alcohol, mp 235°. [a]D14 -84.6° (c = 1.7).
Melting point: mp 235°
Optical Rotation: [a]D14 -84.6° (c = 1.7)
Therap-Cat: Anesthetic (topical).
Keywords: Anesthetic (Local).
Ecgonine Echinenone Echinochrome A Echinomycin Echinopsine

Ecgonidine
Ecgonidine.png
Identifiers
CAS number 484-93-5 YesY
PubChem 101709
ChemSpider 16735787 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C9H13NO2
Molar mass 167.205 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

Ecgonidine (anhydroecgonine) is an alkaloid related to ecgonine and cocaine. It has a structure with a cycloheptene ring, with a nitrogen bridge, and a carboxylic acid side chain.

Methylecgonidine is produced by pyrolysis in the process of smoking crack cocaine, and then subsequently metabolised to ecgonidine, and so these two compounds can be tested for as a specific biomarker for crack cocaine use.[1] Ecgonidine is formed as a metabolite of methylecgonidine, and so the relative concentrations of the two compounds can be used to gauge how recently crack cocaine was smoked. If levels of methylecgonidine are higher, then the drug was smoked recently; however after a longer time period mainly ecgonidine will be present.[2] Ecgonidine has a half-life in the body of around 94–137 minutes, and so can be used to detect use of crack cocaine up to 8–10 hours after the drug is consumed.