Ecgonidine
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Product Description
Ecgonidine (C₉H₁₃NO₂), also known as anhydroecgonine, is a non-psychoactive tropane alkaloid formed in vivo when the crack-cocaine pyrolysis product methylecgonidine is hydrolyzed by esterases. Because methylecgonidine appears only after smoked cocaine base, its longer-lived metabolite ecgonidine provides a specific and durable forensic signature that distinguishes crack smoking from other routes of cocaine use. The compound’s tropane skeleton—an N-bridged cycloheptene bearing a carboxylic acid side chain—makes it a key intermediate in clandestine cocaine chemistry as well as a reliable analytical marker: sensitive GC-MS methods detect ecgonidine in plasma and urine long after the parent pyrolyzate has cleared (t½ 94–137 min versus 18–21 min for methylecgonidine). Recent pre-clinical work further suggests that ecgonidine’s stability and tumor-avid properties could be exploited for molecular imaging, extending its utility from forensic indicator to potential diagnostic tracer.
Synthesis and Production
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Illicit: alkaline hydrolysis of cocaine base during coca-paste “wash-up” → ecgonidine + benzoic acid
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Lab: acid-catalysed dehydration of ecgonine (ecgonine – H₂O)
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In-vivo: esterase hydrolysis of methylecgonidine (crack-smoke pyrolyzate)
Uses and Applications
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Forensic/toxicology biomarker: 8–10 h detection window after crack use; distinguishes smoking from i.v./i.n. cocaine
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Wastewater-based epidemiology: community cocaine-consumption marker
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Clandestine chemistry: re-esterified to regenerate cocaine base
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Exploratory molecular imaging: tropane scaffold for tumour-targeting tracers
Properties and Characteristics
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Formula: C₉H₁₃NO₂ MW: 167.2 g mol⁻¹ CAS: 484-93-5
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IUPAC: (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid
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White/off-white crystals; freely soluble in hot H₂O, EtOH, acetone, CHCl₃; LogP –1.5; pKa ≈ 4–5
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Stable months at –80 °C; slow decarboxylation in hot strong acid/base
Other Information
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GC-MS EI m/z 167 (M⁺), 124, 82; CCS 136.14 Ų [M+H]⁺
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Plasma t½ 94–137 min (sheep); renal excretion
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Detected in sewage (ng L⁻¹); on NORMAN Suspect List
Safety and Handling
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Controlled precursor (listed in many schedules)
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PPE: gloves, dust mask; store –20 °C or below, dry, amber glass
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Add 0.1 % NaF to biological samples to block in-vitro formation
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Dispose as controlled-drug waste