Benzoylecgonine
Basic information
- CAS
519-09-5- Standard SMILES
CN1[C@H]2CC[C@@H]1[C@@H](C(=O)O)[C@@H](OC(=O)c1ccccc1)C2- InChIKey
GVGYEFKIHJTNQZ-RFQIPJPRSA-N- Molecular formula
- C16H19NO4
- Average molar mass
- 289.33 g/mol
- Monoisotopic mass
- 289.13140809
Overview
Ecgonine benzoate is a benzoate ester metabolite of cocaine formed by hydrolysis of the methyl ester group, catalysed by carboxylesterases. It has a role as an epitope, a plant metabolite, a human xenobiotic metabolite and a marine xenobiotic metabolite. It is a benzoate ester and a tropane alkaloid. It is functionally related to an ecgonine.
Names & identifiers
- Preferred name
- Benzoylecgonine
- IUPAC
- (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
- English name
- Benzoylecgonine
- Molecular formula
- C16H19NO4
- Molecular weight
- 289.33
Names & synonyms
benzoylecgonineEcgonine benzoate519-09-5(-)-Benzoylecgonineo-Benzoyl-(-)-ecgoninebenzoyl ecgonineDTXSID7046758CHEBI:410015353I8I6YS(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acidDTXCID5026758(1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Show more names
1alphaH,5alphaH-Tropane-2beta-carboxylic acid, 3beta-hydroxy-, benzoate (ester)O-BenzoylecgoninBenzoylecogonineBenzoylecgonine-13C6Benzoylecgonine (CRM)benzoylecgonine solutionBenzoylecgonine tetrahydrate
(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acid(1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acid(1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid(1R,2R,3S,5S)-8-methyl-3-((phenylcarbonyl)oxy)-8-azabicyclo(3.2.1)octane-2-carboxylic acidRefChem:5592(2R,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acid(1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azoniabicyclo(3.2.1)octane-2-carboxylate208-263-5
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 419
Experimental & physicochemical properties
Chemical ClassesStimulant
Drugs
DEA NFLIS-Drug Category -> Narcotics
Pharmaceuticals -> Illicit drugs
Pharmaceuticals -> Listed in ZINC15
Human DrugsPharmaceuticals
Collision Cross Section
167.3 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
168.36 Ų [M+H]+
Physicochemical properties
- Melting point
- 1950 C · 1950C (dec)
- Boiling point
- 431.49 °C · 431.49°C (rough estimate)
- Density
- 1.1267 · 1.1267 (rough estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- Flash point
- 11 °C · 11 °C
- storage temp.
- 2 · 2-8°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 3 mg/ml
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- wgk
- 1
- ridadr
- UN 1230 3/PG 2
- risk_code
- 11-23/24/25-39/23/24/25-25
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- hazard_code
- F,T
- safety_code
- 16-36/37-45-7
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard statements
- H225-H301+H311+H331-H370-H301-H311-H331
- Precautionary statements
- P210-P260-P280-P301+P310-P311
Chemistry & industry
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesA metabolite of Cocaine. Controlled substance
Additional notes
DefinitionChEBI: A benzoate ester metabolite of cocaine formed by hydrolysis of the methyl ester group, catalysed by carboxylesterases.
Related reactions
1 records
Compound notes
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