Basic information
- CAS
43021-26-7- Standard SMILES
COC(=O)C1=CC[C@@H]2CC[C@H]1N2C- InChIKey
MPSNEAHFGOEKBI-VXNVDRBHSA-N- Molecular formula
- C10H15NO2
- Average molar mass
- 181.23 g/mol
- Monoisotopic mass
- 181.11027872
Overview
Anhydroecgonine methyl ester is a N-alkylpyrrolidine.
Names & identifiers
- Preferred name
- (-)-Anhydroecgonine methyl ester
- IUPAC
- methyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
- English name
- Ecgonidine methyl ester mesylate
- Molecular formula
- C10H15NO2
- Molecular weight
- 181.23
Names & synonyms
Anhydroecgonine methyl ester43021-26-7Anhydromethylecgonine(-)-Anhydroecgonine Methyl Ester58C337KP3E8-Azabicyclo(3.2.1)oct-2-ene-2-carboxylic acid, 8-methyl-, methyl ester, (1R,5S)-RefChem:817738MethylecgonidineEcgonidine Methyl Estermethyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylateMethyl EcgonidineEcgonidine Methyl Ester (1.0mg/ml in Acetonitrile)
Show more names
(R)-MethylecgonidineEcgonidine methyl ester mesylateAnhydroecgonine methyl ester solutionecgonidine methyl ester mesylate saltANHYDROECGONINEMETHYLESTER,1.0MG/MLINACETONITRILEAnhydroecgonine methyl ester (exempt preparation)Ecgonidine Methyl Ester (1 mg/ml in Acetonitrile)
UNII-58C337KP3EDTXSID20276220METHYL-ECGONIDINEMETHYLESTERECGONINEECGONIDINE-METHYL-ESTERCHEMBL451136orb3021450SCHEMBL1009981
Database identifiers
- CAS
43021-26-7- PubChem CID
- 119478
- DTXSID
DTXSID20276220- ChEMBL
CHEMBL451136- ChEBI
CHEBI:191065- UNII
- 58C337KP3E
- EC Number
- 636-970-2
- Nikkaji
- J356.372C
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 260
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Biochemical Research
DrugsDEA NFLIS-Drug Category -> Narcotics
Physical DescriptionMesylate: White solid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Boiling point
- 124 · 124-126 °C(Press: 10 Torr)
- Density
- 1.112 · 1.112±0.06 g/cm3(Predicted)
- Flash point
- 2 ℃ · 2℃
- storage temp.
- 20 °C · −20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 7.97 · 7.97±0.40(Predicted)
- color
- Colourless to Light Yellow
- FDA UNII
- 58 C337KP3E · 58C337KP3E
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300+H310+H330-H317
- Precautionary statements
- 260 · P260-P262-P264-P280-P302+P352+P310-P304+P340+P310
- Hazard Codes
- T+,Xn,F
- Risk Statements
- 26 · 26/27/28-43-36-20/21/22-11
- Safety Statements
- 22 · 22-36/37/39-45-36/37-26-16
- RIDADR
- 1544 · UN 1544 6.1/PG 2
- WGK Germany
- 3 · 3
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P261, P262, P264, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P333+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards Summary
Mesylate: May cause irritation and skin sensitization; Highly toxic by ingestion, inhalation, and skin absorption; May pose a reproductive hazard; [Sigma-Aldrich MSDS] A mesylate is any of the esters of an acid CH4SO3 including some in which it is combined with a drug. [Merriam-Webster Medical Dictionary] See Cocaine.
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Safety data
- wgk
- 3
- ridadr
- UN 1544 6.1/PG 2
- risk_code
- 26/27/28-43-36-20/21/22-11
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+,Xn,F
- safety_code
- 22-36/37/39-45-36/37-26-16
- Hazard statements
- H300+H310+H330-H317
- Precautionary statements
- P260-P262-P264-P280-P302+P352+P310-P304+P340+P310
Chemistry & industry
Uses & manufacturing
UsesAnhydroecgonine methyl ester (AEME) is a unique marker following smoked cocaine . . . {Reference #1]
Applications
UsesA metabolite of Cocaine (COC). It is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a metabolite.Controlled substance in some countries.
UsesEcgonidine methyl ester mesylate is a metabolite of Cocaine (COC). It is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a metabolite. Controlled substance in some countries.
Additional notes
DefinitionChEBI: Anhydroecgonine methyl ester is a N-alkylpyrrolidine.
Related reactions
10 records
Compound notes
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