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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23NO4
Molecular Weight 329.3902
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CINNAMOYLCOCAINE

SMILES

COC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC(=O)\C=C\C3=CC=CC=C3)N2C

InChI

InChIKey=MQIXMJWNEKUAOZ-UYCDZTDFSA-N
InChI=1S/C19H23NO4/c1-20-14-9-10-15(20)18(19(22)23-2)16(12-14)24-17(21)11-8-13-6-4-3-5-7-13/h3-8,11,14-16,18H,9-10,12H2,1-2H3/b11-8+/t14-,15+,16-,18+/m0/s1

HIDE SMILES / InChI
Molecular Formula C19H23NO4
Molecular Weight 329.3902
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Approval Year

Unknown
149124
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:14:44 GMT 2025
Edited
by admin
on Mon Mar 31 21:14:44 GMT 2025
Record UNII
O3I44O988U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINNAMOYLCOCAINE
MI  
Common Name English
CINNAMIC ACID, ESTER WITH ECGONINE METHYL ESTER
Preferred Name English
COCAINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 8-METHYL-3-((1-OXO-3-PHENYL-2-PROPENYL)OXY)-, METHYL ESTER, (1R-(1.ALPHA.,2.ALPHA.,3.ALPHA.(E),5.ALPHA.))-
Systematic Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 8-METHYL-3-(((2E)-1-OXO-3-PHENYL-2-PROPENYL)OXY)-, METHYL ESTER, (1R,2R,3S,5S)-
Systematic Name English
TRANS-CINNAMOYLCOCAINE
Common Name English
PHENYLACETYLMETHYLESTER ECGONINE
Common Name English
CINNAMOYLECGONINE METHYL ESTER
Common Name English
ECGONINE PHENYLACETYLMETHYLESTER
Common Name English
ECGONINE CINNAMATE METHYL ESTER
Common Name English
CINNAMOYLCOCAINE, (E)-
Common Name English
Methylecgonine cinnamate
Common Name English
CINNAMOYLCOCAINE [MI]
Common Name English
Code System Code Type Description
PUBCHEM
6440936
Created by admin on Mon Mar 31 21:14:44 GMT 2025 , Edited by admin on Mon Mar 31 21:14:44 GMT 2025
PRIMARY
FDA UNII
O3I44O988U
Created by admin on Mon Mar 31 21:14:44 GMT 2025 , Edited by admin on Mon Mar 31 21:14:44 GMT 2025
PRIMARY
CAS
50763-20-7
Created by admin on Mon Mar 31 21:14:44 GMT 2025 , Edited by admin on Mon Mar 31 21:14:44 GMT 2025
PRIMARY
WIKIPEDIA
Methylecgonine cinnamate
Created by admin on Mon Mar 31 21:14:44 GMT 2025 , Edited by admin on Mon Mar 31 21:14:44 GMT 2025
PRIMARY Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant.[1] Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is said to be pharmacologically inactive.[2] But some studies funded by anti-drug agencies imply that it is active when smoked.[citation needed] Furthermore, the discovery of differing impurity products yielding methylecgonine cinnamate in confiscated cocaine have led enforcing agencies to postulate that illicit manufacturers have changed their oxidation procedures when refining cocaine from a crude form.[3] Methylecgonine cinnamate can dimerize to the truxillic acid derivative truxilline.
MERCK INDEX
m651
Created by admin on Mon Mar 31 21:14:44 GMT 2025 , Edited by admin on Mon Mar 31 21:14:44 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID701334867
Created by admin on Mon Mar 31 21:14:44 GMT 2025 , Edited by admin on Mon Mar 31 21:14:44 GMT 2025
PRIMARY
CAS
521-67-5
Created by admin on Mon Mar 31 21:14:44 GMT 2025 , Edited by admin on Mon Mar 31 21:14:44 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
Related Record Type Details
Structure of COCAINE HYDROCHLORIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
NIH
NCATS
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