Compound
cocaine
An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.
Structure
Loading the model…
- Class
- Organic compound, cation
- Formula
- C17H22NO4
- Mass
- 304.366 g/mol
- Charge
- +1
- InChIKey
- ZPUCINDJVBIVPJ-LJISPDSOSA-O
- SMILES
- [H][C@]12CC[C@]([H])([C@@H](C(=O)OC)[C@@H](OC(=O)c3ccccc3)C1)[NH+]2C
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
4 entities
4 entities reached.
0 reported hops4 assembled from the scaffold
What the reference databases state
Regulatory determinations
LiverTox likelihood score A [HD]LiverTox
LiverTox Likelihood Score A [HD] — well known, well described and well reported to cause liver injury. Hepatotoxic at overdose specifically, not at recommended use. Chapter: "Cocaine". Source: LiverTox Master List (NBK571102).
The document·Public Domain (NLM/NIH)·Transcribed, not assessed
Statements
6 statements
6 statements · 2 reference databases · Subject: cocaine · Sources: Human-GEM, Rhea
- cocaine is metabolised by CES1ProteinHuman-GEM MAR08643Inferred only
- cocaine is metabolised by CES2ProteinHuman-GEM MAR08643Inferred only
- cocaine is metabolised by CES2ProteinHuman-GEM MAR08645Inferred only
- cocaine is metabolised by CES2ProteinRhea RHEA:27506Inferred only
- cocaine is metabolised by CES3ProteinHuman-GEM MAR08643Inferred only
- cocaine is metabolised by CES5AProteinHuman-GEM MAR08643Inferred only
Reactions
7 reactions
cocaine+waterbenzoic acid+ecgonine methyl ester+proton
Catalysed by CES5A or CES3 or CES2 or CES1
Reaction pageLeft to rightBalancedEC 3.1.1.1, 3.1.1.84, 3.1.1.56cytosol
Human-GEM MAR08643CC BY 4.0Reference data
cocaine+waterbenzoic acid+ecgonine methyl ester+proton
Catalysed by CES2
Reaction pageLeft to rightBalancedEC 3.1.1.84endoplasmic reticulum
Human-GEM MAR08645CC BY 4.0Reference data
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR11975CC BY 4.0Reference data
Reaction pageReversibleBalancedextracellular space, cytosol
Human-GEM MAR11976CC BY 4.0Reference data
Reaction pageReversibleBalancedcytosol, endoplasmic reticulum
Human-GEM MAR11977CC BY 4.0Reference data
cocaine+waterecgonine methyl ester+benzoic acid+hydron
Catalysed by CES2
Reaction pageDirection not assertedBalanced
Rhea RHEA:27506CC BY 4.0Reference data
ecgonine methyl ester+benzoyl-CoAcocaine+coenzyme A(4-)
Reaction pageDirection not assertedBalanced
Rhea RHEA:81559CC BY 4.0Reference data
Other names
2 names
Resolves to: cocaine
- Also called
- cocaine cation
- Systematic name
- (1R,2R,3S,5S)-3-(benzoyloxy)-2-(methoxycarbonyl)-8-methyl-8-azoniabicyclo[3.2.1]octane