ChemFOnt: Showing chemical card for Cocaine (CFc000009353)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:28 UTC

Chemfont ID

CFc000009353

Molecule Identification

Common Name

Cocaine

Definition

Cocaine, also known as coke, is an alkaloid ester obtained from the leaves of the coca plant (PMID: 20857618 ). It is a weakly alkaline compound and can therefore combine with acidic compounds to form white salts or powders (which is how it is typically sold and consumed). Cocaine is a strong stimulant that is most frequently used as a recreational drug. It is the second most frequently used illegal drug globally, after cannabis. The stimulant and hunger suppression properties of cocaine and coca leaf extracts have been known for thousands of years by indigenous groups in central and South America. The coca leaf was, and still is, chewed almost universally by some indigenous communities. Cocaine acts by inhibiting the reuptake of serotonin, norepinephrine, and dopamine. This inhibition leads to a number of mental and physical effects that may include loss of contact with reality, an intense feeling of happiness, periods of agitation, along with a rapid heart rate, sweating, and dialated pupils. Cocaine is highly addictive due to its effect on the reward pathway in the brain (PMID: 22856655 ). Cocaine addiction occurs through overexpression of the FosB protein in the nucleus accumbens of the brain, which results in altered transcriptional regulation in neurons within the nucleus accumbens. Cocaine is harmful. Its use increases the risk of stroke, myocardial infarction, lung problems (in those who smoke it), blood infections, and sudden cardiac death. Medically, cocaine is infrequently used as a local anesthetic and vasoconstrictor to cause loss of feeling or numbness before certain medical procedures (e.g., biopsy, stitches, wound cleaning) (PMID: 28956316 ). Topical cocaine is occasionally used as a local numbing agent to help with painful procedures in the mouth or nose. Cocaine is now predominantly used for nasal and lacrimal duct surgery. It works quickly to numb certain areas of the body (e.g., nose, ear, or throat) about 1-2 minutes after application. Cocaine functions as an anesthesia by reversibly binding to and inactivating sodium channels, thereby inhibiting excitation of nerve endings or by blocking conduction in peripheral nerves. Cocaine and its major metabolites are only found in individuals that have used or taken this drug.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Cocaine	ChEBI
2-Methyl-3beta-hydroxy-1alphah,5alphah-tropane-2beta-carboxylate benzoate (ester)	ChEBI
[1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester	ChEBI
Benzoylmethylecgonine	ChEBI
beta-Cocain	ChEBI
Cocain	ChEBI
Cocaina	ChEBI
Cocainum	ChEBI
Kokain	ChEBI
L-Cocain	ChEBI
L-Cocaine	ChEBI
Methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate	ChEBI
Methyl benzoylecgonine	ChEBI
Neurocaine	ChEBI
2-Methyl-3b-hydroxy-1alphah,5alphah-tropane-2b-carboxylate benzoate (ester)	Generator
2-Methyl-3b-hydroxy-1alphah,5alphah-tropane-2b-carboxylic acid benzoic acid (ester)	Generator
2-Methyl-3beta-hydroxy-1alphah,5alphah-tropane-2beta-carboxylic acid benzoic acid (ester)	Generator
2-Methyl-3β-hydroxy-1alphah,5alphah-tropane-2β-carboxylate benzoate (ester)	Generator
2-Methyl-3β-hydroxy-1alphah,5alphah-tropane-2β-carboxylic acid benzoic acid (ester)	Generator
[1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, methyl ester	Generator
b-Cocain	Generator
Β-cocain	Generator
Methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	Generator
(−)-cocaine	HMDB
Cocaine HCL	HMDB
Hydrochloride, cocaine	HMDB
Cocaine hydrochloride	HMDB
HCL, Cocaine	HMDB

Chemical Formula

C₁₇H₂₁NO₄

Average Molecular Weight

303.3529

Monoisotopic Molecular Weight

303.147058165

IUPAC Name

methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Traditional Name

cocaine

CAS Registry Number

50-36-2

SMILES

[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(=O)OC)N2C

InChI Identifier

InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1

InChI Key

ZPUCINDJVBIVPJ-LJISPDSOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Piperidinecarboxylic acid
Tropane alkaloid
Benzoyl
Dicarboxylic acid or derivatives
Piperidine
N-alkylpyrrolidine
Methyl ester
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:27958 )
tropane alkaloid (CHEBI:27958 )
methyl ester (CHEBI:27958 )
benzoate ester (CHEBI:27958 )
Tropane alkaloids (C01416 )
Alkaloids (C01416 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015043)
Membrane (HMDB: HMDB0015043)

Source

Exogenous

Exogenous (HMDB: HMDB0015043)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cocaine Action Pathway (PathBank: SMP0000395)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.03 g/L	ALOGPS
logP	1.97	ALOGPS
logP	2.28	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	8.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.16 m³·mol⁻¹	ChemAxon
Polarizability	32.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon