(-)-Cocaine hydrochloride (CED0000833)

Record Information

Version

1.0

Creation Date

2016-05-22 06:48:39 UTC

Update Date

2026-04-05 17:28:12 UTC

Accession Number

CHEM020120

Identification

Common Name

(-)-Cocaine hydrochloride

Class

Small Molecule

Description

(-)-Cocaine hydrochloride belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It is a benzenoid with the chemical formula C17H22ClNO4 and an average molecular weight of 339.82 g/mol.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cocain-chlorhydrat	ChEBI
Cocaine chloride	ChEBI
Cocaine HCL	ChEBI
Cocaine muriate	ChEBI
L-Cocaine hydrochloride	ChEBI
Cocaine muriic acid	Generator
Methyl (1S,3S,4R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid;hydrochloride	Generator
Hydrochloride, cocaine	MeSH
Cocaine hydrochloride	MeSH
Cocaine	MeSH
HCL, Cocaine	MeSH

Chemical Formula

C₁₇H₂₂ClNO₄

Average Molecular Mass

339.820 g/mol

Monoisotopic Mass

339.124 g/mol

CAS Registry Number

53-21-4

IUPAC Name

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

Traditional Name

cocaine hydrochloride

SMILES

Cl.[H][C@@]12CC[C@@]([H])(N1C)[C@@]([H])(C(=O)OC)[C@]([H])(C2)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H21NO4.ClH/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;1H/t12-,13+,14-,15+;/m0./s1

InChI Key

PIQVDUKEQYOJNR-VZXSFKIWSA-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
Pyrrolidine
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrochloride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydrochloride (CHEBI:613010 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	31.96 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-cbfde8793ed15ce4cf5f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-cbfde8793ed15ce4cf5f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-cbfde8793ed15ce4cf5f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-5a2a109e872188f49979	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-5a2a109e872188f49979	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-5a2a109e872188f49979	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
822.0	Log mg/kg	[460:1500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	1.08989
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	1.16774
Click to view 3D structure	Norepinephrine transporter	Q9WTR4	Rattus norvegicus	Predicted (SEA)	0.700643
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	2.95827
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	3.97031
Click to view 3D structure	Sodium-dependent dopamine transporter	P27922	Bos taurus	Predicted (SEA)	0.155698
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	5.2159
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	34.9543
Click to view 3D structure	Sodium-dependent dopamine transporter	Q9GJT6	Macaca fascicularis	Predicted (SEA)	0.155698
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P08482	Rattus norvegicus	Predicted (SEA)	4.04816
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	59.4768
Click to view 3D structure	Acetylcholine-binding protein	P58154	Lymnaea stagnalis	Predicted (SEA)	2.56902
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P10980	Rattus norvegicus	Predicted (SEA)	13.5458
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P08483	Rattus norvegicus	Predicted (SEA)	5.3716
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	65.7826
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	54.728
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	38.9246
Click to view 3D structure	Transporter	Q63380	Rattus norvegicus	Predicted (SEA)	14.0129
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08485	Rattus norvegicus	Predicted (SEA)	5.60514
Click to view 3D structure	Sodium-dependent dopamine transporter	Q61327	Mouse	Predicted (SEA)	6.22794
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	71.0763
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	75.2023
Click to view 3D structure	Muscarinic acetylcholine receptor M3	Q8VH26	Cavia porcellus	Predicted (SEA)	10.2761
Click to view 3D structure	Neuronal acetylcholine receptor subunit alpha-7	P36544	Humans	Predicted (SEA)	66.2497
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	163.406