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Cocaine Hydrochloride

CAT: 0572-TRC-C633500-1GSize: 1 gDry Ice: NoHazardous: No
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CAT#:0572-TRC-C633500-1GSize:1 g
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
53-21-4
Synonyms
Cocaine Hydrochloride; Cocaine hydrochloride; 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, hydrochloride (1:1), (1R,2R,3S,5S)-; 1alphaH,5alphaH-Tropane-2beta-carboxylic acid, 3beta-hydroxy-, methyl ester, benzoate (ester), hydrochloride (8CI); 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, hydrochloride, (1R,2R,3S,5S)- (9CI); 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, hydrochloride, [1R-(exo,exo)]-; (-)-Cocaine hydrochloride; Cocaine chloride; Cocaine muriate; MCV 4526; NIH 8211; NSC 25263; Sal de Merck; l-Cocaine hydrochloride
Hazard Statement
Toxic if swallowed; UN number: UN1544; Packing Group: III
Purity
>95% (HPLC)
Smiles
Cl.COC(=O)[C@H]1[C@H](C[C@@H]2CC[C@H]1N2C)OC(=O)c3ccccc3
Molecular Formula
C17 H21 N O4 . Cl H
Molecular Weight
339.81
InChI
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
Additionnal Information
IUPAC name: methyl (1S,3S,4R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate;hydrochloride
Shipping Conditions
Room Temperature
Storage Conditions
-20°C

Chemical Information

(-)-Cocaine hydrochloride

Cocaine Hydrochloride is the hydrochloride salt form of the tropane alkaloid cocaine, with central nervous systems (CNS) stimulating and local anesthetic activity. Cocaine binds to the dopamine, serotonin, and norepinephrine transport proteins and inhibits the re-uptake of dopamine, serotonin, and norepinephrine into pre-synaptic neurons. This leads to an accumulation of the respective neurotransmitters in the synaptic cleft and may result in increased postsynaptic receptor activation. Its effect on dopamine levels causes CNS stimulation and euphoria, and ultimately dependence. The mechanism of action through which cocaine exerts its local anesthetic effects is by binding to and blocking the voltage-gated sodium channels in the neuronal cell membrane. By stabilizing neuronal membranes, cocaine inhibits the initiation and conduction of nerve impulses and produces a reversible loss of sensation.

CAS Number53-21-4
PubChem CID656832
IUPAC Namemethyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate;hydrochloride
Molecular FormulaC17H22ClNO4
Molecular Weight339.8
Topological Polar Surface Area55.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Heavy Atom Count23
Formal Charge0
Complexity432
SMILES
CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC.Cl
InChI
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
InChIKey
PIQVDUKEQYOJNR-VZXSFKIWSA-N
Chemical Structure
2D Structure
2D structure of (-)-Cocaine hydrochloride
CAS: 53-21-4
CID: 656832
Formula: C17H22ClNO4
MW: 339.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight339.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass339.1237359
Monoisotopic Mass339.1237359
Topological Polar Surface Area55.8 Ų
Heavy Atom Count23
Formal Charge0
Complexity432
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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