C5776

Sigma-Aldrich

Cocaine hydrochloride

Synonym(s):
Ecgonine methyl ester benzoate hydrochloride
Empirical Formula (Hill Notation):
C17H21NO4 · HCl
CAS Number:
Molecular Weight:
339.81
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

drug control

USDEA Schedule II; Home Office Schedule 2; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; estupefaciente (Spain); Decreto Lei 15/93: Tabela IB (Portugal)

Featured Industry

Forensics and Toxicology

SMILES string

Cl.COC(=O)[C@H]1[C@H](C[C@@H]2CC[C@H]1N2C)OC(=O)c3ccccc3

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

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Biochem/physiol Actions

Inhibits the dopamine, norepinephrine, and serotonin transporters with Kis of about 300 nM, 900 nM, and 400 nM, respectively. Unlike amphetamines, it has no effect on catecholamine release.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Target Organs

Central nervous system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1544PSN2 6.1 / PGIII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Ernest T Chivero et al.
Frontiers in cell and developmental biology, 8, 573-573 (2020-08-28)
MicroRNA-124 (miR-124), a brain-enriched microRNA, is known to regulate microglial quiescence. Psychostimulants such as cocaine have been shown to activate microglia by downregulating miR-124, leading, in turn, to neuroinflammation. We thus rationalized that restoring the levels of miR-124 could function...
Billy T Chen et al.
Nature, 496(7445), 359-362 (2013-04-05)
Loss of control over harmful drug seeking is one of the most intractable aspects of addiction, as human substance abusers continue to pursue drugs despite incurring significant negative consequences. Human studies have suggested that deficits in prefrontal cortical function and...
Elena Martín-García et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 39(10), 2317-2330 (2014-03-19)
High-frequency intake and high drug-induced seeking are associated with cocaine addiction in both human and animals. However, their relationships and neurobiological underpinnings remain hypothetical. The medial prefrontal cortex (mPFC), basolateral amygdala (BLA), and nucleus accumbens (NAc) have been shown to...
Emmanuelle Jordi et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(23), 9511-9516 (2013-05-22)
Drugs of abuse, such as cocaine, induce changes in gene expression and epigenetic marks including alterations in histone posttranslational modifications in striatal neurons. These changes are thought to participate in physiological memory mechanisms and to be critical for long-term behavioral...
Tifei Yuan et al.
Neuron, 80(4), 1025-1038 (2013-11-05)
Drug-evoked synaptic plasticity in the mesolimbic dopamine (DA) system reorganizes neural circuits that may lead to addictive behavior. The first cocaine exposure potentiates AMPAR excitatory postsynaptic currents (EPSCs) onto DA neurons of the VTA but reduces the amplitude of NMDAR-EPSCs....

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