All Photos(1)

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.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Repr. 2 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Michel Engeln et al.
Biological psychiatry, 87(11), 992-1000 (2019-12-21)
We previously showed that the transcription factor Egr3 (early growth response 3) is oppositely regulated in nucleus accumbens (NAc) cell subtypes 24 hours following cocaine exposure and bidirectionally mediates cocaine-related behaviors in male rodents. Overexpressing Egr3 in D2 receptor-containing medium...
Benoît Forget et al.
Progress in neurobiology, 197, 101898-101898 (2020-08-26)
Cocaine addiction is a chronic and relapsing disorder with an important genetic component. Human candidate gene association studies showed that the single nucleotide polymorphism (SNP) rs16969968 in the α5 subunit (α5SNP) of nicotinic acetylcholine receptors (nAChRs), previously associated with increased...
Maria E Burkovetskaya et al.
ACS chemical neuroscience, 11(15), 2231-2242 (2020-07-02)
Cocaine addiction remains a major public concern throughout the world especially in developed countries. In the last three decades, significant achievements have led to a greater understanding of the signaling pathways involved in the development of cocaine addiction; however, there...
Maria E Burkovetskaya et al.
Neuroscience letters, 728, 134951-134951 (2020-04-13)
The evidence showing the involvement of microglial activation in the development of drug addiction remain scarce as microglia have not been systematically investigated in self-administered mice, a gold standard rodent model for drug addiction. Here we established the stable cocaine...
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...

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