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C5776

Sigma-Aldrich

Cocaine hydrochloride

Synonyme(s) :

Ecgonine methyl ester benzoate hydrochloride

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About This Item

Formule empirique (notation de Hill):
C17H21NO4 · HCl
Numéro CAS:
53-21-4
Poids moléculaire :
339.81
Numéro CE :
200-167-1
Numéro MDL:
MFCD00058119
Code UNSPSC :
12352200
ID de substance PubChem :
329775099
Nomenclature NACRES :
NA.77

Forme

powder

Contrôle du médicament

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)

Application(s)

forensics and toxicology

Chaîne SMILES 

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

Clé InChI

PIQVDUKEQYOJNR-VZXSFKIWSA-N

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Application

Cocaine hydrochloride has been used:
  • in saline control to study the effects of cocaine self-administration in mouse brain
  • as adopamine (DA), noradrenaline (NA), and serotonin (5-HT) reuptake inhibitor to evoke neurotransmitter release in artificial fish cerebrospinal fluid (aCSF)
  • to examine conditioning to intravenous cocaine hydrochloride

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H300 + H330,H336,H361d

Classification des risques

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

Organes cibles

Central nervous system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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
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
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