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53-21-4

53-21-4 Structure

53-21-4 Structure
IdentificationBack Directory
[Name]

COCAINE HYDROCHLORIDE
[CAS]

53-21-4
[Synonyms]

MCV 4526
NIH 8211
NSC 25263
(ester)hcl
saldemerck
Cocaine HCl
Sal de Merc
cocainemuriate
cocainechloride
cocain-chlorhydrat
COCAINE HYDROCHLORIDE
l-cocainehydrochloride
COCAINIUM HYDROCHLORIDE
COCAINEHYDROCHLORIDE,USP
Hydrochloric acid cocaine
cocaine hydrochloride solution
Cocaine Hydrochloride (CII), USP
er,benzoate(ester),hydrochloride
Cocaine Hydrochloride CII (250 mg)
cocainehydrochloridemethanolsolution
COCAINE HYDROCHLORIDE--DEA SCHEDULEII IT EM
ECGONINE METHYL ESTER BENZOATE HYDROCHLORIDE
COCAINE HYDROCHLORIDE >97% ECGONINE METH YL ESTER
METHYL (2R,3S)-3-BENZOYLOXY-8-METHYL-8-AZABICYCLO[3.2.1]OCTANE-2-CARBO
methyl3-beta-hydroxy-1-alpha-h,5-alpha-h-tropan-2-beta-carboxylate,benzoate
3β-Hydroxy-1αH,5αH-tropane-2β-carboxylicacidmethylesterbenzoatehydrochloride
1aH,5aH-Tropane-2b-carboxylic acid, 3b-hydroxy-, methyl ester, benzoate (ester), hydrochloride (8CI)
(1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl Ester Hydrochloride
8-Azabicyclo3.2.1octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, hydrochloride, (1R,2R,3S,5S)-
8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, hydrochloride, [1R-(exo,exo)]-
1.alpha.H,5.alpha.H-Tropane-2.beta.-carboxylic acid, 3.beta.-hydroxy-, methyl ester, benzoate (ester), hydrochloride
1.alpha.-H,5.alpha.-H-Tropane-2.beta.-carboxylic acid, 3.beta.-hydroxy-, methyl ester, benzoate(ester), hydrochloride
8-Azabicyclo[3.2.1]octane-2-carboxylicacid, 3-(benzoyloxy)-8-Methyl-, Methyl ester, hydrochloride (1:1),(1R,2R,3S,5S)-
[EINECS(EC#)]

200-167-1
[Molecular Formula]

C17H22ClNO4
[MDL Number]

MFCD00058119
[MOL File]

53-21-4.mol
[Molecular Weight]

339.81
Chemical PropertiesBack Directory
[Appearance]

White Solid
[Melting point ]

200-2020C
[alpha ]

D -72° (c = 2 in aq soln pH 4.5)
[storage temp. ]

2-8°C
[solubility ]

Very soluble in water, freely soluble in alcohol, slightly soluble in methylene chloride.
[form ]

Powder
[Water Solubility ]

Soluble to 100 mM in water
[CAS DataBase Reference]

53-21-4
[EPA Substance Registry System]

8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, hydrochloride (1:1), (1R,2R,3S,5S)- (53-21-4)
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Uses]

Inhibits the dopamine, norepinephrine, and serotonin transporters. Unlike amphetamines, it has no effect on catecholamine release. Controlled substance. Anesthetic (local)
[Definition]

ChEBI: The hydrochloride salt of cocaine. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is drug of abuse.
[Biological Activity]

Competitive inhibitor of monoamine neurotransmitter transporters. Inhibits dopamine (DAT), serotonin (SERT) and noradrenalin (NET) transporters with K i values are 267, 392 and 872 nM respectively. Psychostimulant.
[Description]

Cocaine (hydrochloride) (Item No. 22165) is an analytical reference standard categorized as a tropane. Cocaine has a high potential for abuse and has been found in samples seized by law enforcement. Cocaine is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications.
Questions And AnswerBack Directory
[Characteristics]

Cocaine hydrochloride (benzoylmethylecgonine hydrochloride) occurs naturally as a white crystalline solid that is highly soluble in water:
1. Used exclusively via topical application. Injection of cocaine is contraindicated because of the ready availability of more effective and much less toxic local anesthetics. Cocaine is an ester local anesthetic.
2. Onset of topical anesthetic action is quite rapid, usually occurring within 1 minute.
3. Duration of anesthetic action may be as long as 2 hours. 4. Absorbed rapidly but eliminated slowly (elimination half-life 42 minutes).
5. Undergoes metabolism in the liver and plasma.
6. Unmetabolized cocaine may be found in the urine.
7. Cocaine is the only local anesthetic consistently demonstrated to produce vasoconstriction, which develops as a result of its ability to potentiate the actions of endogenous epinephrine and norepinephrine. Addition of vasoconstrictors to cocaine is therefore unnecessary and is potentially dangerous, increasing the likelihood of dysrhythmias, including ventricular fibrillation.
8. Classified as a Schedule II drug under the Controlled Substances Act. Repeated use results in psychological dependence and tolerance.
9. Overdose of cocaine is not uncommon following illicit use, primarily because the drug is readily absorbed from mucous membranes and its dosage is not carefully monitored.
10. Clinical manifestations of mild overdose include euphoria, excitement, restlessness, tremor, hypertension, tachycardia, and tachypnea.
11. Clinical manifestations of acute cocaine overdose include excitement, restlessness, confusion, tremor, hypertension, tachycardia, tachypnea, nausea and vomiting, abdominal pain, exophthalmos, and mydriasis; these are followed by depression (CNS, cardiovascular, respiratory) and death from respiratory arrest.
12. It is available in concentrations ranging from 1% to 10%.
13. It is recommended that the concentration of cocaine should not exceed 4% for topical application to oral mucous membranes.
14. Solutions of cocaine are unstable and deteriorate on standing.
15. Because of the extreme abuse potential of cocaine, its use as a topical anesthetic in dentistry is not recommended.
16. Cocaine is occasionally applied topically prior to surgical procedures by otolaryngologists and ophthalmologists.
Safety DataBack Directory
[Hazard Codes ]

T,F
[Risk Statements ]

60-25-43-39/23/24/25-23/24/25-11
[Safety Statements ]

7-16-36/37-45-22-53
[RIDADR ]

UN 1544 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

YM3050000
[HazardClass ]

6.1(a)
[PackingGroup ]

II
[HS Code ]

2939710000
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Azimsulfuron-->8-METHYL-8-AZABICYCLO[3.2.1]OCTANE
[Preparation Products]

(-)-2-BETA-CARBOMETHOXY-3-BETA-(4-FLUOROPHENYL)TROPANE-->ECGONINE HYDROCHLORIDE AMINO ALCOHOL POR TION-->Coca leaf extract,decocainized
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