U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO4.ClH
Molecular Weight 339.8145
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COCAINE HYDROCHLORIDE

SMILES

CN1[C@@]2([H])CC[C@]1([H])[C@]([H])([C@]([H])(C2)OC(=O)c3ccccc3)C(=O)OC.Cl

InChI

InChIKey=PIQVDUKEQYOJNR-VZXSFKIWSA-N
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

HIDE SMILES / InChI

Molecular Formula C17H21NO4
Molecular Weight 303.3536
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11895133 | https://www.ncbi.nlm.nih.gov/pubmed/12067559 | https://www.ncbi.nlm.nih.gov/pubmed/17255098 | https://www.ncbi.nlm.nih.gov/pubmed/19897082

Cocaine is an alkaloid ester extracted from the leaves of plants including coca. Cocaine 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 a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake. Cocaine is addictive due to its effect on the reward pathway in the brain. After a short period of use, there is a high risk that dependence will occur. Its use also increases the risk of stroke, myocardial infarction, lung problems in those who smoke it, blood infections, and sudden cardiac death. Cocaine sold on the street is commonly mixed with local anesthetics, cornstarch, quinine, or sugar which can result in additional toxicity. Following repeated doses, a person may have decreased the ability to feel pleasure and be very physically tired. Cocaine acts by inhibiting the reuptake of serotonin, norepinephrine, and dopamine. This results in greater concentrations of these three neurotransmitters in the brain. It can easily cross the blood-brain barrier and may lead to the breakdown of the barrier.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
155.0 nM [Ki]
108.0 nM [Ki]
274.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Cocaine

Approved Use

INDICATIONS AND USAGE. Cocaine hydrochloride topical solution is indicated for the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
550 ng/mL
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
COCAINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
840 ng × h/mL
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
COCAINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
78.9 min
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
COCAINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
25 mg single, intravenous
Dose: 25 mg
Route: intravenous
Route: single
Dose: 25 mg
Sources:
healthy, 30-43 years
n = 6
Health Status: healthy
Age Group: 30-43 years
Sex: M
Population Size: 6
Sources:
32 mg single, intranasal
Dose: 32 mg
Route: intranasal
Route: single
Dose: 32 mg
Sources:
healthy, 30-43 years
n = 6
Health Status: healthy
Age Group: 30-43 years
Sex: M
Population Size: 6
Sources:
42 mg single, respiratory
Dose: 42 mg
Route: respiratory
Route: single
Dose: 42 mg
Sources:
healthy, 30-43 years
n = 6
Health Status: healthy
Age Group: 30-43 years
Sex: M
Population Size: 6
Sources:
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources: Page: p. 56, 74
unhealthy, 45 years (range: 17- 83 years)
n = 275
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Population Size: 275
Sources: Page: p. 56, 74
Other AEs: Headache, Epistaxis...
Other AEs:
Headache (1.5%)
Epistaxis (0.7%)
Anxiety (0.7%)
Foreign body sensation in eyes (0.4%)
Facial pain (0.4%)
Neck pain (0.4%)
Dizziness (0.4%)
Nasal congestion (0.4%)
Sources: Page: p. 56, 74
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Sex: M
Population Size: 1
Sources:
Other AEs: Adverse event...
Other AEs:
Adverse event (grade 5)
Sources:
160 mg single, intranasal
Recommended
Dose: 160 mg
Route: intranasal
Route: single
Dose: 160 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Other AEs: Drug abuse...
AEs

AEs

AESignificanceDosePopulation
Dizziness 0.4%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources: Page: p. 56, 74
unhealthy, 45 years (range: 17- 83 years)
n = 275
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Population Size: 275
Sources: Page: p. 56, 74
Facial pain 0.4%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources: Page: p. 56, 74
unhealthy, 45 years (range: 17- 83 years)
n = 275
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Population Size: 275
Sources: Page: p. 56, 74
Foreign body sensation in eyes 0.4%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources: Page: p. 56, 74
unhealthy, 45 years (range: 17- 83 years)
n = 275
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Population Size: 275
Sources: Page: p. 56, 74
Nasal congestion 0.4%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources: Page: p. 56, 74
unhealthy, 45 years (range: 17- 83 years)
n = 275
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Population Size: 275
Sources: Page: p. 56, 74
Neck pain 0.4%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources: Page: p. 56, 74
unhealthy, 45 years (range: 17- 83 years)
n = 275
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Population Size: 275
Sources: Page: p. 56, 74
Anxiety 0.7%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources: Page: p. 56, 74
unhealthy, 45 years (range: 17- 83 years)
n = 275
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Population Size: 275
Sources: Page: p. 56, 74
Epistaxis 0.7%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources: Page: p. 56, 74
unhealthy, 45 years (range: 17- 83 years)
n = 275
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Population Size: 275
Sources: Page: p. 56, 74
Headache 1.5%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources: Page: p. 56, 74
unhealthy, 45 years (range: 17- 83 years)
n = 275
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Population Size: 275
Sources: Page: p. 56, 74
Adverse event grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Sex: M
Population Size: 1
Sources:
Drug abuse
160 mg single, intranasal
Recommended
Dose: 160 mg
Route: intranasal
Route: single
Dose: 160 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes [IC50 1.2 uM]
unlikely (co-administration study)
Comment: the relatively low plasma concentrations of cocaine resulting from therapeutic doses of GOPRELTO are not expected to raise significant drug-drug interaction concerns
Page: 27.0
yes [IC50 7.85 uM]
unlikely (co-administration study)
Comment: the relatively low plasma concentrations of cocaine resulting from therapeutic doses of GOPRELTO are not expected to raise significant drug-drug interaction concerns
Page: 27.0
yes [Ki 85 uM]
yes [Ki >1000 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Symptomatic overlap of cocaine intoxication and acute schizophrenia at emergency presentation.
1999
Endogenous opioids implicated in the dynamics of experimental drug addiction: an in vivo autoradiographic analysis.
1999
Microbial keratitis following cocaine abuse in a soft contact lens wearer.
1999 Apr
Sequential neuromotor examination in children with intrauterine cocaine/polydrug exposure.
1999 Apr
Amlodipine treatment of cocaine dependence.
1999 Apr-Jun
Comparison of dopamine receptor antagonists on hyperlocomotion induced by cocaine, amphetamine, MK-801 and the dopamine D1 agonist C-APB in mice.
1999 Aug
Role of cocaethylene in toxic symptoms due to repeated subcutaneous cocaine administration modified by oral doses of ethanol.
1999 Aug
Sex and menstrual cycle differences in the subjective effects from smoked cocaine in humans.
1999 Aug
Cocaine-induced hypertension: role of the peripheral sympathetic system.
1999 Aug
Cocaine pharmacokinetics in men and in women during the follicular and luteal phases of the menstrual cycle.
1999 Aug
Cocaine-induced severe angioedema and urticaria.
1999 Aug
Effects of AMPA/kainate glutamate receptor antagonists on cocaine-induced convulsions and lethality in mice.
1999 Dec 15
Gender differences in treatment-seeking cocaine abusers--implications for treatment and prognosis.
1999 Fall
pH-dependent cocaine-induced cardiotoxicity.
1999 Jul
Inhibition by ginsenosides Rb1 and Rg1 of cocaine-induced hyperactivity, conditioned place preference, and postsynaptic dopamine receptor supersensitivity in mice.
1999 Jul
Effects of the competitive N-methyl-D-aspartate receptor antagonist, CPP, on the development and expression of conditioned hyperactivity and sensitization induced by cocaine.
1999 Jul
Total occlusion of the left main coronary artery in a young cocaine user.
1999 Jul 1
The effects of continuous cocaine dose on the induction of behavioral tolerance and dopamine autoreceptor function.
1999 Jul 9
Effects of dopamine receptor antagonists (D1 and D2) on the demand for smoked cocaine base in rhesus monkeys.
1999 Jun
U69593, a kappa-opioid agonist, decreases cocaine self-administration and decreases cocaine-produced drug-seeking.
1999 Jun
5-HT2 receptor antagonism reduces hyperactivity induced by amphetamine, cocaine, and MK-801 but not D1 agonist C-APB.
1999 Jun
Role of gender in the toxicity of norcocaine.
1999 Jun
Antisocial personality disorder and psychopathy in cocaine-dependent women.
1999 Jun
Triggering of myocardial infarction by cocaine.
1999 Jun 1
Choreoathetoid movements in cocaine dependence.
1999 Jun 15
Cocaine-seeking behavior and Fos expression in the amygdala produced by cocaine or a cocaine self-administration environment.
1999 Jun 29
Cocaine is self-administered into the shell region of the nucleus accumbens in Wistar rats.
1999 Jun 29
Phasic accumbal firing may contribute to the regulation of drug taking during intravenous cocaine self-administration sessions.
1999 Jun 29
[Centrofacial necrosis secondary to cocaine use].
1999 Jun-Jul
Acute ischaemic colitis following intravenous cocaine use.
1999 May
Neuropsychological deficits in withdrawn cocaine-dependent males.
1999 May
Chronic inhaled cocaine abuse may predispose to the development of pancreatic adenocarcinoma.
1999 Nov
The effects of cocaine on mood and sleep in cocaine-dependent males.
1999 Nov
The effects of benzamide analogues on cocaine self-administration in rhesus monkeys.
1999 Nov
Pramipexole treatment for cocaine cravings.
1999 Nov
Dopamine transporter mRNA in autopsy studies of chronic cocaine users.
1999 Nov 10
Antagonism of 5-hydroxytryptamine(4) receptors attenuates hyperactivity induced by cocaine: putative role for 5-hydroxytryptamine(4) receptors in the nucleus accumbens shell.
1999 Oct
Effects of the long-acting monoamine reuptake inhibitor indatraline on cocaine self-administration in rhesus monkeys.
1999 Oct
A role for the bed nucleus of the stria terminalis, but not the amygdala, in the effects of corticotropin-releasing factor on stress-induced reinstatement of cocaine seeking.
1999 Oct 15
Effects of chronic 'Binge' cocaine administration on plasma ACTH and corticosterone levels in mice deficient in DARPP-32.
1999 Sep
Long-term changes in connexin32 gap junction protein and mRNA expression following cocaine self-administration in rats.
1999 Sep
Cocaine induced myocardial infarction.
1999 Sep
Association of depressive symptoms during abstinence with the subjective high produced by cocaine.
1999 Sep
Cocaine-induced erythrocytosis and increase in von Willebrand factor: evidence for drug-related blood doping and prothrombotic effects.
1999 Sep 13
Postoperative anisocoria in a patient undergoing endoscopic sinus surgery.
1999 Sep-Oct
Cocaine-induced mood disorder: prevalence rates and psychiatric symptoms in an outpatient cocaine-dependent sample.
1999 Spring
Dose-related neurobehavioral effects of chronic cocaine use.
1999 Summer
Using eye movement desensitization and reprocessing to reduce cocaine cravings.
2000 Jan
Effects of prenatal cocaine/crack and other drug exposure on electroencephalographic sleep studies at birth and one year.
2000 Jan
Cocaine induces apoptosis in fetal myocardial cells through a mitochondria-dependent pathway.
2000 Jan
Patents

Sample Use Guides

Cocaine HCl 10% topical solution, up to 4 mL, is applied for 20 minutes via cotton pledget(s)
Route of Administration: Topical
Neuronal cultures were prepared from 18-day-old Sprague–Dawley rat fetuses. Cultures were used for neurotoxicity experiments after 12 days in culture. To assess any toxic effects of cocaine per se, 10 mL aliquots of three different dilutions of the cocaine stock solution (0.1–10 mM final concentration in the medium) were added to cell cultures. Appropriate vehicle controls (same volume of solvent added) were included for each group.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:11:42 UTC 2021
Edited
by admin
on Fri Jun 25 21:11:42 UTC 2021
Record UNII
XH8T8T6WZH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COCAINE HYDROCHLORIDE
EP   MART.   MI   USP   VANDF   WHO-DD  
Common Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(BENZOYLOXY)-8-METHYL-, METHYL ESTER, HYDROCHLORIDE,(1R-(EXO,EXO))-
Common Name English
NUMBRINO
Brand Name English
RX-0041-002
Code English
COCAINE HYDROCHLORIDE [USP]
Common Name English
COCAINE HYDROCHLORIDE CII
USP-RS  
Common Name English
METHYL 3.BETA.-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPAN-2.BETA.-CARBOXYLATE, BENZOATE (ESTER) HYDROCHLORIDE
Common Name English
COCAINUM MURIATICUM
HPUS  
Common Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(BENZOYLOXY)-8-METHYL-, METHYL ESTER, HYDROCHLORIDE, (1R,2R,3S,5S)
Common Name English
COCAINE HYDROCHLORIDE [VANDF]
Common Name English
COCAINE HYDROCHLORIDE [WHO-DD]
Common Name English
COCAINE MURIATE
Common Name English
COCAINE HYDROCHLORIDE CII [USP-RS]
Common Name English
COCAINUM MURIATICUM [HPUS]
Common Name English
COCAINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
COCAINE HCL
Common Name English
COCAINE HYDROCHLORIDE [JAN]
Common Name English
GOPRELTO
Brand Name English
NSC-25263
Code English
MCV 4526
Code English
COCAINE HYDROCHLORIDE [MART.]
Common Name English
COCAINE HYDROCHLORIDE [MI]
Common Name English
METHYL (1R,2R,3S,5S)-3- (BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1) OCTANE-2-CARBOXYLATE, HYDROCHLORIDE
Common Name English
NIH 8211
Code English
COCAINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
DEA NO. 9041
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
NCI_THESAURUS C47795
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
Code System Code Type Description
MERCK INDEX
M3710
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY Merck Index
DRUG BANK
DBSALT001521
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY
EPA CompTox
53-21-4
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY
NCI_THESAURUS
C81016
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY
EVMPD
SUB13417MIG
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY
PUBCHEM
656832
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY
CAS
53-21-4
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY
RXCUI
81985
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY RxNorm
FDA UNII
XH8T8T6WZH
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY
USP_CATALOG
1143008
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
200-167-1
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL370805
Created by admin on Fri Jun 25 21:11:42 UTC 2021 , Edited by admin on Fri Jun 25 21:11:42 UTC 2021
PRIMARY
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IMPURITY -> PARENT
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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