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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO4
Molecular Weight 303.3536
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COCAINE

SMILES

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

InChI

InChIKey=ZPUCINDJVBIVPJ-LJISPDSOSA-N
InChI=1S/C17H21NO4/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/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

Description
Curator's Comment:: 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

TargetsConditions

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
Health Status: healthy
Age Group: 30-43 years
Sex: M
Sources:
32 mg single, intranasal
Dose: 32 mg
Route: intranasal
Route: single
Dose: 32 mg
Sources:
healthy, 30-43 years
Health Status: healthy
Age Group: 30-43 years
Sex: M
Sources:
42 mg single, respiratory
Dose: 42 mg
Route: respiratory
Route: single
Dose: 42 mg
Sources:
healthy, 30-43 years
Health Status: healthy
Age Group: 30-43 years
Sex: M
Sources:
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources:
unhealthy, 45 years (range: 17- 83 years)
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Sources:
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:
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
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:
unhealthy, 45 years (range: 17- 83 years)
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Sources:
Facial pain 0.4%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources:
unhealthy, 45 years (range: 17- 83 years)
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Sources:
Foreign body sensation in eyes 0.4%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources:
unhealthy, 45 years (range: 17- 83 years)
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Sources:
Nasal congestion 0.4%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources:
unhealthy, 45 years (range: 17- 83 years)
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Sources:
Neck pain 0.4%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources:
unhealthy, 45 years (range: 17- 83 years)
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Sources:
Anxiety 0.7%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources:
unhealthy, 45 years (range: 17- 83 years)
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Sources:
Epistaxis 0.7%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources:
unhealthy, 45 years (range: 17- 83 years)
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Sources:
Headache 1.5%
8 % single, intranasal
Highest studied dose
Dose: 8 %
Route: intranasal
Route: single
Dose: 8 %
Sources:
unhealthy, 45 years (range: 17- 83 years)
Health Status: unhealthy
Age Group: 45 years (range: 17- 83 years)
Sex: M+F
Sources:
Adverse event grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
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
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
yes [Ki 85 uM]
yes [Ki >1000 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Symptomatic overlap of cocaine intoxication and acute schizophrenia at emergency presentation.
1999
Prolonged perioperative myocardial ischemia in a young male: due to topical intranasal cocaine?
1999 Aug
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
Acute injection of drugs with low addictive potential (delta(9)-tetrahydrocannabinol, 3,4-methylenedioxymethamphetamine, lysergic acid diamide) causes a much higher c-fos expression in limbic brain areas than highly addicting drugs (cocaine and morphine).
1999 Aug 25
Brief report: frequency of maternal cocaine use during pregnancy and infant neurobehavioral outcome.
1999 Dec
Nasolacrimal duct obstruction and orbital cellulitis associated with chronic intranasal cocaine abuse.
1999 Dec
Cocaine-induced acute renal failure without rhabdomyolysis.
1999 Dec
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
Distinct features of seizures induced by cocaine and amphetamine analogs.
1999 Jul 21
Selective inhibition of cocaine-seeking behaviour by a partial dopamine D3 receptor agonist.
1999 Jul 22
A case of mutism subsequent to cocaine abuse.
1999 Jul-Sep
U69593, a kappa-opioid agonist, decreases cocaine self-administration and decreases cocaine-produced drug-seeking.
1999 Jun
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
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
Pramipexole treatment for cocaine cravings.
1999 Nov
Level of in utero cocaine exposure and neonatal ultrasound findings.
1999 Nov
Dopamine transporter mRNA in autopsy studies of chronic cocaine users.
1999 Nov 10
Alcohol plus cocaine prenatally is more deleterious than either drug alone.
1999 Nov-Dec
The effect of prenatal cocaine exposure on neurobehavioral outcome: a meta-analysis.
1999 Nov-Dec
Serotonin(2C) receptors appear to mediate genetic sensitivity to cocaine-induced convulsions.
1999 Oct
Prenatal cocaine and neuromotor outcome at four months: effect of duration of exposure.
1999 Oct
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
Urticarial vasculitis following cocaine use.
1999 Sep
Homozygosity at the dopamine DRD3 receptor gene in cocaine dependence.
1999 Sep
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
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures.
1999 Sep
Rapid induction of behavioral and neurochemical tolerance to cocaethylene, a model compound for agonist therapy of cocaine dependence.
1999 Sep 1
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
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 22:37:54 UTC 2021
Edited
by admin
on Fri Jun 25 22:37:54 UTC 2021
Record UNII
I5Y540LHVR
Record Status Validated (UNII)
Record Version
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Name Type Language
COCAINE
HSDB   MART.   MI   USP   VANDF   WHO-DD  
Common Name English
COCAINE [VANDF]
Common Name English
RX-0041
Code English
RX0041
Code English
(R)-(-)-COCAINE
Common Name English
COCAINE [WHO-DD]
Common Name English
COCAINE [MI]
Common Name English
COCAINUM [HPUS]
Common Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(BENZOYLOXY)-8-METHYL-, METHYL ESTER, (1R-(EXO,EXO))-
Common Name English
METHYL (1R,2R,3S,5S)-3- (BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1) OCTANE-2-CARBOXYLATE
Systematic Name English
COCAINE [USP]
Common Name English
NEUROCAINE
Common Name English
METHYL 3B-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLATE BENZOATE (ESTER)
Common Name English
3.BETA.-HYDROXY-2.BETA.-TROPANECARBOXYLIC ACID METHYL ESTER BENZOATE (ESTER)
Common Name English
COCAINUM
HPUS  
Common Name English
COCAINE [MART.]
Common Name English
ECGONINE METHYL ESTER BENZOATE (ESTER)
Common Name English
BENZOYLMETHYLECGONINE
Common Name English
COCAINE [HSDB]
Common Name English
IDS-NC-004
Code English
Classification Tree Code System Code
WHO-ATC R02AD03
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
WHO-ATC S02DA02
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
WHO-VATC QS02DA02
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
WHO-VATC QN01BC01
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
YELLOW LIST NC 004
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
NCI_THESAURUS C47795
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
WHO-ATC S01HA01
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
WHO-VATC QR02AD03
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
WHO-VATC QS01HA01
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
DEA NO. 9041
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
WHO-ATC N01BC01
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
CFR 21 CFR 862.3250
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
Code System Code Type Description
LACTMED
Cocaine
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
MESH
D003042
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
IUPHAR
2286
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
FDA UNII
I5Y540LHVR
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
EVMPD
SUB13416MIG
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
NCI_THESAURUS
C80153
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
MERCK INDEX
M3710
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
200-032-7
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
DRUG CENTRAL
723
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
ChEMBL
CHEMBL370805
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
WIKIPEDIA
COCAINE
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
HSDB
6469
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
DRUG BANK
DB00907
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
CAS
50-36-2
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
EPA CompTox
50-36-2
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
PUBCHEM
446220
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY
RXCUI
2653
Created by admin on Fri Jun 25 22:37:54 UTC 2021 , Edited by admin on Fri Jun 25 22:37:54 UTC 2021
PRIMARY RxNorm
Related Record Type Details
INHIBITOR -> TARGET
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
PARENT -> SALT/SOLVATE
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
TRANSPORTER -> INHIBITOR
PARENT -> SALT/SOLVATE
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
ANALOGUE->TARGET
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE ACTIVE -> PARENT
PARENT -> METABOLITE
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT) Cocaine is a methyl ester of benzoylecgonine (an alkaloid found in coca leaves or prepared by synthesis from ecgonine). as per INCB
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
Related Record Type Details
ACTIVE MOIETY