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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO4.H2O4S
Molecular Weight 401.431
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COCAINE SULFATE

SMILES

OS(O)(=O)=O.COC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC(=O)C3=CC=CC=C3)N2C

InChI

InChIKey=OHOXZHVORBDIEV-VZXSFKIWSA-N
InChI=1S/C17H21NO4.H2O4S/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;1-5(2,3)4/h3-7,12-15H,8-10H2,1-2H3;(H2,1,2,3,4)/t12-,13+,14-,15+;/m0./s1

HIDE SMILES / InChI

Molecular Formula C17H21NO4
Molecular Weight 303.3529
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.078
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
[Acute myocardial infarction related to cocaine use].
1999 Apr
'Research' versus 'real-world' patients: representativeness of participants in clinical trials of treatments for cocaine dependence.
1999 Apr 1
Dopamine D2/D3 receptors modulate cocaine's reinforcing and discriminative stimulus effects in rhesus monkeys.
1999 Apr 1
Two novel sigma receptor ligands, BD1047 and LR172, attenuate cocaine-induced toxicity and locomotor activity.
1999 Apr 16
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
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
Initial validation of the Voris Cocaine Craving Scale: a preliminary report.
1999 Jan
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
Total occlusion of the left main coronary artery in a young cocaine user.
1999 Jul 1
A case of mutism subsequent to cocaine abuse.
1999 Jul-Sep
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
Antisocial personality disorder and psychopathy in cocaine-dependent women.
1999 Jun
Myocardial perfusion imaging with technetium-99m sestamibi in patients with cocaine-associated chest pain.
1999 Jun
Pharmacological characterization of nicotine's interaction with cocaine and cocaine analogs.
1999 Jun
Selegiline effects on cocaine-induced changes in medial temporal lobe metabolism and subjective ratings of euphoria.
1999 Jun
Effects of the 5-HT2C/2B antagonist SB 206553 on hyperactivity induced by cocaine.
1999 Jun
Effects of contingent and non-contingent cocaine on drug-seeking behavior measured using a second-order schedule of cocaine reinforcement in rats.
1999 Jun
Choreoathetoid movements in cocaine dependence.
1999 Jun 15
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
Neuronal and behavioural abnormalities in striatal function in DARPP-32-mutant mice.
1999 Mar
Neuropsychological deficits in withdrawn cocaine-dependent males.
1999 May
Gender effects on persistent cerebral metabolite changes in the frontal lobes of abstinent cocaine users.
1999 May
Bilateral saccular cysts after cocaine use.
1999 May
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine.
1999 May
Magnetic resonance imaging evidence of "silent" cerebrovascular toxicity in cocaine dependence.
1999 May 1
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
Prenatal cocaine and neuromotor outcome at four months: effect of duration of exposure.
1999 Oct
Effects of the long-acting monoamine reuptake inhibitor indatraline on cocaine self-administration in rhesus monkeys.
1999 Oct
Homozygosity at the dopamine DRD3 receptor gene in cocaine dependence.
1999 Sep
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures.
1999 Sep
Cocaine-induced erythrocytosis and increase in von Willebrand factor: evidence for drug-related blood doping and prothrombotic effects.
1999 Sep 13
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 Sat Dec 16 08:29:47 GMT 2023
Edited
by admin
on Sat Dec 16 08:29:47 GMT 2023
Record UNII
GG6P4Q1KNT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COCAINE SULFATE
Common Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(BENZOYLOXY)-8-METHYL-, METHYL ESTER, (1R-(EXO,EXO))-, SULFATE (1:1)
Systematic Name English
1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLIC ACID, 3.BETA.-HYDROXY-, METHYL ESTER, BENZOATE (ESTER), SULFATE (1:1)
Common Name English
Code System Code Type Description
FDA UNII
GG6P4Q1KNT
Created by admin on Sat Dec 16 08:29:47 GMT 2023 , Edited by admin on Sat Dec 16 08:29:47 GMT 2023
PRIMARY
PUBCHEM
56841038
Created by admin on Sat Dec 16 08:29:47 GMT 2023 , Edited by admin on Sat Dec 16 08:29:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID70974567
Created by admin on Sat Dec 16 08:29:47 GMT 2023 , Edited by admin on Sat Dec 16 08:29:47 GMT 2023
PRIMARY
CAS
5913-65-5
Created by admin on Sat Dec 16 08:29:47 GMT 2023 , Edited by admin on Sat Dec 16 08:29:47 GMT 2023
PRIMARY
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