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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO4.BH3O3
Molecular Weight 365.186
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COCAINE BORATE

SMILES

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

InChI

InChIKey=ZBDPRNDGRCEKTB-VZXSFKIWSA-N
InChI=1S/C17H21NO4.BH3O3/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;2-1(3)4/h3-7,12-15H,8-10H2,1-2H3;2-4H/t12-,13+,14-,15+;/m0./s1

HIDE SMILES / InChI

Molecular Formula BH3O3
Molecular Weight 61.833
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Midfacial complications of prolonged cocaine snorting.
1999 Apr
RGS mRNA expression in rat striatum: modulation by dopamine receptors and effects of repeated amphetamine administration.
1999 Apr
Amlodipine treatment of cocaine dependence.
1999 Apr-Jun
Prolonged perioperative myocardial ischemia in a young male: due to topical intranasal cocaine?
1999 Aug
Cocaine-induced hypertension: role of the peripheral sympathetic system.
1999 Aug
Comparative effects of sodium bicarbonate and sodium chloride on reversing cocaine-induced changes in the electrocardiogram.
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
Inhibition by ginsenosides Rb1 and Rg1 of cocaine-induced hyperactivity, conditioned place preference, and postsynaptic dopamine receptor supersensitivity in mice.
1999 Jul
A case of mutism subsequent to cocaine abuse.
1999 Jul-Sep
5-HT2 receptor antagonism reduces hyperactivity induced by amphetamine, cocaine, and MK-801 but not D1 agonist C-APB.
1999 Jun
Effects of the 5-HT2C/2B antagonist SB 206553 on hyperactivity induced by cocaine.
1999 Jun
Phasic accumbal firing may contribute to the regulation of drug taking during intravenous cocaine self-administration sessions.
1999 Jun 29
Stress-induced craving and stress response in cocaine dependent individuals.
1999 Mar
Bilateral saccular cysts after cocaine use.
1999 May
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine.
1999 May
The effects of cocaine on mood and sleep in cocaine-dependent males.
1999 Nov
Pramipexole treatment for cocaine cravings.
1999 Nov
Dopamine transporter mRNA in autopsy studies of chronic cocaine users.
1999 Nov 10
Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice.
1999 Nov 15
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
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
Rapid induction of behavioral and neurochemical tolerance to cocaethylene, a model compound for agonist therapy of cocaine dependence.
1999 Sep 1
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
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 11:10:48 GMT 2023
Edited
by admin
on Sat Dec 16 11:10:48 GMT 2023
Record UNII
2RT6KC9AZ6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COCAINE BORATE
Common Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(BENZOYLOXY)-8-METHYL-, METHYL ESTER, (1R-(EXO,EXO))-, COMPD. WITH BORIC ACID (H3BO3)
Systematic Name English
BORIC ACID, COMPD. WITH COCAINE
Common Name English
1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLIC ACID, 3.BETA.-HYDROXY-, METHYL ESTER, BENZOATE (ESTER), BORATE
Common Name English
BORIC ACID (H3BO3), COMPD. WITH (1R-(EXO,EXO))-METHYL 3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLATE
Common Name English
Code System Code Type Description
CAS
6696-60-2
Created by admin on Sat Dec 16 11:10:48 GMT 2023 , Edited by admin on Sat Dec 16 11:10:48 GMT 2023
PRIMARY
PUBCHEM
167713242
Created by admin on Sat Dec 16 11:10:48 GMT 2023 , Edited by admin on Sat Dec 16 11:10:48 GMT 2023
PRIMARY
FDA UNII
2RT6KC9AZ6
Created by admin on Sat Dec 16 11:10:48 GMT 2023 , Edited by admin on Sat Dec 16 11:10:48 GMT 2023
PRIMARY
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