COCAINE

First marketed in 1860

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 Search

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
Sources: https://www.drugbank.ca/drugs/DB00907
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin transporter 164 Target ID: CHEMBL313 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559	Inhibitor 7728	155.0 nM [Ki]
Norepinephrine transporter 175 Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559	Inhibitor 7728	108.0 nM [Ki]
Dopamine transporter 164 Target ID: CHEMBL338 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559	Inhibitor 7728	274.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cocaine-related disorders 14 Sources: https://clinicaltrials.gov/ct2/show/NCT00000270	Primary		Phase IV 63	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.
Procedures and surgeries on or through accessible mucous membranes of the nasal cavities 3 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=24faa247-fe12-4574-881d-445b078b3e87	Primary		Approved 8043	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.

C_max

Value	Dose	Co-administered	Analyte	Population
550 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7242115/	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

Value	Dose	Co-administered	Analyte	Population
840 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7242115/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
78.9 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7242115/	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

Dose	Population	Adverse events
25 mg single, intravenous Dose: 25 mg Route: intravenous Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	healthy, 30-43 years n = 6 Health Status: healthy Age Group: 30-43 years Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	Sources: https://pubmed.ncbi.nlm.nih.gov/8926741
32 mg single, intranasal Dose: 32 mg Route: intranasal Route: single Dose: 32 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	healthy, 30-43 years n = 6 Health Status: healthy Age Group: 30-43 years Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	Sources: https://pubmed.ncbi.nlm.nih.gov/8926741
42 mg single, respiratory Dose: 42 mg Route: respiratory Route: single Dose: 42 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	healthy, 30-43 years n = 6 Health Status: healthy Age Group: 30-43 years Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	Sources: https://pubmed.ncbi.nlm.nih.gov/8926741
8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/4443787	unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4443787	Other AEs: Adverse event... Other AEs: Adverse event (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/4443787
160 mg single, intranasal Recommended Dose: 160 mg Route: intranasal Route: single Dose: 160 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf	Other AEs: Drug abuse... Other AEs: Drug abuse Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf

AEs

AE	Significance	Dose	Population
Dizziness	0.4%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Facial pain	0.4%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Nasal congestion	0.4%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Neck pain	0.4%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Anxiety	0.7%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Epistaxis	0.7%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Headache	1.5%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Adverse event	grade 5	2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/4443787	unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4443787
Drug abuse		160 mg single, intranasal Recommended Dose: 160 mg Route: intranasal Route: single Dose: 160 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1601	inhibitor 1604	inhibitor 1702	inhibitor 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1383 CYP2A6 627 CYP2B6 717 CYP2C8 818 CYP2C19 1325 CYP2E1 790 CYP3A4/5 241 P-gp 1330 BCRP 643 OAT1 554 OAT3 588 OATP1B1 733 OATP1B3 657 OCT2 594 OCT1 480 OCT3 140	CES2 23 P-gp 1400 BCRP 515 OAT1 294 OAT3 305 OATP1B1 370 OATP1B3 319 OCT2 316

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BCRP 713	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=28 Page: 28.0	no
CYP1A2 1532	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2A6 659	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2B6 884	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2C19 1392	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2C8 865	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2C9 1648	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2E1 871	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP3A4/5 293	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT1 558	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT3 590	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B1 748	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B3 666	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
P-gp 1514	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=28 Page: 28.0	no
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0
OCT2 595	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0
OCT1 495	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/16581093/	yes [Ki 85 uM]
OCT3 140	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/16581093/	yes [Ki >1000 uM]

Drug as victim

Target	Modality	Activity	Metabolite
BCRP 515	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT1 294	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT3 305	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B1 370	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B3 319	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OCT2 316	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
P-gp 1400	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CES2 23	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf#page=12 Page: 12.0	yes
CYP3A4 1601	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf#page=12 Page: 12.0	yes
P-gp 1400	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	yes	BE 3

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1507	inhibitor 1489 Sources: https://pubmed.ncbi.nlm.nih.gov/11561083/

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L9JBL
Alfa Chemistry	ACM53214
Aurora Fine Chemicals LLC	A17.902.496	http://online.aurorafinechemicals.com/info?ID=A17.902.496
ChemMol	30107819	http://www.chemmol.com/chemmol/30107819.html
ChemMol	99097714	http://www.chemmol.com/chemmol/99097714.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0602073
Compound Cloud	122142
Compound Cloud	23724835
Compound Cloud	446220
Hangzhou Yuhao Chemical Technology	RT7155
LGC Standards	LGCAMP1345.05-11	https://www.lgcstandards.com/US/en/p/LGCAMP1345.05-11
LGC Standards	LGCAMP1345.05-12	https://www.lgcstandards.com/US/en/p/LGCAMP1345.05-12
LGC Standards	LGCFOR1345.05	https://www.lgcstandards.com/US/en/p/LGCFOR1345.05
NovoSeek	446220
Sigma Aldrich	1143008\|USP
Sigma Aldrich	19330\|SIAL
Sigma Aldrich	51621\|SIAL
Sigma Aldrich	C-008\|CERILLIAN
Sigma Aldrich	C1528\|SIAL
Sigma-Aldrich	C-008_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/c008?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C8912_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/c8912?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S524154	http://www.smolecule.com/products/s524154
THE BioTek	bt-264235	https://www.thebiotek.com/product/inhibitors/bt-264235
Tetrahedron	TS78461
Tocris	2833
Toronto Research Chemicals	A634018
Toronto Research Chemicals	C633500
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	CC-1775E
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0777
ZINC	ZINC000003875336	http://zinc15.docking.org/substances/ZINC000003875336

PubMed

Title	Date	PubMed
Microbial keratitis following cocaine abuse in a soft contact lens wearer.	1999 Apr	10450397
Amlodipine treatment of cocaine dependence.	1999 Apr-Jun	10437993
Prolonged perioperative myocardial ischemia in a young male: due to topical intranasal cocaine?	1999 Aug	10526815
Comparison of dopamine receptor antagonists on hyperlocomotion induced by cocaine, amphetamine, MK-801 and the dopamine D1 agonist C-APB in mice.	1999 Aug	10494572
Role of cocaethylene in toxic symptoms due to repeated subcutaneous cocaine administration modified by oral doses of ethanol.	1999 Aug	10478337
Sex and menstrual cycle differences in the subjective effects from smoked cocaine in humans.	1999 Aug	10472516
Cocaine-induced hypertension: role of the peripheral sympathetic system.	1999 Aug	10433872
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	10521585
Brief report: frequency of maternal cocaine use during pregnancy and infant neurobehavioral outcome.	1999 Dec	10608102
Nasolacrimal duct obstruction and orbital cellulitis associated with chronic intranasal cocaine abuse.	1999 Dec	10604666
Severe avascular necrosis of the nasal chambers secondary to cocaine abuse.	1999 Dec	10604166
Comparative effects of sodium bicarbonate and sodium chloride on reversing cocaine-induced changes in the electrocardiogram.	1999 Dec	10598131
Cocaine-induced acute renal failure without rhabdomyolysis.	1999 Dec	10570114
Effects of AMPA/kainate glutamate receptor antagonists on cocaine-induced convulsions and lethality in mice.	1999 Dec 15	10618468
Gender differences in treatment-seeking cocaine abusers--implications for treatment and prognosis.	1999 Fall	10598213
pH-dependent cocaine-induced cardiotoxicity.	1999 Jul	10452435
Distinct features of seizures induced by cocaine and amphetamine analogs.	1999 Jul 21	10456426
The effects of continuous cocaine dose on the induction of behavioral tolerance and dopamine autoreceptor function.	1999 Jul 9	10448878
A case of mutism subsequent to cocaine abuse.	1999 Jul-Sep	10435258
Effects of dopamine receptor antagonists (D1 and D2) on the demand for smoked cocaine base in rhesus monkeys.	1999 Jun	10435411
U69593, a kappa-opioid agonist, decreases cocaine self-administration and decreases cocaine-produced drug-seeking.	1999 Jun	10435406
[Centrofacial necrosis secondary to cocaine use].	1999 Jun-Jul	10491482
Chronic inhaled cocaine abuse may predispose to the development of pancreatic adenocarcinoma.	1999 Nov	10612544
The effects of cocaine on mood and sleep in cocaine-dependent males.	1999 Nov	10609968
The effects of benzamide analogues on cocaine self-administration in rhesus monkeys.	1999 Nov	10591881
Pramipexole treatment for cocaine cravings.	1999 Nov	10553755
Level of in utero cocaine exposure and neonatal ultrasound findings.	1999 Nov	10545554
Dopamine transporter mRNA in autopsy studies of chronic cocaine users.	1999 Nov 10	10581411
Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice.	1999 Nov 15	10578459
Alcohol plus cocaine prenatally is more deleterious than either drug alone.	1999 Nov-Dec	10560774
The effect of prenatal cocaine exposure on neurobehavioral outcome: a meta-analysis.	1999 Nov-Dec	10560768
Serotonin(2C) receptors appear to mediate genetic sensitivity to cocaine-induced convulsions.	1999 Oct	10541732
Prenatal cocaine and neuromotor outcome at four months: effect of duration of exposure.	1999 Oct	10533991
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	10490917
Effects of the long-acting monoamine reuptake inhibitor indatraline on cocaine self-administration in rhesus monkeys.	1999 Oct	10490887
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	10516337
Urticarial vasculitis following cocaine use.	1999 Sep	10583098
Homozygosity at the dopamine DRD3 receptor gene in cocaine dependence.	1999 Sep	10523822
Effects of chronic 'Binge' cocaine administration on plasma ACTH and corticosterone levels in mice deficient in DARPP-32.	1999 Sep	10516482
Long-term changes in connexin32 gap junction protein and mRNA expression following cocaine self-administration in rats.	1999 Sep	10510198
Cocaine induced myocardial infarction.	1999 Sep	10505926
Association of depressive symptoms during abstinence with the subjective high produced by cocaine.	1999 Sep	10484960
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures.	1999 Sep	10454489
Rapid induction of behavioral and neurochemical tolerance to cocaethylene, a model compound for agonist therapy of cocaine dependence.	1999 Sep 1	10485969
Cocaine-induced erythrocytosis and increase in von Willebrand factor: evidence for drug-related blood doping and prothrombotic effects.	1999 Sep 13	10493323
Postoperative anisocoria in a patient undergoing endoscopic sinus surgery.	1999 Sep-Oct	10499761
Dose-related neurobehavioral effects of chronic cocaine use.	1999 Summer	10440013
Using eye movement desensitization and reprocessing to reduce cocaine cravings.	2000 Jan	10618047
Effects of prenatal cocaine/crack and other drug exposure on electroencephalographic sleep studies at birth and one year.	2000 Jan	10617702
Cocaine induces apoptosis in fetal myocardial cells through a mitochondria-dependent pathway.	2000 Jan	10604926

Patents

Sample Use Guides

In Vivo Use Guide

Cocaine HCl 10% topical solution, up to 4 mL, is applied for 20 minutes via cotton pledget(s)

Route of Administration: Topical

In Vitro Use Guide

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

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

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