COCAINE CITRATE

First marketed in 1860

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C17H21NO4.C6H8O7
Molecular Weight	798.8294
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.COC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC(=O)C3=CC=CC=C3)N2C.COC(=O)[C@@H]4[C@H]5CC[C@@H](C[C@@H]4OC(=O)C6=CC=CC=C6)N5C

InChI

InChIKey=ABRXXTCCHNTUTK-QJHKOLHCSA-N

InChI=1S/2C17H21NO4.C6H8O7/c2*1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11;7-3(8)1-6(13,5(11)12)2-4(9)10/h2*3-7,12-15H,8-10H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t2*12-,13+,14-,15+;/m00./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	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 183 Target ID: CHEMBL313 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559	Inhibitor 8504	155.0 nM [Ki]
Norepinephrine transporter 197 Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559	Inhibitor 8504	108.0 nM [Ki]
Dopamine transporter 183 Target ID: CHEMBL338 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559	Inhibitor 8504	274.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cocaine-related disorders 19 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 8 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=24faa247-fe12-4574-881d-445b078b3e87	Primary		Approved 8583	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 Health Status: healthy Age Group: 30-43 years Sex: M 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 Health Status: healthy Age Group: 30-43 years Sex: M 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 Health Status: healthy Age Group: 30-43 years Sex: M 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	unhealthy, 45 years (range: 17- 83 years) Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf	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
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 Health Status: unhealthy Age Group: adult Sex: M 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	unhealthy, 45 years (range: 17- 83 years) Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf
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	unhealthy, 45 years (range: 17- 83 years) Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf
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	unhealthy, 45 years (range: 17- 83 years) Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf
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	unhealthy, 45 years (range: 17- 83 years) Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf
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	unhealthy, 45 years (range: 17- 83 years) Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf
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	unhealthy, 45 years (range: 17- 83 years) Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf
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	unhealthy, 45 years (range: 17- 83 years) Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf
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	unhealthy, 45 years (range: 17- 83 years) Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf
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 Health Status: unhealthy Age Group: adult Sex: M 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 1946	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 CYP3A4/5 296 P-gp 1741 BCRP 910 OAT1 725 OAT3 747 OATP1B1 1079 OATP1B3 961 OCT2 779 OCT1 620 OCT3 159	CES2 33 P-gp 2052 BCRP 697 OAT1 395 OAT3 391 OATP1B1 503 OATP1B3 435 OCT2 434

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=28 Page: 28.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=28 Page: 28.0	no
CYP2D6 2546	inhibitor 4027 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 782	inhibitor 4027 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 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16581093/	yes [Ki 85 uM]
OCT3 161	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16581093/	yes [Ki >1000 uM]

Drug as victim

Target	Modality	Activity	Metabolite
BCRP 697	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT1 395	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT3 391	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OCT2 434	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CES2 33	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf#page=12 Page: 12.0	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf#page=12 Page: 12.0	yes
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	yes	BE 8

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 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
Chemieliva Pharmaceutical Co., Ltd	PBCM0602073
ChemMol	30107819	http://www.chemmol.com/chemmol/30107819.html
ChemMol	99097714	http://www.chemmol.com/chemmol/99097714.html
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	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
Sigma Aldrich	1143008\|USP
Sigma Aldrich	19330\|SIAL
Sigma Aldrich	51621\|SIAL
Sigma Aldrich	C-008\|CERILLIAN
Sigma Aldrich	C1528\|SIAL
Smolecule	S524154	http://www.smolecule.com/products/s524154
Tetrahedron	TS78461
THE BioTek	bt-264235	https://www.thebiotek.com/product/inhibitors/bt-264235
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
Using eye movement desensitization and reprocessing to reduce cocaine cravings.	2000-01	10618047
Effects of prenatal cocaine/crack and other drug exposure on electroencephalographic sleep studies at birth and one year.	2000-01	10617702
Cocaine induces apoptosis in fetal myocardial cells through a mitochondria-dependent pathway.	2000-01	10604926
Effects of AMPA/kainate glutamate receptor antagonists on cocaine-induced convulsions and lethality in mice.	1999-12-15	10618468
Brief report: frequency of maternal cocaine use during pregnancy and infant neurobehavioral outcome.	1999-12	10608102
Nasolacrimal duct obstruction and orbital cellulitis associated with chronic intranasal cocaine abuse.	1999-12	10604666
Severe avascular necrosis of the nasal chambers secondary to cocaine abuse.	1999-12	10604166
Comparative effects of sodium bicarbonate and sodium chloride on reversing cocaine-induced changes in the electrocardiogram.	1999-12	10598131
Cocaine-induced acute renal failure without rhabdomyolysis.	1999-12	10570114
Alcohol plus cocaine prenatally is more deleterious than either drug alone.	1999-11-24	10560774
The effect of prenatal cocaine exposure on neurobehavioral outcome: a meta-analysis.	1999-11-24	10560768
Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice.	1999-11-15	10578459
Dopamine transporter mRNA in autopsy studies of chronic cocaine users.	1999-11-10	10581411
Chronic inhaled cocaine abuse may predispose to the development of pancreatic adenocarcinoma.	1999-11	10612544
The effects of cocaine on mood and sleep in cocaine-dependent males.	1999-11	10609968
The effects of benzamide analogues on cocaine self-administration in rhesus monkeys.	1999-11	10591881
Pramipexole treatment for cocaine cravings.	1999-11	10553755
Level of in utero cocaine exposure and neonatal ultrasound findings.	1999-11	10545554
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.	1999-10-15	10516337
Serotonin(2C) receptors appear to mediate genetic sensitivity to cocaine-induced convulsions.	1999-10	10541732
Prenatal cocaine and neuromotor outcome at four months: effect of duration of exposure.	1999-10	10533991
Antagonism of 5-hydroxytryptamine(4) receptors attenuates hyperactivity induced by cocaine: putative role for 5-hydroxytryptamine(4) receptors in the nucleus accumbens shell.	1999-10	10490917
Effects of the long-acting monoamine reuptake inhibitor indatraline on cocaine self-administration in rhesus monkeys.	1999-10	10490887
Postoperative anisocoria in a patient undergoing endoscopic sinus surgery.	1999-09-28	10499761
[Centrofacial necrosis secondary to cocaine use].	1999-09-24	10491482
Cocaine-induced erythrocytosis and increase in von Willebrand factor: evidence for drug-related blood doping and prothrombotic effects.	1999-09-13	10493323
Rapid induction of behavioral and neurochemical tolerance to cocaethylene, a model compound for agonist therapy of cocaine dependence.	1999-09-01	10485969
Urticarial vasculitis following cocaine use.	1999-09	10583098
Homozygosity at the dopamine DRD3 receptor gene in cocaine dependence.	1999-09	10523822
Effects of chronic 'Binge' cocaine administration on plasma ACTH and corticosterone levels in mice deficient in DARPP-32.	1999-09	10516482
Long-term changes in connexin32 gap junction protein and mRNA expression following cocaine self-administration in rats.	1999-09	10510198
Cocaine induced myocardial infarction.	1999-09	10505926
Association of depressive symptoms during abstinence with the subjective high produced by cocaine.	1999-09	10484960
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures.	1999-09	10454489
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).	1999-08-25	10521585
Amlodipine treatment of cocaine dependence.	1999-08-07	10437993
A case of mutism subsequent to cocaine abuse.	1999-08-06	10435258
Prolonged perioperative myocardial ischemia in a young male: due to topical intranasal cocaine?	1999-08	10526815
Comparison of dopamine receptor antagonists on hyperlocomotion induced by cocaine, amphetamine, MK-801 and the dopamine D1 agonist C-APB in mice.	1999-08	10494572
Role of cocaethylene in toxic symptoms due to repeated subcutaneous cocaine administration modified by oral doses of ethanol.	1999-08	10478337
Sex and menstrual cycle differences in the subjective effects from smoked cocaine in humans.	1999-08	10472516
Cocaine-induced hypertension: role of the peripheral sympathetic system.	1999-08	10433872
Distinct features of seizures induced by cocaine and amphetamine analogs.	1999-07-21	10456426
The effects of continuous cocaine dose on the induction of behavioral tolerance and dopamine autoreceptor function.	1999-07-09	10448878
pH-dependent cocaine-induced cardiotoxicity.	1999-07	10452435
Effects of dopamine receptor antagonists (D1 and D2) on the demand for smoked cocaine base in rhesus monkeys.	1999-06	10435411
U69593, a kappa-opioid agonist, decreases cocaine self-administration and decreases cocaine-produced drug-seeking.	1999-06	10435406
Microbial keratitis following cocaine abuse in a soft contact lens wearer.	1999-04	10450397
Gender differences in treatment-seeking cocaine abusers--implications for treatment and prognosis.	1999	10598213
Dose-related neurobehavioral effects of chronic cocaine use.	1999	10440013

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 `Mon Mar 31 23:40:51 GMT 2025` Edited by `admin` on `Mon Mar 31 23:40:51 GMT 2025`
Record UNII	WM3M8W3FYR
Record Status	`Validated (UNII)`
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Name

Type

Language

COCAINE CITRATE

Common Name

English

8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(BENZOYLOXY)-8-METHYL-, METHYL ESTER, (1R-(EXO,EXO))-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (2:1)

Preferred Name

English

Code System Code Type Description

CAS

5988-00-1

Created by admin on Mon Mar 31 23:40:51 GMT 2025 , Edited by admin on Mon Mar 31 23:40:51 GMT 2025

PRIMARY

PUBCHEM

167713243

Created by admin on Mon Mar 31 23:40:51 GMT 2025 , Edited by admin on Mon Mar 31 23:40:51 GMT 2025

PRIMARY

FDA UNII

WM3M8W3FYR

Created by admin on Mon Mar 31 23:40:51 GMT 2025 , Edited by admin on Mon Mar 31 23:40:51 GMT 2025

PRIMARY

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					I5Y540LHVR

COCAINE

PARENT -> SALT/SOLVATE

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Related Record Type Details


					I5Y540LHVR

COCAINE

ACTIVE MOIETY

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OverviewOther

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Tox targets

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PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator