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{{Infobox drug
[[파일:Cocaine.svg|섬네일]]
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477165921
| drug_name =
| IUPAC_name = Methyl (1''R'',2''R'',3''S'',5''S'')-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
| image = Kokain - Cocaine.svg
| image2 = Cocaine-from-xtal-1983-3D-balls.png
 
<!--Clinical data-->
| pronounce = kəʊˈkeɪn
| Drugs.com = {{drugs.com|CONS|cocaine}}
| tradename = Neurocaine,<ref>{{cite book |last1=Nordegren |first1=Thomas |title=The A-Z Encyclopedia of Alcohol and Drug Abuse |date=2002 |publisher=Universal-Publishers |isbn=9781581124040 |page=461 |url=https://books.google.ca/books?id=4yaGePenGKgC&pg=PA461 |language=en}}</ref> other
| pregnancy_US = C
| legal_AU = Schedule 8
| legal_CA = Schedule I
| legal_DE = Anlage III
| legal_NZ = Class A
| legal_UK = Class A
| legal_US = Schedule II<ref name=DEA2017Sched>{{cite web|title=DEA / Drug Scheduling|url=https://www.dea.gov/druginfo/ds.shtml|website=www.dea.gov|access-date=7 August 2017|deadurl=no|archive-url=https://web.archive.org/web/20170809044016/https://www.dea.gov/druginfo/ds.shtml|archive-date=9 August 2017|df=dmy-all}}</ref>
| legal_UN = N I III
| legal_status =
| dependency_liability = {{plainlist|
*[[Physical dependence|Physical]]: none<ref>{{cite book |vauthors=Malenka RC, Nestler EJ, Hyman SE |veditors=Sydor A, Brown RY | title = Molecular Neuropharmacology: A Foundation for Clinical Neuroscience | year = 2009 | publisher = McGraw-Hill Medical | location = New York | isbn = 978-0-07-148127-4 | edition = 2nd | chapter = Chapter 15: Reinforcement and Addictive Disorders | page = 367 | quote= While physical dependence and withdrawal occur with some drugs of abuse (opiates, ethanol), these phenomena are not useful in the diagnosis of addiction because they do not occur with other drugs of abuse (cocaine, amphetamine) and can occur with many drugs that are not abused (propranolol, clonidine).}}</ref>
*[[Psychological dependence|Psychological]]: High<ref name=Gho2010>{{cite book| first1 = Hamid | last1 = Ghodse | name-list-format = vanc | title = Ghodse's Drugs and Addictive Behaviour: A Guide to Treatment|date=2010|publisher=Cambridge University Press|isbn=978-1-139-48567-8|page=91|edition=4|url=https://books.google.com/books?id=WYQ23OMjWbcC&pg=PA91|deadurl=no|archive-url=https://web.archive.org/web/20170910234911/https://books.google.com/books?id=WYQ23OMjWbcC&pg=PA91|archive-date=10 September 2017|df=dmy-all}}</ref>}}
| addiction_liability = High<ref>{{cite book|title=Introduction to Pharmacology Third Edition|date=2007|publisher=CRC Press|location=Abingdon|isbn=978-1-4200-4742-4|pages=222–223|url=https://books.google.com/books?id=qfrLBQAAQBAJ&pg=PA222|deadurl=no|archive-url=https://web.archive.org/web/20170910234921/https://books.google.com/books?id=qfrLBQAAQBAJ&pg=PA222|archive-date=10 September 2017|df=dmy-all}}</ref>
| routes_of_administration = [[Topical]], [[route of administration#Oral|oral]], [[insufflation (medicine)|insufflation]], [[intravenous]]
| class = {{plainlist|
*{{abbr|CNS|central nervous system}} [[stimulant]]
*[[Local anesthetic]]}}
 
<!--Pharmacokinetic data-->
| bioavailability = {{plainlist|
*[[route of administration#Oral|By mouth]]: 33%<ref name="fattinger2000">{{cite journal | vauthors = Fattinger K, Benowitz NL, Jones RT, Verotta D | title = Nasal mucosal versus gastrointestinal absorption of nasally administered cocaine | journal = European Journal of Clinical Pharmacology | volume = 56 | issue = 4 | pages = 305–10 | date = July 2000 | pmid = 10954344 | doi = 10.1007/s002280000147 }}</ref>
*[[Insufflation (medicine)|insufflated]]: 60<ref>{{cite journal | vauthors = Barnett G, Hawks R, Resnick R | title = Cocaine pharmacokinetics in humans | journal = Journal of Ethnopharmacology | volume = 3 | issue = 2–3 | pages = 353–66 | year = 1981 | pmid = 7242115 | doi = 10.1016/0378-8741(81)90063-5 }}</ref>–80%<ref>{{cite journal | vauthors = Jeffcoat AR, Perez-Reyes M, Hill JM, Sadler BM, Cook CE | title = Cocaine disposition in humans after intravenous injection, nasal insufflation (snorting), or smoking | journal = Drug Metabolism and Disposition | volume = 17 | issue = 2 | pages = 153–9 | year = 1989 | pmid = 2565204 }}</ref>
*[[Nasal spray]]: 25<ref>{{cite journal | vauthors = Wilkinson P, Van Dyke C, Jatlow P, Barash P, Byck R | title = Intranasal and oral cocaine kinetics | journal = Clinical Pharmacology and Therapeutics | volume = 27 | issue = 3 | pages = 386–94 | date = March 1980 | pmid = 7357795 | doi = 10.1038/clpt.1980.52 }}</ref>–43%<ref name="fattinger2000" />}}
| metabolism = [[liver]] [[CYP3A4]]
| metabolites = [[Norcocaine]], [[benzoylecgonine]], [[cocaethylene]]
| onset = seconds to minutes<ref name="Zimmerman2012"/>
| elimination_half-life = 1 hour
| duration_of_action=5 to 90 minutes<ref name="Zimmerman2012"/>
| excretion = Kidney
 
<!--Identifiers-->
| index_label =
| index2_label =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 50-36-2
| CAS_number2 = 53-21-4
| ATC_prefix = N01
| ATC_suffix = BC01
| ATC_supplemental = {{ATC|R02|AD03}}, {{ATC|S01|HA01}}, {{ATC|S02|DA02}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27958
| PubChem = 446220
| IUPHAR_ligand = 2286
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00907
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10194104
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = I5Y540LHVR
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00110
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 370805
| PDB_ligand = COC
 
<!--Chemical data-->
| C=17 |H=21 |N=1 |O=4
| molecular_weight = 303.353&nbsp;g/mol
| smiles = CN1[C@H]2CC[C@@H]1[C@@H](C(OC)=O)[C@@H](OC(C3=CC=CC=C3)=O)C2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZPUCINDJVBIVPJ-LJISPDSOSA-N
| synonyms = Benzoylmethylecgonine, coke
| melting_point = 98<!--Pubchem-->
| boiling_point = 187
| solubility = ~1.8<!--Pubchem-->
}}
 
'''코카인'''({{llang|en|cocaine}})은 [[코카나무]] 잎에서 추출하는 [[알칼로이드]]이다. [[중추 신경]]을 자극하여 [[식욕 감퇴]]를 일으켜 쾌감을 일으킨다. 19세기에서 20세기까지는 국소 마취제로 쓰기도 했다. 중독성이 있기 때문에 전 세계적으로 의학적인 용도 이외로 코카인을 소지하는 것은 불법이다. 화학식은 C<sub>17</sub>H<sub>21</sub>NO<sub>4</sub>이다.