Cocaine

Cocaine
Clinical data
Pronunciation	kə(ʊ)ˈkeɪn
Trade names	Neurocaine, Goprelto, Numbrino, others
Synonyms	Coke, blow, snow, yay, crack (in free base form)
AHFS/Drugs.com	Micromedex Detailed Consumer Information
License data	US DailyMed: Cocaine;
Dependence; liability	Physical: Low Psychological: High
Addiction; liability	High
Routes of; administration	Topical, by mouth, insufflation, intravenous, inhalation
Drug class	SNDRI;; Stimulant;; Local anesthetic;
ATC code	N01BC01 (WHO) R02AD03 (WHO), S01HA01 (WHO), S02DA02 (WHO);
Legal status
Legal status	AU: S8 (Controlled drug) ; BR: F1 ; CA: Schedule I ; DE: Anlage III (Special prescription form required) ; NZ: Class A ; UK: Class A ; US: Schedule II ; UN: Narcotic Schedules I and III ;
Pharmacokinetic data
Bioavailability	By mouth: 33%; Insufflated: 60–80%; Nasal spray: 25–43%;
Metabolism	Liver, CYP3A4
Metabolites	Norcocaine, benzoylecgonine, cocaethylene
Onset of action	Seconds to minutes
Duration of action	20 to 90 minutes
Excretion	Kidney
Identifiers
	IUPAC name Methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate;
CAS Number	50-36-2 ;
PubChem CID	446220;
IUPHAR/BPS	2286;
DrugBank	DB00907 ;
ChemSpider	10194104 ;
UNII	I5Y540LHVR;
KEGG	D00110 ;
ChEBI	CHEBI:27958 ;
ChEMBL	ChEMBL370805 ;
PDB ligand	COC (PDBe, RCSB PDB);
ECHA InfoCard	100.000.030
Chemical and physical data
Formula	C17H21NO4
Molar mass	303.36 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	98 °C (208 °F)
Boiling point	187 °C (369 °F)
Solubility in water	1.8g/L (22 °C)
	SMILES CN1[C@H]2CC[C@@H]1[C@@H](C(OC)=O)[C@@H](OC(C3=CC=CC=C3)=O)C2;
	InChI 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 ; Key:ZPUCINDJVBIVPJ-LJISPDSOSA-N ;
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Cocaine (also cocain) is a strong stimulant drug that is made from coca leaves. It is illegal in most countries. Cocaine is usually a white powder. Because it is a stimulant, cocaine gives people energy. It also makes people feel very happy when it is taken. When used this way, cocaine is very addictive. However, cocaine can also be used as a local anesthetic if it is applied topically (onto the skin or gums) and this was how it was first used.^[13] The name comes from: "coca" - the plant it comes from - and "-ine" - anesthetic.

↑ Ghodse H (2010). Ghodse's Drugs and Addictive Behaviour: A Guide to Treatment (4 ed.). Cambridge University Press. p. 91. ISBN 978-1-139-48567-8. Archived from the original on 10 September 2017.
↑ Introduction to Pharmacology (3 ed.). Abingdon: CRC Press. 2007. pp. 222–223. ISBN 978-1-4200-4742-4. Archived from the original on 10 September 2017.
↑ Nordegren T (2002). The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal-Publishers. p. 461. ISBN 978-1-58112-404-0. Archived from the original on 8 July 2024. Retrieved 3 September 2020.
↑ Cite error: The named reference Goprelto FDA label was used but no text was provided for refs named (see the help page).
↑ Cite error: The named reference Numbrino FDA label was used but no text was provided for refs named (see the help page).
↑ Azizi SA (December 2020). "Monoamines: Dopamine, Norepinephrine, and Serotonin, Beyond Modulation, "Switches" That Alter the State of Target Networks". The Neuroscientist. 28 (2): 121–143. doi:10.1177/1073858420974336. ISSN 1073-8584. PMID 33292070. S2CID 228080727.
↑ "DEA / Drug Scheduling". www.dea.gov. Archived from the original on 9 August 2017. Retrieved 7 August 2017.
↑ ^8.0 ^8.1 Fattinger K, Benowitz NL, Jones RT, Verotta D (July 2000). "Nasal mucosal versus gastrointestinal absorption of nasally administered cocaine". European Journal of Clinical Pharmacology. 56 (4): 305–10. doi:10.1007/s002280000147. PMID 10954344. S2CID 20708443.
↑ Barnett G, Hawks R, Resnick R (1981). "Cocaine pharmacokinetics in humans". Journal of Ethnopharmacology. 3 (2–3): 353–66. doi:10.1016/0378-8741(81)90063-5. PMID 7242115.
↑ Jeffcoat AR, Perez-Reyes M, Hill JM, Sadler BM, Cook CE (1989). "Cocaine disposition in humans after intravenous injection, nasal insufflation (snorting), or smoking". Drug Metabolism and Disposition. 17 (2): 153–9. PMID 2565204.
↑ Wilkinson P, Van Dyke C, Jatlow P, Barash P, Byck R (March 1980). "Intranasal and oral cocaine kinetics". Clinical Pharmacology and Therapeutics. 27 (3): 386–94. doi:10.1038/clpt.1980.52. PMID 7357795. S2CID 29851205.
↑ ^12.0 ^12.1 Cite error: The named reference Zimmerman2012 was used but no text was provided for refs named (see the help page).
↑ Macmillan Dictionary for Students Macmillan, Pan Ltd. (1981), page 192. Retrieved 2010-7-21.

[Gho2010-1] Ghodse H (2010). Ghodse's Drugs and Addictive Behaviour: A Guide to Treatment (4 ed.). Cambridge University Press. p. 91. ISBN 978-1-139-48567-8. Archived from the original on 10 September 2017.

[2] Introduction to Pharmacology (3 ed.). Abingdon: CRC Press. 2007. pp. 222–223. ISBN 978-1-4200-4742-4. Archived from the original on 10 September 2017.

[3] Nordegren T (2002). The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal-Publishers. p. 461. ISBN 978-1-58112-404-0. Archived from the original on 8 July 2024. Retrieved 3 September 2020.

[Goprelto_FDA_label-4] Cite error: The named reference Goprelto FDA label was used but no text was provided for refs named (see the help page).

[Numbrino_FDA_label-5] Cite error: The named reference Numbrino FDA label was used but no text was provided for refs named (see the help page).

[Monoamines:_Dopamine,_Norepinephrin-6] Azizi SA (December 2020). "Monoamines: Dopamine, Norepinephrine, and Serotonin, Beyond Modulation, "Switches" That Alter the State of Target Networks". The Neuroscientist. 28 (2): 121–143. doi:10.1177/1073858420974336. ISSN 1073-8584. PMID 33292070. S2CID 228080727.

[DEA2017Sched-7] "DEA / Drug Scheduling". www.dea.gov. Archived from the original on 9 August 2017. Retrieved 7 August 2017.

[fattinger2000-8] 8.0 ^8.1 Fattinger K, Benowitz NL, Jones RT, Verotta D (July 2000). "Nasal mucosal versus gastrointestinal absorption of nasally administered cocaine". European Journal of Clinical Pharmacology. 56 (4): 305–10. doi:10.1007/s002280000147. PMID 10954344. S2CID 20708443.

[9] Barnett G, Hawks R, Resnick R (1981). "Cocaine pharmacokinetics in humans". Journal of Ethnopharmacology. 3 (2–3): 353–66. doi:10.1016/0378-8741(81)90063-5. PMID 7242115.

[10] Jeffcoat AR, Perez-Reyes M, Hill JM, Sadler BM, Cook CE (1989). "Cocaine disposition in humans after intravenous injection, nasal insufflation (snorting), or smoking". Drug Metabolism and Disposition. 17 (2): 153–9. PMID 2565204.

[Intranasal_and_oral_cocaine_kinetic-11] Wilkinson P, Van Dyke C, Jatlow P, Barash P, Byck R (March 1980). "Intranasal and oral cocaine kinetics". Clinical Pharmacology and Therapeutics. 27 (3): 386–94. doi:10.1038/clpt.1980.52. PMID 7357795. S2CID 29851205.

[Zimmerman2012-12] 12.0 ^12.1 Cite error: The named reference Zimmerman2012 was used but no text was provided for refs named (see the help page).

[13] Macmillan Dictionary for Students Macmillan, Pan Ltd. (1981), page 192. Retrieved 2010-7-21.

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