Cocaine

Title: Cocaine
CAS Registry Number: 50-36-2
CAS Name: [1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester
Additional Names: 3b-hydroxy-1aH,5aH-tropane-2b-carboxylic acid methyl ester benzoate; 2b-carbomethoxy-3b-benzoxytropane; ecgonine methyl ester benzoate; l-cocaine; b-cocaine; benzoylmethylecgonine
Molecular Formula: C17H21NO4
Molecular Weight: 303.35
Percent Composition: C 67.31%, H 6.98%, N 4.62%, O 21.10%
Literature References: From the leaves of Erythroxylon coca Lam. and other species of Erythroxylon, Erythroxylaceae or by synthesis. Extraction procedure: Squibb, Pharm. J. [3] 15, 775, 796; 16, 67 (1885); Emde in Ullmanns Encyklopädie der technischen Chemie Schwyzer, Die Fabrikation pharmazeutischer und chemisch-technischer Produkte (Berlin, 1931). Configuration: Findlay, J. Am. Chem. Soc. 76, 2855 (1954); O. Kovacs et al., Helv. Chim. Acta 37, 892 (1954). Synthesis: R. Willstätter et al., Ann. 434, 111 (1923). Stereospecific synthesis of dl-form: J. J. Tufariello et al., Tetrahedron Lett. 1978, 1733; eidem, J. Am. Chem. Soc. 101, 2435 (1979). Biosynthesis: E. Leete, S. H. Kim, J. Am. Chem. Soc. 110, 2976 (1988). Absorption spectrum: J. J. Dobbie, J. J. Fox, J. Chem. Soc. 103, 1193 (1913); Fischer, Arch. Exp. Pathol. Pharmakol. 170, 610 (1933). Toxicity: C. L. Rose et al., J. Lab. Clin. Med. 15, 731 (1930). Vapor pressure studies: A. H. Lawrence et al., Can. J. Chem. 62, 1886 (1984). Comprehensive description: F. J. Muhtadi, A. A. Al-Badr, Anal. Profiles Drug Subs. 15, 151-231 (1986). Review of pharmacology and pharmacotherapies for abuse: M. Rocío et al., Bioorg. Med. Chem. 12, 5019-5030 (2004).
Properties: Monoclinic tablets from alcohol, mp 98°. Volatile, esp above 90°, but the sublimate is not crystalline. bp0.1 187-188°. [a]D18 -35° (50% alcohol); [a]D20 -16° (c = 4 in chloroform). Aq solns are alkaline to litmus. pKa (15°) 8.61. pKb (15°) 5.59. One gram dissolves in 600 ml water, 270 ml water at 80°, 6.5 ml alcohol, 0.7 ml chloroform, 3.5 ml ether, 12 ml oil turpentine, 12 ml olive oil, 30-50 ml liquid petrolatum. Also sol in acetone, ethyl acetate, carbon disulfide. LD50 i.v. in rats: 17.5 mg/kg (Rose).
Melting point: mp 98°
Boiling point: bp0.1 187-188°
pKa: pKa (15°) 8.61; pKb (15°) 5.59
Optical Rotation: [a]D18 -35° (50% alcohol); [a]D20 -16° (c = 4 in chloroform)
Toxicity data: LD50 i.v. in rats: 17.5 mg/kg (Rose)
Derivative Type: Hydrochloride
CAS Registry Number: 53-21-4
Additional Names: Cocaine muriate
Molecular Formula: C17H21NO4.HCl
Molecular Weight: 339.81
Percent Composition: C 60.09%, H 6.53%, N 4.12%, O 18.83%, Cl 10.43%
Properties: Crystals, granules, or powder; saline, slightly bitter taste; numbs tongue and lips. mp ~195°. [a]D -72° (c = 2 in aq soln pH 4.5). One gram dissolves in 0.4 ml water; 3.2 ml cold, 2 ml hot alcohol; 12.5 ml chloroform. Also sol in glycerol, acetone. Insol in ether or oils. Avoid heat in preparing soln as it decomposes. Preserve in well-closed, light-resistant containers.
Melting point: mp ~195°
Optical Rotation: [a]D -72° (c = 2 in aq soln pH 4.5)
NOTE: This is a controlled substance: 21 CFR, 1308.12.
Therap-Cat: Anesthetic (local).
Therap-Cat-Vet: Topical anesthetic (ophthalmic).
Keywords: Anesthetic (Local).
Cocillana Coclaurine Cocoa Coconut Oil Cod Liver Oil

Cocaine
Kokain - Cocaine.svg
Cocaine3Dan.gif
Systematic (IUPAC) name
methyl (1R,2R,3S,5S)-3- (benzoyloxy)-8-methyl-8-azabicyclo[3.2.1] octane-2-carboxylate
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. C
Legal status Controlled (S8) (AU) Schedule I (CA) A (UK) Schedule II (US) Narcotic Schedules I and III (UN)
Dependence liability High
Routes Topical, oral, insufflation, IV, PO
Pharmacokinetic data
Bioavailability Oral: 33%[1]
Insufflated: 60[2]–80%[3]
Nasal spray: 25[4]–43%[1]
Metabolism Hepatic CYP3A4
Half-life 1 hour
Excretion Renal (benzoylecgonine and ecgonine methyl ester)
Identifiers
CAS number 50-36-2 YesY
ATC code N01BC01 R02AD03, S01HA01, S02DA02
PubChem CID 5760
IUPHAR ligand 2286
DrugBank DB00907
ChemSpider 10194104 YesY
UNII I5Y540LHVR YesY
KEGG D00110 YesY
ChEBI CHEBI:27958 YesY
ChEMBL CHEMBL120901 N
Synonyms methylbenzoylecgonine, benzoylmethylecgonine, ecgonine methyl ester benzoate, 2b-Carbomethoxy −3b-benzoyloxy tropane
Chemical data
Formula C17H21NO4 
Mol. mass 303.353 g/mol
Physical data
Melt. point 98 °C (208 °F)
Boiling point 187 °C (369 °F)
Solubility in water HCl: 1800–2500 mg/mL (20 °C)
 N (what is this?)  (verify)

Cocaine (INN) (benzoylmethylecgonine, an ecgonine derivative) is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant.[5] The name comes from "coca" and the alkaloid suffix "-ine", forming "cocaine". It is a stimulant, an appetite suppressant, and a nonspecific voltage gated sodium channel blocker, which in turn causes it to produce anaesthesia at low doses. Biologically, cocaine acts as a serotonin–norepinephrine–dopamine reuptake inhibitor, also known as a triple reuptake inhibitor (TRI). It is addictive because of its effect on the mesolimbic reward pathway.[6] It is markedly more dangerous than other CNS stimulants, including the entire amphetamine drug class,[7] at high doses due to its effect on sodium channels, as blockade of Nav1.5 can cause sudden cardiac death.[8]

Unlike most molecules, cocaine has pockets[clarification needed] with both high hydrophilic and lipophilic efficiency, violating the rule of hydrophilic-lipophilic balance. This causes it to cross the blood–brain barrier far better than other psychoactive chemicals[citation needed] and may even induce blood-brain barrier breakdown.[9][10]

It is controlled internationally by the Single Convention on Narcotic Drugs (Schedule I, preparation in Schedule III).