FANDOM


Cocaine
Cocaine-wiki
Synonyms Coke, crack and numerous others
Brand names None notable
IUPAC name

IUPAC name
methyl (1S,3S,4R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate
ChemSpider

10194104

DrugBank

DB00907

PubChem

446220

PDB fields

N/A

Formula

C17H21NO4

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
InChIKey
InChIKey
ZPUCINDJVBIVPJ-LJISPDSOSA-N
SMILES
SMILES
CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC
(Jmol 3D structure)
Mol. mass

303.3529 g/mol

Erythroxylum coca

Erythroxylum coca

Cocaine is the second most commonly-used illicit drug, with the first being cannabis. It is derived from the coca tree (scientific name: Erythroxylum coca) of South America and is primarily used, medically, for its local anaesthetic properties, that is, its ability to numb a region of the body to which it is applied/injected. It is generally snorted when abused, although intravenous abuse and smoking has been reported and its short-term effect are predominantly sympathomimetic in nature, although it is believed to be particularly toxic in cases of overdoses due to its local anaesthetic actions and their disruptive effects on the electrical cycle of the heart. Traditionally coca leaves are chewed and this slowly releases the drug into one’s bloodstream, producing only mild stimulant actions. Via this route addiction is rare. Smoking and injecting are believed to be the most addictive routes of administration for cocaine.[1]


Therapeutic useEdit

It is generally used during surgery of the ear, nose or throat, so as to relieve the discomfort and is sometimes used in a mouthwash so as to relieve pain from ulcers in the mouth that occur as a result of cancer chemotherapy. It is sometimes given via an injection into or near to the spine so as to relieve severe pain associated with a terminal illness like cancer.[1]

Short-term effectsEdit

Its positive effects include: peaceful euphoria, energy and alertness. Although, as with other stimulants a comedown period often occurs after cocaine use. People can have a greater desire for pleasurable activities like dancing, having sex, drinking alcohol and smoking. It increases ones risk for seizures, if epileptic. People often report that it numbs their mouth or throat if smoked or chewed. It can fatally interact with serotonergic drugs like antidepressants, certain painkillers (like pethidine and tramadol), etc. to cause serotonin syndrome.[1]

Long-term consequences of useEdit

Overall snorting cocaine causes addiction in approximately 16% of people that try it. It is sometimes abused along with heroin in attempts to amplify the euphoria generated by both drugs. Dangerous complications of cocaine abuse include: cocaine cardiomyopathy (which has led to some deaths), psychosis, depression, anxiety disorders, aggression, seizures, hypertension, brain damage and damage to the nasal passages. Damage to the nasal passages is unlikely to heal on its own due to the fact that cocaine is a vasoconstrictor, hence reducing blood supply to the tissues of the nose.

Fetal consequences of maternal useEdit

There is also an increased risk of complications in children born to cocaine-abusing mothers, including: stillbirth, miscarriage, premature labour and placental abruption (basically when the placenta becomes detached from the uterus). This is likely due to the vasoconstrictive effects of cocaine. These babies are often lighter than usual and have a higher risk of cardiovascular birth defects (i.e., congenital heart defects, which can be fatal) and developmental delay.

PharmacologyEdit

Its effects have been potentiated by concurrent use of cannabis, as THC seems to aid its penetration across the blood-brain barrier. Smoking cocaine is also associated with a risk of burning one’s lips, mouth and lungs.[1]

PropertiesEdit

It is a weakly alkaline substance derived from the coca leaf; its freebase form is insoluble in water but very soluble in alcohol. Its hydrochloride salt is the most commonly used form (called “coke,” “blow,” “snow,” “nose candy,” and “yayo” on the street) and is a white powder that is soluble one in 0.5 water. Both forms degrade upon contact with light and moisture. Coke is usually extracted from coca leaves by treating them with hydrochloric acid (which is also found in stomach acid and used in pools) as this converts cocaine in freebase form to its hydrochloride salt. It is usually fairly cheap on the streets, according to Goodman and Gilman.

Its half-life varies significantly from person-to-person and from dose-to-dose but is usually in the range of 0.5-2 hours. Its bioavailability via insufflation (that is, by snorting it) is roughly 30-60%, partly limited via its vasoconstrictive effects, which limits the amount that can get its way into the blood vessels of the nose. It is usually not smoked in its hydrochloride form, as the boiling point for this form is so high that at these temperatures the drug degrades substantially. Via insufflation the effects peak about 14.6 minutes after insufflation, whereas after injection its effects peak roughly 3.1 minutes after administration. Freebase cocaine can be smoked and its effects peak roughly 1.4 minutes after inhalation. Its purity on the streets, in the U.S. at least, is estimated to be 50-60% and a single dose can cost as little as $2.7-5.3 AUD.[2][3]

It achieves its effects inhibiting the reuptake of serotonin, noradrenaline and dopamine.[4][5]

An unfortunate adulterant (that is, a substance used to “cut” the drug) that seems rather common in the U.S. and Canada, at least, is levamisole, an anti-worming agent used in veterinary medicine and previously used in human medicine as an anti-worming and anti-cancer agent. Levamisole is unfortunate as an adulterant in that it causes people to suffer from agranulocytosis in an unacceptably high proportion of cases. This side effect is usually reversible (that is, it goes away if people discontinue the drug) and is more common in women, than in men. It is likely used as an adulterant due to the fact that levamisole has similar properties (including colour and melting point) to cocaine and is cheap.[6][7]

Treatments for addictionEdit

Currently the only widely-accepted treatment for cocaine addiction is psychosocial interventions such as variants of the Alcoholics Anonymous 12-step program, CBT and CT. Some drug treatments that have shown some promise in treating cocaine addiction include: acetylcysteine, bupropion (in combination with CT), citalopram (in combination with CT), desipramine (in combination with CT), dexamfetamine, disulfiram, levodopa-carbidopa (CB, in combination with CT), metamfetamine and topiramate. All of these treatments have only shown promise in relatively small clinical trials, this is why none of them has actually received regulatory approval (by regulatory administrations such as the FDA or TGA) in any country.[4]

It is worth noting, however, that the antidepressants citalopram and desipramine were found in a recent Cochrane review to be ineffective in the treatment of cocaine dependence.[8]

StructuresEdit

Another 2D structure
Cocaine S3D
2D structure
Cocaine


Static 3D
Cocaine3D
Animated 3D
250px cocaine



External linksEdit

Reference listEdit

  1. 1.0 1.1 1.2 1.3 Brayfield, A, ed. (13 December 2013). "Cocaine". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 5 April 2014.
  2. Brunton, LL; Chabner, BA; Knollmann, BC, eds. (2010). Goodman & Gilman's Pharmacological Basis of Therapeutics. (12th ed.). New York, USA: McGraw-Hill Professional. ISBN 978-0-07-162442-8.
  3. Brayfield, A, ed. (13 December 2013). "Cocaine". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 5 April 2014.
  4. 4.0 4.1 Ciccarone, D (March 2011). "Stimulant abuse: pharmacology, cocaine, methamphetamine, treatment, attempts at pharmacotherapy.". Primary Care 38 (1): 41–58, v–vi. doi:10.1016/j.pop.2010.11.004. PMC 3056348. PMID 21356420.
  5. Kazimir, M; Talano, JV; Hayes, S (19 July 2013). "Cocaine-Related Cardiomyopathy". In Sander, GE; Talavera, F; Ooi, HH. Medscape Reference. WebMD. Retrieved 8 June 2014.
  6. Wolford, A; McDonald, TS; Eng, H; Hansel, S; Chen, Y; Bauman, J; Sharma, R; Kalgutkar, AS (June 2012). "Immune-mediated agranulocytosis caused by the cocaine adulterant levamisole: a case for reactive metabolite(s) involvement.". Drug Metabolism and Disposition 40 (6): 1067–75. doi:10.1124/dmd.112.045021. PMID 22393119.
  7. Larocque, A; Hoffman, RS (April 2012). "Levamisole in cocaine: unexpected news from an old acquaintance.". Clinical Toxicology 50 (4): 231–41. doi:10.3109/15563650.2012.665455. PMID 22455354.
  8. Pani, PP; Trogu, E; Vecchi, S; Amato, L (December 2011). "Antidepressants for cocaine dependence and problematic cocaine use.". The Cochrane Database of Systematic Reviews (12): CD002950. doi:10.1002/14651858.CD002950.pub3. PMID 22161371.

Ad blocker interference detected!


Wikia is a free-to-use site that makes money from advertising. We have a modified experience for viewers using ad blockers

Wikia is not accessible if you’ve made further modifications. Remove the custom ad blocker rule(s) and the page will load as expected.