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Overload

Cocaine

Category: Medicines

Type

Involuntary and voluntary

Introduction and description

Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. 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.

Cocaine was once extensively prescribed for pain relief.  It was also historically used as a topical anaesthetic in eye and nasal surgery.  It is still used in nasal and lacrimal duct surgery.

“The major disadvantages of this use are cocaine's intense vasoconstrictor activity and potential for cardiovascular toxicity”.

In Australia it is currently prescribed for use as a local anaesthetic for conditions such as mouth and lung ulcers. Some ENT specialists occasionally use cocaine within the practice when performing procedures such as nasal cauterization. In this scenario dissolved cocaine is soaked into a ball of cotton wool, which is placed in the nostril for the 10–15 minutes immediately before the procedure, thus performing the dual role of both numbing the area to be cauterized, and vasoconstriction. Even when used this way, some of the used cocaine may be absorbed through oral or nasal mucosa and give systemic effects.

Background

SNDRI -  Cocaine is a dopamine transporter and norepinephrine transporter blocker that competitively inhibits dopamine uptake to increase the lifetime of dopamine in the system.  It can increase the amount of dopamine in the system by up to 150 percent.  It acts as a serotonin–norepinephrine–dopamine reuptake inhibitor.  

It is addicting in the way that all reuptake inhibitors are addicting but is unusual because it  crosses the blood-brain barrier with vastly superior reinforcement than many other reuptake inhibitors meaning it has the potential to both be more effective, but also do more damage.

For more details I urge you to read the section on Serotonin imbalance, as this section describes the effects of cocaine use

Legality - Its possession, cultivation, and distribution are illegal for non-medicinal and non-government sanctioned purposes in virtually all parts of the world. “Although its free commercialization is illegal and has been severely penalized in virtually all countries, its use worldwide remains widespread in many social, cultural, and personal settings”.

Cocaethylene (ethylbenzoylecgonine) is structurally similar to cocaine, and formed in vivo when cocaine and ethyl alcohol have been ingested simultaneously.  It is a ‘recreational drug’  and a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).  Cocaethylene appears to, in most users, produce more euphoria and possess a longer duration of action than cocaine. Some studies “suggest that it may be more cardiotoxic than cocaine”. I am unsure how anything can be 'more' cardiotoxic - cocaine is extremely high on the list. Cocaethylene is more potent than cocaine at binding to the dopamine transporter, however it is less potent at binding to the serotonin transporter and norepinephrine transporter.

Analogues  - There are also a very large number of anlogues of cocaine, a small sample are listed below:

  • 4'-Fluorococaine has only around the same potency as cocaine as an inhibitor of dopamine reuptake, but is a much stronger serotonin reuptake inhibitor than cocaine
  • CFT - (–)-2-β-Carbomethoxy-3-β-(4-fluorophenyl)tropane (β-CFT, WIN 35,428) is a dopamine reuptake inhibitor and is structurally derived from cocaine. It is around 3-10x more potent than cocaine and lasts around 7 times longer
  • FE-β-CPPIT  - N-(2'-Fluoroethyl-#-3β-#4'-chlorophenyl#-2β-#3'-phenylisoxazol-5'-yl#nortropane
  • FP-β-CPPIT  - N-(3'-Fluoropropyl-#-3β-#4'-chlorophenyl#-2β-#3'-phenylisoxazol-5'-yl#nortropane 
  • pFBT  - (3β-(p-Fluorobenzoyloxy)tropane, 8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 4-fluorobenzoic acid ester, 4-fluorotropacocaine, 3-pseudotropyl-4-fluorobenzoate) -  first reported as a designer drug analogue of cocaine by the European Monitoring Centre for Drugs and Drug Addiction in 2008.
  • RTI range - RTI-112 , RTI-113, RTI-120, RTI-121, RTI 126, RTI-150, RTI-177, RTI-229 , RTI-274 , RTI-31 , RTI-32, RTI-336RTI-352, RTI-353, RTI-371, RTI-51, RTI-55, for example:
    • RTI-55 [iometopane] is “ used in scientific research” and is a DRI.  It is one of the most potent stimulants commercially available, which “limits its use in humans, as it might have significant abuse potential if used outside of a strictly controlled medical setting”  In contrast to RTI-31 which is predominantly dopaminergic, it also has an affinity for the SERT, while retaining mostly all of its DAT blocking activity
  • Salicylmethylecgonine, (2'-Hydroxycocaine) is a synthetic analogue and a possible active metabolite of cocaine.   Its potency in vitro is around 10x that of cocaine.
  • WF-11 - 2β-Propanoyl-3β-(4-tolyl)-tropane also known as PTT is a cocaine analogue 20 times more potent than cocaine at binding to the dopamine transporter with increased selectivity for the norepinephrine transporters
  • WF-23 - 2β-Propanoyl-3β-(2-naphthyl)-tropane is a cocaine analogue. It is claimed to be several hundred times more potent than cocaine at being serotonin-norepinephrine-dopamine reuptake inhibitor
  • WF-31 - 2-Propanoyl-3-(4-isopropylphenyl)-tropane;  PIT is a cocaine analogue, approximately ten times more potent than cocaine at binding to serotonin and at inhibiting serotonin uptake
  • WF-33 - 2α-(Propanoyl)-3β-(2-(6-methoxynaphthyl))-tropane is a cocaine analogue. It, along with WF-23  , are considered the more potent of the WF series cocaine analogues.

How it works

Whether administered by a doctor or voluntarily taken, overdosing on cocaine can produce hallucinations, visions or worse.

Short term any hallucinations etc are caused by the cardiological effects - hypoxia being the main outcome.  Long term use, however, can result in permanent brain damage, liver damage, and permanent heart problems.  You can also become permanently psychotic.  It is a form of poisoning.

Neurotoxic and cardiotoxic effects of cocaine and ethanol - Farooq MU, Bhatt A, Patel M;  Department of Neurology and Ophthalmology, Michigan State University, East Lansing, MI, USA.
INTRODUCTION:  Concurrent abuse of alcohol and cocaine results in the formation of cocaethylene, a powerful cocaine metabolite. Cocaethylene potentiates the direct cardiotoxic and indirect neurotoxic effects of cocaine or alcohol alone.
CASE REPORT:  A 44-year-old female with history of cocaine and alcohol abuse presented with massive stroke in the emergency department. CT scan revealed extensive left internal carotid artery dissection extending into the left middle and anterior cerebral arteries resulting in a massive left hemispheric infarct, requiring urgent decompressive craniectomy. The patient had a stormy hospital course with multiple episodes of torsades de pointes in the first 4 days requiring aggressive management. She survived all events and was discharged to a nursing home with residual right hemiplegia and aphasia.
CONCLUSION:  The combination of ethanol and cocaine has been associated with a significant increase in the incidence of neurological and cardiac emergencies including cerebral infarction, intracranial hemorrhage, myocardial infarction, cardiomyopathy, and cardiac arrhythmias. The alteration of cocaine pharmacokinetics and the formation of cocaethylene have been implicated, at least partially, in the increased toxicity of this drug combination

and

Cognitive and executive dysfunctions in cocaine dependence: a case-control study].- [Article in Spanish] - Madoz-Gurpide A, Ochoa-Mangado E;  Centro de Salud Mental San Blas, Madrid, Espana.
INTRODUCTION. In the past, various studies have related chronic cocaine use to diverse types of neuropsychological impairment. However, the majority of these studies offer partial results using batteries of tests of little ecological weight.
AIM. To investigate neuropsychological impairment (and of executive functions in particular) amongst severe chronic cocaine users, measured by means of more ecological tests and in a more global manner, taking confounding factors into account, such as age, years of schooling, gender, race, opioid dependence and alcohol consumption.
SUBJECTS AND METHODS. We performed an observational study, comparing the cocaine dependence group (n = 24) with a non-cocaine use control group (n = 27).
RESULTS. The principal results revealed significant differences in the direct and reverse digit span tests (p = 0.008 and p < 0.001 respectively), and in the Cards Test (p < 0.001). They also showed a significance result in the Zoo Map Test (p = 0.001), and in different measurements but not in all forming part of the Wisconsin test (number of correct responses and number of errors).
CONCLUSIONS. These results confirm that the chronic use of cocaine per se causes neuropsychological impairment that is manifested in classical and ecologically-valid tests. This impairment may influence patients' functionality and prognosis, and also therapeutic failure.

References and further reading

The EROWID cocaine entry

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