Providing straightforward information pertaining to drugs, drug use & drug policy. The Grey Pages promotes drug-related literacy and advocates a system of viable and tolerant drug policies. This is my personal collection of commentaries, essays, tid-bits, and other such writings on everything ranging from drug use, drug policy and drug-myths, to drug-science, addiction, human behavior, and the workings of the human brain. I started this blog with a particular focus on opioids, and over the past year have found my interest gravitate toward the intriguing, ever-changing world of designer intoxicants (i.e. "research chemicals" or "designer drugs").

Monday, March 12, 2012

Bupropion Vault

Basic: Popularly known as Wellbutrin or Amfebutamone. Bupropion is a mild psychostimulant compound with antidepressant properties. It is used medicinally in the US in the treatment of depression and nicotine withdrawal/cravings. 

Properties: Like other related sympathomimetic phenethylamines, bupropion increases synaptic concentrations of dopamine and norepinephrine. Its specific mode of action is norepinephrine and dopamine reuptake inhibition. Bupropion has also been reported to be a dopamine/norepinephrine releasing agent. Additionally, it acts as an antagonist at nicotinic-acetylcholine receptors.

Use: Catecholaminergic properties have made bupropion a popular adjunct to SSRI compounds such as fluoxetine, sertraline, and paroxetine - It has been assumed to enhance their antidepressant efficacy; more than likely by reducing the symptoms of amotivation, anhedonia, or chronic fatiguge that are common in many patients taking the SSRIs. Bupropion is often useful 'off label' for treating protracted withdrawal in abstinent methamphetamine or cocaine users. Most of the clinically used bupropion products are administered orally, usually in tablet form. Both immediate release pills and long acting (controlled release) pills are available.

Despite its structural and pharmacological similarity to other amphetamine-type psychostimulants, bupropion is not classified as a controlled substance, though its close relative diethylpropion is a schedule IV controlled substance. The reinforcing and dependence producing properties of bupropion are relatively mild compared to other phenethylamines such as cathinone, methamphetamine and amphetamine, and its psychostimulant properties are more stable, drawn out, and less pronounced, especially when the drug is taken orally and/or the controlled release tablets are used. However there are plenty of anecdotal reports involving intranasal and even intravenous administration of the tablets. Many individuals have reported a short-lived euphoric experience, in some cases an initial "rush", similar to amphetamine. Bupropion was able to maintain self administration in a manner consistent with cocaine when given intravenously in primates. Bupropion is known to lower the seizure threshold; and has caused seizures when crushed, snorted, injected, or otherwise taken in doses well in excess of its labeling. However, the incidence of seizures was reported to be 0.35% to 0.44% of all individuals taking oral bupropion in daily doses of 450 mg  or less.

Chemistry: Bupropion is a sympathomimetic phenethylamine and is structurally related to drugs of the aminopropiophenone (cathinone) and amphetamine classes. Chemically, bupropion can be considered a halogenated N-butyl analogue of cathinone. The structural similarities between these compounds is illustrated below.

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