Talk:Bupropion

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Bupropion is known to cause extremely unpleasant if not dangerous experiences when used recreationally and especially at high doses.

Please use responsible use practices such as always having a trip sitter when trying this substance.

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Bupropion
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Chemical Nomenclature
Common names Wellbutrin, Zyban, Aplenzin, bupropion
Systematic name (RS)-2-(tert-Butylamino)-1-(3-chlorophenyl)propan-1-one
Class Membership
Psychoactive class Stimulant
Chemical class Substituted cathinone
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



Oral
Dosage
Threshold
(These values are for immediate-release bupropion.)
75 mg
Light 75 - 100 mg
Common 100 - 175 mg
Strong 250 - 325 mg
Heavy 325 mg + Warning: Heavy risk of death by seizures
Duration
Total (These values are for immediate-release bupropion.) 8 - 12 hours
Onset 40 - 60 minutes
Peak 90 minutes
Offset 5 - 8 hours
After effects 1 - 2 days









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.


Bupropion, sold as Wellbutrin (in sustained-release, immediate-release, or extended-release form), Zyban, and known also as amfebutamone, is a cathinone[1] medication used on-label for major depressive disorder and smoking cessation. Bupropion is also used off-label for seasonal affective disorder and ADHD. Bupropion is also taken recreationally for its deliriant-like and stimulant effects. It is a norepinephrine-dopamine reuptake inhibitor (NDRI) and nicotinic acetylcholine receptor antagonist. [2][3] It may exert its deliriant-like actions through antagonism of the nicotinic acetylcholine receptors.

History and culture

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Bupropion was invented by Nariman Mehta of Burroughs Wellcome (now GlaxoSmithKline) in 1969, and the US patent for it was granted in 1974. It was approved by the U.S. Food and Drug Administration as an antidepressant on 30 December 1985, and marketed under the name Wellbutrin. However, a significant incidence of seizures at the originally recommended dosage (400–600 mg/day) caused the withdrawal of the drug in 1986. Subsequently, the risk of seizures was found to be highly dose-dependent, and bupropion was re-introduced to the market in 1989 with a lower maximum recommended daily dose of 450 mg/day.

Chemistry

Bupropion, is a molecule of the cathinone class with substituted a chlorine atom at R3 of its phenyl ring, and a tert-btylamine at the amino group. Cathinones are a sub-category of amphetamines, sharing the core amphetamine structure of a phenyl ring bound to an amino (NH2) group through an ethyl chain and an additional methyl substitution at Rα. Bupropion and other cathinones are differentiated by their ketone substitution on the beta carbon of the amphetamine skeleton, meaning they are β-keto-amphetamines

Pharmacology

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Bupropion binds to norepinephrine transporter (NET) and dopamine transporter (DAT), therefore inhibiting the reuptake of both monoamines. It also binds to nicotinic acetylcholine receptors as an antagonist. [3] Bupropion is extensively metabolized to hydroxybupropion, threohydrobupropion, and erythrohydrobupropion. It exerts its deliriant-like actions through antagonism of the nicotinic acetylcholine receptors, inhibiting the action of acetylcholine. The nAChRs it antagonizes are α3β2, α3β4, α4β2 nicotinic acetylcholine receptors. It also, very weakly, antagonizes the nicotinic acetylcholine receptor α7. [4][5] It is likely this antagonism of the nAChRs that causes bupropion to make users hallucinate and have vivid dreams.

Subjective effects

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Bupropion has an effects profile similar to diphenhydramine at high doses; in low doses, it acts as a mild and usually pleasant substance, but in high doses, delirium begins to take over and make for an extremely uncomfortable experience.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects
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Visual effects
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Cognitive effects
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Auditory effects
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Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

Toxicity and harm potential

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Note: Always conduct independent research and use harm reduction practices if using this substance.

It is strongly recommended that one use harm reduction practices when using bupropion; bupropion can cause seizures and therefore should not be combined with other substances that lower the seizure threshold such as tramadol or be used during GABAergic withdrawal.

Lethal dosage

Bupropion, despite having a relatively average LD50 for rats and mice,[7] is still very dangerous in overdose due to the risk of monoamine flood, seizures, and heart attacks or strokes.

Tolerance and addiction potential

Theoretically, bupropion is addictive because of its activity as an NDRI.

Dangerous interactions

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Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

  • Stimulants (Amphetamine, lisdexamfetamine, methylphenidate, cocaine) - This combination can increase the chance of a heart attack, stroke, or adrenergic flood. These agents often individually lowers the seizure threshold and may have additive effects when combined with Bupropion.
  • Tramadol, tapentadol, or any other drug or substance that lowers the seizure threshold such as dextropropoxyphene or lithium. - This combination can increase the risk of seizures, death from seizures, or status epilepticus (seizure lasting longer than five minutes).
  • Sedatives (Alprazolam, clonazolam, diazepam, opioids, phenobarbital, secobarbital, quetiapine) - Bupropion's effects are masked by sedatives such as benzodiazepines, barbiturates, alcohol, and antipsychotics. If the effects of sedatives wear off before bupropion's, bupropion's effects may seem or become more pronounced.
  • Alcohol - This combination increases the risk of atypical and unpleasant or dangerous side effects such as seizures, paranoia, or depression.
  • Depressive and/or manic disorders - Bupropion can increase the risk of suicide in depressed patients or users. It can also increase the risk of positive or negative mania.
  • DXM - Bupropion is a potent inhibitor of CYP2D6, the enzyme primarily responsible for breaking down DXM. This can lead to prolonged effects and excessive accumulation of DXM in the bloodstream.[8]

Legal status

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Internationally, bupropion is usually not controlled, but it is prescription-only.

See also

External links

Literature

References

  1. Iverson, of the ACMD, L. (2010, March 31). Consideration of the Cathinones. Retrieved from https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/119173/acmd-cathinodes-report-2010.pdf
  2. MedlinePlus. (2017, July 27). Retrieved from https://medlineplus.gov/druginfo/meds/a695033.html
  3. 3.0 3.1 I, C. F., E, B. B., W, M. S., A, N. H., J, L. R., & I, D. M. (2014). Bupropion and bupropion analogs as treatments for CNS disorders. Retrieved from https://www.ncbi.nlm.nih.gov/pubmed/24484978
  4. Lemke, Thomas L., Williams, David A. (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 611–613.
  5. I, C. F., E, B. B., W, M. S., A, N. H., J, L. R., & I, D. M. (2014). Bupropion and bupropion analogs as treatments for CNS disorders. Retrieved from https://www.ncbi.nlm.nih.gov/pubmed/24484978
  6. Ebbert, J. O., MD, MSc, Hatsukami, D. K., Ph.D., Croghan, I. T., Ph.D., Schroeder, D. R., MS, Allen, S. S., MD, Hays, T. J., MD, & Hurt, R. D., MD. (2014, January 8). Combination Varenicline and Bupropion SR for Tobacco Dependence Treatment in Cigarette Smokers: A Randomized Trial. Retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3959999/
  7. Cayman Chemicals. (2012, July 19). Retrieved from https://www.caymanchem.com/msdss/10488m.pdf
  8. Journal of Clinical Psychopharmacology (June 2005). Inhibition of CYP2D6 activity by bupropion; Retrieved from https://pubmed.ncbi.nlm.nih.gov/15876900/


Discussion