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{{Talk:SubstanceBox/Yohimbine}}
{{Talk:SubstanceBox/Yohimbine}}


'''Yohimbine''' hydrochloride (also known as '''quebrachine''') is a [[naturally-occurring]] [[Psychoactive class::stimulant]] substance of the [[chemical class::indole]] class derived from the bark of the African tree [[wikipedia:Pausinystalia johimbe|''Pausinystalia johimbe'']]. It is the major active constituent of the bark, with the active ingredient being yohimbine hydrochloride. It has various uses including as an aphrodisiac and a weight loss agent. Yohimbine is also used as a mydriatic and sympatholytic and has been suggested as an antidote to [[clonidine]] and [[wikipedia:xylazine|xylazine]] overdose.
'''Yohimbine''' (also known as '''quebrachine''') is a [[naturally-occurring]] [[Psychoactive class::stimulant]] substance of the [[chemical class::indoloquinolizidine]] class.  It has various uses including as an aphrodisiac and a weight loss agent. Most often, yohimbine is used in the form of hydrochloride.
 
Yohimbine, an alpha-2 [[adrenergic]] [[receptor]] [[antagonist]], is an indole [[alkaloid]] found in numerous botanical sources. It is the predominant alkaloid in extracts from the bark of the [[wikipedia:Pausinystalia johimbe|''Pausinystalia johimbe'']] tree, and can also be found in [[wikipedia:Rauwolfia|''Rauwolfia'']] root.<ref>Yohimbine | https://www.sciencedirect.com/science/article/pii/B9780128012383988627</ref> Many of its effects are attributed to its α2-adrenergic receptor antagonist activity, which increases central sympathetic outflow and raises [[Increased blood pressure|blood pressure]], [[Increased heart rate|heart rate]], and [[norepinephrine]] levels.<ref name="Interactions">Interactions between Nutraceuticals/Nutrients and Therapeutic Drugs | https://www.sciencedirect.com/science/article/pii/B9780128021477000607</ref>
 
Yohimbine is also used as a mydriatic and sympatholytic and has been suggested as an antidote to [[clonidine]] and [[wikipedia:xylazine|xylazine]] overdose.<ref>Encyclopedia of Toxicology. Yohimbine | https://www.sciencedirect.com/science/article/pii/B9780123864543007995</ref>
 
While some reviewers noted that this extract did help them maintain an erection, lose weight or increase their energy level, many noted that the side effects they experienced outweighed any benefits they received. Some took a dosage that was considerably lower than recommended and still had unwanted side effects.


==Chemistry==
==Chemistry==
{{chemistry}}
{{chemistry}}
Yohimbine is an indole alkaloid molecule of the indole chemical class. It is structurally related to [[wikipedia:mitragynine|mitragynine]] but shows a totally different pharmacology.  
Yohimbine is an indole [[alkaloid]] molecule of the indoloquinolizidine chemical class. Analyses of yohimbe bark indicate that the average total indole alkaloid content is approximately 3–6%, with approximately 10–15% of the alkaloids being yohimbine. In addition to yohimbine and its isomers (α-yohimbine, β-yohimbine, allo-yohimbine), these alkaloids include ajmaline, dihydroyohimbine, corynantheidine, dihydrocorynantheine, and corynanthine (rauhimbin).<ref name="Interactions"/>  Most often, yohimbine is used in the form of hydrochloride.
 
Yohimbine has been used for a variety of medical purposes, including as a treatment for erectile dysfunction, sexual dysfunction caused by selective serotonin reuptake inhibitors (SSRIs), and as a treatment for xerostomia (dry mouth). It has also been used as a performance-enhancing supplement in bodybuilding and athletics, as well as a weight loss supplement. However, there is limited scientific evidence to support the effectiveness of yohimbine for these purposes.
 
Yohimbine is believed to work by blocking alpha-2 adrenergic receptors, which can increase blood flow and improve circulation. However, it can also cause side effects such as anxiety, high blood pressure, and rapid heart rate. It may also interact with certain medications, such as antidepressants and medications for high blood pressure.
 
Despite its potential medical uses, yohimbine is not regulated by the FDA and is considered a dietary supplement. As with all supplements, it is important to discuss the use of yohimbine with a healthcare provider before taking it.
 
Yohimbine has been found to be effective in treating erectile dysfunction in men. It is believed to work by blocking alpha-2 adrenergic receptors, which can increase blood flow and improve circulation. This can improve the symptoms of erectile dysfunction. However, more research is needed to fully understand the effectiveness and safety of yohimbine for this purpose.
 
Studies have also found that yohimbine may be effective in treating sexual dysfunction caused by SSRIs. It is believed to work by increasing the release of neurotransmitters such as dopamine and norepinephrine, which can improve sexual function. However, more research is needed to confirm these findings.
 
In addition to its potential medical uses, yohimbine is also used as a performance-enhancing supplement in bodybuilding and athletics, as well as a weight loss supplement. However, there is limited scientific evidence to support the effectiveness of yohimbine for these purposes.
 
As with all supplements, it is important to discuss the use of yohimbine with a healthcare provider before taking it. Yohimbine can cause side effects such as anxiety, high blood pressure, and rapid heart rate. It may also interact with certain medications, such as antidepressants and medications for high blood pressure.


==Pharmacology==
==Pharmacology==
{{pharmacology}}
The primary and most researched mechanism of yohimbine is antagonism of a class of receptors known as alpha-2 [[adrenergic]] [[receptors]], thus it increases [[noradrenaline]] levels by preventing their uptake into subsequent neurons. Blocking alpha-2 adrenoceptors increases blood pressure, releases insulin, and decreases blood sugar levels. Yohimbine also, however, blocking alpha-1 adrenergic receptors, albeit with lower affinity. It also has been shown to weak [[MAOI|inhibit monoamine oxidase]].<ref name="Toxic">Encyclopedia of Toxicology | https://www.sciencedirect.com/science/article/pii/B9780123864543007995</ref>
Yohimbine antagonize alpha-2 [[adrenergic]] [[receptors]], leading to increased blood flow to the genital area, where blocking the presynaptic alpha-2 receptors will lead to an increase in both nitric oxide and [[noradrenaline]] release. Blocking alpha-2 adrenoceptors increases blood pressure, releases insulin, and decreases blood sugar levels. Yohimbine also, however, interacts with alpha-1 adrenergic receptors, albeit with lower affinity, therefore, at higher doses an α<sub>1</sub> blockade can occur and overwhelm the effects of the α<sub>2</sub> blockade, making it difficult to predict the response (alpha-1 antagonism reduces blood pressure and overall CNS stimulation). It also has been shown to weak [[MAOI|inhibit monoamine oxidase]].<ref name="Toxic">Encyclopedia of Toxicology | https://www.sciencedirect.com/science/article/pii/B9780123864543007995</ref>


In high concentrations yohimbine behaves as an [[antagonist]] at [[dopamine]] D<sub>2</sub> and D<sub>3</sub> [[receptors]], [[serotonin]] 5-HT<sub>1B</sub>, 5-HT<sub>1D</sub>, and 5-HT<sub>2B</sub> receptors, and as a partial [[agonist]] at 5-HT<sub>1A</sub>.<ref>Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/10611634</ref>
In high concentrations yohimbine behaves as an [[antagonist]] at [[dopamine]] D<sub>2</sub> and D<sub>3</sub> [[receptors]], [[serotonin]] 5-HT<sub>1B</sub>, 5-HT<sub>1D</sub>, and 5-HT<sub>2B</sub> receptors, and as a partial [[agonist]] at 5-HT<sub>1A</sub>.<ref>Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/10611634</ref>
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==Subjective effects==
==Subjective effects==
{{EffectStub}}
{{EffectStub}}
Compared to other [[stimulants]], yohimbine can be described as less recreational. For many users, it is unpleasant, and often even with a small dosage causes [[anxiety]] and [[irritability]].
{{Preamble/SubjectiveEffects}}                                                                             
{{Preamble/SubjectiveEffects}}                                                                             
{{effects/base
{{effects/base


|{{effects/physical|
|{{effects/physical|
*'''[[Effect::Stimulation]]''' - Stimulation is especially noticeable once you begin an activity that increase adrenaline output, such as training.
Yohimbine pretty much gives body energy while doing very little for mind.
*'''[[Effect::Appetite suppression]]'''<ref>Yohimbine and rauwolscine reduce food intake of genetically obese (obob) and lean mice. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/6145164</ref>
*'''[[Effect::Appetite suppression]]'''<ref>Yohimbine and rauwolscine reduce food intake of genetically obese (obob) and lean mice. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/6145164</ref>
*'''[[Effect::Dizziness]]'''<ref name="Toxic"/>
*'''[[Effect::Dizziness]]'''<ref name="Toxic"/>
*'''[[Effect::Frequent urination]]'''<ref name="Biomedical"/>
*'''[[Effect::Headaches]]'''<ref name="Toxic"/>
*'''[[Effect::Headaches]]'''<ref name="Toxic"/>
*'''[[Effect::Increased blood pressure]]'''<ref name="Biomedical"/>
*'''[[Effect::Hyperthermia]]'''
*'''[[Effect::Decreased blood pressure]]'''
*'''[[Effect::Increased blood pressure]]'''<ref name="Biomedical">Reference Module in Biomedical Sciences | https://www.sciencedirect.com/science/article/pii/B9780128012383988627</ref>
*'''[[Effect::Increased heart rate]]'''<ref name="Toxic"/>
*'''[[Effect::Increased heart rate]]'''<ref name="Toxic"/>
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Increased salivation]]''' - The mechanism by which yohimbine increases submaxillary secretion appears to involve inhibition of presynaptic a2-ARs located on the chorda tympani, which inhibit cholinergic transmission.<ref name="Review">Yohimbine: a clinical review | https://www.sciencedirect.com/science/article/pii/S0163725801001565</ref>
*'''[[Effect::Motor control loss|Incoordination]]'''<ref name="Toxic"/>
*'''[[Effect::Nausea]]'''<ref name="Toxic"/>
*'''[[Effect::Pupil dilation]]'''<ref name="Toxic"/>
*'''[[Effect::Seizures]]'''<ref name="Toxic"/> - In extremely high dose, yohimbine can induce seizures.
*'''[[Effect::Stamina enhancement]]'''
*'''[[Effect::Stamina enhancement]]'''
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the user, yohimbine is usually considered to be mildly to moderately energetic and stimulating in a fashion that is considerably weaker in comparison to that of traditional recreational stimulants such as [[amphetamine]] or [[cocaine]], but stronger than [[caffeine]].
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Vasoconstriction]]'''
*'''[[Effect::Vasoconstriction]]'''
*'''[[Effect::Vasodilation]]'''
*'''[[Effect::Increased salivation]]'''<ref>Evidence for activation of both adrenergic and cholinergic nervous pathways by yohimbine, an alpha 2-adrenoceptor antagonist. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/7557820</ref>
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Nausea]]'''<ref name="Toxic"/>
*'''[[Effect::Pupil dilation]]'''<ref name="Toxic"/>
*'''[[Effect::Seizures]]''' - In high doses.<ref name="Toxic"/>
*'''[[Effect::Motor control loss|Incoordination]]'''<ref name="Toxic"/>
*'''[[Effect::Frequent urination]]'''<ref name="Biomedical"/>


}}
}}
|{{effects/cognitive|
|{{effects/cognitive|
*'''[[Effect::Anxiety suppression]]''' - Yohimbine decrease social anxiety and increased mood. <ref>Yohimbine enhancement of exposure therapy for social anxiety disorder: a randomized controlled trial. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/24237691</ref><ref>Cognitive Enhancers for Anxiety Disorders (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3114287/</ref>
*'''[[Effect::Analysis enhancement]]'''<ref>Differential effects of noradrenergic drugs on anxiety and arousal in healthy volunteers with high and low anxiety. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/9004342</ref>
*'''[[Effect::Analysis enhancement]]'''<ref>Differential effects of noradrenergic drugs on anxiety and arousal in healthy volunteers with high and low anxiety. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/9004342</ref>
*'''[[Effect::Anxiety]]'''<ref name="Toxic"/>
*'''[[Effect::Anxiety]]'''<ref name="Toxic"/> - Yohimbine exerts a stimulating action on the emotions and may increase anxiety.
*'''[[Effect::Cognitive dysphoria]]'''
*'''[[Effect::Cognitive euphoria]]''' - Generally, this effect is rare and less pronounced than with classical [[stimulants]].
*'''[[Effect::Disinhibition]]''' - Yohimbine can increase impulsivity.<ref name="Sport">An Overview of Yohimbine in Sports Medicine | https://www.sciencedirect.com/science/article/pii/B9780128054130000156</ref>
*'''[[Effect::Dream potentiation]]''' - Many users report that yohimbine in a dosage of up to 1 mg has a positive effect on the brightness of sleep and its memory.
*'''[[Effect::Ego inflation]]'''
*'''[[Effect::Emotion enhancement]]''' - Yohimbine makes whatever cognitive, especially emotional, sensation more intense. That sensation intensified could be positive or negative, it just depends on the context.
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Irritability]]'''
*'''[[Effect::Irritability]]'''
*'''[[Effect::Memory enhancement]]''' - Yohimbine improve long-term memory by increasing norepinephrine levels.<ref>Stimulation of the noradrenergic system enhances and blockade reduces memory for emotional material in man. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/10576300</ref>
*'''[[Effect::Motivation enhancement]]''' - Yohimbine can get motivation and mood levels up.
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Cognitive dysphoria]]'''
*'''[[Effect::Emotion enhancement]]'''
}}
}}
}}
}}
===Experience reports===
===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:
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
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==Toxicity and harm potential==
==Toxicity and harm potential==
Yohimbine has a [[Toxicity::low toxicity]] relative to dose. Side effects associated with the use of yohimbine include anxiety, an increased urinary frequency, and increases in blood pressure at higher doses.<ref name="Biomedical">Reference Module in Biomedical Sciences | https://www.sciencedirect.com/science/article/pii/B9780128012383988627</ref> Higher doses (200 – 5,000 mg) result in stronger side effects and can be toxic to the brain. Extremely high doses (above 5,000 mg) can be lethal.<ref>Case study: two fatal case reports of acute yohimbine intoxication. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/23846025</ref>
{{toxicity}}
Yohimbine has a [[Toxicity::low toxicity]] relative to dose. Various studies have shown that in reasonable doses in a careful context, it presents few negative cognitive, psychiatric or toxic physical consequences, though some exist. The side effects of yohimbine are clearly dose-dependent, are generally apparent at doses much higher than the claimed therapeutic doses. Generally all reported side effects of yohimbine are reversible and resolve spontaneously within a relatively short time after termination of the drug therapy<ref name="Review"/>, and most individuals who experience the inadvertent use of toxic doses will recover after a relatively short period of expectant restoration, which is measured in hours. Deaths from yohimbine overdosing are uncommonly reported but nonetheless published.<ref name="Sport"/> Higher doses (200 – 5,000 mg) result in stronger side effects and can be toxic to the brain. Extremely high doses (above 5,000 mg) can be lethal.<ref name="Intoxication">Case study: two fatal case reports of acute yohimbine intoxication. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/23846025</ref>
 
Not recommended for individuals who have bleeding conditions as it can increase the risk of bleeding. For this reason, it is also dangerous for individuals who recently had a surgery. For those already taking this supplement, it is advised to stop intake two weeks before the scheduled surgery.
 
It is strongly recommended that one be familiar with [[responsible drug use|harm reduction practices]] when using this drug.


===Dependence and abuse potential===
===Dependence and abuse potential===
Yohimbine may potentially be [[Addiction potential::mildly habit forming]] and the desire to use it may actually ''increase'' with use. However, in comparison to other more traditional [[stimulants]] such as [[amphetamine]] or [[methylphenidate]], it is not nearly as addictive or compulsive.
Yohimbine is not known to be [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.
 
Tolerance to the effects of yohimbine are quickly built [[Time to full tolerance::after repeated and frequent usage]]. After that, it takes about [[Time to half tolerance::7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::14 days]] to be back at baseline (in the absence of further consumption). Yohimbine does not produce cross-tolerance with most other [[stimulants]].


===Dangerous interactions===
===Dangerous interactions===
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==Legal status==
==Legal status==
{{LegalStub}}
According to [https://erowid.org/plants/yohimbe/yohimbe_law.shtml 1], yohimbine is uncontrolled in the United States, meaning it is legal to buy, sell or possess without a license or prescription. However, it is illegal to market it as a treatment for erectile dysfunction without getting FDA approval [https://en.wikipedia.org/wiki/Yohimbine 2]. Yohimbine is also unscheduled in the U.K., making it legal to buy, sell or possess [https://erowid.org/plants/yohimbe/yohimbe_law.shtml 1].
However, yohimbine is banned in some other countries, such as Australia [https://nootriment.com/yohimbine-australia/ 1], Canada [https://nootriment.com/yohimbine-canada/ 2], New Zealand, Germany and Austria. In these countries, yohimbine can only be obtained with a prescription or not at all.


==See also==
==See also==
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==External links==
==External links==
*[[wikipedia:Yohimbine|Yohimbine (Wikipedia)]]
*[[wikipedia:Yohimbine|Yohimbine (Wikipedia)]]
*[https://isomerdesign.com/PiHKAL/explore.php?id=5410 Yohimbine (PiHKAL / Isomer Design)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=5410 Yohimbine (Isomer Design)]


==References==
==References==
<references />
<references />
[[Category:Psychoactive substance]]
 
[[Category:Naturally occurring]]
[[Category:Alkaloid]]
[[Category:Tryptamine]]
[[Category:beta-Carboline]]
[[Category:Stimulant]]
[[Category:Stimulant]]
[[Category:MAOI]]
[[Category:MAOI]]
[[Category:Articles in talk page]]
[[Category:Approval]]
[[Category:Approval]]
[[Category:Proofread]]


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