Alpha-GPC: Difference between revisions

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| ''[[Choline bitartrate/Summary|Summary sheet: Alpha GPC]]''
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'''Alpha GPC''', ('''Alpha-glycerophosphocholine'''), ('''choline alfoscerate''') is a water soluble nutrient which serves within the brain as a precursor to both [[choline]] and glycerophosphate. To humans, choline is an essential nutrient, as its role in reducing the risk of neural tube defects, fatty liver disease, and other pathologies have been documented. <ref>http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2782876/</ref> Alpha GPC is one of the three choline-containing phospholipids that can be orally supplemented (the other two being [[Citicoline]] and Phosphatidylcholine).


Alpha-GPC is mostly marketed due to it being the most efficient choline prodrug (able to influence both systemic and brain concentrations of choline). Due to the provision of the other half of the alpha-GPC molecule (glycerophosphate), alpha-GPC also appears to support the structure of cellular membranes, similarly to [[citicoline]].
'''''Alpha''-GPC''' ('''L-''alpha''-glycerophosphocholine''', '''choline alfoscerate''') is a water-soluble nutrient which serves as a precursor to both [[choline]] and glycerophosphate within the brain. In humans, choline is considered to be an essential nutrient as its role in reducing the risk of neural tube defects, fatty liver disease, and other pathologies has been well-documented.<ref>{{cite journal | vauthors=((Zeisel, S. H.)), ((Costa, K.-A. da)) | journal=Nutrition Reviews | title=Choline: an essential nutrient for public health | volume=67 | issue=11 | pages=615–623 | date= November 2009 | url=https://academic.oup.com/nutritionreviews/article-lookup/doi/10.1111/j.1753-4887.2009.00246.x | issn=00296643 | doi=10.1111/j.1753-4887.2009.00246.x}}</ref>


Athletes are interested in alpha-GPC due to its ability to enhance growth hormone production and to enhance power output, which has a lone pilot study in support of 600 mg alpha-GPC prior to exercise. <ref>http://jissn.biomedcentral.com/articles/10.1186/1550-2783-5-S1-P15</ref>
Notably, alpha-GPC is one of the three choline-containing phospholipids that can be orally supplemented (the other two being [[citicoline]] and phosphatidylcholine) and its popularity may be due to it being the most efficient pro-drug of choline (with the ability to influence both systemic and brain concentrations of choline). Due to the provision of the other half of the alpha-GPC molecule (glycerophosphate), it also appears to support the structure and maintenance of cellular membranes, similarly to [[citicoline]].


When taken as supplement, this compound has [[psychoactive class::nootropic]] effects. It is easily available and commonly sold for this purpose through the use of online supplement vendors.
Athletes have been known to use alpha-GPC due to its purported ability to enhance growth hormone production and to enhance power output (which is based on a lone pilot study in support of subjects ingesting 600 mg alpha-GPC prior to exercise<ref>{{cite journal | vauthors=((Ziegenfuss, T.)), ((Landis, J.)), ((Hofheins, J.)) | journal=Journal of the International Society of Sports Nutrition | title=Acute supplementation with alpha-glycerylphosphorylcholine augments growth hormone response to, and peak force production during, resistance exercise | volume=5 | issue=sup1 | pages=P15 | date=17 September 2008 | url=https://www.tandfonline.com/doi/full/10.1186/1550-2783-5-S1-P15 | issn=1550-2783 | doi=10.1186/1550-2783-5-S1-P15}}</ref>).
 
When taken as a supplement, this compound has [[psychoactive class::nootropic]] effects which may have the potential for the treatment of Alzheimer's disease<ref>{{cite journal | vauthors=((Parnetti, L.)), ((Mignini, F.)), ((Tomassoni, D.)), ((Traini, E.)), ((Amenta, F.)) | journal=Journal of the Neurological Sciences | title=Cholinergic precursors in the treatment of cognitive impairment of vascular origin: Ineffective approaches or need for re-evaluation? | volume=257 | issue=1–2 | pages=264–269 | date= June 2007 | url=https://linkinghub.elsevier.com/retrieve/pii/S0022510X07000597 | issn=0022510X | doi=10.1016/j.jns.2007.01.043}}</ref> and other related disorders.<ref>{{cite journal | vauthors=((Doggrell, S. A.)), ((Evans, S.)) | journal=Expert Opinion on Investigational Drugs | title=Treatment of dementia with neurotransmission modulation | volume=12 | issue=10 | pages=1633–1654 | date= October 2003 | url=http://www.tandfonline.com/doi/full/10.1517/13543784.12.10.1633 | issn=1354-3784 | doi=10.1517/13543784.12.10.1633}}</ref> It is easily available and commonly sold for this purpose via online supplement and nootropic vendors.
==Chemistry==
==Chemistry==
{{chemistry}}
Alpha-GPC is a naturally-occurring choline compound found endogenously (naturally) in the brain which is also made and used for oral consumption. Structurally, Alpha-GPC is comprised of a choline group bound to a glycerol molecule via a phosphate group.  
Alpha-GPC is a choline molecule bound to a glycerol molecule via a phosphate group. It is Phosphatidylcholine (a lecithin molecule) without its two fatty acids. The molar mass of Alpha-GPC is 257.221g, and is 40% choline by weight (ie. 1,000mg Alpha-GPC confers 400mg free choline).
 
Choline is a quaternary ammonium salt, containing a positively charged ammonium cation substituted with three methyl groups and a hydroxyethyl chain. Glycerol is a polysubstituted alcohol consisting of propane with one hydroxyl (-OH) group bound to each carbon in the chain.  
 
In alpha-GPC, the terminal oxygen of the choline chain and a primary hydroxyl group of glycerol are integrated as bridging oxygen into a phosphate group. This phosphate group is a quaternary-substituted phosphorus atom connected to four oxygen atoms, two of which serve to bind the choline, glycerol, and phosphate groups into a unified molecule.
 
==Pharmacology==
==Pharmacology==
Alpha GPC breaks down into two key components: [[Choline]] and glycerophosphate.
Alpha-GPC breaks down into two key components, [[choline]] and glycerophosphate.
Choline and its metabolites are needed for three main physiological purposes: structural integrity and signaling roles for cell membranes, cholinergic neurotransmission ([[acetylcholine]] synthesis).<ref>https://dx.doi.org/10.1002%2Fmnfr.201200636</ref> This may explain why supplementing this compound results in [[nootropic]] effects.
Choline and its metabolites are needed for three main physiological purposes: structural integrity and signaling roles for cell membranes as well as cholinergic neurotransmission ([[acetylcholine]] synthesis).<ref>{{cite journal | vauthors=((Glier, M. B.)), ((Green, T. J.)), ((Devlin, A. M.)) | journal=Molecular Nutrition & Food Research | title=Methyl nutrients, DNA methylation, and cardiovascular disease | volume=58 | issue=1 | pages=172–182 | date= January 2014 | url=https://onlinelibrary.wiley.com/doi/10.1002/mnfr.201200636 | issn=16134125 | doi=10.1002/mnfr.201200636}}</ref> This process essentially allows acetylcholine to accumulate at higher levels than it otherwise would. As acetylcholine is involved in the function of memory and other essential cognitive functions, this could potentially account for its [[nootropic]] effects.


Glycerophosphate, the other component, can also help with production of cellular membranes, but it is not a very well investigated topic.
Glycerophosphate, the other component, can also help with the production of cellular membranes, but this remains largely unstudied and is not well understood by the scientific literature.


==Subjective effects==
==Subjective effects==
The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|contributors]]. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.   
{{Preamble/SubjectiveEffects}}   
====Physical effects====
{{effects/base
|{{effects/physical|
*'''[[Effect::Bodily control enhancement]]'''  
*'''[[Effect::Bodily control enhancement]]'''  
*'''[[Effect::Stimulation]]''' - The stimulation which Alpha-GPC presents can be considered as primarily subtle, about that of [[caffeine]].
*'''[[Effect::Stimulation]]''' - The stimulation which alpha-GPC presents can be considered as primarily subtle and similar to that of [[caffeine]].
*'''[[Effect::Stamina enhancement]]'''
*'''[[Effect::Stamina enhancement]]'''
*'''[[Effect::Headaches]]'''
*'''[[Effect::Headaches]]'''
*'''[[Effect::Body odor alteration]]''' - In some populations, especially those suffering from trimethylaminuria. [[Choline]] (a bi-product of Alpha GPC) is a precursor to trimethylamine, which some persons are not able to easily break down, often resulting in a "fishy smell."
*'''[[Effect::Teeth grinding]]'''
*'''[[Effect::Body odor alteration]]''' - This can be caused in some populations, especially those suffering from trimethylaminuria. [[Choline]] (a byproduct of alpha-GPC) is a precursor to trimethylamine, which those with trimethylaminuria are not able to easily break down, oftening resulting in smelling similar to fish.
 
}}


====Cognitive effects====
|{{effects/cognitive|
*'''[[Effect::Wakefulness]]''' - In comparison to [[Citicoline]], Alpha-GPC manifests itself primarily in a physically stimulating manner over a mental stimulation.
*'''[[Effect::Wakefulness]]''' - In comparison to [[citicoline]], alpha-GPC manifests itself primarily in a physically stimulating manner over a mental stimulation.
*'''[[Effect::Dream potentiation]]'''
*'''[[Effect::Dream potentiation]]'''
*'''[[Effect::Focus enhancement]]'''<ref>http://www.scirp.org/journal/PaperInformation.aspx?paperID=19921</ref>
*'''[[Effect::Focus enhancement]]'''<ref>{{cite journal | vauthors=((McGlade, E.)), ((Locatelli, A.)), ((Hardy, J.)), ((Kamiya, T.)), ((Morita, M.)), ((Morishita, K.)), ((Sugimura, Y.)), ((Yurgelun-Todd, D.)) | journal=Food and Nutrition Sciences | title=Improved Attentional Performance Following Citicoline Administration in Healthy Adult Women | volume=03 | issue=06 | pages=769–773 | date= 2012 | url=http://www.scirp.org/journal/doi.aspx?DOI=10.4236/fns.2012.36103 | issn=2157-944X | doi=10.4236/fns.2012.36103}}</ref>
*'''[[Effect::Mindfulness]]'''  
*'''[[Effect::Mindfulness]]'''  
*'''[[Effect::Memory enhancement]]'''
*'''[[Effect::Memory enhancement]]'''
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Motivation enhancement]]'''
}}
}}
===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:
* [https://www.erowid.org/experiences/subs/exp_alphaGPC.shtml Erowid Experience Vaults: alpha-GPC]


==Toxicity and harm potential==
==Toxicity and harm potential==
Alpha GPC is non-addictive, is not known to cause harm, and has an [[Toxicity::extremely low toxicity]] relative to dose. Similar to many other [[nootropics]] drugs, there are relatively few physical side effects associated with acute choline exposure. Various studies have shown that in reasonable doses in a careful context, it presents no negative cognitive, psychiatric or toxic physical consequences of any sort.  
Alpha-GPC is non-addictive, is not known to cause harm, and has an [[Toxicity::extremely low toxicity]] relative to dose. Similar to many other [[nootropic]] substances, there are relatively few physical side effects associated with acute choline exposure. Various studies have shown that in reasonable doses in a particular context, it presents no negative cognitive, psychiatric or toxic physical consequences of any sort.  


Regardless, it is strongly recommended that one be familiar with [[responsible drug use|harm reduction practices]] when using this drug.
Regardless, it is strongly recommended that one is familiar with and uses [[responsible drug use|harm reduction practices]] when using this substance.
===Tolerance and addiction potential===
===Tolerance and addiction potential===
Alpha GPC is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.  
Alpha-GPC is [[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 alpha-GPC is built [[Time to full tolerance::after prolonged and repeated 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). Alpha-GPC presents cross-tolerance with [[Cross-tolerance::no other known compounds]], meaning that after the use of Alpha-GPC all other psychoactive compounds will not have a reduced effect.


Tolerance to the effects of Alpha GPC are built [[Time to full tolerance::after prolonged and repeated 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). Alpha GPC presents cross-tolerance with [[Cross-tolerance::no other known compounds]], meaning that after the consumption of Alpha GPC all other psychoactive compounds will not have a reduced effect.
===Dangerous interactions===
==Legal issues==
''alpha''-GPC is a suspected monoaminergic substance.<ref>{{cite journal | vauthors=((Tayebati, S. K.)), ((Tomassoni, D.)), ((Nwankwo, I. E.)), ((Di Stefano, A.)), ((Sozio, P.)), ((Cerasa, L. S.)), ((Amenta, F.)) | journal=CNS & neurological disorders drug targets | title=Modulation of monoaminergic transporters by choline-containing phospholipids in rat brain | volume=12 | issue=1 | pages=94–103 | date=1 February 2013 | issn=1996-3181 | doi=10.2174/1871527311312010015}}
</ref><ref>{{cite journal | vauthors=((Trabucchi, M.)), ((Govoni, S.)), ((Battaini, F.)) | journal=Il Farmaco; Edizione Scientifica | title=Changes in the interaction between CNS cholinergic and dopaminergic neurons induced by L-alpha-glycerylphosphorylcholine, a cholinomimetic drug | volume=41 | issue=4 | pages=325–334 | date= April 1986 | issn=0430-0920}}</ref> Alpha-GPC and [[MAOIs]] are a potentially dangerous combination. It is likely that MAOIs could increase the effects of Alpha-GPC unpredictably. Taking this chemical while on prescription MAOIs is strongly discouraged.
 
==Legal status==
{{legalStub}}
{{legalStub}}
*'''United States''' - Alpha-GPC is completely legal to purchase in the United States as a dietary supplement.
*'''Canada''' - Alpha-GPC is completely legal to purchase in Canada as a dietary supplement.
==See also==
==See also==
*[[Citicoline]]
*[[Citicoline]]
*[[Choline]]
*[[Choline]]
*[[Nootropic]]
*[[Nootropic]]
==External links==
*[https://en.wikipedia.org/wiki/Alpha-GPC Alpha-GPC (Wikipedia)]
*[https://examine.com/supplements/alpha-gpc/ Alpha-GPC (Examine)]
*[https://www.reddit.com/r/nootropics/wiki/beginners#wiki_alpha-gpc Alpha-GPC (r/Nootropics FAQ)]
==Literature==
* Parker, A. G., Byars, A., Purpura, M., & Jäger, R. (2015). The effects of alpha-glycerylphosphorylcholine, caffeine or placebo on markers of mood, cognitive function, power, speed, and agility. Journal of the International Society of Sports Nutrition, 12(Suppl 1), P41. https://doi.org/10.1186/1550-2783-12-S1-P41
* Onishchenko, L. S., Gaikova, O. N., & Yanishevskii, S. N. (2008). Changes at the focus of experimental ischemic stroke treated with neuroprotective agents. Neuroscience and Behavioral Physiology, 38(1), 49–54. https://doi.org/10.1007/s11055-008-0007-1
* Ziegenfuss, T., Landis, J., & Hofheins, J. (2008). Acute supplementation with alpha-glycerylphosphorylcholine augments growth hormone response to, and peak force production during, resistance exercise. Journal of the International Society of Sports Nutrition, 5(Suppl 1), P15. https://doi.org/10.1186/1550-2783-5-S1-P15
* Lopez, C. M., Govoni, S., Battaini, F., Bergamaschi, S., Longoni, A., Giaroni, C., & Trabucchi, M. (1991). Effect of a new cognition enhancer, alpha-glycerylphosphorylcholine, on scopolamine-induced amnesia and brain acetylcholine. Pharmacology, Biochemistry and Behavior, 39(4), 835–840. https://doi.org/10.1016/0091-3057(91)90040-9
==== Relevant non-specific literature ====
* Doggrell, S. a, & Evans, S. (2003). Treatment of dementia with neurotransmission modulation. Expert Opinion on Investigational Drugs, 12(10), 1633–54. https://doi.org/10.1517/13543784.12.10.1633
* Parnetti, L., Mignini, F., Tomassoni, D., Traini, E., & Amenta, F. (2007). Cholinergic precursors in the treatment of cognitive impairment of vascular origin: Ineffective approaches or need for re-evaluation? Journal of the Neurological Sciences, 257(1–2), 264–269. https://doi.org/10.1016/j.jns.2007.01.043
* Zeisel, S. H., & Da Costa, K. A. (2009). Choline: An essential nutrient for public health. Nutrition Reviews, 67(11), 615–623. https://doi.org/10.1111/j.1753-4887.2009.00246.x
* Glier, M. B., Green, T. J., & Devlin, A. M. (2014). Methyl nutrients, DNA methylation, and cardiovascular disease. Molecular Nutrition and Food Research, 58(1), 172–182. https://doi.org/10.1002/mnfr.201200636


==References==
==References==
<references />
<references />
[[Category:Cholinergic]][[Category:Psychoactive substance]][[Category:Substance]][[Category:Stimulant]][[Category:Nootropic]]
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