Alpha-GPC
| Summary sheet: Alpha-GPC |
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| Chemical Nomenclature | |||||||||||||||||||||||||
| Common names | Alpha-GPC, Choline Alfoscerate, L-Alpha Glycerylphosphorylcholine | ||||||||||||||||||||||||
| Systematic name | [(2R)-2,3-Dihydroxypropyl] 2-trimethylazaniumylethyl phosphate | ||||||||||||||||||||||||
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| Psychoactive class | Nootropic | ||||||||||||||||||||||||
| Chemical class | Choline derivative | ||||||||||||||||||||||||
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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.[1]
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.
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[2]).
When taken as a supplement, this compound has nootropic effects which may have the potential for the treatment of Alzheimer's disease[3] and other related disorders.[4] It is easily available and commonly sold for this purpose via online supplement and nootropic vendors.
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.
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
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 as well as cholinergic neurotransmission (acetylcholine synthesis).[5] 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 the production of cellular membranes, but this remains largely unstudied and is not well understood by the scientific literature.
Subjective effects
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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- Bodily control enhancement
- Stimulation - The stimulation which alpha-GPC presents can be considered as primarily subtle and similar to that of caffeine.
- Stamina enhancement
- Headaches
- Teeth grinding
- 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 
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- Wakefulness - In comparison to citicoline, alpha-GPC manifests itself primarily in a physically stimulating manner over a mental stimulation.
- Dream potentiation
- Focus enhancement[6]
- Mindfulness
- Memory enhancement
- 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:
Toxicity and harm potential
Alpha-GPC is non-addictive, is not known to cause harm, and has an 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 is familiar with and uses harm reduction practices when using this substance.
Tolerance and addiction potential
Alpha-GPC is 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 after prolonged and repeated usage. After that, it takes about 7 days for the tolerance to be reduced to half and 14 days to be back at baseline (in the absence of further consumption). Alpha-GPC presents cross-tolerance with no other known compounds, meaning that after the use of Alpha-GPC all other psychoactive compounds will not have a reduced effect.
Dangerous interactions
alpha-GPC is a suspected monoaminergic substance.[7][8] 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
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This legality section is a stub. As such, it may contain incomplete or wrong information. You can help by expanding it. |
- 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
External links
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
- ↑ Zeisel, S. H., Costa, K.-A. da (November 2009). "Choline: an essential nutrient for public health". Nutrition Reviews. 67 (11): 615–623. doi:10.1111/j.1753-4887.2009.00246.x. ISSN 0029-6643.
- ↑ Ziegenfuss, T., Landis, J., Hofheins, J. (17 September 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 (sup1): P15. doi:10.1186/1550-2783-5-S1-P15. ISSN 1550-2783.
- ↑ Parnetti, L., Mignini, F., Tomassoni, D., Traini, E., Amenta, F. (June 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. doi:10.1016/j.jns.2007.01.043. ISSN 0022-510X.
- ↑ Doggrell, S. A., Evans, S. (October 2003). "Treatment of dementia with neurotransmission modulation". Expert Opinion on Investigational Drugs. 12 (10): 1633–1654. doi:10.1517/13543784.12.10.1633. ISSN 1354-3784.
- ↑ Glier, M. B., Green, T. J., Devlin, A. M. (January 2014). "Methyl nutrients, DNA methylation, and cardiovascular disease". Molecular Nutrition & Food Research. 58 (1): 172–182. doi:10.1002/mnfr.201200636. ISSN 1613-4125.
- ↑ McGlade, E., Locatelli, A., Hardy, J., Kamiya, T., Morita, M., Morishita, K., Sugimura, Y., Yurgelun-Todd, D. (2012). "Improved Attentional Performance Following Citicoline Administration in Healthy Adult Women". Food and Nutrition Sciences. 03 (06): 769–773. doi:10.4236/fns.2012.36103. ISSN 2157-944X.
- ↑ Tayebati, S. K., Tomassoni, D., Nwankwo, I. E., Di Stefano, A., Sozio, P., Cerasa, L. S., Amenta, F. (1 February 2013). "Modulation of monoaminergic transporters by choline-containing phospholipids in rat brain". CNS & neurological disorders drug targets. 12 (1): 94–103. doi:10.2174/1871527311312010015. ISSN 1996-3181.
- ↑ Trabucchi, M., Govoni, S., Battaini, F. (April 1986). "Changes in the interaction between CNS cholinergic and dopaminergic neurons induced by L-alpha-glycerylphosphorylcholine, a cholinomimetic drug". Il Farmaco; Edizione Scientifica. 41 (4): 325–334. ISSN 0430-0920.