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'''Piracetam''' ('''2-oxo-1-pyrrolidine acetamide''') is a [[psychoactive class::nootropic]] drug in the [[chemical class::racetam]]s group which is a derivative of [[GABA]]. Piracetam was first synthesized in 1964 by Corneliu E. Giurgea and other scientists at the Belgian pharmaceutical company UCB. As a "smart drug", it is reported to enhance cognitive functions including memory, intelligence, and attention.<ref>Piracetam FAQ - Fooling the Bladder Cops by Christ Schoon (maintained by Erowid) | https://www.erowid.org/smarts/piracetam/piracetam_faq.shtml</ref>
'''Piracetam''' ('''2-oxo-1-pyrrolidine acetamide''') is a [[psychoactive class::nootropic]] substance of the [[chemical class::racetam]] class. It is a derivative of [[GABA]].  


In the U.K., piracetam is prescribed mainly for myoclonus (spasmodic jerky contraction of groups of muscles),<ref>Nootropil (piracetam) - Net Doctor | http://www.netdoctor.co.uk/medicines/100001864.html</ref> but is used off-label for other conditions. In the United States, it is not approved by the Food and Drug Administration for any medical use and it is not permitted to be sold as a dietary supplement. However, it is still readily available and sold through online vendors.
Piracetam was first synthesized in 1964 by Corneliu E. Giurgea and other scientists at the Belgian pharmaceutical company UCB.{{citation needed}}
 
In the United Kingdom, piracetam is prescribed mainly for myoclonus (spasmodic jerky contraction of groups of muscles),<ref>{{Citation | vauthors=((Henderson, D. R.)) | year=2012 | title=Nootropil (piracetam) | url=http://www.netdoctor.co.uk/medicines/brain-and-nervous-system/news/a7226/nootropil-piracetam/}}</ref> but is used off-label for other conditions. In the United States, it is not approved by the Food and Drug Administration for any medical use and it is not permitted to be sold as a dietary supplement. However, it is still readily available and sold through online vendors. As a "smart drug", it is reported to enhance cognitive functions including memory, intelligence, and attention.<ref>{{Citation | title=Erowid Piracetam Vault : FAQ : Frequently Asked Questions v0.7 | url=https://www.erowid.org/smarts/piracetam/piracetam_faq.shtml}}</ref>
 
The active dose of piracetam is 100 times than that of [[noopept]],{{citation needed}} making it both the earliest and least potent [[racetam]]. The standard piracetam dose for adults is between 1,200-4,800mg a day. The largest effective dose is 1,600mg taken three times a day for a total of 4,800mg.


Piracetam's dosage is 100x less potent than that of [[noopept]], making it both the earliest and least potent [[racetam]]. The standard piracetam dose for adults is between 1,200-4,800mg a day. The largest effective dose is 1,600mg taken three times a day for a total of 4,800mg.
==Chemistry==
==Chemistry==
Piracetam, or 2-oxo-1-pyrrolidine-acetamide, is a synthetic compound of the [[racetam]] family. Racetams share a pyrrolidine nucleus, a five member nitrogenous ring with a ketone bonded oxygen at R<sub>2</sub>.<ref>Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders. | http://www.ncbi.nlm.nih.gov/pubmed/20166767</ref> This 2-pyrrolidone ring is bound to the terminal carbon of an acetamide group, an ethyl amide chain with a ketone bond (C=O) at the alpha carbon.  
Piracetam, or 2-oxo-1-pyrrolidine-acetamide, is a synthetic compound of the [[racetam]] family. Racetams share a [[pyrrolidine]] nucleus, a five member nitrogenous ring with a ketone bonded oxygen at R<sub>2</sub>.<ref>{{cite journal | vauthors=((Malykh, A. G.)), ((Sadaie, M. R.)) | journal=Drugs | title=Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders | volume=70 | issue=3 | pages=287–312 | date=12 February 2010 | issn=1179-1950 | doi=10.2165/11319230-000000000-00000}}</ref> This 2-pyrrolidone ring is bound to the terminal carbon of an acetamide group, an ethyl amide chain with a ketone bond (C=O) at the alpha carbon.  


Piracetam shares structural similarity to the neurotransmitter [[GABA]], its pyrrolidine core is the cyclic counterpart of [[GABA]] and could theoretically be converted into an acetamide chain through a hydrolysis reaction into [[GABA]].
Piracetam shares structural similarity to the neurotransmitter [[GABA]], its pyrrolidine core is the cyclic counterpart of [[GABA]] and could theoretically be converted into an acetamide chain through a hydrolysis reaction into [[GABA]].


==Pharmacology==
==Pharmacology==
Piracetam's mechanism of action, as with [[racetam]]s in general, is not fully understood. The drug influences neuronal and vascular functions and influences cognitive function without acting as a [[sedative]] or [[stimulant]].<ref>Piracetam: a review of pharmacological properties and clinical uses (NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/16007238</ref> Piracetam is a positive allosteric modulator of the AMPA receptor.<ref>Piracetam defines a new binding site for allosteric modulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptors (NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/20163115</ref> It is hypothesized to act on ion channels or ion carriers, thus leading to increased neuron excitability.<ref>Piracetam and other structurally related nootropics (NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/8061686</ref> [[GABA]] brain metabolism and GABA receptors are not affected by piracetam.<ref>http://onlinelibrary.wiley.com/doi/10.1002/ddr.430020505/abstract;jsessionid=B9BF0E3214F13C8DD3692A776A0A5B78.f02t01</ref>
Piracetam's mechanism of action, as with [[racetam]]s in general, is not fully understood. The drug influences neuronal and vascular functions and influences cognitive function without acting as a [[sedative]] or [[stimulant]].<ref>{{cite journal | vauthors=((Winblad, B.)) | journal=CNS drug reviews | title=Piracetam: a review of pharmacological properties and clinical uses | volume=11 | issue=2 | pages=169–182 | date= 2005 | issn=1080-563X | doi=10.1111/j.1527-3458.2005.tb00268.x}}</ref> Piracetam is a positive allosteric modulator of the AMPA receptor.<ref>{{cite journal | vauthors=((Ahmed, A. H.)), ((Oswald, R. E.)) | journal=Journal of Medicinal Chemistry | title=Piracetam defines a new binding site for allosteric modulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptors | volume=53 | issue=5 | pages=2197–2203 | date=11 March 2010 | issn=1520-4804 | doi=10.1021/jm901905j}}</ref> It is hypothesized to act on ion channels or ion carriers, thus leading to increased neuron excitability.<ref>{{cite journal | vauthors=((Gouliaev, A. H.)), ((Senning, A.)) | journal=Brain Research. Brain Research Reviews | title=Piracetam and other structurally related nootropics | volume=19 | issue=2 | pages=180–222 | date= May 1994 | doi=10.1016/0165-0173(94)90011-6}}</ref> [[GABA]] brain metabolism and GABA receptors are not affected by piracetam.<ref>{{cite journal | vauthors=((Giurgea, C. E.)) | journal=Drug Development Research | title=The nootropic concept and its prospective implications | volume=2 | issue=5 | pages=441–446 | date= 1982 | url=https://onlinelibrary.wiley.com/doi/10.1002/ddr.430020505 | issn=0272-4391 | doi=10.1002/ddr.430020505}}</ref>


Among other things, it has also been found to increase blood flow and oxygen consumption in parts of the brain, but this may be a side effect of increased brain activity rather than a primary effect or mechanism of action for the drug.<ref>Cerebral blood flow effects of piracetam, pentifylline, and nicotinic acid in the baboon model compared with the known effect of acetazolamide (NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/8876930</ref> Piracetam also improves the function of the neurotransmitter [[acetylcholine]] via muscarinic cholinergic (ACh) receptors, which are implicated in memory processes.<ref>Piracetam--an old drug with novel properties? (NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/16459490</ref>
Among other things, it has also been found to increase blood flow and oxygen consumption in parts of the brain, but this may be a side effect of increased brain activity rather than a primary effect or mechanism of action for the drug.<ref>{{cite journal | vauthors=((Jordaan, B.)), ((Oliver, D. W.)), ((Dormehl, I. C.)), ((Hugo, N.)) | journal=Arzneimittel-Forschung | title=Cerebral blood flow effects of piracetam, pentifylline, and nicotinic acid in the baboon model compared with the known effect of acetazolamide | volume=46 | issue=9 | pages=844–847 | date= September 1996 | issn=0004-4172}}</ref> Piracetam also improves the function of the neurotransmitter [[acetylcholine]] via muscarinic cholinergic (ACh) receptors, which are implicated in memory processes.<ref>{{cite journal | vauthors=((Winnicka, K.)), ((Tomasiak, M.)), ((Bielawska, A.)) | journal=Acta Poloniae Pharmaceutica | title=Piracetam--an old drug with novel properties? | volume=62 | issue=5 | pages=405–409 | date= October 2005 | issn=0001-6837}}</ref>


Although it is not fully understood how, it's these multiple complex mechanisms of action which result in piracetams [[nootropic]] effects.
Although it is not fully understood how, it's these multiple complex mechanisms of action which result in piracetams [[nootropic]] effects.
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{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}


In comparison to the effects of other [[racetam]] nootropics such as [[noopept]], this compound can be described as focusing primarily on physical stimulation over that of cognitive stimulation.
In comparison to the effects of other nootropics such as [[noopept]], this compound can be described as focusing primarily on physical stimulation over that of cognitive stimulation.
===Sensory effects===
{{effects/base
|{{effects/physical|
*'''[[Effect::Stimulation]]''' - The stimulation which piracetam presents can be considered as primarily subtle, comparable to that of [[caffeine]].
*'''[[Effect::Headaches]]''' - Some users suggest that this effect may be alleviated with a choline source such as [[choline bitartrate]], [[alpha-GPC]] or [[citicoline]].
*'''[[Effect::Muscle spasms]]'''
 
}}
{{effects/sensory|


*'''[[Effect::Acuity enhancement]]'''
*'''[[Effect::Acuity enhancement]]'''
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*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Tactile enhancement]]'''


===Physical effects===
}}
*'''[[Effect::Stimulation]]''' - The stimulation which piracetam presents can be considered as primarily subtle, comparable to that of [[caffeine]].
|{{effects/cognitive|
*'''[[Effect::Headaches]]''' - Some users suggest that this effect may be alleviated with a choline source such as [[choline bitartrate]], [[alpha-GPC]] or [[citicoline]].
*'''[[Effect::Muscle spasms]]'''
 
===Cognitive effect===
*'''[[Effect::Anxiety suppression]]''' or '''[[Effect::Anxiety]]'''
*'''[[Effect::Anxiety suppression]]''' or '''[[Effect::Anxiety]]'''
*'''[[Effect::Dream potentiation]]'''
*'''[[Effect::Dream potentiation]]'''
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*'''[[Effect::Thought connectivity]]'''
*'''[[Effect::Thought connectivity]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''
}}
}}
===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_Piracetam.shtml Erowid Experience Vaults: Piracetam]


==Toxicity and harm potential==
==Toxicity and harm potential==
Adverse effects, although rare and of short duration are limited to [[anxiety]], [[wakefulness|insomnia]], [[sedation|drowsiness]], [[headaches]] and [[irritability|agitation]]. It may be safe for up to 18 months in humans at doses of 3.2g daily with one year-long study in ambulatory patients with Alzheimer's using 8g daily reporting no side effects.<ref>Long-term efficacy and safety of piracetam in the treatment of progressive myoclonus epilepsy. | http://www.ncbi.nlm.nih.gov/pubmed/11346373</ref> However, a possibility for adverse drug-drug interactions persists for piracetam due to it interacting with blood in an anti-clotting manner (and such, caution should be taken when pairing piracetam with pharmaceutical blood thinning agents such as Warfarin or potent nutraceutical options).
Adverse effects, although rare and of short duration are limited to [[anxiety]], [[wakefulness|insomnia]], [[sedation|drowsiness]], [[headaches]] and [[irritability|agitation]]. It may be safe for up to 18 months in humans at doses of 3.2g daily with one year-long study in ambulatory patients with Alzheimer's using 8g daily reporting no side effects.<ref>{{cite journal | vauthors=((Fedi, M.)), ((Reutens, D.)), ((Dubeau, F.)), ((Andermann, E.)), ((D’Agostino, D.)), ((Andermann, F.)) | journal=Archives of Neurology | title=Long-term efficacy and safety of piracetam in the treatment of progressive myoclonus epilepsy | volume=58 | issue=5 | pages=781–786 | date= May 2001 | issn=0003-9942 | doi=10.1001/archneur.58.5.781}}</ref> However, a possibility for adverse drug-drug interactions persists for piracetam due to it interacting with blood in an anti-clotting manner. Therefore, caution should be taken when pairing piracetam with pharmaceutical blood thinning agents such as Warfarin or potent nutraceutical options and individuals prone to brain hemorrhaging are discouraged from using piracetam.
 
Patients with renal insufficiency should also not use piracetam.


No fatal overdoses associated with piracetam use have been reported as of 2016. In animal models (rodents, dogs, and marmoset), an [[LD50|LD<sub>50</sub>]] failed to be established at the dosage of 8-10g/kg.
No fatal overdoses associated with piracetam use have been reported as of 2016. In animal models (rodents, dogs, and marmoset), an [[LD50|LD<sub>50</sub>]] failed to be established at the dosage of 8-10g/kg.


Regardless, it is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
Regardless, it is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.
 
===Lethal dosage===
===Lethal dosage===
The median lethal dosage (LD50) of piracetam has not been officially published as it has low abuse potential, but the typical dosage is two grams once to three times a day.
The median lethal dosage (LD50) of piracetam has not been officially published as it has low abuse potential, but the typical dosage is two grams once to three times a day.
===Tolerance and addiction potential===
 
===Dependence and abuse potential===
The chronic use of piracetam can be considered as [[Addiction potential::not addictive with a low potential for abuse]]. It does not seem to be capable of causing psychological dependence among certain users.  
The chronic use of piracetam can be considered as [[Addiction potential::not addictive with a low potential for abuse]]. It does not seem to be capable of causing psychological dependence among certain users.  


Tolerance to many of the effects of piracetam [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Piracetam may presents cross-tolerance with [[Cross-tolerance::all [[racetam]] [[nootropic]]s]], meaning that after the consumption of piracetam certain [[nootropics]]s such as [[noopept]] and [[pramiracetam]] may have a reduced effect.
Tolerance to many of the effects of piracetam [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Piracetam may presents cross-tolerance with [[Cross-tolerance::all [[racetam]] [[nootropic]]s]], meaning that after the consumption of piracetam certain [[nootropics]] such as [[aniracetam]] and [[pramiracetam]] may have a reduced effect.


==Legal issues==
===Dangerous interactions===
Piracetam showed nonselective MAO activity in a rat study.<ref>{{cite journal | vauthors=((Stancheva, S. L.)), ((Alova, L. G.)) | journal=Farmakologiia I Toksikologiia | title=[Effect of centrophenoxine, piracetam and aniracetam on the monoamine oxidase activity in different brain structures of rats] | volume=51 | issue=3 | pages=16–18 | date= June 1988 | issn=0014-8318}}</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> Piracetam and [[MAOIs]] are a potentially dangerous combination. It is likely that MAOIs could increase the effects of piracetam unpredictably. Taking this chemical while on prescription MAOIs is strongly discouraged.
 
==Legal status==
{{legalStub}}
{{legalStub}}
Piracetam, being a member of the [[racetam]] family, currently is legally available to buy and sell in most countries, but may still vary by region.
Piracetam, being a member of the [[racetam]] family, currently is legally available to buy and sell in most countries, but may still vary by region.
*'''United Kingdom''' - Piracetam and other racetams are prescription only drugs; however, there is no penalty for possession or importing them.
 
*'''New Zealand''' - Piracetam is considered a prescription drug, and as such will be seized by the Ministry of Health. It is not able to be imported without a signed note from a doctor.
*'''Czech Republic:''' Piracetam is not regulated and can be bought in a pharmacy.
*'''Germany:''' Piracetam is a prescription medicine, according to Anlage 1 AMVV.<ref>{{Citation | title=Anlage 1 AMVV - Einzelnorm | url=https://www.gesetze-im-internet.de/amvv/anlage_1.html}}</ref>
*'''Switzerland:''' Piracetam is listed as a "Abgabekategorie B" pharmaceutical, which requires a prescription.{{citation needed}}
*'''United Kingdom:''' Piracetam and other racetams are prescription only drugs; however, there is no penalty for possession or importing them.
*'''New Zealand:''' Piracetam is considered a prescription drug, and as such will be seized by the Ministry of Health. It is not able to be imported without a signed note from a doctor.


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Noopept]]
*[[Noopept]]
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==External links==
==External links==
*[https://en.wikipedia.org/wiki/Piracetam Piracetam (Wikipedia)]
*[https://en.wikipedia.org/wiki/Piracetam Piracetam (Wikipedia)]
*[http://drugs.tripsit.me/Piracetam Piracetam (TripSit)]
*[https://www.erowid.org/smarts/piracetam/ Piracetam (Erowid Vault)]
*[https://www.erowid.org/smarts/piracetam/ Piracetam (Erowid)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=9985 Piracetam (Isomer Design)]
*[https://examine.com/supplements/piracetam/ Piracetam (Examine)]
*[https://examine.com/supplements/piracetam/ Piracetam (Examine)]


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<references />
<references />
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Substance]]
[[Category:Stimulant]]
[[Category:Stimulant]]
[[Category:Nootropic]]
[[Category:Nootropic]]
[[Category:Pyrrolidine]]
[[Category:Racetam]]
{{#set:Featured=true}}
{{#set:Featured=true}}
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