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    Aniracetam molecular structure

    Aniracetam

    NootropicsApproved (Italy)

    Also known as: Ro 13-5057, Draganon, Sarpul, Ampamet, Memodrin, 1-(4-methoxybenzoyl)-2-pyrrolidinone, 1-p-anisoyl-2-pyrrolidinone

    Aniracetam is a pyrrolidinone in the racetam family, developed by Hoffmann-La Roche under the code Ro 13-5057. The first detailed pharmacology paper, published in 1982 by the Roche group, reported that oral aniracetam prevented or reversed several forms of experimentally induced amnesia in rats and mice, with bell-shaped dose-response curves and roughly ten times the potency of piracetam (PMID: 6817363).

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    $0.186/mg$64.99 for 350mg

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    Half-life: About half an hour for the parent drug in humansRoute: OralMW: 219.24 g/molCAS: 72432-10-1
    Last reviewed:

    Overview

    At A Glance

    Mechanism

    Aniracetam is a positive allosteric modulator of AMPA-type ionotropic glutamate receptors. It binds at the two-fold axis of the GluA2 ligand-binding domain dimer interface, adjacent to the hinge of the clamshell, and stabilizes the closed glutamate-bound conformation, which slows…

    Half-Life
    About half an hour for the parent drug in humans. Plasma elimination half-life was 0.47 to 0.49 hours after a single 400 mg oral dose in 20 healthy male volunteers (PMID: 19025058). Aniracetam is extensively metabolized to N-anisoyl-GABA and anisic acid; in six elderly hospitalized patients with cerebrovascular disease and reduced creatinine clearance, metabolite half-life was 4 to 7 times longer than in young volunteers (PMID: 9062694).
    Routes
    Oral
    Potential Benefits
    Prevented or reversed amnesia from hypercapnia, scopolamine, electroconvulsive shock and protein synthesis inhibitors in rats and mice (PMID: 6817363)Improved delayed-response performance in an eight-arm radial maze in rats (PMID: 1611039)Improved contextual fear conditioning and increased hippocampal gamma-PKC activation in DBA/2J mice (PMID: 11918291)Reversed sleep-deprivation-induced passive avoidance deficits in Wistar rats (PMID: 24079994)Reduced immobility in the forced swim test in aged rats but not young rats, an effect attributed to its metabolites (PMID: 11702095)Improved psychobehavioral scores versus placebo over six months in 109 patients with mild to moderate probable Alzheimer type dementia (PMID: 1822317)

    Overview

    Aniracetam is a pyrrolidinone in the racetam family, developed by Hoffmann-La Roche under the code Ro 13-5057. The first detailed pharmacology paper, published in 1982 by the Roche group, reported that oral aniracetam prevented or reversed several forms of experimentally induced amnesia in rats and mice, with bell-shaped dose-response curves and roughly ten times the potency of piracetam (PMID: 6817363). It went on to be sold as a prescription medicine in parts of Europe under names including Ampamet and Memodrin, indicated for cognitive and behavioral symptoms in older patients, and in Japan under the names Draganon and Sarpul. It has never been approved in the United States. Nearly all of the aniracetam bought by consumers today is bulk powder or capsules supplied as a research chemical rather than a licensed medicine. The best characterized action is positive allosteric modulation of AMPA-type glutamate receptors. Aniracetam potentiated ionotropic quisqualate and AMPA responses in Xenopus oocytes injected with rat brain mRNA, and potentiated excitatory postsynaptic potentials in rat hippocampal slices (PMID: 1975272). Patch-clamp work in guinea pig hippocampal slices showed that it reduces glutamate receptor desensitization and slows the decay of fast excitatory synaptic currents (PMID: 1660156). Cocrystal structures of the GluA2 ligand-binding core later placed aniracetam at the dimer interface, where it stabilizes the closed, glutamate-bound conformation and slows deactivation (PMID: 16192394). Animal work consistently shows restoration of impaired performance rather than improvement of normal performance. Aniracetam improved delayed-response performance in an eight-arm radial maze in rats (PMID: 1611039), improved contextual fear conditioning in DBA/2J mice along with increased membrane-bound hippocampal gamma-PKC (PMID: 11918291), and reversed passive avoidance deficits in sleep-deprived Wistar rats (PMID: 24079994). In healthy animals the picture is different: daily oral aniracetam produced no measurable change across spatial, associative, motor and anxiety tasks in normal C57BL/6J mice (PMID: 25099639), and it had no effect on delayed matching-to-sample performance in neurologically healthy pigeons (PMID: 31002681). The human record is mixed and mostly from the late 1980s and early 1990s. A 109-patient, six-month, placebo-controlled multicenter study in mild to moderate probable Alzheimer type dementia reported significant differences favoring aniracetam on psychobehavioral measures (PMID: 1822317), while a 44-patient double-blind study found no difference from placebo (PMID: 3103163). A 1994 review concluded the evidence supported continued evaluation rather than established efficacy (PMID: 8199398), and a 2010 review of piracetam-like drugs reported that aniracetam and oxiracetam were no longer in clinical use (PMID: 20166767). Two practical points. First, the parent molecule barely survives first-pass metabolism, so most of what circulates is metabolite (PMID: 19025058), and formulation chemists describe aniracetam as having low aqueous solubility and poor oral bioavailability (PMID: 30453664). Second, in February 2019 the United States Food and Drug Administration told a nootropics seller that aniracetam is not a dietary supplement ingredient and that products containing it are unapproved new drugs. In the United States it is a research-use-only compound.

    Potential Research Fields

    Cognitive enhancementAMPA receptor pharmacologyDementiaNootropics

    Chemical Information

    IUPAC Name

    Not yet available

    CAS Number

    72432-10-1

    Molecular Formula

    C12H13NO3

    Molecular Mass

    219.24 g/mol

    Dosing & Protocols

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    Interactions

    Contraindications

    No contraindication list is reproduced here from European product information. Mechanism-based and pharmacokinetic cautions: clearance depends on hepatic metabolism and renal elimination of metabolites, and elderly patients with cerebrovascular disease and low creatinine clearance showed 4 to 7 fold longer metabolite half-lives (PMID: 9062694). Positive modulation of AMPA receptors increases excitatory transmission and slows synaptic current decay (PMID: 1660156), which is a mechanism-based reason for caution in people with seizure disorders. In alcohol-preferring rats, aniracetam increased operant alcohol self-administration and potentiated cue-induced reinstatement of alcohol seeking (PMID: 23126443).

    Research Disclaimer

    This interaction data is compiled from published research and community reports. It may not be exhaustive. Always consult a healthcare professional before combining compounds.

    Best Price

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    Vendors Selling Aniracetam

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    9-Me-BC (9-Methyl-β-carboline)

    NootropicsPreclinical

    9-Methyl--carboline (9-Me-BC) is a synthetic -carboline alkaloid that has drawn nootropic-community interest for a preclinical property that is genuinely unusual among -carbolines: in rodent and cell-culture studies it appears to stimulate the dopaminergic phenotype - raising tyrosine hydroxylase, the number of differentiated dopamine neurons and dopamine content - while also showing neuroprotective, neurorestorative and anti-inflammatory effects, plus in-vitro MAO-A/MAO-B inhibition [PMID:17913302, PMID:20374418, PMID:32285253].

    t½ Not characterized in humans (no pharmacokinetic data). Community/anecdotal only: ~5-25 mg per day, oral. No validated or approved human dose exists.
    6 PubMedView Profile

    Bemethyl (bemitil)

    NootropicsApproved (Russia)

    Bemethyl, known in the Russian literature as bemitil and sold in the region under names including Metaprot, Bemactor and Antihot, is 2-ethylthiobenzimidazole, normally handled as the hydrobromide salt.

    t½ Not established in humans; in healthy volunteers given a single 250 mg oral dose of the Metaprot capsule form, peak serum ethylthiobenzimidazole averaged 0.91 microg/mL at about 1.06 h, and no terminal half-life was reported (PMID: 21870773)
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    Bromantane

    NootropicsRussia Approved

    Bromantane is an atypical psychostimulant and anxiolytic developed in the 1980s at the Zakusov Institute of Pharmacology of the Russian Academy of Medical Sciences, originally created as an adaptogen for Soviet military and elite athletic use and later approved in Russia for the treatment of neurasthenic and asthenic disorders under the trade name Ladasten.

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    Cyclazodone

    NootropicsPreclinical

    Cyclazodone is the N-cyclopropyl derivative of pemoline, a 4-oxazolidinone stimulant.

    PreclinicalView Profile

    Dihexa

    NootropicsPreclinical

    Dihexa is a synthetic peptide analogue of the angiotensin IV metabolite LVV-hemorphin-7, developed at Washington State University.

    t½ Not characterized in humans. Dihexa was engineered for metabolic stability (resistant to plasma and enzymatic degradation) and blood-brain-barrier penetration; in preclinical work its central procognitive effects appear to outlast its plasma presence. 5 to 40 mg oral per day (anecdotal range; no established human dose)
    1 PubMedView Profile

    Fasoracetam (NS-105)

    NootropicsPhase 2

    Fasoracetam is a racetam developed by Nippon Shinyaku in Japan under the code NS-105 and taken into clinical development for vascular dementia.

    t½ Mean terminal half-life 4.82 hours, range 4.06 to 6.99 hours, after single oral doses in adolescents aged 12 to 17, with the drug excreted for the most part unchanged through the kidneys (PMID: 29339723). After intravenous dosing in animals, elimination half-life was 0.67 hours in rats, 2.1 hours in dogs and 1.3 hours in monkeys, with high systemic availability after oral dosing in all three species (PMID: 10604039).
    PreclinicalView Profile

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    Research Score

    30

    0 PubMed results

    Quality Indicators

    Data Completeness

    63%
    Description
    Mechanism of Action
    Chemical Data
    Dosing Protocols
    Safety Profile
    PubMed Results
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    Vendor Listings

    Quick Facts

    Half-Life

    About half an hour for the parent drug in humans. Plasma elimination half-life was 0.47 to 0.49 hours after a single 400 mg oral dose in 20 healthy male volunteers (PMID: 19025058). Aniracetam is extensively metabolized to N-anisoyl-GABA and anisic acid; in six elderly hospitalized patients with cerebrovascular disease and reduced creatinine clearance, metabolite half-life was 4 to 7 times longer than in young volunteers (PMID: 9062694).

    Molecular Weight

    219.24 g/mol

    Administration

    Oral

    CAS Number

    72432-10-1

    Trial Phase

    Approved (Italy)

    0

    Research Disclaimer

    This information is for educational and research purposes only. Not intended as medical advice. Consult a healthcare professional before use.

    Frequently Asked Questions

    What is Aniracetam used for in research?

    Aniracetam is a pyrrolidinone in the racetam family, developed by Hoffmann-La Roche under the code Ro 13-5057. The first detailed pharmacology paper, published in 1982 by the Roche group, reported that oral aniracetam prevented or reversed several forms of experimentally induced amnesia in rats and mice, with bell-shaped dose-response curves and roughly ten times the potency of piracetam (PMID: 6817363). It went on to be sold as a prescription medicine in parts of Europe under names including Ampamet and Memodrin, indicated for cognitive and behavioral symptoms in older patients, and in Japan under the names Draganon and Sarpul. It has never been approved in the United States. Nearly all of the aniracetam bought by consumers today is bulk powder or capsules supplied as a research chemical rather than a licensed medicine.

    The best characterized action is positive allosteric modulation of AMPA-type glutamate receptors. Aniracetam potentiated ionotropic quisqualate and AMPA responses in Xenopus oocytes injected with rat brain mRNA, and potentiated excitatory postsynaptic potentials in rat hippocampal slices (PMID: 1975272). Patch-clamp work in guinea pig hippocampal slices showed that it reduces glutamate receptor desensitization and slows the decay of fast excitatory synaptic currents (PMID: 1660156). Cocrystal structures of the GluA2 ligand-binding core later placed aniracetam at the dimer interface, where it stabilizes the closed, glutamate-bound conformation and slows deactivation (PMID: 16192394).

    Animal work consistently shows restoration of impaired performance rather than improvement of normal performance. Aniracetam improved delayed-response performance in an eight-arm radial maze in rats (PMID: 1611039), improved contextual fear conditioning in DBA/2J mice along with increased membrane-bound hippocampal gamma-PKC (PMID: 11918291), and reversed passive avoidance deficits in sleep-deprived Wistar rats (PMID: 24079994). In healthy animals the picture is different: daily oral aniracetam produced no measurable change across spatial, associative, motor and anxiety tasks in normal C57BL/6J mice (PMID: 25099639), and it had no effect on delayed matching-to-sample performance in neurologically healthy pigeons (PMID: 31002681).

    The human record is mixed and mostly from the late 1980s and early 1990s. A 109-patient, six-month, placebo-controlled multicenter study in mild to moderate probable Alzheimer type dementia reported significant differences favoring aniracetam on psychobehavioral measures (PMID: 1822317), while a 44-patient double-blind study found no difference from placebo (PMID: 3103163). A 1994 review concluded the evidence supported continued evaluation rather than established efficacy (PMID: 8199398), and a 2010 review of piracetam-like drugs reported that aniracetam and oxiracetam were no longer in clinical use (PMID: 20166767).

    Two practical points. First, the parent molecule barely survives first-pass metabolism, so most of what circulates is metabolite (PMID: 19025058), and formulation chemists describe aniracetam as having low aqueous solubility and poor oral bioavailability (PMID: 30453664). Second, in February 2019 the United States Food and Drug Administration told a nootropics seller that aniracetam is not a dietary supplement ingredient and that products containing it are unapproved new drugs. In the United States it is a research-use-only compound.

    What forms does Aniracetam come in?

    Aniracetam is available in powder form.

    How much does Aniracetam cost?

    Prices start at $64.99 across 1 vendor.

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    Research Tools

    Related Compounds

    View All

    9-Me-BC (9-Methyl-β-carboline)

    NootropicsPreclinical

    9-Methyl--carboline (9-Me-BC) is a synthetic -carboline alkaloid that has drawn nootropic-community interest for a preclinical property that is genuinely unusual among -carbolines: in rodent and cell-culture studies it appears to stimulate the dopaminergic phenotype - raising tyrosine hydroxylase, the number of differentiated dopamine neurons and dopamine content - while also showing neuroprotective, neurorestorative and anti-inflammatory effects, plus in-vitro MAO-A/MAO-B inhibition [PMID:17913302, PMID:20374418, PMID:32285253].

    t½ Not characterized in humans (no pharmacokinetic data). Community/anecdotal only: ~5-25 mg per day, oral. No validated or approved human dose exists.
    6 PubMedView Profile

    Bemethyl (bemitil)

    NootropicsApproved (Russia)

    Bemethyl, known in the Russian literature as bemitil and sold in the region under names including Metaprot, Bemactor and Antihot, is 2-ethylthiobenzimidazole, normally handled as the hydrobromide salt.

    t½ Not established in humans; in healthy volunteers given a single 250 mg oral dose of the Metaprot capsule form, peak serum ethylthiobenzimidazole averaged 0.91 microg/mL at about 1.06 h, and no terminal half-life was reported (PMID: 21870773)
    PreclinicalView Profile

    Bromantane

    NootropicsRussia Approved

    Bromantane is an atypical psychostimulant and anxiolytic developed in the 1980s at the Zakusov Institute of Pharmacology of the Russian Academy of Medical Sciences, originally created as an adaptogen for Soviet military and elite athletic use and later approved in Russia for the treatment of neurasthenic and asthenic disorders under the trade name Ladasten.

    34 PubMedView Profile

    Cyclazodone

    NootropicsPreclinical

    Cyclazodone is the N-cyclopropyl derivative of pemoline, a 4-oxazolidinone stimulant.

    PreclinicalView Profile

    Dihexa

    NootropicsPreclinical

    Dihexa is a synthetic peptide analogue of the angiotensin IV metabolite LVV-hemorphin-7, developed at Washington State University.

    t½ Not characterized in humans. Dihexa was engineered for metabolic stability (resistant to plasma and enzymatic degradation) and blood-brain-barrier penetration; in preclinical work its central procognitive effects appear to outlast its plasma presence. 5 to 40 mg oral per day (anecdotal range; no established human dose)
    1 PubMedView Profile

    Fasoracetam (NS-105)

    NootropicsPhase 2

    Fasoracetam is a racetam developed by Nippon Shinyaku in Japan under the code NS-105 and taken into clinical development for vascular dementia.

    t½ Mean terminal half-life 4.82 hours, range 4.06 to 6.99 hours, after single oral doses in adolescents aged 12 to 17, with the drug excreted for the most part unchanged through the kidneys (PMID: 29339723). After intravenous dosing in animals, elimination half-life was 0.67 hours in rats, 2.1 hours in dogs and 1.3 hours in monkeys, with high systemic availability after oral dosing in all three species (PMID: 10604039).
    PreclinicalView Profile

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