Piracetam

Base Information

• Chemical Name: Piracetam
• CAS No.: 7491-74-9
• Molecular Formula: C6H10N2O2
• Molecular Weight: 142.158
• Hs Code.: 29339900
• European Community (EC) Number: 231-312-7
• NSC Number: 758191
• UNII: ZH516LNZ10
• DSSTox Substance ID: DTXSID5044491
• Nikkaji Number: J8.946J
• Wikipedia: Piracetam
• Wikidata: Q410069
• NCI Thesaurus Code: C66410
• Metabolomics Workbench ID: 152244
• ChEMBL ID: CHEMBL36715
• Mol file: 7491-74-9.mol

Synonyms:2-Pyrrolidone-N-Acetamide;Avigilen;Axonyl;Cerebroforte;Cerepar N;Ciclofalina;Cuxabrain;Dinagen;Gabacet;Geram;Memo Puren;Memo-Puren;Nootrop;Nootropil;Nootropyl;Normabra?n;Piracebral;Piracetam;Piracetam AbZ;Piracetam RPh;Piracetam-RPh;Piracetrop;Pirazetam;Pyracetam;Pyramem;Sinapsan;UCB 6215;UCB-6215;UCB6215

Chemical Property of Piracetam

Chemical Property:

• Vapor Pressure: 7.06E-07mmHg at 25°C
• Melting Point: 151-152 °C
• Refractive Index: 1.523
• Boiling Point: 408.3 °C at 760 mmHg
• PKA: 15.67±0.40(Predicted)
• Flash Point: 200.8 °C
• PSA: 63.40000
• Density: 1.239 g/cm³
• LogP: -0.26770
• Storage Temp.: Store at RT
• Solubility.: Freely soluble in water, soluble in ethanol (96 per cent). It shows polymorphism (5.9).
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 142.074227566
• Heavy Atom Count: 10
• Complexity: 167

Purity/Quality:

99% ^*data from raw suppliers

Piracetam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1)CC(=O)N
• Recent ClinicalTrials: Pharmacovigilance in Gerontopsychiatric Patients
• Recent EU Clinical Trials: A single center, randomized, open-label, comparative study to assess efficacy and safety of piracetam 4.8g/d administered for 6 months as adjuvant to standard vestibular rehabilitation (VR) therapy utilizing Cooksey Cawthorne exercises to adults suffering from moderate to severe vertigo of peripheral origin lasting for at least 3 months.
• Description: Found commercially under the name Nootropil? (UCB Pharma, Slough, UK) Piracetam is available in tablet form (800 mg) and as oral solution (333.3 mg/ mL). Piracetam is initially prescribed at a dose of 7.2 g daily, divided into 2 or 3 doses, and can be gradually increased in steps of 4.8 g daily every 3– 4 days up to a maximum dose of 20 g daily (subsequently, attempts should be made to reduce the dose of concurrent therapy). Piracetam is a nootropic agent with an indication as adjunctive treatment for myoclonus of cortical origin, as well as tardive dyskinesia. However, piracetam is not approved by the FDA for any medical use in the USA. Piracetam should not be prescribed in patients with Huntington disease, those with serious kidney problems, or patients who have experienced a brain haemorrhage. Bleeding problems are a further caution to be taken into account. Most common adverse effects are hyperkinesia, irritability, and weight gain; less commonly, patients can report asthenia, depression, and drowsiness. Although there is little evidence for piracetam’s efficacy in terms of long- term benefits for the treatment of mild cognitive impairments, recent studies showed that it is effective in the treatment of cognitive disorders of cerebrovascular and traumatic origins. With regard to piracetam’s behavioural profile, its beneficial effects on lowering depression and anxiety appear to be higher than its positive effects on memory.
• Uses: antinauseant Nootropic; cortical myoclonus. Piracetam has been used to study crystal structure and physicochemical properties of six co-crystals of piracetam. It has also been used to study its in vitro antioxidant properties.
• Therapeutic Function: Psychotropic
• Clinical Use: Myoclonus

Technology Process of Piracetam

There total 18 articles about Piracetam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) + N,N-dimethyl-N'-(pyrrolid-2-on-1-ylacetyl)formamidine (92884-66-7) → 2-oxo-1-pyrrolidine acetamide (7491-74-9) + N,N-dimethyl-N'-homoveratrylformamidine (61945-49-1)

Guidance literature:

In benzene; for 4h; Ambient temperature;

DOI:10.1007/BF00773015

Reference yield: 97.0%

nitrile of 2-oxopyrrolidine-1-acetic acid (57275-83-9) → 2-oxo-1-pyrrolidine acetamide (7491-74-9)

Guidance literature:

With manganese(IV) oxide; water; In isopropyl alcohol; at 100 ℃; for 0.25h; under 5171.62 Torr;

DOI:10.1021/ol403591c

Reference yield: 93.0%

methyl-2-oxopyrrolidine-1-acetate (59776-88-4) → 2-oxo-1-pyrrolidine acetamide (7491-74-9)

Guidance literature:

With ammonia; In methanol; at 60 ℃; for 4h; Sealed tube;

DOI:10.1021/acs.joc.7b02894

upstream raw materials:

2-(oxo-pyrrolidin-1-yl)-acetic acid ethyl ester

2-(4-chlorobutyramido)acetamide

methyl-2-oxopyrrolidine-1-acetate

2-(3,4-dimethoxyphenyl)-ethylamine

Downstream raw materials:

N-{4,6-dioxo-1-(3-methylphenyl)-2-thioxo-5-trifluoromethyl-2,3,4,5,6,7-hexahydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-(2-oxopyrrolidin-1-yl)acetamide

N-{4,6-dioxo-1-phenyl-2-thioxo-5-trifluoromethyl-2,3,4,5,6,7-hexahydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-(2-oxopyrrolidin-1-yl)acetamide

N-{1-(2-phenylethyl)-2,4,6-trioxo-5-trifluoromethyl-2,3,4,5,6,7-hexahydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-(2-oxopyrrolidin-1-yl)acetamide

N-{1-benzyl-2,4,6-trioxo-5-trifluoromethyl-2,3,4,5,6,7-hexahydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-(2-oxopyrrolidin-1-yl)acetamide

Refernces

• 1、 -. "TYK2 INHIBITORS AND USES THEREOF". Paragraph 00766-00767. . Retrieved 2020/06/19.
• 2、 Liu, Tianqi,Jia, Wenqiang,Xi, Qiumu,Chen, Yonghui,Wang, Xiaojian,Yin, Dali. "Diversity-Oriented Synthesis of Heterocycles: Al(OTf)3-Promoted Cascade Cyclization and Ionic Hydrogenation". . p. 1387 - 1393. Retrieved 2018/02/10.