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P5520 Sigma

Paraldehyde

≥97%

Synonym: 2,4,6-Trimethyl-1,3,5-trioxacyclohexane, s-Trimethyltrioxymethylene, Acetaldehyde trimer, NSC 9799, Paracetaldehyde

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Properties

Related Categories Aldehydes, Building Blocks, C1 to C6, Carbonyl Compounds, Cell Biology,
assay   ≥97%
drug control   USDEA Schedule IV
density   0.994 g/mL at 20 °C(lit.)

Description

Biochem/physiol Actions

Hypnotic with rapid onset; anticonvulsant at high doses; used to treat delirium tremors

Application

Reactant involved in:
• Modified Sanford reaction1
• Synthesis of N-arylbenzoquinaldinium derivatives with antimicrobial activity2
• Hydroformylation of alkenylamines3
• Studies of molecules with inhibitory activity against HIV-1 integrase4
• Irregular Wittig reactions for the formation of α-hydroxyketones5

Price and Availability

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Paraldehyde

Lonza quality, ≥99.5% (GC)

Safety & Documentation

Safety Information

Symbol 
GHS02  GHS02
Signal word 
Warning
Hazard statements 
RIDADR 
UN 1264 3 / PGIII
WGK Germany 
1
RTECS 
YK0525000
Flash Point(F) 
75.2 °F
Flash Point(C) 
24 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Determination of Water Content in Paraldehyde Using Karl Fischer Titration

Aldehydes have a tendency to form acetals. At the same time water is formed. Water is bound in the bisulfite addition. Short chain aldehydes show a strong tendency to acetal formation, aromatic aldeh...
Keywords: Size-exclusion chromatography, Titrations

Peer-Reviewed Papers

References

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1. Preparation of a Family of 10-Hydroxybenzo[h]quinoline Analogues via a Modified Sanford Reaction and Their Excited State Intramolecular Proton Transfer Properties J. Piechowska and D. T. Gryko J. Org. Chem. 76, 10220-10228, (2011)

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2. Synthesis and antimicrobial activity of quaternary N-aryl-5,6-benzoquinaldinium derivatives N. E. Shchepina, et al. Pharmaceut. Chem. J. 45, 159-161, (2011)

3. Hydroformylation of Alkenylamines: Concise Approaches toward Piperidines, Quinolizidines, and Related Alkaloids E. Airiau, et al. J. Org. Chem. 75, 8670-8673, (2010)

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4. Design, synthesis and anti-HIV integrase evaluation of N-(5-chloro-8-hydroxy-2-styrylquinoline-7-yl)benzenesulfonamide derivatives Z. Jiao, et al. Molecules 15, 1903-1917, (2010)

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5. Formation of α-hydroxyketones via irregular Wittig reaction H. Okada, et al. Tetrahedron Lett. 50, 1276-1278, (2009)

Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model. Biagini G, Avoli M, Marcinkiewicz J, et al. J. Neurochem. 76(6), 1814-22, (2001)

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Complications following sedation of paediatric oncology patients undergoing radiotherapy. Adenipekun A, Soyannwo OA, Amanor-Boadu SD, et al. West Afr. J. Med. 17(4), 224-6, (1998)

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Audit of treatment of convulsive status epilepticus. Wanigasinghe J and Liyanage UA Ceylon Med. J. 53(3), 110, (2008)

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Towards evidence based emergency medicine: best BETs from the Manchester Royal Infirmary. Phenytoin or paraldehyde as the second drug for convulsions in children. Townend W and Mackway-Jones K Emerg. Med. J. 19(1), 50, (2002)

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Use of paraldehyde in neonates - an experience. Mishra D and Gupta VK Indian Pediatr. 38(2), 209-10, (2001)

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Type of syringe for giving paraldehyde injection. Dass CR Indian Pediatr. 37(4), 448, (2000)

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Efficacy and safety of intranasal lorazepam versus intramuscular paraldehyde for protracted convulsions in children: an open randomised trial. Ahmad S, Ellis JC, Kamwendo H, et al. Lancet 367(9522), 1591-7, (2006)

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Children presenting with convulsions (including status epilepticus) to a paediatric accident and emergency department: an audit of a treatment protocol. Garr RE, Appleton RE, Robson WJ, et al. Dev. Med. Child Neurol. 41(1), 44-7, (1999)

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Pharmacological management of convulsive status epilepticus in children. Scott RC and Neville BG Dev. Med. Child Neurol. 41(3), 207-10, (1999)

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Characterization of Ehrlichia risticii binding, internalization, and proliferation in host cells by flow cytometry. Messick JB and Rikihisa Y Infect. Immun. 61(9), 3803-10, (1993)

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Review of the efficacy of rectal paraldehyde in the management of acute and prolonged tonic-clonic convulsions. Rowland AG, Gill AM, Stewart AB, et al. Arch. Dis. Child. 94(9), 720-3, (2009)

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Serum creatine kinase levels after a single intramuscular injection--dependence on injection volume. Azzam Z, Krivoy N, Alroy G, et al. Ann. Clin. Biochem. 31 ( Pt 2), 193-4, (1994)

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Classical genetic analyses of responses to sedative-hypnotic drugs in crosses derived from long-sleep and short-sleep mice. de Fiebre CM, Marley RJ, Miner LL, et al. Alcohol. Clin. Exp. Res. 16(3), 511-21, (1992)

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Pervasive seizures caused by hypoxic-ischemic encephalopathy: treatment with intravenous paraldehyde. Armstrong DL and Battin MR J. Child Neurol. 16(12), 915-7, (2001)

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Outcome of status epilepticus in immature rats varies according to the paraldehyde treatment. Kubová H, Rejchrtová J, Redkozubova O, et al. Epilepsia 46 Suppl 5, 38-42, (2005)

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Vibrational spectral assignments of paraldehyde by ab initio and density functional methods. Gunasekaran S, Arunbalaji R, Kumaresan S, et al. J. Mol. Model. 14(5), 375-83, (2008)

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Paraldehyde. Von Burg R and Stout T J. Appl. Toxicol. 11(5), 379-81, (1991)

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Response to diazepam in children with malaria-induced seizures. Ikumi ML, Muchohi SN, Ohuma EO, et al. Epilepsy Res. 82(2-3), 215-8, (2008)

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Neurons projecting to the retrocerebral complex of the adult blow fly, Protophormia terraenovae. Shiga S, Toyoda I, and Numata H Cell Tissue Res. 299(3), 427-39, (2000)

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Determination of paraldehyde by gas chromatography in whole blood from children. Githiga IM, Muchohi SN, Ogutu BR, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 805(2), 365-9, (2004)

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Septicaemia among neonates with tetanus. Antia-Obong OE, Ekanem EE, Udo JJ, et al. J. Trop. Pediatr. 38(4), 173-5, (1992)

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Effects of paraldehyde on the convulsions induced by administration of soman in rats. Carpentier P, Lallement G, Bodjarian N, et al. Fundam. Clin. Pharmacol. 6(7), 309-18, (1992)

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DNA-protein cross-link formation in Burkitt lymphoma cells cultured with benzaldehyde and the sedative paraldehyde. Kuykendall JR, Jarvi EJ, Finley BL, et al. Drug Chem. Toxicol. 30(1), 1-16, (2007)

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Emergency management of seizures in children. Goyal M and Wiznitzer M Lancet 367(9522), 1555-6, (2006)

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The role of paraldehyde and lidocaine in the management of status epilepticus. Thulasimani M and Ramaswamy S Anaesthesia 57(1), 99-100, (2002)

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Merck 14,7027

Beil. 19,V,9,112

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