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Pentobarbital

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Pentobarbital Basic information
Pentobarbital Chemical Properties
  • Melting point:129.5°C
  • Boiling point:367.89°C (rough estimate)
  • Density 1.1376 (rough estimate)
  • refractive index 1.4620 (estimate)
  • Flash point:9℃
  • storage temp. 2-8°C
  • solubility Very slightly soluble in water, freely soluble in ethanol. It forms water-soluble compounds with alkali hydroxides and carbonates and with ammonia.
  • pkapK1:8.11(0) (25°C)
  • Water Solubility 679 mg/L
  • CAS DataBase Reference76-74-4(CAS DataBase Reference)
  • NIST Chemistry ReferencePentobarbital(76-74-4)
  • EPA Substance Registry SystemPentobarbital (76-74-4)
Safety Information
MSDS
Pentobarbital Usage And Synthesis
  • Chemical PropertiesA white or almost white, crystalline powder or colourless crystals
  • OriginatorNembutal,Abbott,US
  • UsesSedative-hypnotic.
  • DefinitionChEBI: A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.
  • Manufacturing ProcessSodium (9.6 parts) was dissolved in butanol (192 parts) and di-n-butyl ethyl 1-methyl-n-butylmalonate (62.8 parts) and urea (14.4 parts) were added to the warm solution with agitation. The mixture was then heated to reflux temperature in three quarters of an hour and maintained for 2 hours. The reaction mass was kept, water (150 parts) added, the aqueous portion separated, and the butanol layer extracted with water (3 x 50 parts). The combined aqueous extracts were then given 3 small extractions with benzene, the aqueous liquors separated, charcoaled, filtered and precipitated with concentrated hydrochloric acid (acid to congopaper). The solid was collected, washed with water, dissolved in N-sodium hydroxide and reprecipitated with carbon dioxide. On recrystallization, from aqueous alcohol, the pentobarbitone was obtained.
  • brand nameNembutal(Ovation)[Name previously used: Pentobarbitone.];Aethaminalum;Barbityral;Barbopent;Burtylonel;Cafergot p.b.;Calpental;Di-barbs;Dipental;Distonocalm;Ergobel plus;Hypnol;Hypnotal;Hyptonal;Insom rapido;Isoamytal;Isom rapido;Iturate;Narcoren;Nembudeine;Nicaphlogyl;Novarectal;Nova-rectal;Novopentobarb;Novo-pentobarb;Or-trin;Palpent;Pembul;Penbon;Pentalgin;Pentanca;Pentodormol;Pentogen;Pentolos;Petab;Petonel;Praecicalm;Prodormol;Somnophyt;Somnotol;S-spac;Stopp-15;Wans;Wigraine-pb;Yastyl.
  • Therapeutic FunctionHypnotic, Sedative
  • World Health Organization (WHO)Pentobarbital is a short-acting barbiturate which is controlled under Schedule III of the 1971 Convention on Psychotropic Substances. See WHO comment for barbiturates. (Reference: (UNCPS3) United Nations Convention on Psychotropic Substances (III), , , 1971)
  • Purification MethodsA solution of the sodium salt in 10% HCl is prepared, and the acid is extracted with ether. Evaporation of the extract gives a solid which is then purified by repeated crystallisation from CHCl3. It sublimes at 95-105o/10-12mm. [Bucket & Sandorfy J Phys Chem 88 3274 1984.] The (+)-and (-)-enantiomers crystallise from 50% aqueous EtOH with m 120-121o and have [] 25 +4.73o to –4.93o (EtOH) [Kleiderer & Shonle J Am Chem Soc 56 1772 1934]. [Beilstein 24
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