| Identification | More | [Name]
Pentobarbitone | [CAS]
76-74-4 | [Synonyms]
5-ETHYL-5-[1-METHYLBUTYL]-2,4,6-TRIOXOHEXAHYDROPYRIMIDINE
5-ethyl-5-(1-methylbutyl)barbituric acid
5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione
PENTOBARBITAL
pentobarbitone
2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylbutyl)-
5-Ethyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
5-Ethyl-5-(1-methylbutyl)barbituric acidcid
5-ethyl-5-(1-methylbutyl)-barbituricaci
5-Ethyl-5-(1-methylbutyl)malonylurea
5-Ethyl-5-(sec-pentyl)barbituric acid
5-ethyl-5-(sec-pentyl)barbituricacid
6(1h,3h,5h)-pyrimidinetrione,5-ethyl-5-(1-methylbutyl)-4
Barbituric acid, 5-ethyl-5-(1-methylbutyl)-
barbituricacid,5-ethyl-5-(2-pentyl)
component of Emesert
Dorsital
Ethaminal
Ethyl-propylmethylcarbinylbarbituric acid
ethyl-propylmethylcarbinylbarbituricacid | [EINECS(EC#)]
200-983-8 | [Molecular Formula]
C11H18N2O3 | [MDL Number]
MFCD00057561 | [Molecular Weight]
226.27 | [MOL File]
76-74-4.mol |
| Chemical Properties | Back Directory | [Appearance]
A white or almost white, crystalline powder or colourless crystals | [Melting point ]
129.5°C | [Boiling point ]
367.89°C (rough estimate) | [density ]
1.1376 (rough estimate) | [refractive index ]
1.4620 (estimate) | [Fp ]
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. | [form ]
A neat solid | [pka]
pK1:8.11(0) (25°C) | [Water Solubility ]
679 mg/L | [CAS DataBase Reference]
76-74-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Pentobarbital(76-74-4) | [EPA Substance Registry System]
76-74-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,F | [Risk Statements ]
R25:Toxic if swallowed.
R63:Possible risk of harm to the unborn child.
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R36/38:Irritating to eyes and skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S7:Keep container tightly closed .
S16:Keep away from sources of ignition-No smoking .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
CQ5775000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
2933530000 | [Hazardous Substances Data]
76-74-4(Hazardous Substances Data) | [Toxicity]
A barbiturate that
causes CNS depression, apparently due to a facilitation of
GABA-ergic inhibition. It appears that the site of action of pentobarbital may be the macromolecular complex made up of a
GABA receptor, chloride channel, benzodiazepine-binding site,
and picrotoxin-binding site. Barbiturates have been shown to
compete for dihydropicrotoxinin-binding sites. In clinical use,
barbiturates such as pentobarbital have been largely replaced
as sedative-hypnotics by the much safer benzodiazepines. The
sedative-hypnotic properties of barbiturates may lead to abuse, as
tolerance and dependence are known to occur. In animals, pentobarbital is routinely used for its anesthetic and anticonvulsant
properties, as well as for euthanasia. Pentobarbital, like other
barbiturates, can induce the metabolism of other compounds by
altering cytochrome P450 activity. The oral LD50 in rats is
118 mg/kg. |
| Hazard Information | Back Directory | [Description]
Pentobarbital (CRM) (Item No. 20966) is a certified reference material categorized as a barbiturate.1,2 Pentobarbital is regulated as a Schedule II compound in the United States. Pentobarbital (CRM) (Item No. 20966) is provided as a DEA exempt preparation. This product is intended for research and forensic applications. | [Chemical Properties]
A white or almost white, crystalline powder or colourless crystals | [Originator]
Nembutal,Abbott,US | [Uses]
Sedative-hypnotic. | [Definition]
ChEBI: 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 Process]
Sodium (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 name]
Nembutal(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 Function]
Hypnotic, 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 Methods]
A 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 |
|