Secbutabarbital

Structural formula
	Structural formula without stereochemistry
General
Non-proprietary name	Secbutabarbital
other names	5-Ethyl-5- (1-methylpropyl) - (1 H , 3 H , 5 H ) -pyrimidine-2,4,6-trione ( IUPAC ); Butabarbital (USAN);
Molecular formula	C 10 H 16 N 2 O 3
External identifiers / databases
EC number	204-738-6
ECHA InfoCard	100.004.308
PubChem	2479
DrugBank	DB00237
Wikidata	Q410608
Drug information
ATC code	N05 CA03
Drug class	barbiturate
properties
Molar mass	212.25 g mol −1
Physical state	firmly
Melting point	165-168 ° C
pK s value	pKa 1 = 8.2; pKa 2 = 12.7;
solubility	poorly in water, soluble in diethyl ether , chloroform , ethanol and aqueous alkalis
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Secbutabarbital ( INN ), also butabarbital (USAN), is a barbiturate . Chemically, it is a barbituric - derivative . Secbutabarbital was patented for Eli Lilly and Company in 1932 .

Stereoisomers

Stereoisomers of secbutabarbital
( R ) stereoisomer
( S ) stereoisomer

The drug is a 1: 1 mixture of the ( R ) - (-) - enantiomer and ( S ) - (+) - enantiomer - i.e. a ( racemate ). This mixture is mostly used as the sodium salt . Secbutabarbital was patented for Eli Lilly and Company in 1932 .

synthesis

Secbutabarbital is produced by the condensation of ethyl (1-methyl-propyl) -malonic acid diethyl ester and urea :

Synthesis of butabarbital

Legal status

Secbutabarbital is a marketable narcotic drug in the Federal Republic of Germany due to its listing in Appendix 2 BtMG , but not a prescription drug. Internationally, secbutabarbital falls under the Convention on Psychotropic Substances .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on Secbutabarbital. In: Römpp Online . Georg Thieme Verlag, accessed on June 18, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ AW Frahm, HHJ Hager, F. v. Bruchhausen, M. Albinus, H. Hager: Hager's Handbook of Pharmaceutical Practice: Volume 4: Substances AK. , Birkhäuser, 1999, ISBN 978-3-540-52688-9 , p. 70.
↑ BtMG - single standard. In: gesetze-im-internet.de. Retrieved June 9, 2016 .
↑ International Narcotics Control Board: List of psychotropic substances under international control . ( Memento of August 31, 2012 in the Internet Archive ) (PDF) 23rd edition, August 2003.

[Römpp-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on Secbutabarbital. In: Römpp Online . Georg Thieme Verlag, accessed on June 18, 2014.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] AW Frahm, HHJ Hager, F. v. Bruchhausen, M. Albinus, H. Hager: Hager's Handbook of Pharmaceutical Practice: Volume 4: Substances AK. , Birkhäuser, 1999, ISBN 978-3-540-52688-9 , p. 70.

[4] BtMG - single standard. In: gesetze-im-internet.de. Retrieved June 9, 2016 .

[5] International Narcotics Control Board: List of psychotropic substances under international control . ( Memento of August 31, 2012 in the Internet Archive ) (PDF) 23rd edition, August 2003.