Heptabarbital

Structural formula
General
Non-proprietary name	Heptabarbital
other names	5- (1-cycloheptene-1-yl) -5-ethyl- (1 H , 3 H , 5 H ) -pyrimidine-2,4,6-trione
Molecular formula	C 13 H 18 N 2 O 3
Brief description	white, odorless powder with a bitter taste
External identifiers / databases
EC number	208-107-6
ECHA InfoCard	100.007.371
PubChem	10518
DrugBank	DB01354
Wikidata	Q410829
Drug information
ATC code	N05 CA11
Drug class	barbiturate
properties
Molar mass	250.29 g · mol -1
Physical state	firmly
Melting point	174 ° C
pK s value	7.4 (at 25 ° C)
solubility	very bad in water (250 mg l −1 at 25 ° C); soluble in ethanol , acetone , chloroform ; very soluble in alkaline solutions;
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
Toxicological data	> 800 mg kg −1 ( LD 50 , mouse , oral ) ; > 5 g kg −1 ( LD 50 , rat , oral ) ; 700 μg kg −1 ( TD Lo , human , oral ) ; 50 mg kg −1 ( LD Lo , human , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Heptabarbital is a chemical compound from the group of barbiturates and thus a derivative of barbituric acid . The substance and its mono -sodium salt (trade name Medomin ^® ) were classified as short-acting drug against falling asleep used. No preparation with heptabarbital is currently in use in Germany.

history

In 1946 the company has Geigy the patent registered for this substance. Like many other derivatives of barbituric acid , heptabarbital was also used in the form of its sodium salt as a sleep aid and sedative . Since barbiturates lead to a certain dependency and, moreover, abuse has occurred, heptabarbital (Medomin ^® ) is no longer produced and used today.

Extraction and presentation

Theoretically, it can be represented by the reaction of urea with the previously appropriately alkylated diethyl malonate ( diethyl malonate ).

An example of the theoretical production:

use

In the past, sodium heptabarbital, similar to pentobarbital , cyclobarbital and aprobarbital , was used as a sleeping and sedative. The mean dose was between 100 and 200 mg. However, the substance leads to physical dependence, which is comparable to alcoholism . Withdrawal leads to nervousness, tremors, impaired responsiveness, and irritability. In extreme cases, delirium tremens can even occur. Overdoses can also lead to death.

Like many other barbiturates , heptabarbital is therefore no longer used today.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f F. v. Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hagers Handbook of Pharmaceutical Practice. Volume 8: Substances E-O. 5th edition, 1993, Springer, ISBN 3-540-52640-4 , pp. 422-423.
↑ ^a ^b ^c ^d Entry on heptabarbital in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Drug Research . Vol. 21, pp. 1727, 1971.
↑ ^a ^b Irving S. Rossoff: Encyclopedia of clinical toxicology: a comprehensive guide and reference. Informa Health Care, 2002, ISBN 1-84214-101-5 , p. 515.

[hager-1] ↑ ^a ^b ^c ^d ^e ^f F. v. Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hagers Handbook of Pharmaceutical Practice. Volume 8: Substances E-O. 5th edition, 1993, Springer, ISBN 3-540-52640-4 , pp. 422-423.

[chemid-2] Entry on heptabarbital in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Drug Research . Vol. 21, pp. 1727, 1971.

[Rossoff-5] Irving S. Rossoff: Encyclopedia of clinical toxicology: a comprehensive guide and reference. Informa Health Care, 2002, ISBN 1-84214-101-5 , p. 515.