Carbromal

Carbromal
Names
	IUPAC name 2-Bromo-N-carbamoyl-2-ethylbutanamide
Identifiers
CAS Number	77-65-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1697828 ;
ChemSpider	6243 ;
ECHA InfoCard	100.000.952
EC Number	201-046-6;
KEGG	D02619 ;
MeSH	carbromal
PubChem CID	6488;
UNII	0Y299JY9V3 ;
CompTox Dashboard (EPA)	DTXSID8020252 ;
	InChI InChI=1S/C7H13BrN2O2/c1-3-7(8,4-2)5(11)10-6(9)12/h3-4H2,1-2H3,(H3,9,10,11,12) Key: OPNPQXLQERQBBV-UHFFFAOYSA-N ;
	SMILES CCC(Br)(CC)C(=O)NC(N)=O;
Properties
Chemical formula	C7H13BrN2O2
Molar mass	237.097 g·mol−1
Appearance	White crystals
Odor	Odorless
Density	1.544 g/cm3
Melting point	119 °C (246 °F; 392 K)
Solubility in water	Soluble
Solubility	soluble in chloroform, ether, acetone, benzene
log P	1.623
Acidity (pKa)	10.69
Basicity (pKb)	3.31
Structure
Crystal structure	rhombic
Pharmacology
ATC code	N05CM04 (WHO)
Related compounds
Related ureas	Bromisoval
Related compounds	3-Ureidopropionic acid; beta-Ureidoisobutyric acid; Carbamoyl aspartic acid; N-Acetylaspartic acid; Aceglutamide; N-Acetylglutamic acid; Citrulline;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer and subsequently marketed as Adalin.^[1]^[2] The drug was later sold by Parke-Davis in combination with pentobarbital, under the name Carbrital.^[3]

Synthesis

Carbromal synthesis:^[2]^[4]^[5] Literature:^[6]^[7]

Diethylmalonic acid [510-20-3] (1) is decarboxylated to 2-ethylvaleric acid [20225-24-5] (2). The Hell-Volhard-Zelinsky reaction converts this to 2-Bromo-2-Ethylbutyryl Bromide [26074-53-3] (3). Reaction with urea with affords carbromal (4).

References

^ Borrie P (March 1955). "A purpuric drug eruption caused by carbromal". British Medical Journal. 1 (4914): 645–6. doi:10.1136/bmj.1.4914.645. PMC 2061381. PMID 13230580.
^ ^a ^b DE 22571, "Verfahren dur Darstellung von Bromodiäthylacetylharnstoff [Method for the preparation of bromodiethylacetylurea]", published 1910-09-17, assigned to Friedrich Bayer & Co.
^ Physicians' Desk Reference (33 ed.). Oradell, N.J.: Medical Economics Co. 1979. p. 1266. ISBN 0-87489-999-0. OCLC 4636066.
^ Frdl. 10, 1160
^ Chem. Zentralbl. 1910, II, 1008.
^ Slotta H (1931). Bauer KH (ed.). Grundriss der modernen Arzneistoff-Synthese. Stuttgart: Verlag Ferd. Enke.
^ H. P. Kaufmann, Arzneimittel-Synthese (Berlin, 1953).

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[1] Borrie P (March 1955). "A purpuric drug eruption caused by carbromal". British Medical Journal. 1 (4914): 645–6. doi:10.1136/bmj.1.4914.645. PMC 2061381. PMID 13230580.

[patent225710-2] DE 22571, "Verfahren dur Darstellung von Bromodiäthylacetylharnstoff [Method for the preparation of bromodiethylacetylurea]", published 1910-09-17, assigned to Friedrich Bayer & Co.

[3] Physicians' Desk Reference (33 ed.). Oradell, N.J.: Medical Economics Co. 1979. p. 1266. ISBN 0-87489-999-0. OCLC 4636066.

[4] Frdl. 10, 1160

[5] Chem. Zentralbl. 1910, II, 1008.

[6] Slotta H (1931). Bauer KH (ed.). Grundriss der modernen Arzneistoff-Synthese. Stuttgart: Verlag Ferd. Enke.

[7] H. P. Kaufmann, Arzneimittel-Synthese (Berlin, 1953).

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Carbromal

Synthesis

See also

References