MedKoo Cat#: 329216 | Name: Bromisoval
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bromisoval, also known as bromovalerylurea, is a bromide-containing sedative-hypnotic that is occasionally combined with non-steroidal anti-inflammatory drugs in over-the-counter products. Bromisoval suppresses expression of many kinds of pro- and anti-inflammatory mediators in LPS- or interferon-γ activated alveolar and peritoneal macrophages. Bromisoval is used to treat anxiety.

Chemical Structure

Bromisoval
Bromisoval
CAS#496-67-3

Theoretical Analysis

MedKoo Cat#: 329216

Name: Bromisoval

CAS#: 496-67-3

Chemical Formula: C6H11BrN2O2

Exact Mass: 222.0004

Molecular Weight: 223.07

Elemental Analysis: C, 32.31; H, 4.97; Br, 35.82; N, 12.56; O, 14.34

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
25g USD 450.00 2 Weeks
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Related CAS #
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Synonym
Bromisoval; bromovalerylurea; Isobromyl; Bromaral; BRN 1773255; BRN-1773255; BRN1773255
IUPAC/Chemical Name
2-bromo-N-carbamoyl-3-methylbutanamide
InChi Key
CMCCHHWTTBEZNM-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H11BrN2O2/c1-3(2)4(7)5(10)9-6(8)11/h3-4H,1-2H3,(H3,8,9,10,11)
SMILES Code
O=C(N)NC(C(Br)C(C)C)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 223.07 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Biyajima M, Satoh S, Morikawa T, Morita Y, Watanabe R, Matsui D, Konno M, Morimoto N, Yatsu Y, Hirasaki A, Yahikozawa H. Bromisoval-induced bromism with status epilepticus mimicking Wernicke's encephalopathy: report of two cases. BMC Neurol. 2022 May 16;22(1):181. doi: 10.1186/s12883-022-02712-3. PMID: 35578314; PMCID: PMC9109394. 2: Mulders TM, Bergman DJ, Poll-The BT, Smit GP, Breimer DD, Mulder GJ, Duran M, Smeitink JA. Abnormal glutathione conjugation in patients with tyrosinaemia type I. J Inherit Metab Dis. 1997 Aug;20(4):473-85. doi: 10.1023/a:1005385009831. PMID: 9266383. 3: Mulders TM, Keizer, Ouwerkerk J, van der Velde EA, Breimer DD, Mulder GJ. Effect of ifosfamide treatment on glutathione and glutathione conjugation activity in patients with advanced cancers. Clin Cancer Res. 1995 Dec;1(12):1525-36. PMID: 9815953. 4: Mulders TM, Venizelos V, Schoemaker R, Cohen AF, Breimer DD, Mulder GJ. Characterization of glutathione conjugation in humans: stereoselectivity in plasma elimination pharmacokinetics and urinary excretion of (R)- and (S)-2-bromoisovalerylurea in healthy volunteers. Clin Pharmacol Ther. 1993 Jan;53(1):49-58. doi: 10.1038/clpt.1993.8. PMID: 8422741. 5: Maurer HH. Identification and differentiation of barbiturates, other sedative-hypnotics and their metabolites in urine integrated in a general screening procedure using computerized gas chromatography-mass spectrometry. J Chromatogr. 1990 Sep 14;530(2):307-26. doi: 10.1016/s0378-4347(00)82334-8. PMID: 2079506. 6: Kurokawa Y, Fukatsu R, Takasaka Y, Chiba T, Yamashita I, Asano Y. Three cases of chronic bromisoval intoxication: clinical symptoms and application of energy dispersive X-ray analysis (EDX) to detect bromine in serum, urine and cerebrospinal fluid. Jpn J Psychiatry Neurol. 1987 Mar;41(1):25-32. doi: 10.1111/j.1440-1819.1987.tb00388.x. PMID: 3626193. 7: Cockaerts P, Roets E, Hoogmartens J. Analysis of a complex analgesic formulation by high-performance liquid chromatography with column-switching. J Pharm Biomed Anal. 1986;4(3):367-76. doi: 10.1016/0731-7085(86)80058-9. PMID: 16867602. 8: van Essen EJ, Csànky-Treels JC, de Krom MC, Tjoeng MM. An acute bromisoval intoxication. Arch Toxicol. 1980 Apr;44(4):299-300. doi: 10.1007/BF00278037. PMID: 7396716. 9: Eichelbaum M, Sonntag B, von Unruh G. Determination of monoureides in biological fluids by high-pressure-liquid-chromatography. Arch Toxicol. 1978 Dec 28;41(3):187-93. doi: 10.1007/BF00354090. PMID: 32863. 10: Käferstein H, Sticht G. Nachweis der Bromureide in Leichenorgranen [Post mortem determination of bromureides (author's transl)]. Z Rechtsmed. 1978 Aug 28;81(4):269-83. German. doi: 10.1007/BF02096433. PMID: 28618. 11: Strubelt O, Schütt A, Iven H, Siegers CP. Vergleich der kardiotoxischen Wirkungen von Carbromal, Bromisoval und Pentobarbital [Comparison of the cardiotoxic effects of carbromal, bromisoval and pentobarbital]. Med Welt. 1978 Jul 28;29(29-30):1184-7. German. PMID: 27695. 12: Blank HJ, Brinkmann OH, Berndt V. Differentialtherapie der Bromcarbamid-- Vergiftungen under Berücksichtigung der primären Detoxikation durch Gastro-bzw. Duodenotomie [Differential therapy of bromcarbamide poisoning with reference to primary detoxication by means of gastro- or duodenotomy]. MMW Munch Med Wochenschr. 1978 May 19;120(20):693-8. German. PMID: 306544. 13: Niederwieser A, Steinmann B, Matasovic A. New bromisoval (bromural) metabolites in human urine: alpha-(cystein-S-yl)isovalerylurea, alpha-(N-acetylcystein-S-yl)isovalerylurea and alpha-(cysteamin-S-yl)isovaleric acid. J Chromatogr. 1978 Jan 11;147:163-76. doi: 10.1016/s0021-9673(00)85128-6. PMID: 621251. 14: Höbel M, Bender G. Separation and quantitative determination of acecarbromal, carbromal, and bromisoval as well as their main metabolites by means of high-pressure liquid chromatographic analysis. Arch Toxicol. 1977 Aug 9;37(4):307-12. doi: 10.1007/BF00330822. PMID: 20869. 15: Grom OL, Znaevskaia AV, Shkol'nik SD. Analiz kofeïnu-benzoatu natriiu, fenobarbitalu, dyfeninu i bromizovalu v bahatokomponentnykh likars'kykh formakh [Analysis of caffeine-benzoate sodium, phenobarbital, diphenine and bromisoval in multi-component medicinal forms]. Farm Zh. 1977 Mar-Apr;(2):77-80. Ukrainian. PMID: 885233. 16: Mrongovius RI, Gaff GA, Rand MJ. Comparison of the bromureide sedative- hypnotic drugs, bromvaletone (bromisoval) and carbromal, and their chloro analogues in mice. Clin Exp Pharmacol Physiol. 1976 Sep-Oct;3(5):443-7. doi: 10.1111/j.1440-1681.1976.tb00621.x. PMID: 10116. 17: Przyborowski L, Smajkiewicz A. Colorimetric determination of bromisoval and carbromal. Pol J Pharmacol Pharm. 1975 Nov-Dec;27(6):645-8. PMID: 1716. 18: Srch M. Vysetrovánizvratků [Examination of vomits]. Soud Lek. 1975 Aug;20(3):46-8. Czech. PMID: 1209290. 19: Grabowska I, Kaliszan R. Dimorphism of ureides. alpha-Bromisovalerylurea (bromisoval) and alpha-bromdiaethylacetylcarbamide (carbromal). Pol J Pharmacol Pharm. 1974 Jul-Aug;26(5):527-30. PMID: 4154437. 20: Poser S, Müller-Oerlinghausen B. Proceedings: Clinical investigations on the chronic intoxication with bromocarbamides (carbromal and bromisoval). Naunyn Schmiedebergs Arch Pharmacol. 1974;282(Suppl):suppl 282:R75. PMID: 4152368. 1: Biyajima M, Satoh S, Morikawa T, Morita Y, Watanabe R, Matsui D, Konno M, Morimoto N, Yatsu Y, Hirasaki A, Yahikozawa H. Bromisoval-induced bromism with status epilepticus mimicking Wernicke's encephalopathy: report of two cases. BMC Neurol. 2022 May 16;22(1):181. doi: 10.1186/s12883-022-02712-3. PMID: 35578314; PMCID: PMC9109394. 2: Mulders TM, Bergman DJ, Poll-The BT, Smit GP, Breimer DD, Mulder GJ, Duran M, Smeitink JA. Abnormal glutathione conjugation in patients with tyrosinaemia type I. J Inherit Metab Dis. 1997 Aug;20(4):473-85. doi: 10.1023/a:1005385009831. PMID: 9266383. 3: Mulders TM, Keizer, Ouwerkerk J, van der Velde EA, Breimer DD, Mulder GJ. Effect of ifosfamide treatment on glutathione and glutathione conjugation activity in patients with advanced cancers. Clin Cancer Res. 1995 Dec;1(12):1525-36. PMID: 9815953. 4: Mulders TM, Venizelos V, Schoemaker R, Cohen AF, Breimer DD, Mulder GJ. Characterization of glutathione conjugation in humans: stereoselectivity in plasma elimination pharmacokinetics and urinary excretion of (R)- and (S)-2-bromoisovalerylurea in healthy volunteers. Clin Pharmacol Ther. 1993 Jan;53(1):49-58. doi: 10.1038/clpt.1993.8. PMID: 8422741. 5: Maurer HH. Identification and differentiation of barbiturates, other sedative-hypnotics and their metabolites in urine integrated in a general screening procedure using computerized gas chromatography-mass spectrometry. J Chromatogr. 1990 Sep 14;530(2):307-26. doi: 10.1016/s0378-4347(00)82334-8. PMID: 2079506. 6: Kurokawa Y, Fukatsu R, Takasaka Y, Chiba T, Yamashita I, Asano Y. Three cases of chronic bromisoval intoxication: clinical symptoms and application of energy dispersive X-ray analysis (EDX) to detect bromine in serum, urine and cerebrospinal fluid. Jpn J Psychiatry Neurol. 1987 Mar;41(1):25-32. doi: 10.1111/j.1440-1819.1987.tb00388.x. PMID: 3626193. 7: Cockaerts P, Roets E, Hoogmartens J. Analysis of a complex analgesic formulation by high-performance liquid chromatography with column-switching. J Pharm Biomed Anal. 1986;4(3):367-76. doi: 10.1016/0731-7085(86)80058-9. PMID: 16867602. 8: van Essen EJ, Csànky-Treels JC, de Krom MC, Tjoeng MM. An acute bromisoval intoxication. Arch Toxicol. 1980 Apr;44(4):299-300. doi: 10.1007/BF00278037. PMID: 7396716. 9: Eichelbaum M, Sonntag B, von Unruh G. Determination of monoureides in biological fluids by high-pressure-liquid-chromatography. Arch Toxicol. 1978 Dec 28;41(3):187-93. doi: 10.1007/BF00354090. PMID: 32863. 10: Käferstein H, Sticht G. Nachweis der Bromureide in Leichenorgranen [Post mortem determination of bromureides (author's transl)]. Z Rechtsmed. 1978 Aug 28;81(4):269-83. German. doi: 10.1007/BF02096433. PMID: 28618. 11: Strubelt O, Schütt A, Iven H, Siegers CP. Vergleich der kardiotoxischen Wirkungen von Carbromal, Bromisoval und Pentobarbital [Comparison of the cardiotoxic effects of carbromal, bromisoval and pentobarbital]. Med Welt. 1978 Jul 28;29(29-30):1184-7. German. PMID: 27695. 12: Blank HJ, Brinkmann OH, Berndt V. Differentialtherapie der Bromcarbamid-- Vergiftungen under Berücksichtigung der primären Detoxikation durch Gastro-bzw. Duodenotomie [Differential therapy of bromcarbamide poisoning with reference to primary detoxication by means of gastro- or duodenotomy]. MMW Munch Med Wochenschr. 1978 May 19;120(20):693-8. German. PMID: 306544. 13: Niederwieser A, Steinmann B, Matasovic A. New bromisoval (bromural) metabolites in human urine: alpha-(cystein-S-yl)isovalerylurea, alpha-(N-acetylcystein-S-yl)isovalerylurea and alpha-(cysteamin-S-yl)isovaleric acid. J Chromatogr. 1978 Jan 11;147:163-76. doi: 10.1016/s0021-9673(00)85128-6. PMID: 621251. 14: Höbel M, Bender G. Separation and quantitative determination of acecarbromal, carbromal, and bromisoval as well as their main metabolites by means of high-pressure liquid chromatographic analysis. Arch Toxicol. 1977 Aug 9;37(4):307-12. doi: 10.1007/BF00330822. PMID: 20869. 15: Grom OL, Znaevskaia AV, Shkol'nik SD. Analiz kofeïnu-benzoatu natriiu, fenobarbitalu, dyfeninu i bromizovalu v bahatokomponentnykh likars'kykh formakh [Analysis of caffeine-benzoate sodium, phenobarbital, diphenine and bromisoval in multi-component medicinal forms]. Farm Zh. 1977 Mar-Apr;(2):77-80. Ukrainian. PMID: 885233. 16: Mrongovius RI, Gaff GA, Rand MJ. Comparison of the bromureide sedative- hypnotic drugs, bromvaletone (bromisoval) and carbromal, and their chloro analogues in mice. Clin Exp Pharmacol Physiol. 1976 Sep-Oct;3(5):443-7. doi: 10.1111/j.1440-1681.1976.tb00621.x. PMID: 10116. 17: Przyborowski L, Smajkiewicz A. Colorimetric determination of bromisoval and carbromal. Pol J Pharmacol Pharm. 1975 Nov-Dec;27(6):645-8. PMID: 1716. 18: Srch M. Vysetrovánizvratků [Examination of vomits]. Soud Lek. 1975 Aug;20(3):46-8. Czech. PMID: 1209290. 19: Grabowska I, Kaliszan R. Dimorphism of ureides. alpha-Bromisovalerylurea (bromisoval) and alpha-bromdiaethylacetylcarbamide (carbromal). Pol J Pharmacol Pharm. 1974 Jul-Aug;26(5):527-30. PMID: 4154437. 20: Poser S, Müller-Oerlinghausen B. Proceedings: Clinical investigations on the chronic intoxication with bromocarbamides (carbromal and bromisoval). Naunyn Schmiedebergs Arch Pharmacol. 1974;282(Suppl):suppl 282:R75. PMID: 4152368.