Bromisoval
Chemical compound
From Wikipedia, the free encyclopedia
Bromisoval (INN), commonly known as bromovalerylurea, is a hypnotic and sedative of the bromoureide group discovered by Knoll in 1907 and patented in 1909.[1] It is marketed over the counter in Asia under various trade names (such as Brovarin[2]), usually in combination with nonsteroidal anti-inflammatory drugs.
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| IUPAC name | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
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| ChemSpider | |
| ECHA InfoCard | 100.007.115 |
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| KEGG | |
| MeSH | Bromisovalum |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C6H11BrN2O2 | |
| Molar mass | 223.070 g·mol−1 |
| log P | 1.057 |
| Acidity (pKa) | 10.536 |
| Basicity (pKb) | 3.461 |
| Pharmacology | |
| N05CM03 (WHO) | |
| Oral | |
| Related compounds | |
Related ureas |
Carbromal |
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bromisoval can be prepared by bromination of isovaleric acid by the Hell-Volhard-Zelinsky reaction followed by reaction with urea.
Toxicity
Chronic use of bromisoval has been associated with bromine poisoning.[3][4][5][6]
It was commonly used in Japan for suicide by overdose. In the 1950s and 1960s, ~4,000 people died each year from bromide poisoning, most commonly from bromvalerylurea.[7] In Japan, one popular formulation was Calmotin [カルモチン]. Osamu Dazai attempted a double complex suicide with Shimeko Tanabe by overdosing on Calmotin, then drowning at sea. Only Shimeko died. This became the basis for The Flowers of Buffoonery.
The drug was also referred to as the suicide drug in several literature works, including Freezing Point (suicide attempt of the heroine 陽子), The Sea of Fertility (suicide attempt of the heroine's maid, 蓼科).
