Mebutamate: Difference between revisions
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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number'). |
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{{short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
| Verifiedfields = changed |
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| Watchedfields = changed |
| Watchedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 457633911 |
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| IUPAC_name = 2-''sec''-Butyl-2-methylpropane-1,3-diyl dicarbamate |
| IUPAC_name = 2-''sec''-Butyl-2-methylpropane-1,3-diyl dicarbamate |
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| image = Mebutamate.svg |
| image = Mebutamate.svg |
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| legal_US = Schedule IV |
| legal_US = Schedule IV |
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| legal_status = |
| legal_status = |
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| routes_of_administration = |
| routes_of_administration = |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_number_Ref = {{cascite| |
| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = |
| CAS_number = 64-55-1 |
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| ATC_prefix = N05 |
| ATC_prefix = N05 |
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| ATC_suffix = BC04 |
| ATC_suffix = BC04 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
| DrugBank = |
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| UNII_Ref = {{fdacite| |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 5H8F175RER |
| UNII = 5H8F175RER |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D01807 |
| KEGG = D01807 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = |
| ChEMBL = 1200922 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 5919 |
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<!--Chemical data--> |
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| C=10 | H=20 | N=2 | O=4 |
| C=10 | H=20 | N=2 | O=4 |
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| smiles = CCC(C)C(C)(COC(=O)N)COC(=O)N |
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| molecular_weight = 232.277 g/mol |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C10H20N2O4/c1-4-7(2)10(3,5-15-8(11)13)6-16-9(12)14/h7H,4-6H2,1-3H3,(H2,11,13)(H2,12,14) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = LEROTMJVBFSIMP-UHFFFAOYSA-N |
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}} |
}} |
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'''Mebutamate'''<ref>{{ cite book | title = The Merck Index | edition = 14 | publisher = Merck Publishers | isbn = 978-0-911910-00-1 | at = 5813 }}</ref> is a [[sedative]] and [[anxiolytic]] drug with anti-[[hypertension|hypertensive]] (blood pressure lowering) effects. It has effects comparable to those of [[barbiturates]] such as [[secobarbital]], but is only around 1/3 the potency of secobarbital as a sedative. Side effects include [[dizziness]] and [[headaches]].<ref>{{ cite pmid |6037393 }}</ref> |
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'''Mebutamate''' ('''Capla''', '''Dormate''') is an [[anxiolytic]] and [[sedative]] [[drug]] with [[antihypertensive]] effects of the carbamate class.<ref name="TaylorFrancis2000">{{cite book | title = Index Nominum 2000: International Drug Directory | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA634 | date = January 2000 | publisher = Taylor & Francis | isbn = 978-3-88763-075-1 | page = 634}}</ref><ref>{{ cite book | title = The Merck Index | edition = 14 | publisher = Merck Publishers | isbn = 978-0-911910-00-1 | at = 5813 | date = 2006-11-03 }}</ref> It has effects comparable to those of [[barbiturate]]s such as [[secobarbital]], but is only around 1/3 the potency of secobarbital as a sedative. Side effects include [[dizziness]] and [[headaches]].<ref>{{cite journal | vauthors = Tetreault L, Richer P, Bordeleau JM | title = Hypnotic properties of mebutamate: a comparative study of mebutamate, secobarbital and placebo in psychiatric patients | journal = Canadian Medical Association Journal | volume = 97 | issue = 8 | pages = 395–8 | date = August 1967 | pmid = 6037393 | pmc = 1923261 }}</ref> |
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Mebutamate is one of many [[Gabaergic|GABAergic]] drugs which act via [[allosteric]] agonism of the [[GABAA receptor|GABA<sub>A</sub> receptor]] at the β-subreceptor similar to barbiturates. In contrast, [[benzodiazepines]] act at the α-subreceptor. As such, carbamates and barbiturates, possess [[analgesic]] properties while the benzodiazepine class of drugs are strictly psychoactive. |
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Other carbamates with the same mechanism of action and pharmacological properties include [[meprobamate]], [[carisoprodol]], [[felbamate]], and [[tybamate]]. |
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==Synthesis== |
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[[File:Mebutamate synthesis.svg|thumb|center|700px|Mebutamate synthesis: Berger, Ludwig, {{US patent|2878280}} (1959 to [[Carter-Wallace|Carter Prod]].).]] |
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==Structural analogs== |
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*[[Lorbamate]] |
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*[[Carisoprodol]] |
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*[[Pentabamate]] |
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*[[Meprobamate]] |
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*[[Felbamate]] |
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*[[Tybamate]] |
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== References == |
== References == |
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{{ |
{{Reflist}} |
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{{Anxiolytics}} |
{{Anxiolytics}} |
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{{GABAAR PAMs}} |
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[[Category:Anxiolytics]] |
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[[Category:Carbamates]] |
[[Category:Carbamates]] |
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[[Category:GABAA receptor positive allosteric modulators]] |
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{{sedative-stub}} |
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{{nervous-system-drug-stub}} |