Mebutamate: Difference between revisions - Wikipedia

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{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 407756678457633911

| IUPAC_name = 2-''sec''-Butyl-2-methylpropane-1,3-diyl dicarbamate

| image = Mebutamate.svg

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| legal_US = Schedule IV

| legal_status =

| routes_of_administration =

<!--Pharmacokinetic data-->

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| metabolism =

| elimination_half-life =

| excretion =

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correctchanged|??}}

| CAS_number = <!-- blanked - oldvalue: 64-55-1 -->

| ATC_prefix = N05

| ATC_suffix = BC04

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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| UNII_Ref = {{fdacite|changedcorrect|FDA}}

| UNII = 5H8F175RER

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| KEGG = D01807

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| ChEMBL = <!-- blanked - oldvalue: 1200922 -->

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 5919

<!--Chemical data-->

| C=10 | H=20 | N=2 | O=4

| smiles = CCC(C)C(C)(COC(=O)N)COC(=O)N

| molecular_weight = 232.277 g/mol

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| 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)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = LEROTMJVBFSIMP-UHFFFAOYSA-N

}}

'''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>

'''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>

Mebutamate is one of many [[Gabaergic|GABAergic]] drugs which act via [[allosteric]] agonism of the [[GABAA receptor|GABA_A 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.

Other carbamates with the same mechanism of action and pharmacological properties include [[meprobamate]], [[carisoprodol]], [[felbamate]], and [[tybamate]].

==Synthesis==

[[File:Mebutamate synthesis.svg|thumb|center|700px|Mebutamate synthesis: Berger, Ludwig, {{US patent|2878280}} (1959 to [[Carter-Wallace|Carter Prod]].).]]

==Structural analogs==

*[[Lorbamate]]

*[[Carisoprodol]]

*[[Pentabamate]]

*[[Meprobamate]]

*[[Felbamate]]

*[[Tybamate]]

== References ==

{{reflistReflist}}

{{Anxiolytics}}

{{GABAAR PAMs}}

[[Category:Anxiolytics]]

[[Category:Carbamates]]

[[Category:GABAA receptor positive allosteric modulators]]

{{sedative-stub}}

{{nervous-system-drug-stub}}