Mebutamate

Last updated
Mebutamate
Mebutamate.svg
Clinical data
ATC code
Legal status
Legal status
Identifiers
  • 2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.534 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H20N2O4
Molar mass 232.280 g·mol−1
3D model (JSmol)
  • CCC(C)C(C)(COC(=O)N)COC(=O)N
  • InChI=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) X mark.svgN
  • Key:LEROTMJVBFSIMP-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Mebutamate (Capla, Dormate) is an anxiolytic and sedative drug with antihypertensive effects of the carbamate class. [1] [2] 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. [3]

Contents

Mebutamate is one of many GABAergic drugs which act via allosteric agonism of the GABAA 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

Mebutamate synthesis: Berger, Ludwig, U.S. patent 2,878,280 (1959 to Carter Prod.). Mebutamate synthesis.svg
Mebutamate synthesis: Berger, Ludwig, U.S. patent 2,878,280 (1959 to Carter Prod.).

Structural analogs

Related Research Articles

<span class="mw-page-title-main">Hypnotic</span> Drug whose use induces sleep

Hypnotic, or soporific drugs, commonly known as sleeping pills, are a class of psychoactive drugs whose primary function is to induce sleep and to treat insomnia (sleeplessness).

An antispasmodic is a pharmaceutical drug or other agent that suppresses muscle spasms.

<span class="mw-page-title-main">Sedative</span> Drug that reduces excitement without inducing sleep

A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are CNS depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but the majority of them affect the neurotransmitter gamma-aminobutyric acid (GABA). In spite of the fact that each sedative acts in its own way, most produce relaxing effects by increasing GABA activity.

<span class="mw-page-title-main">Ethchlorvynol</span> Group of stereoisomers

Ethchlorvynol is a GABA-ergic sedative and hypnotic/soporific medication first developed by Pfizer in the 1950s. In the United States it was sold by Abbott Laboratories under the trade name Placidyl. Placidyl was available in 200 mg, 500 mg, and 750 mg strength gel filled capsules. While the 500 mg and 750 mg strength capsules were for use in reducing sleep latency, the 200 mg strength capsules were intended to be used to re-induce sleep in case of early awakening. Abbott discontinued production in 1999, due to it being replaced by the benzodiazepine family and its widespread abuse, after which Placidyl was available for about a year in the United States. Although, theoretically, ethchlorvynol could be manufactured for sale in the United States by another pharmaceutical company, no pharmaceutical company has chosen to do so. Individuals with a valid prescription for the substance may legally transport a reasonable amount of ethclorvynol with them into the United States.

Colloquially known as "downers", depressants or central depressants are drugs that lower neurotransmission levels, or depress or reduce arousal or stimulation in various areas of the brain. Depressants do not change the mood or mental state of others. Stimulants, or "uppers", increase mental or physical function, hence the opposite drug class from depressants are stimulants, not antidepressants.

<span class="mw-page-title-main">Carbamate</span> Chemical group (>N–C(=O)–O–)

In organic chemistry, a carbamate is a category of organic compounds with the general formula R2NC(O)OR and structure >N−C(=O)−O−, which are formally derived from carbamic acid. The term includes organic compounds, formally obtained by replacing one or more of the hydrogen atoms by other organic functional groups; as well as salts with the carbamate anion H2NCOO.

<span class="mw-page-title-main">Carisoprodol</span> Muscle relaxant medication

Carisoprodol, sold under the brand name Soma among others, is a medication used for musculoskeletal pain. Use is only approved for up to three weeks. Effects generally begin within half an hour and last for up to six hours. It is taken orally.

Physical dependence is a physical condition caused by chronic use of a tolerance-forming drug, in which abrupt or gradual drug withdrawal causes unpleasant physical symptoms. Physical dependence can develop from low-dose therapeutic use of certain medications such as benzodiazepines, opioids, stimulants, antiepileptics and antidepressants, as well as the recreational misuse of drugs such as alcohol, opioids and benzodiazepines. The higher the dose used, the greater the duration of use, and the earlier age use began are predictive of worsened physical dependence and thus more severe withdrawal syndromes. Acute withdrawal syndromes can last days, weeks or months. Protracted withdrawal syndrome, also known as post-acute-withdrawal syndrome or "PAWS", is a low-grade continuation of some of the symptoms of acute withdrawal, typically in a remitting-relapsing pattern, often resulting in relapse and prolonged disability of a degree to preclude the possibility of lawful employment. Protracted withdrawal syndrome can last for months, years, or depending on individual factors, indefinitely. Protracted withdrawal syndrome is noted to be most often caused by benzodiazepines. To dispel the popular misassociation with addiction, physical dependence to medications is sometimes compared to dependence on insulin by persons with diabetes.

<span class="mw-page-title-main">Meprobamate</span> Carbamate derivative used as an anxiolytic drug

Meprobamate—marketed as Miltown by Wallace Laboratories and Equanil by Wyeth, among others—is a carbamate derivative used as an anxiolytic drug. It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benzodiazepines due to their wider therapeutic index and lower incidence of serious side effects.

<span class="mw-page-title-main">Methocarbamol</span> Medication for musculoskeletal pain

Methocarbamol, sold under the brand name Robaxin among others, is a medication used for short-term musculoskeletal pain. It may be used together with rest, physical therapy, and pain medication. It is less preferred in low back pain. It has limited use for rheumatoid arthritis and cerebral palsy. Effects generally begin within half an hour. It is taken by mouth or injection into a vein.

<span class="mw-page-title-main">Secobarbital</span> Obsolete sedative-hypnotic

Secobarbital is a short-acting barbiturate derivative drug that was patented in 1934 in the United States. It possesses anaesthetic, anticonvulsant, anxiolytic, sedative, and hypnotic properties. In the United Kingdom, it was known as quinalbarbitone. It is the most frequently used drug in physician-assisted suicide within the United States. Secobarbital is considered to be an obsolete sedative-hypnotic, and as a result, it has largely been replaced by the benzodiazepine family. Seconal was widely abused, known on the street as "red devils" or "reds".

<span class="mw-page-title-main">Butabarbital</span> Chemical compound

Butabarbital is a prescription barbiturate sleep aid and anxiety medication. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia, relieving general anxiety and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its intermediate duration of action gives butabarbital an abuse potential slightly lower than secobarbital. Butabarbital can be hydrolyzed to valnoctamide.

<span class="mw-page-title-main">Chlordiazepoxide</span> Benzodiazepine class sedative and hypnotic medication

Chlordiazepoxide, trade name Librium among others, is a sedative and hypnotic medication of the benzodiazepine class; it is used to treat anxiety, insomnia and symptoms of withdrawal from alcohol and other drugs.

<span class="mw-page-title-main">GABA receptor agonist</span> Category of drug

A GABA receptor agonist is a drug that is an agonist for one or more of the GABA receptors, producing typically sedative effects, and may also cause other effects such as anxiolytic, anticonvulsant, and muscle relaxant effects. There are three receptors of the gamma-aminobutyric acid. The two receptors GABA-α and GABA-ρ are ion channels that are permeable to chloride ions which reduces neuronal excitability. The GABA-β receptor belongs to the class of G-Protein coupled receptors that inhibit adenylyl cyclase, therefore leading to decreased cyclic adenosine monophosphate (cAMP). GABA-α and GABA-ρ receptors produce sedative and hypnotic effects and have anti-convulsion properties. GABA-β receptors also produce sedative effects. Furthermore, they lead to changes in gene transcription.

<span class="mw-page-title-main">Barbiturate</span> Class of depressant drugs derived from barbituric acid

Barbiturates are a class of depressant drugs that are chemically derived from barbituric acid. They are effective when used medically as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as well as overdose potential among other possible adverse effects. They have been used recreationally for their anti-anxiety and sedative effects, and are thus controlled in most countries due to the risks associated with such use.

<span class="mw-page-title-main">Fenadiazole</span> Chemical compound

Fenadiazole, also known as phénadiazole and sold under the brand names Hypnazol, Eudormil, and Viodor, is a hypnotic and sedative medication which has been used to treat insomnia but is no longer marketed. It is described as a non-barbiturate hypnotic with marked or profound hypnotic and sedative properties in animals, variable hypnotic effects in humans, additional anticonvulsant, antithermal, and spasmolytic effects, and a generally well-tolerated profile in humans. The drug was synthesized, pharmacologically characterized, patented, and marketed by the French pharmaceutical company Laboratoires Jacques Logeais between 1960 and 1962. As a hypnotic and sedative, fenadiazole has a unique oxadiazole-based chemical structure. It may be chemically related to certain other hypnotics and sedatives with atypical chemical structures.

<span class="mw-page-title-main">Fenpentadiol</span> Chemical compound

Fenpentadiol (INN), also known as phenpentanediol, is a drug described as a tranquilizer and antidepressant that was formerly marketed in Europe. It also has stimulant, sedative, and anxiolytic effects, with the latter two occurring only at higher doses.

Barbiturate dependence develops with regular use of barbiturates. This in turn may lead to a need for increasing doses of the drug to get the original desired pharmacological or therapeutic effect. Barbiturate use can lead to both addiction and physical dependence, and as such they have a high potential for excess or non-medical use, however, it does not affect all users. Management of barbiturate dependence involves considering the affected person's age, comorbidity and the pharmacological pathways of barbiturates.

An anxiotropic agent is one that modifies anxiety, a human emotion that has homologous processes in animals. In psychopharmacology anxiotropic agents consist of two categories of psychoactive drugs: anxiolytics that reduce anxiety and may be used therapeutically, and anxiogenic compounds that increase anxiety.

GABA<sub>A</sub> receptor positive allosteric modulator GABAA receptor positive modulators

In pharmacology, GABAA receptor positive allosteric modulators, also known as GABAkines or GABAA receptor potentiators, are positive allosteric modulator (PAM) molecules that increase the activity of the GABAA receptor protein in the vertebrate central nervous system.

References

  1. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 634. ISBN   978-3-88763-075-1.
  2. The Merck Index (14 ed.). Merck Publishers. 2006-11-03. 5813. ISBN   978-0-911910-00-1.
  3. Tetreault L, Richer P, Bordeleau JM (August 1967). "Hypnotic properties of mebutamate: a comparative study of mebutamate, secobarbital and placebo in psychiatric patients". Canadian Medical Association Journal. 97 (8): 395–8. PMC   1923261 . PMID   6037393.