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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| verifiedrevid = 413310317
| verifiedrevid = 477317940
| IUPAC_name = 5,5-diprop-2-enyl-1,3-diazinane-2,4,6-trione
| IUPAC_name = 5,5-di(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
| image = Allobarbital.svg
| image = Allobarbital.svg
| image_class = skin-invert-image
| width = 120
| width = 120
| image2 = Allobarbital ball-and-stick animation.gif
| image2 = Allobarbital ball-and-stick animation.gif
| width2 = 160
| width2 = 160

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
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| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_BR = B1
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule IV
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US = Schedule III
| legal_DE = Anlage III
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =
| class = [[Barbiturate]]

<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
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| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =

<!--Identifiers-->
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 52-43-7
| CAS_number = 52-43-7
| ATC_prefix = N05
| ATC_prefix = N05
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 267719
| ChEMBL = 267719

<!--Chemical data-->
<!--Chemical data-->
| C=10 | H=12 | N=2 | O=3
| C=10 | H=12
| N=2 | O=3
| molecular_weight = 208.214 g/mol
| smiles = O=C1NC(=O)NC(=O)C1(C\C=C)C\C=C
| smiles = O=C1NC(=O)NC(=O)C1(C\C=C)C\C=C
| InChI = 1/C10H12N2O3/c1-3-5-10(6-4-2)7(13)11-9(15)12-8(10)14/h3-4H,1-2,5-6H2,(H2,11,12,13,14,15)
| InChIKey = FDQGNLOWMMVRQL-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H12N2O3/c1-3-5-10(6-4-2)7(13)11-9(15)12-8(10)14/h3-4H,1-2,5-6H2,(H2,11,12,13,14,15)
| StdInChI = 1S/C10H12N2O3/c1-3-5-10(6-4-2)7(13)11-9(15)12-8(10)14/h3-4H,1-2,5-6H2,(H2,11,12,13,14,15)
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| synonyms = 5,5-Diallylbarbituric acid, Allobarbital
| synonyms = 5,5-Diallylbarbituric acid, Allobarbital
}}
}}
'''Allobarbital''', also known as '''allobarbitone''' and branded as '''Cibalgine''' or '''Dial-Ciba''' (in combination with [[ethyl carbamate]]), is a [[barbiturate]] derivative invented in 1912 by Ernst Preiswerk and Ernst Grether working for [[Ciba Specialty Chemicals|CIBA]]. It was used primarily as an [[anticonvulsant]] <ref>Chocholova L, Radil-Weiss T. Effect of allobarbital on focal epilepsy in rats. Physiologia Bohemoslovaca. 1971;20(4):325-34.</ref> although it has now largely been replaced by newer drugs with improved safety profiles. Other uses for allobarbital included as an adjutant to boost the activity of [[analgesic]] drugs, and use in the treatment of [[insomnia]] and [[anxiety]].
'''Allobarbital''', also known as '''allobarbitone''' and branded as '''Dial''', '''Cibalgine''' (in combination with [[aminophenazone]]), or '''Dial-Ciba''' (in combination with [[ethyl carbamate]]), is a [[barbiturate]] derivative invented in 1912 by Ernst Preiswerk and Ernst Grether working for [[Ciba Specialty Chemicals|CIBA]]. It was used primarily as an [[anticonvulsant]]<ref>{{cite journal | vauthors = Chocholová L, Radil-Weiss T | title = Effect of allobarbital on focal epilepsy in rats | journal = Physiologia Bohemoslovaca | volume = 20 | issue = 4 | pages = 325–34 | year = 1971 | pmid = 4335127 }}</ref> although it has now largely been replaced by newer drugs with improved safety profiles. Other uses for allobarbital included as an adjutant to boost the activity of [[analgesic]] drugs, and use in the treatment of [[insomnia]] and [[anxiety]].


Allobarbital was never particularly widely used compared to better known barbiturates such as [[phenobarbital]] and [[secobarbital]], although it saw more use in some European countries such as [[Bulgaria]] and [[Slovakia]],<ref>Getova D, Georgiev V. GABA-ergic mechanisms in the anticonvulsive activity of newly-synthesized barbiturates. I. Effects of barbiturates on the convulsive action of GABA-antagonists. Acta Physiologica et Pharmacologica Bulgarica. 1987;13(3):43-50.</ref> and is still used in for example Poland, but only as compound.<ref>{{Citation
Allobarbital was never particularly widely used compared to better known barbiturates such as [[phenobarbital]] and [[secobarbital]], although it saw more use in some European countries such as [[Bulgaria]] and [[Slovakia]],<ref>{{cite journal | vauthors = Getova D, Georgiev V | title = GABA-ergic mechanisms in the anticonvulsive activity of newly-synthesized barbiturates. I. Effects of barbiturates on the convulsive action of GABA-antagonists | journal = Acta Physiologica et Pharmacologica Bulgarica | volume = 13 | issue = 3 | pages = 43–50 | year = 1987 | pmid = 3439474 }}</ref> and is still used in for example Poland, but only as compound.<ref>{{cite web|title=APTECZKA BABUNI - KROPLE ŻOŁĄDKOWE KROPLE 20 G |trans-title=GRANDMA'S FIRST AID KIT - DROPS - STOMACH DROPS 20 G |website=Domzdrowia.pl |language=Polish |url=http://www.domzdrowia.pl/29439,apteczka-babuni-krople-zoladkowe-krople-20-g.html |archive-url=https://web.archive.org/web/20071031195035/http://www.domzdrowia.pl/29439%2Capteczka-babuni-krople-zoladkowe-krople-20-g.html |archive-date=October 31, 2007 |access-date=March 10, 2013 |url-status=live }}</ref>
|last= |first= |year= |title=APTECZKA BABUNI - KROPLE ŻOŁĄDKOWE KROPLE 20 G |publisher= |publication-place= |language=Polish |url=http://www.domzdrowia.pl/29439,apteczka-babuni-krople-zoladkowe-krople-20-g.html |archiveurl=http://web.archive.org/web/20071031195035/http://www.domzdrowia.pl/29439,apteczka-babuni-krople-zoladkowe-krople-20-g.html |archivedate=October 31, 2007 |accessdate=March 10, 2013 }}</ref>


==References==
== References ==
{{reflist}}
{{reflist}}


{{barbiturates}}
{{Hypnotics and sedatives}}
{{Hypnotics and sedatives}}
{{GABAAR PAMs}}


[[Category:Barbiturates]]
[[Category:Barbiturates]]
[[Category:Allyl compounds]]

Latest revision as of 19:20, 11 January 2025

Allobarbital
Clinical data
Other names5,5-Diallylbarbituric acid, Allobarbital
Drug classBarbiturate
ATC code
Legal status
Legal status
Identifiers
  • 5,5-di(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.129 Edit this at Wikidata
Chemical and physical data
FormulaC10H12N2O3
Molar mass208.217 g·mol−1
3D model (JSmol)
  • O=C1NC(=O)NC(=O)C1(C\C=C)C\C=C
  • InChI=1S/C10H12N2O3/c1-3-5-10(6-4-2)7(13)11-9(15)12-8(10)14/h3-4H,1-2,5-6H2,(H2,11,12,13,14,15) checkY
  • Key:FDQGNLOWMMVRQL-UHFFFAOYSA-N checkY
  (verify)

Allobarbital, also known as allobarbitone and branded as Dial, Cibalgine (in combination with aminophenazone), or Dial-Ciba (in combination with ethyl carbamate), is a barbiturate derivative invented in 1912 by Ernst Preiswerk and Ernst Grether working for CIBA. It was used primarily as an anticonvulsant[2] although it has now largely been replaced by newer drugs with improved safety profiles. Other uses for allobarbital included as an adjutant to boost the activity of analgesic drugs, and use in the treatment of insomnia and anxiety.

Allobarbital was never particularly widely used compared to better known barbiturates such as phenobarbital and secobarbital, although it saw more use in some European countries such as Bulgaria and Slovakia,[3] and is still used in for example Poland, but only as compound.[4]

References

[edit]
  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Chocholová L, Radil-Weiss T (1971). "Effect of allobarbital on focal epilepsy in rats". Physiologia Bohemoslovaca. 20 (4): 325–34. PMID 4335127.
  3. ^ Getova D, Georgiev V (1987). "GABA-ergic mechanisms in the anticonvulsive activity of newly-synthesized barbiturates. I. Effects of barbiturates on the convulsive action of GABA-antagonists". Acta Physiologica et Pharmacologica Bulgarica. 13 (3): 43–50. PMID 3439474.
  4. ^ "APTECZKA BABUNI - KROPLE ŻOŁĄDKOWE KROPLE 20 G" [GRANDMA'S FIRST AID KIT - DROPS - STOMACH DROPS 20 G]. Domzdrowia.pl (in Polish). Archived from the original on October 31, 2007. Retrieved March 10, 2013.
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