Barbituric acid, 5-allyl-

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MedKoo CAT#: 581610

CAS#: 2565-43-7

Description: Barbituric acid, 5-allyl-, arbituric acid is discontinued (DEA controlled substance). It is an odourless powder and is soluble in water. It has a very high pharmacological activity and can be used to synthesize addition derivatives of it, to be used in novel drug discovery. It basically acts on the central nervous system (CNS) depressants, thereby possessing a wide range from mild sedation to total anaesthesia.


Price and Availability

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Pricing updated 2020-10-26. Prices are subject to change without notice.

Barbituric acid, 5-allyl- is discontinued (DEA controlled substance).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 581610
Name: Barbituric acid, 5-allyl-
CAS#: 2565-43-7
Chemical Formula: C7H8N2O3
Exact Mass: 168.0535
Molecular Weight: 168.15
Elemental Analysis: C, 50.00; H, 4.80; N, 16.66; O, 28.54


Synonym: Barbituric acid, 5-allyl-; 5-Allylbarbituric acid; 5-Allyl-2,4,6-pyrimidinetrione; Deallylallobarbitone.

IUPAC/Chemical Name: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(2-propenyl)-

InChi Key: JLXDSDWQIIJSHV-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H8N2O3/c1-2-3-4-5(10)8-7(12)9-6(4)11/h2,4H,1,3H2,(H2,8,9,10,11,12)

SMILES Code: O=C1NC(C(CC=C)C(N1)=O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.03.00


References

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7: Nourmahnad A, Stern AT, Hotta M, Stewart DS, Ziemba AM, Szabo A, Forman SA. Tryptophan and Cysteine Mutations in M1 Helices of α1β3γ2L γ-Aminobutyric Acid Type A Receptors Indicate Distinct Intersubunit Sites for Four Intravenous Anesthetics and One Orphan Site. Anesthesiology. 2016 Dec;125(6):1144-1158. PubMed PMID: 27753644; PubMed Central PMCID: PMC5117677.

8: Stern AT, Forman SA. A Cysteine Substitution Probes β3H267 Interactions with Propofol and Other Potent Anesthetics in α1β3γ2L γ-Aminobutyric Acid Type A Receptors. Anesthesiology. 2016 Jan;124(1):89-100. doi: 10.1097/ALN.0000000000000934. PubMed PMID: 26569173; PubMed Central PMCID: PMC4681607.

9: Jayakar SS, Zhou X, Savechenkov PY, Chiara DC, Desai R, Bruzik KS, Miller KW, Cohen JB. Positive and Negative Allosteric Modulation of an α1β3γ2 γ-Aminobutyric Acid Type A (GABAA) Receptor by Binding to a Site in the Transmembrane Domain at the γ+-β- Interface. J Biol Chem. 2015 Sep 18;290(38):23432-46. doi: 10.1074/jbc.M115.672006. Epub 2015 Jul 30. PubMed PMID: 26229099; PubMed Central PMCID: PMC4645599.

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12: Chiara DC, Jayakar SS, Zhou X, Zhang X, Savechenkov PY, Bruzik KS, Miller KW, Cohen JB. Specificity of intersubunit general anesthetic-binding sites in the transmembrane domain of the human α1β3γ2 γ-aminobutyric acid type A (GABAA) receptor. J Biol Chem. 2013 Jul 5;288(27):19343-57. doi: 10.1074/jbc.M113.479725. Epub 2013 May 15. PubMed PMID: 23677991; PubMed Central PMCID: PMC3707639.

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20: Dain JG, Bhuta SI, Coombs RA, Talbot KC, Dugger HA. Metabolism of butalbital, 5-allyl-5-isobutylbarbituric acid, in the dog. Drug Metab Dispos. 1980 Jul-Aug;8(4):247-52. PubMed PMID: 6105059.