T2019 Sigma

Thebaine

powder

Synonym: Paramorphine

Properties

Related Categories Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Neurobiology, Neuroscience,
form   powder
drug control   USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
solubility   alcohol: soluble1 in 10 of alcohol
  benzene: soluble1 in 18 in benzene
  chloroform: soluble50 mg/ml, clear, yellow
  diethyl ether: soluble1 in 135 of ether
  H2O: insoluble

Description

Biochem/physiol Actions

The (-)-isomer of thebaine is the naturally-occurring constituent of opium that is a precursor of morphine. It has poor antinociceptive activity and induces convulsions. It binds to μ and δ opioid receptors in vitro.

Preparation Note

Thebaine dissolves in chloroform at 50 mg/ml to yield a clear, yellow solution. It soluble in alcohol, ether, and benzene at 1:10, 1: 135, and 1:18 parts respectively. However, thebaine does not dissolve in water.

Physical form

Alkaloid powder

Application

Thebaine has been used for the synthesis of neopinone/codeinone ring systems1. Thebaine has also been used as a 1 mg/ml standard in methanol for urine thebaine analysis in individuals who had consumed poppy seeds2.

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