THEBAINE

Description

The naturally occurring opiate alkaloid thebaine is present in high concentrations in poppy straw; lower concentrations of the co deine alkaloid are present.

Description

Thebaine (Item No. 14043) is an analytical reference material categorized as a precursor in the synthesis of morphine (Item Nos. ISO60147 | 15464) and codeine (Item Nos. ISO60140 | 15459). Thebaine is a potential impurity in the illicit synthesis of heroin (Item Nos. ISO60187 | 9001543 | 9003076). Thebaine is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications.

Chemical Properties

Tan Solid

Uses

Thebaine is present in opium at 0.3–1.5%.It is extracted from opium or from latex ofthe plant Papaver bracteatum, in which it ispresent at up to 26%. It is used to producecodeine.

Uses

Controllled substance (opiate).

Uses

Thebaine is used in the manufacture of other opiate pharmaceuticals, such as bupren and morphine, and caused contact dermatitis in a laboratory worker at an opiate-manufacturing pharmaceutical company, who was also sensitive to co deine.

Definition

ChEBI: Thebaine is a morphinane alkaloid and an organic heteropentacyclic compound. It is a conjugate base of a thebaine(1+).

Hazard

Toxic by ingestion, may induce addiction.

Health Hazard

Although thebaine has a morphine- orcodeine-like structure, its pharmacologyaction is somewhat different. It is a convulsantpoison like strychnine, rather thana narcotic. High doses can cause ataxia andconvulsion
LD50 value, intraperitoneal (mice): 42 mg/kg
Thebaine is a habit-forming compound. Itis a controlled substance (opiate) listed underU.S. Code of Federal Regulations (Title 21Part 1308.12, 1985).

Contact allergens

The naturally occurring opiate alkaloid thebaine is present in concentrated poppy straw, and in small concentrations in codeine alkaloid. It is used in the manufacture of other opiate pharmaceuticals, such as buprenorphine and morphine, and caused contact dermatitis in a laboratory worker at an opiates manufacturing pharmaceutical company, also sensitive to codeine.

Purification Methods

Crystallise Thebaine from Et2O or EtOH. Sublime it at 170-180o. The hydrochloride decomposes >182o (from MeOH/Et2O). [Beilstein 27 II 177, 27 III/IV 2271.] It is a NARCOTIC.

References

Pelletier, Thiboumery., Annalen, 16,38 (1835)
Kane., ibid, 19, 9 (1836)
Anderson., ibid, 86, 184 (1853)
Howerd., Ber., 17,527 (1884)
Pschorr, Zeidler., ibid, 27,2961 (1894)
Freund, Michaels, Gobel., ibid, 30, 1357 (1897)
Knorr., ibid, 36, 3074 (1903)
Freund, Holthof., ibid, 37, 2780 (1904)
Pschorr, Pfaff, Herrschmann., ibid, 38, 3163 (1905)
Reichard., Pharm. Zeit., 47,623 (1906)
Hildebrandt., Arch. expo Path. Pharm., 65,54 (1911)
Kruger, Eddy, Sumwalt., Suppl. No. 165, Public Health Reports, Washington (1943)
Flieschhacker, Pasal, Vieboeck., Monatsh., 99, 300 (1968)
Eppenberger, Warren, Repoport., Helv. Chim. Acta, 51,381 (1968)