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[top]Introduction to Thebaine



Thebaine, also known as Paramorphine is a white, crystalline, slightly water-soluble (in pure form after a synthesis), poisonous alkaloid, with the molecular Formular: C19H21NO3,[1] present in opium in small quantities.[2] The Thebaine-Constituent of Raw-Opium is normally between 0.2% and 1.5% But higher amounts up to 6% have also been reported.[3]


[top]Using of Thebaine



Thebaine is not used for therapeutic or recreational purposes, but is converted industrially into a variety of compounds including oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine and etorphine. [1]


[top]Metabolism



Thebaine is metabolized via O-demethylation [1]


[top]Effects of Thebaine



Thebaine has more strychnin-like "convulsive" properties (see warnings!) rather than any narcotic effect, and possesses a sharp astringent taste and a tetanic action like strychnine.

Thebaine was long believed to have no morphine-like agonistic properties and many studies, old and recent, are supportive of this view. [3]

However, it is now evident that it has a meaningful dependence potential, both physical and psychological, when large doses are ingested over a certain period. (ie. in Poppy/ Poppyseed-tea)


[top]Pharmacology of Thebaine


LD50 (mg/kg) [1]:
Rabbit : 14 subcutaneously (hydrochloride monohydrate)


[top]Chemistry of Thebaine


Systematic (IUPAC) name:(5[alpha])-6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan
Synonyms:paramorphine
Molecular Formula:C19H21NO3
Molar mass: 311.38 g/mol, 365.85 g/mol (hydrochloride monohydrate), 820.89 g/mol (oxalate hexahydrate), 419.43 g/mol (binoxalate monohydrate), 479.48 g/mol (bitartrate monohydrate), 449.50 g/mol (salicylate)
CAS Registry Number:115-37-7
Melting Point:193C (rapid heating)
Boiling Point:no data
Flash Point:no data
Solubility:Freebase : 1 g dissolves in 1460 mL water (15C), 15 mL hot alcohol, 25 mL benzene, about 200 mL ether, 13 mL chloroform, 12 mL pyridine; almost insoluble in petroleum ether. Hyrochloride monohydrate : soluble in about 12 parts water, soluble in alcohol. Oxalate hexahydrate : soluble in about 10 parts water, soluble in alcohol; almost insoluble in ether. Binoxalate monohydrate : soluble in 45 parts water. Bitartrate monohydrate : soluble in about 130 parts water; quite soluble in hot water, hot alcohol. Salicylate : soluble in 750 parts water.
Additionnal data:Freebase : sublimation at 170-180C (atmospheric pressure), pK (15C) 6.05, pH of saturated water solution 7.6. Hydrochloride monohydrate : pH (0.05 molar solution) 4.95.
Notes:Freebase aspect : orthorhombic, rectangular plates by sublimation. Hydrochloride monohydrate aspect : orthorhombic prisms from alcohol. Oxalate hexahydrate aspect : prisms. Binoxalate monohydrate aspect : prisms. Bitartrate monohydrate aspect : prisms. Salicylate aspect : crystals.
[1]


[top]Different uses for Thebaine


Thebaine is used only in synthesis into other pharmaceutical drugs. People should avoid contact with thebaine itself due to the toxicity of thebaine.


[top]The Dangers of Thebaine



Thebaine is far more toxic (ten times higher) than morphine. Compared to morphine sulfate, thebaine is 10 times more lethal: Morphine sulfate anhydrous: oral rat LD50: 461 mg/kg; oral mouse LD50: 600 mg/kg!


(!) Thebaine is the most poisonous opium alkaloid.

The UNHDOC mentioned[3] that the LD. 50 of Thebaine in mice is 31 mg/kg s.c. and 20 mg/kg i.p.; other authors have reported an intraperitoneal
(the area that contains the abdominal organs.) LD50 of 42 mg/kg in mice.

In rabbits, the intravenous LLD50 is 3-4 mg/kg and is dependent on the age of the animals. In the dog the lethal doses are reported to be 10-30 mg/kg s.c. and 5-7 mg/kg i.v.. In chicken embryo, Thebaine has been reported to induce pseudohyperfeminization (change of the Gender-features).


[top]Legal status of Thebaine


Thebaine is a controlled substance : 21 CFR 1308.12

[top]Status in the USA



Thebaine is a controlled substance (opiate), Schedule 2. listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.12 [1]

[top]Status in Europe



It is controlled in Schedule II of the Controlled Substances Act as well as under international law.

Thebaine is listed as a Class A drug under the Misuse of Drugs Act 1971 in the United Kingdom [1]


[top]History of Thebaine



So called from a kind of Egyptian opium produced at Thebes. "Opium Thebacium" and Thebaine share only the origin of the name, the first is the Roman Trade-name!


[top]Further Information



Papaver bracteatum Lindl., is a Highly Rich Source of Thebaine
Papaver somniferum strain with high concentration of thebaine (and oripavine)

[top]The latest Thebaine threads


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Attached Images
File Type: jpg thebaine.jpg (48.4 KB, 701 views)
Created by Jasim Gold member, 25-04-2010 at 23:12
Last edited by John_bob, 23-04-2014 at 19:34
Last comment by NeuroChi on 11-05-2010 at 14:53
4 Comments, 36,187 Views

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