[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: C19
, present in opium
in small quantities. The Thebaine-Constituent of Raw-Opium is normally between 0.2% and 1.5% But higher amounts up to 6% have also been reported.
Thebaine is not used for therapeutic or recreational purposes, but is converted industrially into a variety of compounds including oxycodone
, nalbuphine, naloxone, naltrexone, buprenorphine
Thebaine is metabolized via O-demethylation
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.
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
[top]Pharmacology of Thebaine
LD50 (mg/kg) :
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|
|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:||193°C (rapid heating)|
|Boiling Point:||no data|
|Flash Point:||no data|
|Solubility:||Freebase : 1 g dissolves in 1460 mL water (15°C), 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 170-180°C (atmospheric pressure), pK (15°C) 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.|
[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 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
[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
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!
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
, fifteenth edition (2013)
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