[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)
You may not create new articles
You may not edit articles
You may not protect articles
You may not post comments
You may not post attachments
You may not edit your comments
HTML code is Off