Thebaine
Thebaine, apparently named after an Egyptian opium produced in Thebes, is also known as paramorphine and is chemically analogous to codeine and morphine, as it is derived from opium. However, the drug has an opposing effect to morphine as it is stimulatory rather than depressing, thus, being known as paramorphine. The drug itself has no therapeutic uses; however, it is commercially used as a starting point for the industrial production of many compounds that are Thebaine derived, for example oxycodone (a drug used for pain relief in cancer patients ), nalaxone (a drug to counteract opioid overdose), naltrexone (a drug used to manage alcohol and opioid dependence) and etorphine(a drug 1500 – 3000 times more powerful than morphine used to immobilise large mammals such as elephants).
Under the Misuse of Drugs Act 1971 in the UK, Thebaine is categorised as a Class A drug. At higher doses, Thebaine produces strychnine-like convulsions rather than narcosis, which occurs with a morphine overdose.
| Thebaine | |
|---|---|
| |
| General | |
| Systematic name | 4,5α-epoxy-3,6-dimethoxy-17-methyl-morphina-6,8(14)-diene |
| Other names | Thebain, paramorphine |
| Molecular formula | C19H21NO3 |
| SMILES | O.Cl.COC1=CC=C2[C@H]3Cc4ccc(OC)c5O[C@@H]1[C@]2(CCN3C)c45 |
| Molar mass | 311.38g/mole |
| Appearance | {{{Appearance}}} |
| CAS number | {{{CASNo}}} |
| Properties | |
| Density & phase | {{{Density}}} g/cm³ |
| Solubility in water | {{{Sol_Water}}} g/100 ml (25°C) |
| Melting point | {{{Mp}}} K |
| Boiling point | {{{Bp}}} K |
| Acidity (pKa) | {{{pKa}}} |
| Basicity (pKb) | {{{pKb}}} |
| Chiral rotation [α]D | {{{Rotation}}}° |
| Viscosity | {{{Viscosity}}} cP at 25°C |
| Structure | |
| Molecular shape | heterocyclic |
| Coordination geometry |
{{{Coordination}}} |
| Crystal structure | {{{Crystal_Structure}}} |
| Dipole moment | {{{DM}}} D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | {{{Hazards}}} |
| NFPA 704 | {{{NFPA}}} |
| Flash point | {{{Fp}}}°C |
| R/S statement | R: {{{R-S}}} S: ? |
| RTECS number | {{{RTECS}}} |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Other anions | {{{Other_anion}}} |
| Other cations | {{{Ohter_cation}}} |
| Related compounds | {{{Relative_Compounds}}} |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
| Structure | |
|---|---|
| Molecular shape | {{{MolShape}}} |
| Coordination geometry |
{{{Coordination}}} |
| Crystal structure | {{{CrystalStruct}}} |
| Dipole moment | {{{Dipole}}} D |
Synthesis
http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/alkaloid/thebaine.html
References
http://www.emolecules.com/cgi-bin/more?vid=10589283 http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/alkaloid/thebaine.html