| Identification | Back Directory | [Name]
THEBAINE | [CAS]
115-37-7 | [Synonyms]
Tebain
C06173
Thebain
THEBAINE
Thenaine
p-Morphine
(-)-thebain
PARAMORPHINE
thebaine (90%)
Thebaine (CRM)
thebaine base (92-96%)
THEBAINE ALKALOID CONSTITUENT OF OPIUM
THEBAINE ALKALOID POWDER--DEA SCHEDULE*I I ITEM
6,7,8,14-Tetradehydro-4,5α-epoxy-3,6-dimethoxy-17-methylmorphinan
6,7,8,14-tetradehydro-4,5-alpha-epoxy-3,6-dimethoxy-17-methyl-morphina
6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-morphina(5-alpha
Morphinan, 6,7,8,14-tetradehydro-4,5alpha-epoxy-3,6-dimethoxy-17-methyl-
Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-, (5alpha)-
(4R,12bS)-7,9-dimethoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline
(4aR,8R,9cS)-3,5-Dimethoxy-12-methyl-4a,8,9,9c-tetrahydro-8,9c-(iminoethano)phenanthro[4,5-bcd]furan | [EINECS(EC#)]
204-084-1 | [Molecular Formula]
C19H21NO3 | [MDL Number]
MFCD00027409 | [MOL File]
115-37-7.mol | [Molecular Weight]
311.37 |
| Chemical Properties | Back Directory | [Melting point ]
183-186°C (dec.) | [alpha ]
D15 -219° (p = 2 in alc); D23 -230° (p = 5 in chloroform) | [Boiling point ]
451.42°C (rough estimate) | [density ]
1.3050 | [refractive index ]
1.5000 (estimate) | [storage temp. ]
Controlled Substance, -20°C Freezer | [solubility ]
H2O: 2.2 mg/mL, slightly soluble
| [form ]
powder
| [pka]
6.05(at 15℃) | [Water Solubility ]
<10mg/L(room temperature) | [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. | [EPA Substance Registry System]
Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-,(5.alpha.)- (115-37-7) |
| Hazard Information | Back Directory | [Chemical Properties]
Tan Solid | [Uses]
Controllled substance (opiate). | [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. | [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). | [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) |
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