115-37-7

Name	THEBAINE
CAS	115-37-7
EINECS(EC#)	204-084-1
Molecular Formula	C19H21NO3
MDL Number	MFCD00027409
Molecular Weight	311.37
MOL File	115-37-7.mol

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

Chemical Properties

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. less more
EPA Substance Registry System	Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-,(5.alpha.)- (115-37-7)

Safety Data

Hazard Codes	T+
Risk Statements	26/27/28 less more
Safety Statements	22-36/37/39-45 less more
RIDADR	UN 1544 6.1/PG 2
WGK Germany	3
RTECS	QD2975000
HazardClass	6.1(b)
PackingGroup	III

Hazard Information

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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