THEBAINE

Base Information

• Chemical Name: THEBAINE
• CAS No.: 115-37-7
• Molecular Formula: C19H21 N O3
• Molecular Weight: 311.381
• European Community (EC) Number: 204-084-1
• UNII: 2P9MKG8GX7
• DSSTox Substance ID: DTXSID7046099
• Nikkaji Number: J5.266C
• Wikipedia: Thebaine
• Wikidata: Q410169
• NCI Thesaurus Code: C871
• Metabolomics Workbench ID: 53479
• ChEMBL ID: CHEMBL403893
• Mol file: 115-37-7.mol

Synonyms:Morphinan,6,7,8,14-tetradehydro-4,5a-epoxy-3,6-dimethoxy-17-methyl- (8CI); (-)-Thebaine; Paramorphine;Thebain; Thebaine

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of THEBAINE

Chemical Property:

• Vapor Pressure: 6.4E-09mmHg at 25°C
• Melting Point: 183-186°C (dec.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 467.6°Cat760mmHg
• PKA: 6.05(at 15℃)
• Flash Point: 141°C
• PSA: 30.93000
• Density: 1.3g/cm³
• LogP: 2.36240
• Storage Temp.: Controlled Substance, -20°C Freezer
• Solubility.: H2O: 2.2 mg/mL, slightly soluble
• Water Solubility.: <10mg/L(room temperature)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 311.15214353
• Heavy Atom Count: 23
• Complexity: 585

Purity/Quality:

Safty Information:

• Pictogram(s): Toxic by ingestion, may induce addiction.
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)OC)O4)OC
• Isomeric SMILES: CN1CC[C@]23[C@@H]4C(=CC=C2[C@H]1CC5=C3C(=C(C=C5)OC)O4)OC
• Recent EU Clinical Trials: Androgen metabolism and doping tests
• Description: The naturally occurring opiate alkaloid thebaine is present in high concentrations in poppy straw; lower concentrations of the co deine alkaloid are present. 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.
• Uses: Controllled substance (opiate). Thebaine is present in opium at 0.3–1.5%.It is extracted from opium or from latex ofthe plant Papaver bracteatum, in which it ispresent at up to 26%. It is used to producecodeine. Thebaine is used in the manufacture of other opiate pharmaceuticals, such as bupren and morphine, and caused contact dermatitis in a laboratory worker at an opiate-manufacturing pharmaceutical company, who was also sensitive to co deine.

Technology Process of THEBAINE

There total 38 articles about THEBAINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

codeine-6-methyl ether (2859-16-7) → thebaine (115-37-7)

Guidance literature:

With manganese(IV) oxide; In tetrahydrofuran;

DOI:10.1071/CH03246

Reference yield: 90.0%

5-trimethylsilylthebaine (503588-47-4) → thebaine (115-37-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/jo020704m

Reference yield: 87.0%

thebaine N-oxide hydrochloride → northebaine (2579-67-1) + thebaine (115-37-7)

Guidance literature:

With ferroceneacetic acid; In chloroform; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1055/s-0032-1316590

upstream raw materials:

diazomethane

oripavine

4,5α-epoxy-3,6,6-trimethoxy-17-methyl-morphin-7-ene

formaldehyd

Downstream raw materials:

(-)-(R_a,6Ξ)-2,12-dimethoxy-7-methyl-6-phenyl-6,7,8,9-tetrahydro-5H-dibenz[d,f]azonin-1-ol

2,12-dimethoxy-7-methyl-6-phenyl-6,7,8,9-tetrahydro-5H-dibenzo[d,f]azonin-1-ol

thevinone

nepenthone

Refernces

• 1、 Singer, Robert D,Scammells, Peter J. "Alternative methods for the MnO2 oxidation of codeine methyl ether to thebaine utilizing ionic liquids". . p. 6831 - 6833. Retrieved 2001.
• 2、 Martin et al.. "-". . p. 4726. Retrieved 1964.
• 3、 Chen, Weibin,Wu, Huifang,Bernard, Denzil,Metcalf, Matthew D.,Deschamps, Jeffrey R.,Flippen-Anderson, Judith L.,MacKerell Jr., Alexander D.,Coop, Andrew. "Rearrangement of 5-trimethylsilylthebaine on treatment with L-selectride: An efficient synthesis of (+)-bractazonine". . p. 1929 - 1932. Retrieved 2003.
• 4、 Kok, Gaik B.,Pye, Cory C.,Singer, Robert D.,Scammells, Peter J.. "Two-step iron(0)-mediated N-demethylation of N -methyl alkaloids". . p. 4806 - 4811. Retrieved 2010.
• 5、 Hemeon, Ivan,Barnett, Neil W.,Gathergood, Nicholas,Scammells, Peter J.,Singer, Robert D.. "Manganese dioxide allylic and benzylic oxidation reactions in ionic liquids". . p. 125 - 128. Retrieved 2004.
• 6、 Rapoport et al.. "-". . . Retrieved 1967.
• 7、 Kok, Gaik B.,Scammells, Peter J.. "Polonovski-type N-demethylation of N-methyl alkaloids using substituted ferrocene redox catalysts". experimental part. p. 2587 - 2594. Retrieved 2012/09/22.
• 8、 Moiseev,Shishkov,Kalinin. "On the features of reactivity of 8-[(1E)-2-phenylethenyl]-substituted thebaine and codeinone derivatives". body text. p. 557 - 560. Retrieved 2011/11/05.