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115-37-7

115-37-7

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115-37-7 Usage

Description

Different sources of media describe the Description of 115-37-7 differently. You can refer to the following data:
1. The naturally occurring opiate alkaloid thebaine is present in high concentrations in poppy straw; lower concentrations of the co deine alkaloid are present.
2. 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.

Chemical Properties

Tan Solid

Uses

Different sources of media describe the Uses of 115-37-7 differently. You can refer to the following data:
1. Controllled substance (opiate).
2. 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.
3. 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.

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 andconvulsionLD50 value, intraperitoneal (mice): 42 mg/kgThebaine is a habit-forming compound. Itis a controlled substance (opiate) listed underU.S. Code of Federal Regulations (Title 21Part 1308.12, 1985).

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.

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)

Check Digit Verification of cas no

The CAS Registry Mumber 115-37-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 5 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 115-37:
(5*1)+(4*1)+(3*5)+(2*3)+(1*7)=37
37 % 10 = 7
So 115-37-7 is a valid CAS Registry Number.
InChI:InChI=1/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13-,18+,19+/m1/s1

115-37-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name thebaine

1.2 Other means of identification

Product number -
Other names Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-, (5α)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:115-37-7 SDS

115-37-7Related news

Simultaneous chemiluminescence determination of THEBAINE (cas 115-37-7) and noscapine using support vector machine regression08/31/2019

In this work, a batch chemiluminescence (CL) method has been proposed for the simultaneous determination of two structurally similar alkaloids, noscapine and thebaine. The method is based on the kinetic distinction of the CL reactions of noscapine and thebaine with Ru(bipy)32+ and Ce(IV) system ...detailed

THEBAINE (cas 115-37-7) in hair as a marker for chronic use of illegal opium poppy substances08/30/2019

Opium poppy products are often illegally used for both recreational and medicinal purposes. In order to demonstrate the ingestion of opium poppy substances, morphine, codeine and their metabolites have been identified. However, morphine and codeine also originate from the ingestion of therapeuti...detailed

Short communicationProspects of in vitro production of THEBAINE (cas 115-37-7) in opium poppy (Papaver somniferum L.)08/29/2019

A variant plant of opium poppy (Papaver somniferum L.) having high thebaine was obtained from the dose of 10 kR (kilo rad) + 0.4% EMS during an extensive mutation breeding experiment. The M2 seeds of variant plant were subjected to in vitro studies to investigate the prospects of thebaine produc...detailed

Developmental accumulation of THEBAINE (cas 115-37-7) and some gene transcripts in different organs of Papaver bracteatum08/28/2019

Noted as a rich source of thebaine and a potential alternative to Papaver somniferum for production of codeine and some semi-synthetic antagonist drugs (namely naloxone and naltrexone), Papaver bracteatum is a perennial species belongs to the section oxytona. Benzylisoquinoline alkaloids (BIAs) ...detailed

Comparative study for stability and adaptability through different models in developed high THEBAINE (cas 115-37-7) lines of opium poppy (Papaver somniferum L.)08/27/2019

Successful development of stable and adaptable crop varieties solely depend on the positive results obtained from the interaction between genotype and environment that consequently has significant impact on breeding strategies. GEI is a finest breeding approach that helps in the development of v...detailed

Full length articleReactions of THEBAINE (cas 115-37-7) derivatives with trifluoroacetyl acetylenes: [4+2]-addition solely08/25/2019

Trifluoroacetyl acetylenes, highly reactive dienophiles and electrophiles, were used as the probe for study competitive [4+2] vs nucleophilic addition reactions in thebaine series. Unlike thebaine itself that reacts with these electron deficient acetylenes giving rise to the adducts resulted fro...detailed

Structure ReportCrystal structure of THEBAINE (cas 115-37-7) 6-O-demethylase from the morphine biosynthesis pathway08/24/2019

Thebaine 6-O-demethylase (T6ODM) from Papaver somniferum (opium poppy), which belongs to the non-heme 2-oxoglutarate/Fe(II)-dependent dioxygenases (ODD) family, is a key enzyme in the morphine biosynthesis pathway. Initially, T6ODM was characterized as an enzyme catalyzing O-demethylation of the...detailed

Biocatalysts screening of Papaver bracteatum flora for THEBAINE (cas 115-37-7) transformation to codeine and morphine08/23/2019

The aim of this study was to find biocatalyst which uses thebaine and extract of different parts of Papaver bracteatum to synthesize morphine alkaloids. The thebaine-resistant strains were obtained from microbial flora of different parts of P.bracteatum. They were purified and treated utilizing ...detailed

A novel highly sensitive THEBAINE (cas 115-37-7) sensor based on MWCNT and dandelion-like Co3O4 nanoflowers fabricated via solvothermal synthesis08/22/2019

For this study, the synthesis of dandelion-like Co3O4 nanoflowers is presented via the straightforward solvothermal approach and specified by various analytical methods. Furthermore, electrochemical activity of dandelion-like Co3O4 nanoflowers and multiwall carbon nanotubes (MWCNT) concerning th...detailed

115-37-7Relevant articles and documents

-

Israilov,I.A. et al.

, (1977)

-

A novel synthesis of thebaine from codeine

Coop, Andrew,Rice, Kenner C.

, p. 43 - 47 (1998)

Codeine was converted into thebaine through methylation of the enolate of codeinone.

-

Fleischhacker,Markut

, p. 587 (1971)

-

Relationship of pharmacokinetic and metabolic parameters to the absence of physical dependence liability with thebaine 3H

Misra,Pontani,Mule

, p. 1108 - 1110 (1973)

The rapid metabolism, excretion and elimination of thebaine from rat brain produces no biochemical changes in the cells of the central nervous system, which could be the reason for its low physiological tolerance.

ESR ANALYSIS OF THE KINETIC ALKALINITY OF PSEUDOEPHEDRINE

Masalimov, A. S.,Nikol'skii, S. N.,Abdykarimova, A. P.,Prokof'ev, A. I.,Muldakhmetov, Z. M.

, p. 1559 - 1562 (1992)

The kinetics of protonation of pseudoephedrine by 3,6-di-tert-butyl-2-hydroxyphenoxyl have been analyzed by the ESR technique.It was shown that protolysis of the radical produced closed ionic pairs with the pseudoephedrine cation in a dimer state. Keywords: ESR, pseudoephedrine, 3,6-di-tert-butyl-2-hydroxyphenoxyl, ion pairs.

Closure of the oxide bridge in morphine biosynthesis

Lenz, Rainer,Zenk, Meinhart H.

, p. 3897 - 3900 (1994)

A highly substrate specific enzyme has been discovered and purified to homogeneity, which transfers the acetyl-moiety from acetyl-coenzyme A to the 7-OH group of salutaridinol. The formed 7-O-acetyl-salutaridinol spontaneously closes the oxide bridge at pH 8-9 by allylic elimination furnishing the morphine precursor thebaine.

A Regio- and Diastereoselective Anodic Aryl–Aryl Coupling in the Biomimetic Total Synthesis of (?)-Thebaine

Lipp, Alexander,Ferenc, Dorota,Gütz, Christoph,Geffe, Mario,Vierengel, Nina,Schollmeyer, Dieter,Sch?fer, Hans J.,Waldvogel, Siegfried R.,Opatz, Till

supporting information, p. 11055 - 11059 (2018/08/21)

The biosynthesis of thebaine is based on the regioselective, intramolecular, oxidative coupling of (R)-reticuline. For decades, chemists have sought to mimic this coupling by using stoichiometric oxidants. However, all approaches to date have suffered from low yields or the formation of undesired regioisomers. Electrochemistry would represent a sustainable alternative in this respect but all attempts to accomplish an electrochemical synthesis of thebaine have failed so far. Herein, a regio- and diastereoselective anodic coupling of 3′,4′,5′-trioxygenated laudanosine derivatives is presented, which finally enables electrochemical access to (?)-thebaine.

On the features of reactivity of 8-[(1E)-2-phenylethenyl]-substituted thebaine and codeinone derivatives

Moiseev,Shishkov,Kalinin

body text, p. 557 - 560 (2011/11/05)

An improved method for the synthesis of 8-[(1E)-2-phenylethenyl]codeinone dimethyl ketal was described. The ability of [(1E)-2-phenylethenyl] substituent to stabilize effectively the π-system of the ring C is responsible for the essential difference in both the reactivity and the compositions of products formed in the reactions of the corresponding substituted and unsubstituted codeinone and thebaine derivatives.