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T2019

Sigma-Aldrich

Thebaine

powder

Synonym(s):

Paramorphine

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About This Item

Empirical Formula (Hill Notation):
C19H21NO3
CAS Number:
115-37-7
Molecular Weight:
311.37
EC Number:
204-084-1
MDL number:
MFCD00027409
UNSPSC Code:
12352200
PubChem Substance ID:
24900006
NACRES:
NA.77

form

powder

drug control

USDEA Schedule II; Home Office Schedule 2; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; estupefaciente (Spain); Decreto Lei 15/93: Tabela IA (Portugal)

solubility

alcohol: soluble 1 in 10 of alcohol
benzene: soluble 1 in 18 in benzene
chloroform: soluble 50 mg/ml, clear, yellow
diethyl ether: soluble 1 in 135 of ether
H2O: insoluble

SMILES string

[H][C@@]12Oc3c(OC)ccc4C[C@H]5N(C)CC[C@]1(C5=CC=C2OC)c34

InChI

1S/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

InChI key

FQXXSQDCDRQNQE-VMDGZTHMSA-N

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Application

Thebaine has been used for the synthesis of neopinone/codeinone ring systems. Thebaine has also been used as a 1 mg/ml standard in methanol for urine thebaine analysis in individuals who had consumed poppy seeds.

Biochem/physiol Actions

The (-)-isomer of thebaine is the naturally-occurring constituent of opium that is a precursor of morphine. It has poor antinociceptive activity and induces convulsions. It binds to μ and δ opioid receptors in vitro.

Physical form

Alkaloid powder

Preparation Note

Thebaine dissolves in chloroform at 50 mg/ml to yield a clear, yellow solution. It soluble in alcohol, ether, and benzene at 1:10, 1: 135, and 1:18 parts respectively. However, thebaine does not dissolve in water.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Morphine support studies. 2. Formation of the neopinone/codeinone ring system via intramolecular 1, 6-addition of an amino moiety to a dienyl ketone.
Toth, J. E., and Fuchs, P. L.
The Journal of Organic Chemistry, 51(13), 2594-2596 (1986)
G Cassella et al.
Journal of analytical toxicology, 21(5), 376-383 (1997-09-01)
The consumption of poppy seeds in various foods may lead to a positive opiate result in urine subjected to testing for drugs of abuse. As a natural constituent of poppy seeds, thebaine was investigated as a possible marker for poppy
Ali Reza Fakhari et al.
Journal of separation science, 33(14), 2153-2159 (2010-06-17)
This study investigated the use of ultrasound-assisted extraction to improve the extraction efficiency of morphine, codeine and thebaine from the papaver plants. Extraction conditions such as type of solvent, temperature, duration, frequency and power level of ultrasonic were optimized and
Gaik B Kok et al.
Bioorganic & medicinal chemistry letters, 20(15), 4499-4502 (2010-06-30)
Under Polonovski-type conditions, ferrocene has been found to be a convenient and efficient catalyst for the N-demethylation of a number of N-methyl alkaloids such as opiates and tropanes. By judicious choice of solvent, good yields have been obtained for dextromethorphan
Veniero Gambaro et al.
Planta medica, 78(12), 1395-1398 (2012-07-06)
In this paper, we report a case of misidentification of medicinal plants involving dried petals of Papaver rhoeas (red poppy) contaminated with Papaver bracteatum (scarlet poppy) petals. Preliminary TLC analysis indicated the presence of thebaine either in the fluid extracts
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