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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

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Xucong Lin et al.
Journal of separation science, 30(17), 3011-3017 (2007-10-27)
A method for the separation and determination of five major opium alkaloids (narcotine, papaverine, thebaine, codeine, and morphine) in pericarpium papaveris by pressurized CEC (pCEC) with monolithic column has been developed. Under the optimum condition, linear calibration ranges of narcotine
Gaik B Kok et al.
Organic & biomolecular chemistry, 9(4), 1008-1011 (2010-12-28)
Further investigations into the direct synthesis of N-nororipavine from oripavine using iron powder under non-classical Polonovski conditions have been conducted. The stoichiometry, solvents and iron oxidation rates were found to have a dramatic effect on the rate of N-demethylation as
Gilbert Stork et al.
Journal of the American Chemical Society, 131(32), 11402-11406 (2009-07-25)
Total syntheses of the morphine alkaloids are described that use a direct stereoselective formation of the phenanthrofuran system via an intramolecular 4 + 2 cycloaddition of a diene tethered to the 4-position of a 7-methoxybenzofuran-3-carboxylic acid ester.
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)
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