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Sigma-Aldrich

Thebain

powder

Synonym(e):

Paramorphin

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About This Item

Empirische Formel (Hill-System):
C19H21NO3
CAS-Nummer:
115-37-7
Molekulargewicht:
311.37
EG-Nummer:
204-084-1
MDL-Nummer:
MFCD00027409
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24900006
NACRES:
NA.77
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Form

powder

Arzneimittelkontrolle

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)

Löslichkeit

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

InChIKey

FQXXSQDCDRQNQE-VMDGZTHMSA-N

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Anwendung

Thebaine has been used for the synthesis of neopinone/codeinone ring systems[1]. Thebaine has also been used as a 1 mg/ml standard in methanol for urine thebaine analysis in individuals who had consumed poppy seeds[2].

Biochem./physiol. Wirkung

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.

Physikalische Form

Alkaloid powder

Angaben zur Herstellung

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.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H301

Gefahreneinstufungen

Acute Tox. 3 Oral

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

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Analysenzertifikate (COA)

Lot/Batch Number
0000387736
0000348513
0000387736
0000348513
SLCN4470

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Die Dokumentenbibliothek aufrufen

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
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)
Jihyun Shim et al.
The journal of physical chemistry. B, 115(22), 7487-7496 (2011-05-14)
Despite being studied for over 30 years, a consensus structure-activity relationship (SAR) that encompasses the full range peptidic and nonpeptidic μ-opioid receptor ligands is still not available. To achieve a consensus SAR the Conformationally Sampled Pharmacophore (CSP) method was applied
Nadja Grobe et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(18), 8147-8152 (2010-04-28)
It has been firmly established that humans excrete a small but steady amount of the isoquinoline alkaloid morphine in their urine. It is unclear whether it is of dietary or endogenous origin. There is no doubt that a simple isoquinoline
David Rennison et al.
Journal of medicinal chemistry, 50(21), 5176-5182 (2007-09-25)
A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7alpha-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with
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