Thebaine

Thebaine
Names


IUPAC names 6,7,8,14-tetradehydro-4,5a-epoxy- 3,6-dimethoxy-17-methylmorphinan
Other names Paramorphine
Identifiers
CAS Number	115-37-7^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:9519^Y
ChEMBL	ChEMBL403893^Y
ChemSpider	4481822^Y 4479543^Y
ECHA InfoCard	100.003.713
KEGG	C06173^N
MeSH	Thebaine
PubChem	5324289
UNII	2P9MKG8GX7^Y
InChI 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^Y Key: FQXXSQDCDRQNQE-VMDGZTHMSA-N^Y 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 Key: FQXXSQDCDRQNQE-VMDGZTHMBG Key: FQXXSQDCDRQNQE-VMDGZTHMSA-N
SMILES COC1=CC=C2[C@@H](C3)N(C)CC[C@@]24C5=C3C=CC(OC)=C5O[C@@H]14
Properties
Chemical formula	C₁₉H₂₁NO₃
Molar mass	311.37 g/mol
Pharmacology
Dependence liability	Low
Pharmacokinetics:
Metabolism	O-demethylation
Legal status	AU: S8 (Controlled) CA: Schedule I UK: Class A US: Schedule II
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Thebaine (paramorphine), also known as codeine methyl enol ether, is an opiate alkaloid, its name coming from the Greek Θῆβαι, Thēbai (Thebes), an ancient city in Upper Egypt. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects. At high doses, it causes convulsions similar to strychnine poisoning. The synthetic enantiomer (+)-thebaine does show analgesic effects apparently mediated through opioid receptors, unlike the inactive natural enantiomer (−)-thebaine. While thebaine is not used therapeutically, it is the main alkaloid extracted from Papaver bracteatum (Iranian poppy) and can be converted industrially into a variety of compounds, including oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine and etorphine. Butorphanol can also be derived from thebaine and is scheduled separately from butorphanol derived by other processes.

Thebaine is controlled under international law, is listed as a Class A drug under the Misuse of Drugs Act 1971 in the United Kingdom, is controlled as an analog of a Schedule II drug per the Analog Act in the United States, and is controlled with its derivatives and salts, as a Schedule I substance of the Controlled Drugs and Substances Act in Canada. The 2013 US Drug Enforcement Administration (DEA) aggregate manufacturing quota for thebaine (ACSCN 9333) was unchanged from the previous year at 145 metric tons.

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