Thebaine

Thebaine
Names
	IUPAC name 3,6-Dimethoxy-17-methyl-6,7,8,14-tetradehydro-4,5α-epoxymorphinan
	Systematic IUPAC name (4R,7aR,12bS)-7,9-Dimethoxy-3-methyl-2,3,4,7a-tetrahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline
	Other names Paramorphine
Identifiers
CAS Number	115-37-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9519 ;
ChEMBL	ChEMBL403893 ;
ChemSpider	4481822 ;
ECHA InfoCard	100.003.713
KEGG	C06173 ;
MeSH	Thebaine
PubChem CID	5324289;
UNII	2P9MKG8GX7 ;
CompTox Dashboard (EPA)	DTXSID7046099 ;
	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 Key: FQXXSQDCDRQNQE-VMDGZTHMSA-N ; 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 drug); BR: Class A1 (Narcotic drugs); 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). 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 opium / Persian poppy) and can be converted industrially into a variety of compounds that do have medicinal value.