Conorfone

Conorfone

Systematic (IUPAC) name
(5α,8β)-17-(Cyclopropylmethyl)-8-ethyl-3-methoxy-4,5-epoxymorphinan-6-one
Identifiers
CAS Number	72060-05-0
ATC code	None
PubChem	CID: 172964
ChemSpider	151049
ChEMBL	CHEMBL2106064
Chemical data
Formula	C23H29NO3
Molecular mass	367.481 g/mol
SMILES O=C4[C@@H]5Oc1c2c(ccc1OC)CC3N(CC[C@]25[C@H]3[C@@H](CC)C4)CC6CC6

Conorfone (INN; TR-5109), also known as conorphone and codorphone, as well as conorphone hydrochloride (USAN), is an opioid analgesic that was never marketed. It is an analogue of hydrocodone substituted with an 8-ethyl group and an N-cyclopropylmethyl group. It acts as a mixed agonist-antagonist at the μ-opioid receptor, and is slightly more potent than codeine in analgesic effects but associated with somewhat greater side effects.

Synthesis

File:Codorphone synthesis.svg

Codorphone synthesis:

Exposure of thebaine (1) to mild acid leads to hydrolysis of the enol ether function followed by migration of the double bond to yield the conjugated enone (2). Addition of lithium diethylcuprate proceeds by 1,4-addition from the less hindered side to give the intermediate 3. Treatment of that with cyanogen bromide under von Braun reaction conditions leads to the isolable aminocyanide. This is the converted to the secondary amine (4) by treatment with aqueous base. Alkylation of that intermediate with cyclopropylmethyl chloride affords the analgesic codorphone (5).

See also

• Hydrocodone