Substituted morphinans

Generic structure of morphinan molecule

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Morphinans are a class of psychoactive drugs consisting of opioid analgesics, cough suppressants, and dissociative hallucinogens, among others.

Chemistry

Morphinans are made up of the morphinan molecule with altering functional groups attached on the numbered carbons. Morphinan is comprised of a 1-benzylisoquinoline backbone with two additional ring closures. It features three benzene rings, where two are partially unsaturated, as well as a piperidine ring. It can have various substitutions at R₃ and R₆, and it is commonly substituted at R_N with a methyl group and at R₄ and R₅ with an ether linkage to form products of varying potency, affinity, efficacy and half-life. It is a very flexible molecule with five chiral centers, which results in a lot of different configurations of the bonds.

Pharmacology

The morphinans are a large chemical class and compounds within it have differing pharmacological effects. Active morphinan derivatives often act upon the NMDA receptor, the μ-opioid receptor and the σ1 and σ2 sigma receptors.

List of substituted morphinans

Compound	R₃	R₄	R₅	R₆	R₇	R₈	R₁₄	R₁₇
Morphinan	H	H	H	H	H	H	H	H
Morphine	OH	O-	-	OH	-	-	H	CH₃
Codeine	OCH₃	O-	-	OH	-	-	H	CH₃
Ethylmorphine	OCH₂CH₃	O-	-	OH	-	-	H	CH₃
Heroin	OCOCH₃	O-	-	OCOCH₃	-	-	H	CH₃
Naloxone	OH	O-	-	=O	-	-	OH	CH₂CH=CH₂
Desomorphine	OH	O-	-	H	H	H	H	CH₃
Hydromorphone	OH	O-	-	=O	H	H	H	CH₃
Hydrocodone	OCH₃	O-	-	=O	H	H	H	CH₃
Dihydrocodeine	OCH₃	O-	-	OH	H	H	H	CH₃
Oxycodone	OCH₃	O-	-	=O	H	H	OH	CH₃
Oxymorphone	OH	O-	-	=O	H	H	OH	CH₃
Buprenorphine	OH	O-	-	(CH₂-)OCH₃	C(OH)(CH₃)C(CH₃)₃	H	CH₂-	CH₂C₃H₅
DXO	OH	H	H	H	H	H	H	CH₃
DXM	OCH₃	H	H	H	H	H	H	CH₃