Substituted morphinans

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

Generic structure of morphinan molecule

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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	Structure
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

See also

• Responsible use
• Opioids
• Dissociatives

External links

• Morphinan (Wikipedia)

References

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