Substituted morphinans

Generic structure of morphinan molecule

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Morphinans are a class of psychoactive drugs consisting of opiate 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	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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