Substituted morphinans

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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 RN 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
Morphine OH O- - OH - - H CH3 Morphine.svg
Codeine OCH3 O- - OH - - H CH3 Codeine.svg
Ethylmorphine OCH2CH3 O- - OH - - H CH3 Ethylmorphine.svg
Heroine OCOCH3 O- - OCOCH3 - - H CH3 Diamorphine.svg
Naloxone OH O- - =O - - OH CH2CH=CH2 Naloxone.svg
Desomorphine OH O- - H H H H CH3 Desomorphine.svg
Hydromorphone OH O- - =O H H H CH3 Hydromorphone.svg
Hydrocodone OCH3 O- - =O H H H CH3 Hydrocodone.svg
Dihydrocodeine OCH3 O- - OH H H H CH3 Dihydrocodeine.svg
Oxycodone OCH3 O- - =O H H OH CH3 Oxycodone.svg
Oxymorphone OH O- - =O H H OH CH3 Oxymorphone.svg
Buprenorphine OH O- - (CH2-)OCH3 C(OH)(CH3)C(CH3)3 H CH2- CH2C3H5 Buprenorphine.svg
DXO OH H H H H H H CH3 Dextrorphan.svg
DXM OCH3 H H H H H H CH3 DXM.svg

See also

External links

References

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