Providing straightforward information pertaining to drugs, drug use & drug policy. The Grey Pages promotes drug-related literacy and advocates a system of viable and tolerant drug policies. This is my personal collection of commentaries, essays, tid-bits, and other such writings on everything ranging from drug use, drug policy and drug-myths, to drug-science, addiction, human behavior, and the workings of the human brain. I started this blog with a particular focus on opioids, and over the past year have found my interest gravitate toward the intriguing, ever-changing world of designer intoxicants (i.e. "research chemicals" or "designer drugs").

Wednesday, February 16, 2011

Chemistry Series In Laymans Terms Part I of 3

Basic Chemistry of Morphinan Phenanthrene Based Opioids
Phenanthrene Base Structure
The traditional opiate family includes naturally opium derived compounds and semi-synthetic compounds which are built off of the natural compounds. All drugs of the immediate opiate class are built off of the phenanthrene skeleton, which is a fusion of 3 benzene rings.

Note of Interest: Phenanthrene is anaturally occurring compound in cigarette smoke.


Morphinan Base Structure:
All opiates f the morphine
and codeine class are built
off of his strucure. It is also
the parent compound for a
large family of synthetic
CNS compounds which
include opioid agonists,
opioid antagonists, and
NMDA antagonists
Addition of a third ring closure (i.e. nitrogen) and saturation of the double bonds of the asymmetric benzene (B ring) and C ring creates the 'morphinan' base structure; although morphinan is used as the base of its own synthetic class, each compound of the morphine and codeine family (i.e. epoxymorphinan) shares this base structure - this is reflected by the inclusion of morphinan in the nomenclature - morphinan is included in the name.

If an opiate molecule is a building: phenanthrene would be the concrete foundation, and morphinan would be the structural frame.

The morphinan base structure is easily synthesized; there also exists a fully synthetic class of morphine-like compounds based off of morphinan.
click for large view

Note of Interest: Levorphanol Tartrate is a potent fully synthetic (lab-created) opioid of the synthetic morphinan series. It is currently the only opioid of this particular series available on the market. It's molecular structure is extremely simple - it differs from the morphinan base only with the addition of an N-Methyl group at the 17 position and a hydroxyl group at the 3 position; both groups are major determinents in mu opioid recognition - for example, morphinan itself has little to no opioid activity, however in the case of levorphanol, the simple addition of an N-methyl and 3-HO boosts the compound's potency to 5x that of morphine. Certain further modifications to levorphanol will yield compounds dozens to hundreds of times more potent than morphinE. Levorphanol itself is 5 to 7.5 times more potent than morphinE.
click for large view

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