C₃₁H₃₇NO₄
Founded in 2017, Sigma Chemical Co., Ltd. supplies over 100 countries with high-quality chemicals. We are dedicated to safety, innovation, and global cooperation.
Product Description
(alphaR,5alpha,7alpha)-4,5-Epoxy-3,6-dimethoxy-alpha,17-dimethyl-alpha-(2-phenylethyl)-6,14-ethenomorphinan-7-methanol—better known by its common name 7-PET—is a semi-synthetic orvinol derived from the opium-poppy alkaloid thebaine. This highly constrained morphinan carries a 6,14-etheno bridge that locks the molecule into a rigid, potent conformation, while methoxy groups at C-3 and C-6, an α-2-phenylethyl substituent, and a C-7 hydroxymethyl group confer extraordinary μ-opioid affinity. With a molecular formula of C₃₁H₃₇NO₄ (CAS 13965-63-4, UNII EA1GYF3V3I, PubChem CID 203125), 7-PET is reported to be roughly 300 times more potent than morphine by weight, placing it in the same ultrapotent class as etorphine and necessitating stringent legal controls because of its narrow therapeutic index and high overdose risk.
Other Information
-
Stereochemistry: The specified stereochemistry (alphaR,5alpha,7alpha) is critical for its biological activity, as opioid receptor binding is highly stereospecific.
-
Related Compounds: It is structurally related to well-known opioids such as Buprenorphine (a partial agonist used for therapy) and Etorphine (a super-potent agonist used in veterinary medicine), sharing the core 6,14-ethenomorphinan-7-methanol structure but differing in the substituents on the nitrogen and the C-19 side chain.
Synthesis and Production
-
Synthetic Intermediate: This compound is not a naturally occurring substance but is a semi-synthetic derivative. It is synthesized from natural opiate alkaloid precursors, most notably thebaine.
-
Precursor Role: It serves as a crucial synthetic intermediate or precursor in organic and medicinal chemistry for the production of other, more complex opioids, particularly those within the orvinol family (e.g., etorphine, buprenorphine).
-
Structural Modifications: The synthesis involves complex chemical steps to build the characteristic 6,14-etheno bridge and introduce the specific substituents at the C-19 position (the methyl and 2-phenylethyl groups) and the 7-methanol group, all while controlling the critical stereochemistry (alphaR,5alpha,7alpha).
-
Synthetic Intermediate: This compound is not a naturally occurring substance but is a semi-synthetic derivative. It is synthesized from natural opiate alkaloid precursors, most notably thebaine.
-
Precursor Role: It serves as a crucial synthetic intermediate or precursor in organic and medicinal chemistry for the production of other, more complex opioids, particularly those within the orvinol family (e.g., etorphine, buprenorphine).
-
Structural Modifications: The synthesis involves complex chemical steps to build the characteristic 6,14-etheno bridge and introduce the specific substituents at the C-19 position (the methyl and 2-phenylethyl groups) and the 7-methanol group, all while controlling the critical stereochemistry (alphaR,5alpha,7alpha).
Uses and Applications
-
Research Chemical: Its primary use is in scientific research.
-
Pharmaceutical Intermediate: It is used as a building block in the synthesis of other pharmaceutical compounds, especially potent analgesics.
-
PET Imaging Tracer Development: As indicated by its relation to 7-PET, this compound or its close derivatives (such as [¹¹C]PEO and [¹⁸F]FE-PEO) have been investigated as potential radiotracers for Positron Emission Tomography (PET) imaging. These tracers are designed to target and visualize opioid receptors in the brain, aiding neurological and pharmacological research.
Chemical and Physical Properties
-
Molecular Formula: C₃₁H₃₇NO₄
-
Molecular Weight: 487.6 g/mol
-
Physical Properties:
-
XLogP3: 4.5 (Indicates high lipophilicity)
-
Hydrogen Bond Donor Count: 1
-
Hydrogen Bond Acceptor Count: 5
-
Rotatable Bond Count: 6
-
Topological Polar Surface Area: 51.2 Ų
-
-
Structural Properties:
-
Complexity: 903 (Indicates a very complex molecular structure)
-
Defined Atom Stereocenter Count: 7 (Highlights the importance of its specific 3D configuration)
-
-
Pharmacological Properties:
-
Class: It is a morphinan derivative and a member of the orvinol class of synthetic opioids.
-
Mechanism: It acts as a potent opioid receptor agonist, likely with high affinity for μ-opioid (MOR) and κ-opioid (KOR) receptors, similar to other orvinols.
-
Potency: Compounds with this structural scaffold are typically extremely potent, often hundreds to thousands of times more potent than morphine.
-
Safety and Handling
-
High Potency Hazard: Due to its structural class and expected high potency, it must be handled with extreme caution in a laboratory setting. Exposure to even minute quantities could pose severe health risks.
-
Toxicity: The record references toxicological data from ChemIDplus, specifically under "Acute Effects," which typically includes median lethal dose (LD₅₀) data from animal studies. This confirms the compound is considered toxic.
-
Primary Hazards: Based on its pharmacology, the primary hazards associated with accidental exposure would be profound respiratory depression, CNS depression, sedation, and a high risk of dependence and abuse.
-
Regulatory Status: While not explicitly listed, compounds of this nature are almost certainly controlled substances under national and international drug laws (e.g., it would be classified as a controlled substance analogue in the United States).