Β-Methylfentanyl

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Synthetic opioid analgesic


Β-Methylfentanyl
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
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Legal status
CAS Number 79704-88-4
PubChem 62157
DrugBank
ChemSpider 55966
KEGG


β-Methylfentanyl is a potent synthetic opioid analgesic that is structurally related to fentanyl. It was first synthesized in the late 1970s and is known for its high potency and potential for abuse.

Chemical Structure and Properties

Numbering of the fentanyl structure.

β-Methylfentanyl is a derivative of fentanyl, with a methyl group added to the beta position of the piperidine ring. This modification increases its lipophilicity and potency compared to fentanyl. The chemical formula of β-Methylfentanyl is C23H30N2O, and it has a molecular weight of 350.5 g/mol.

Pharmacology

β-Methylfentanyl acts primarily as an agonist at the mu-opioid receptor, similar to other opioids. This interaction is responsible for its analgesic effects as well as its potential for causing respiratory depression, a common risk associated with opioid use. The drug's high potency means that even small doses can have significant effects, which increases the risk of overdose.

Synthesis

The synthesis of β-Methylfentanyl involves the modification of the fentanyl molecule by introducing a methyl group at the beta position of the piperidine ring. This process requires advanced knowledge of organic chemistry and access to controlled substances, as fentanyl and its analogs are regulated due to their potential for abuse.

Legal Status

Due to its high potency and potential for abuse, β-Methylfentanyl is classified as a Schedule I controlled substance in many countries, including the United States. This classification indicates that it is considered to have a high potential for abuse and no accepted medical use.

Health Risks and Abuse

The abuse of β-Methylfentanyl can lead to severe health risks, including addiction, overdose, and death. The drug's potency makes it particularly dangerous, as users may inadvertently consume a lethal dose. Symptoms of overdose include respiratory depression, unconsciousness, and cardiac arrest.

Related Compounds

β-Methylfentanyl is part of a larger class of fentanyl analogs, which includes compounds such as α-Methylfentanyl, 3-Methylfentanyl, and Carfentanil. These analogs vary in potency and pharmacological effects but share a common mechanism of action as opioid receptor agonists.

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Contributors: Prab R. Tumpati, MD