ohmefentanyl

Also known as beta-hydroxy-3-methylfentanyl, β-hydroxy-3-methylfentanyl

Ohmefentanyl (also known as β-hydroxy-3-methylfentanyl, OMF and RTI-4614-4) is an extremely potent opioid analgesic drug which selectively binds to the μ-opioid receptor.

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 447755463
Drug.IUPAC_name: N-[1-(2-hydroxy-2-phenylethyl)-3-methylpiperidin-4-yl]-N-phenylpropanamide
Drug.image: Ohmefentanyl.svg
Drug.image_class: skin-invert-image
Drug.width: 220px
Drug.image2: Ohmyfentanyl 3D Ball and Stick.png
Drug.image_class2: bg-transparent
Drug.width2: 220px
Drug.legal_BR: F1
Drug.legal_CA: Schedule I
Drug.legal_US: Schedule I
Drug.legal_UK: Class A
Drug.legal_DE: Anlage I
Drug.legal_UN: P I
Drug.CAS_number: 78995-14-9
Drug.ATC_prefix: none
Drug.PubChem: 62279

via Wikipedia infobox

Chemical data

Formula: C23H30N2O2
Molecular weight: 366.5 g/mol
IUPAC name: N-[1-(2-hydroxy-2-phenylethyl)-3-methylpiperidin-4-yl]-N-phenylpropanamide
SMILES: CCC(=O)N(C1CCN(CC1C)CC(C2=CC=CC=C2)O)C3=CC=CC=C3
InChIKey: FRPRNNRJTCONEC-UHFFFAOYSA-N
XLogP: 3.6
Polar surface area: 43.8 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

91 papers

[Pharmacokinetics of [3H]ohmefentanyl in rats].Zhongguo yao li xue bao = Acta pharmacologica Sinica · 1990
Ohmefentanyl--a new agonist for mu-opiate receptor.Scientia Sinica. Series B, Chemical, biological, agricultural, medical & earth sciences · 1985
Quantitative comparison of ohmefentanyl isomers induced conditioning place preference in mice.Life sciences · 2001
[3H]ohmefentanyl preferentially binds to mu-opioid receptors but also labels sigma-sites in rat brain sections.European journal of pharmacology · 1991
Ohmefentanyl stereoisomers induce changes of CREB phosphorylation in hippocampus of mice in conditioned place preference paradigm.Cell research · 2003

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 366.2307282

Show 3 more facts

chemical formula: C₂₃H₃₀N₂O₂
canonical SMILES: CCC(=O)N(C1CCN(CC1C)CC(C2=CC=CC=C2)O)C3=CC=CC=C3
Commons category: Ohmefentanyl

Sources (2)

via Wikidata · CC0

~3 min read

Encyclopedic overview

4 sections

Contents

Synthesis
See also
References
External links

Ohmefentanyl (also known as β-hydroxy-3-methylfentanyl, OMF and RTI-4614-4) is an extremely potent opioid analgesic drug which selectively binds to the μ-opioid receptor.

There are eight possible stereoisomers of ohmefentanyl. These stereoisomers are among the most potent μ-opioid receptor agonists known, comparable to super-potent opioids such as carfentanil and etorphine which are only legally used for tranquilizing large animals such as elephants in veterinary medicine. In mouse studies, the most active stereoisomer, 3R,4S,βS-ohmefentanyl, was 28 times more powerful as a painkiller than fentanyl, the chemical from which it is derived, and 6300 times more powerful than morphine. Ohmefentanyl has three stereogenic centers and eight stereoisomers, which are named F9201–F9208. Researchers are studying the different pharmaceutical properties of these isomers.

Excerpted from Wikipedia’s “ohmefentanyl” article, available under the CC BY-SA 4.0 licence.