phenomorphan

Phenomorphan is an opioid analgesic. It is not currently used in medicine, but has similar side-effects to other opiates, which include itching, nausea and respiratory depression.

Chemical data

Formula: C24H29NO
Molecular weight: 347.5 g/mol
IUPAC name: (1R,9R,10R)-17-(2-phenylethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
SMILES: C1CC[C@@]23CCN([C@@H]([C@@H]2C1)CC4=C3C=C(C=C4)O)CCC5=CC=CC=C5
InChIKey: CFBQYWXPZVQQTN-QPTUXGOLSA-N
XLogP: 5.1
Polar surface area: 23.5 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 347.225

Show 4 more facts

chemical formula: C₂₄H₂₉NO
canonical SMILES: C1CCC23CCN(C(C2C1)CC4=C3C=C(C=C4)O)CCC5=CC=CC=C5
isomeric SMILES: C1CC[C@@]23CCN([C@@H]([C@@H]2C1)CC4=C3C=C(C=C4)O)CCC5=CC=CC=C5
Commons category: Phenomorphan

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Encyclopedic overview

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References

Phenomorphan is an opioid analgesic. It is not currently used in medicine, but has similar side-effects to other opiates, which include itching, nausea and respiratory depression.

Phenomorphan is a highly potent drug due to the N-phenethyl group, which boosts affinity to the μ-opioid receptor, and so phenomorphan is around 10x more potent than levorphanol, which is itself 6-8x the potency of morphine. Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than levorphanol, respectively.

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