hydromorphinol

Hydromorphinol (RAM-320, 14-hydroxydihydromorphine), is an opiate analogue that is a derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated. It has similar effects to morphine such as sedation, analgesia and respiratory depression, but is twice as potent as morphine and has a steeper dose-response curve and longer half-life. It is used in medicine as the bitartrate salt (free base conversion ratio 0.643, molecular weight 471.5) and hydrochloride (free base conversion ratio 0.770, molecular weight 393.9)

Chemical data

Formula: C17H21NO4
Molecular weight: 303.35 g/mol
IUPAC name: (4R,4aS,7S,7aR,12bS)-3-methyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
SMILES: CN1CC[C@]23[C@@H]4[C@H](CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)O
InChIKey: AABLHGPVOULICI-BRJGLHKUSA-N
XLogP: -1.1
Polar surface area: 73.2 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 303.147

Show 3 more facts

chemical formula: C₁₇H₂₁NO₄
canonical SMILES: CN1CCC23C4C(CCC2(C1CC5=C3C(=C(C=C5)O)O4)O)O
isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H](CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)O

Sources (2)

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Encyclopedic overview

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Contents

See also
References

Hydromorphinol has also been discovered to occur naturally in trace amounts within opium, although this is a very rare occurrence.

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

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