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{{Short description|Chemical compound}}
{{More citations needed|date=December 2024}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 450105432
| Watchedfields = changed
⚫ | IUPAC_name = 17-(2-(Furan-2-yl)ethyl)-3-hydroxymorphinan
⚫ | verifiedrevid = 414622540
⚫ | image = Furethylnorlevorphanol.svg
⚫ | IUPAC_name = 17-(2-(furan-2-yl)ethyl)-3-hydroxymorphinan
| width = 200px
⚫ | image = Furethylnorlevorphanol.svg
| image2 = Furethylnorlevorphanol 3D BS.png
| width = 240
| width2 = 200px


<!--Clinical data--> <!--Clinical data-->| tradename =
| tradename = | pregnancy_AU =
| pregnancy_AU = | pregnancy_US =
| pregnancy_US = | pregnancy_category =
| legal_AU =
| pregnancy_category =
| legal_AU = | legal_CA =
| legal_CA = | legal_UK =
| legal_UK = | legal_US =
⚫ | legal_status = legal
| legal_US =
⚫ | routes_of_administration = <!--Pharmacokinetic data-->
⚫ | legal_status =
⚫ | bioavailability = 70% oral
⚫ | routes_of_administration =
IV 100%
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life = 11-16h
⚫ | excretion = <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
⚫ | CAS_number = 27767-85-7
⚫ | ATC_prefix =
⚫ | ATC_suffix =
⚫ | PubChem = 20834001


<!--Pharmacokinetic data--> <!--Chemical data-->| C = 22
| H = 27
⚫ | bioavailability =
| N = 1
⚫ | protein_bound =
| O = 2
⚫ | metabolism =
⚫ | smiles = C3CCCC1C35c2cc(O)ccc2CC1N(CC5)CCc4ccco4
⚫ | elimination_half-life =
| excretion = | melting_point =
⚫ | melting_high =

⚫ <!--Identifiers-->
⚫ | CAS_number = 27767-85-7
⚫ | ATC_prefix =
⚫ | ATC_suffix =
⚫ | PubChem = 20834001

<!--Chemical data-->
| C=22 | H=27 | N=1 | O=2
| molecular_weight = 337.454 g/mol
⚫ | smiles = C3CCCC1C35c2cc(O)ccc2CC1N(CC5)CCc4ccco4
| melting_point =
⚫ | melting_high =
}} }}


'''Ro4-1539''' ('''Furethylnorlevorphanol''') is an ] ] drug from the ] series, which was developed by the pharmaceutical company ] in the 1950s.<ref>{{cite patent | US | 2970147 }}</ref> It acts as a potent ] agonist, and was found to be around 30-60x more potent than the related drug ] in animal experiments.<ref></ref><ref>Hellerbach J, Schnider O, Besendorf H, Pellmont B. Synthetic Analgesics. Part IIA. Morphinans. Pergamon Press, 1966.</ref> While it is notable for its high potency, being among the more potent μ-agonist found in the morphinan series of drugs (though not on the scale of ] and other morphinans in the extremity of their level of potency), Ro4-1539 had no particular clinical advantages over other available opioid drugs, and was never commercially marketed. '''Ro4-1539''' ('''furethylnorlevorphanol''') is an ] ] drug from the ] series that was discovered by the pharmaceutical company ] in the 1950s.<ref>{{cite patent | country = US | number = 2970147 | title = 3-hydroxy-N-(heterocyclic-ethyl)-morphinans | pubdate = 1961-01-31 }}</ref> It acts as a potent ] agonist, and was found to be around 30-60 times more potent than the related drug ] in animal experiments.<ref></ref><ref>{{cite book | vauthors = Hellerbach J, Schnider O, Besendorf H, Pellmont B | title = Synthetic Analgesics. Part IIA. | chapter = Morphinans | publisher = Pergamon Press | date = 1966 }}</ref> Although it has high potency, long duration, and good therapeutic index (1100 in animal studies),<ref>Bulletin on Narcotics October–December 1956 page 37</ref> Ro4-1539 had no particular clinical advantages over other available opioid drugs, and was never commercially marketed.


Ro4-1539 has never been formally trialled in humans, but based on its effects in animals it would be expected to produce effects similar to those of other potent opioid agonists, including strong ], ], ], ], ] and also ] which could be harmful or fatal. Ro4-1539 has never formally undergone clinical trials in humans, but based on its effects in animals it would be expected to produce effects similar to those of other potent opioid agonists, including strong ], ], ], ], ], ] and ], which could be harmful or fatal. Due to potential κ-opioid agonism, it may be somewhat dysphoric and cause dissociation.


==See also== ==See also==
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==References== ==References==
{{Reflist|2}}
<references/>


{{opioids}} {{Opioidergics}}


] ]
] ]
] ]
] ]
] ]
] ]
]




Latest revision as of 18:08, 10 December 2024

Chemical compound
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Pharmaceutical compound
Ro4-1539
Legal status
Legal status
  • In general: legal
Pharmacokinetic data
Bioavailability70% oral IV 100%
Elimination half-life11-16h
Identifiers
IUPAC name
  • 17-(2-(Furan-2-yl)ethyl)-3-hydroxymorphinan
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H27NO2
Molar mass337.463 g·mol
3D model (JSmol)
SMILES
  • C3CCCC1C35c2cc(O)ccc2CC1N(CC5)CCc4ccco4
  (verify)

Ro4-1539 (furethylnorlevorphanol) is an opioid analgesic drug from the morphinan series that was discovered by the pharmaceutical company Hoffmann–La Roche in the 1950s. It acts as a potent μ-opioid agonist, and was found to be around 30-60 times more potent than the related drug levorphanol in animal experiments. Although it has high potency, long duration, and good therapeutic index (1100 in animal studies), Ro4-1539 had no particular clinical advantages over other available opioid drugs, and was never commercially marketed.

Ro4-1539 has never formally undergone clinical trials in humans, but based on its effects in animals it would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedation, euphoria, constipation, itching, tachyphylaxis and respiratory depression, which could be harmful or fatal. Due to potential κ-opioid agonism, it may be somewhat dysphoric and cause dissociation.

See also

References

  1. US 2970147, "3-hydroxy-N-(heterocyclic-ethyl)-morphinans", published 1961-01-31 
  2. Nathan B. Eddy, Hedwig Besendorf and Béla Pellmont. Synthetic analgesics - Aralkyl substitution on nitrogen of morphinan. UNODC Bulletin on Narcotics 1958 p 23-42.
  3. Hellerbach J, Schnider O, Besendorf H, Pellmont B (1966). "Morphinans". Synthetic Analgesics. Part IIA. Pergamon Press.
  4. Bulletin on Narcotics October–December 1956 page 37
Opioid receptor modulators
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
  • Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)


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