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Phenomorphan: Difference between revisions

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Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoB
 
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| verifiedrevid = 447927638
| verifiedrevid = 447927638
| IUPAC_name = 17-(2-phenylethyl)morphinan-3-ol
| IUPAC_name = 17-(2-Phenylethyl)morphinan-3-ol
| image = Phenomorphan.svg
| image = Phenomorphan.svg
| width = 190
| width = 230px
| image2 = Phenomorphan 3D BS.png
| width2 = 230px


<!--Clinical data-->
<!--Clinical data-->
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| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = S9
| legal_CA =
| legal_BR = A1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule I
| legal_UK = Class A
| legal_UK = Class A
| legal_US = Schedule I
| legal_US = Schedule I
| legal_status =
| legal_DE = Anlage I
| routes_of_administration =
| routes_of_administration =


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 468-07-5
| CAS_number = 468-07-5
| ATC_prefix = none
| ATC_prefix = none
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| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 26HXE4B73P
| UNII = 26HXE4B73P
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D12688


<!--Chemical data-->
<!--Chemical data-->
| C=24 | H=29 | N=1 | O=1
| C=24 | H=29 | N=1 | O=1
| molecular_weight = 347.493 g/mol
| smiles = Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@H]12)c4c3)CCc5ccccc5
| smiles = Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@H]12)c4c3)CCc5ccccc5
| InChI = 1/C24H29NO/c26-20-10-9-19-16-23-21-8-4-5-12-24(21,22(19)17-20)13-15-25(23)14-11-18-6-2-1-3-7-18/h1-3,6-7,9-10,17,21,23,26H,4-5,8,11-16H2/t21-,23+,24+/m0/s1
| InChIKey = CFBQYWXPZVQQTN-QPTUXGOLBS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H29NO/c26-20-10-9-19-16-23-21-8-4-5-12-24(21,22(19)17-20)13-15-25(23)14-11-18-6-2-1-3-7-18/h1-3,6-7,9-10,17,21,23,26H,4-5,8,11-16H2/t21-,23+,24+/m0/s1
| StdInChI = 1S/C24H29NO/c26-20-10-9-19-16-23-21-8-4-5-12-24(21,22(19)17-20)13-15-25(23)14-11-18-6-2-1-3-7-18/h1-3,6-7,9-10,17,21,23,26H,4-5,8,11-16H2/t21-,23+,24+/m0/s1
Line 50: Line 55:


'''Phenomorphan'''<ref>{{ cite patent
'''Phenomorphan'''<ref>{{ cite patent
| country = US
| country = US
| number = 2885401
| number = 2885401
| status = patent
| status = patent
| title = PROCESS FOR MAKING MORPHINAN DERIVATIVES AND PRODUCTS AVAILABLE THEREBY
| title = Process for making morphinan derivatives and products available thereby
| pubdate = 1956-03-22
| pubdate = 1956-03-22
| gdate = 1959-05-05
| gdate = 1959-05-05
| inventor = Andre Grussner, Joseph Hellerbach, Otto Schnider.
| inventor = Grussner A, Hellerbach J, Schnider O
}}</ref> 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]].
}}</ref> 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<ref>{{ cite patent
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<ref>{{ cite patent
| country = US
| country = US
| number = 2970147
| number = 2970147
| status = patent
| status = patent
| title = 3-HYDROXY-N-(HETEROCYCLIC-ETHYL)-MORPHINANS
| title = 3-hydroxy-N-(heterocyclic-ethyl)-morphinans
| pubdate = 1958-11-26
| pubdate = 1958-11-26
| gdate = 1961-01-31
| gdate = 1961-01-31
| inventor = Andre Grussner, Joseph Hellerbach, Otto Schnider.
| inventor = Andre Grussner, Joseph Hellerbach, Otto Schnider
}}</ref> are even more potent, with the N-(2-(2-[[furan|furyl]])ethyl) and the N-(2-(2-[[thiophene|thienyl]])ethyl) analogues being 60x and 45x stronger than levorphanol respectively.<ref>Hellerbach J, Schnider O, Besendorf H, Pellmont B. Synthetic Analgesics. Part IIA. Morphinans. Pergamon Press, 1966.</ref>
}}</ref> are even more potent, with the [[Ro4-1539|N-(2-(2-furyl)ethyl)]] and the N-(2-(2-[[thiophene|thienyl]])ethyl) analogues being 60x and 45x stronger than levorphanol, respectively.<ref>{{cite book | vauthors = Hellerbach J, Schnider O, Besendorf H, Pellmont B | series= International series of monographs on organic chemistry | title = Synthetic Analgesics: Part IIA. Morphinans | publisher = Pergamon Press | year = 1966 | url=https://www.scribd.com/doc/39966259/Synthetic-Analgesics-1966-Part-IIA-Morphinans }}</ref>


==See also==
==See also==
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==References==
==References==
{{reflist}}
{{Reflist|2}}


{{opioids}}
{{Opioidergics}}


[[Category:Synthetic opioids]]
[[Category:Synthetic opioids]]
[[Category:Morphinans]]
[[Category:Morphinans]]
[[Category:Phenols]]
[[Category:Hydroxyarenes]]
[[Category:Mu-opioid agonists]]
[[Category:Mu-opioid receptor agonists]]


⚫
{{pharm-stub}}


⚫
{{pharm-stub}}
[[sv:Fenomorfan]]

Latest revision as of 18:11, 21 October 2024

Phenomorphan
Clinical data
Other names(-)-3-hydroxy- N- (2-phenylethyl) morphinan
ATC code
  • none
Legal status
Legal status
Identifiers
  • 17-(2-Phenylethyl)morphinan-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.006.732 Edit this at Wikidata
Chemical and physical data
FormulaC24H29NO
Molar mass347.502 g·mol−1
3D model (JSmol)
  • Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@H]12)c4c3)CCc5ccccc5
  • InChI=1S/C24H29NO/c26-20-10-9-19-16-23-21-8-4-5-12-24(21,22(19)17-20)13-15-25(23)14-11-18-6-2-1-3-7-18/h1-3,6-7,9-10,17,21,23,26H,4-5,8,11-16H2/t21-,23+,24+/m0/s1 checkY
  • Key:CFBQYWXPZVQQTN-QPTUXGOLSA-N checkY
  (verify)

Phenomorphan[2] 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[3] 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.[4]

See also

[edit]

References

[edit]
  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ US patent 2885401, Grussner A, Hellerbach J, Schnider O, "Process for making morphinan derivatives and products available thereby", published 1956-03-22, issued 1959-05-05 
  3. ^ US patent 2970147, Andre Grussner, Joseph Hellerbach, Otto Schnider, "3-hydroxy-N-(heterocyclic-ethyl)-morphinans", published 1958-11-26, issued 1961-01-31 
  4. ^ Hellerbach J, Schnider O, Besendorf H, Pellmont B (1966). Synthetic Analgesics: Part IIA. Morphinans. International series of monographs on organic chemistry. Pergamon Press.


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