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{{Short description|Opioid analgesic}}
⚫ {{drugbox | verifiedrevid = 443421073
{{lowercase title}}
|
{{Drugbox
⚫ | IUPAC_name = ''N''-phenyl-''N''-propanamide
⚫ | drug_name = β-Methylfentanyl
⚫ | image = Betamethylfentanyl.svg
⚫ | verifiedrevid = 443422397
| width = 140
⚫ | IUPAC_name = ''N''-Phenyl-''N''-propanamide
| CASNo_Ref = {{cascite}}
⚫ | image = Betamethylfentanyl.svg
| InChI = 1/C23H30N2O/c1-3-23(26)25(21-12-8-5-9-13-21)22-14-16-24(17-15-22)18-19(2)20-10-6-4-7-11-20/h4-13,19,22H,3,14-18H2,1-2H3
| width = 140px
| InChIKey = UXIGUKSHASXDNI-UHFFFAOYAM
| image2 = B-methylfentanyl 3D BS.png
⚫ | CAS_number = 79146-56-8
| width2 = 220px
⚫ | synonyms = β-Methylfentanyl

⚫ | ATC_prefix = none
<!--Clinical data-->
⚫ | ATC_suffix =
| tradename =
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category =
⚫ | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | legal_CA =
⚫ | legal_UK =
| legal_US = ]<ref name=pmid29932611>{{cite journal | title = Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order | journal = Federal Register | volume = 83 | issue = 25 | pages = 5188–92 | date = February 2018 | pmid = 29932611 | last1 = Drug Enforecement Administration | first1 = Department of Justice }}</ref>
⚫ | legal_status =
⚫ | routes_of_administration =
<!--Pharmacokinetic data-->
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
⚫ | CAS_number = 79146-56-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9658A8O6GK
⚫ | ATC_prefix = none
⚫ | ATC_suffix =
⚫ | PubChem = 6425761
⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank =
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 4931228
<!--Chemical data-->
⚫ | C=23 | H=30 | N=2 | O=1
⚫ | smiles = O=C(N(c1ccccc1)C3CCN(CC(c2ccccc2)C)CC3)CC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C23H30N2O/c1-3-23(26)25(21-12-8-5-9-13-21)22-14-16-24(17-15-22)18-19(2)20-10-6-4-7-11-20/h4-13,19,22H,3,14-18H2,1-2H3 | StdInChI = 1S/C23H30N2O/c1-3-23(26)25(21-12-8-5-9-13-21)22-14-16-24(17-15-22)18-19(2)20-10-6-4-7-11-20/h4-13,19,22H,3,14-18H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UXIGUKSHASXDNI-UHFFFAOYSA-N | StdInChIKey = UXIGUKSHASXDNI-UHFFFAOYSA-N
| synonyms = β-Methylfentanyl
⚫ | PubChem = 6425761
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID=4931228
⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank =
⚫ | C = 23 | H = 30 | N = 2 | O = 1
| molecular_weight = 350.497 g/mol
⚫ | smiles = O=C(N(c1ccccc1)C3CCN(CC(c2ccccc2)C)CC3)CC
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category=
⚫ | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | legal_CA =
⚫ | legal_UK =
| legal_US =
⚫ | legal_status =
⚫ | routes_of_administration =
}} }}


'''β-Methylfentanyl''' is an ] ] that is an ] of ]. '''β-Methylfentanyl''' is an ] ] that is an ] of ].


β-Methylfentanyl was sold briefly on the black market in the early 1980s, before the introduction of the ] which for the first time attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared.<ref>Henderson GL. Designer Drugs: Past History and Future Prospects. Journal of Forensic Sciences 1988; 33(2):569-575 </ref> β-Methylfentanyl was sold briefly on the ] in the early 1980s, before the introduction of the ] which, for the first time, attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared.<ref>{{cite journal | vauthors = Henderson GL | title = Designer drugs: past history and future prospects | journal = Journal of Forensic Sciences | volume = 33 | issue = 2 | pages = 569–75 | date = March 1988 | pmid = 3286815 | doi = 10.1520/JFS11976J }}</ref>


]
β-Methylfentanyl has similar effects to fentanyl. Side effects of fentanyl analogues are similar to those of fentanyl itself, which include ], ], and ], which can be serious and even life-threatening.

β-Methylfentanyl has similar effects to fentanyl.<ref>{{Cite web|title=3-Methylfentanyl|url=https://www.drugbank.ca/drugs/DB01571|access-date=2020-07-25|website=www.drugbank.ca}}</ref> Side effects of ] analogs are similar to those of fentanyl itself, which include ], ] and potentially serious ], which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.<ref>{{cite journal | vauthors = Mounteney J, Giraudon I, Denissov G, Griffiths P | title = Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe | journal = The International Journal on Drug Policy | volume = 26 | issue = 7 | pages = 626–31 | date = July 2015 | pmid = 25976511 | doi = 10.1016/j.drugpo.2015.04.003 | url = http://www.ijdp.org/article/S0955-3959%2815%2900097-3/abstract }}</ref>


== References == == References ==
{{Reflist}}
<references />

{{Opioidergics}}


{{DEFAULTSORT:Methylfentanyl, β-}}
] ]
] ]
] ]
] ]
] ]

Latest revision as of 18:25, 15 September 2024

Opioid analgesic Pharmaceutical compound
β-Methylfentanyl
Clinical data
Other namesβ-Methylfentanyl
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • N-Phenyl-N-propanamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H30N2O
Molar mass350.506 g·mol
3D model (JSmol)
SMILES
  • O=C(N(c1ccccc1)C3CCN(CC(c2ccccc2)C)CC3)CC
InChI
  • InChI=1S/C23H30N2O/c1-3-23(26)25(21-12-8-5-9-13-21)22-14-16-24(17-15-22)18-19(2)20-10-6-4-7-11-20/h4-13,19,22H,3,14-18H2,1-2H3
  • Key:UXIGUKSHASXDNI-UHFFFAOYSA-N
  (verify)

β-Methylfentanyl is an opioid analgesic that is an analogue of fentanyl.

β-Methylfentanyl was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which, for the first time, attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared.

The chemical structure of fentanyl has been used as a basis in modern chemistry for the discovery and nomenclature of many new fentanyl analogues, sometimes called fentalogs.

β-Methylfentanyl has similar effects to fentanyl. Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.

References

  1. Drug Enforecement Administration, Department of Justice (February 2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–92. PMID 29932611.
  2. Henderson GL (March 1988). "Designer drugs: past history and future prospects". Journal of Forensic Sciences. 33 (2): 569–75. doi:10.1520/JFS11976J. PMID 3286815.
  3. "3-Methylfentanyl". www.drugbank.ca. Retrieved 2020-07-25.
  4. Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–31. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
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