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{{Short description|Chemical compound}}
{{drugbox | verifiedrevid = 443660279
{{lowercasetitle}}
|
{{Drugbox
| IUPAC_name = ''N''-phenyl-''N''-[1-(1-thiophen-2-ylpropan-2-yl)-4-piperidyl]propanamide
| drug_name = α-Methylthiofentanyl
| image = alphamethylthiofentanyl.svg
| verifiedrevid = 443661467
| width = 100
| IUPAC_name = ''N''-Phenyl-''N''-[1-(1-thiophen-2-ylpropan-2-yl)-4-piperidyl]propanamide
| image = alphamethylthiofentanyl.svg

<!--Clinical data-->
| 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_BR = F1
| legal_CA = Schedule I
| legal_UK = Class A
| legal_US = Schedule I
| legal_DE = Anlage I
| routes_of_administration =

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

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 103963-66-2

| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NF684LIF79

| ATC_prefix = none
| ATC_suffix =
| PubChem = 62309
| KEGG = C22789
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01470
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 56104
| ChemSpiderID = 56104

| InChI = 1/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)19-11-13-22(14-12-19)17(2)16-20-10-7-15-25-20/h4-10,15,17,19H,3,11-14,16H2,1-2H3
<!--Chemical data-->
| C=21 | H=28 | N=2 | O=1 | S=1
| smiles = O=C(N(c1ccccc1)C2CCN(CC2)C(Cc3sccc3)C)CC
| smiles = O=C(N(c1ccccc1)C2CCN(CC2)C(Cc3sccc3)C)CC
| InChIKey = YPOXDUYRRSUFFG-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)19-11-13-22(14-12-19)17(2)16-20-10-7-15-25-20/h4-10,15,17,19H,3,11-14,16H2,1-2H3
| StdInChI = 1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)19-11-13-22(14-12-19)17(2)16-20-10-7-15-25-20/h4-10,15,17,19H,3,11-14,16H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YPOXDUYRRSUFFG-UHFFFAOYSA-N
| StdInChIKey = YPOXDUYRRSUFFG-UHFFFAOYSA-N
| synonyms =
| CAS_number = 103963-66-2
| synonyms = α-methyl-thiofentanyl
| ATC_prefix = none
| ATC_suffix =
| PubChem = 62309
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01470
| C = 21 | H = 28 | N = 2 | O = 1 | S = 1
| molecular_weight = 356.526 g/mol
| 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 = Schedule I
| legal_UK = Class A
| legal_US = Schedule I
| legal_status =
| routes_of_administration =
}}
}}


'''α-methyl-thiofentanyl''' is an [[opioid]] [[analgesic]] that is an [[analog (chemistry)|analogue]] of [[fentanyl]].
'''α-Methylthiofentanyl''' is an [[opioid]] [[analgesic]] that is an [[analog (chemistry)|analogue]] of [[fentanyl]].


α-methyl-thiofentanyl 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. <ref> Henderson GL. Designer Drugs: Past History and Future Prospects. Journal of Forensic Sciences 1988; 33(2):569-575 </ref>
α-Methylthiofentanyl 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.<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 | doi = 10.1520/JFS11976J | pmid = 3286815 }}</ref>


α-methyl-thiofentanyl has similar effects to fentanyl. Side effects of fentanyl analogues are similar to those of fentanyl itself, which include [[itching]], [[nausea]] and potentially serious [[respiratory depression]] which can be life-threatening.
α-Methylthiofentanyl 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.<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 }}</ref>

==See also==
*[[3-Methylthiofentanyl]]


== References ==
== References ==
{{Reflist|1}}
<references />


{{Opioidergics}}


[[Category:Synthetic opioids]]
[[Category:Synthetic opioids]]
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[[Category:Anilides]]
[[Category:Anilides]]
[[Category:Propionamides]]
[[Category:Propionamides]]
[[Category:Mu-opioid agonists]]
[[Category:Mu-opioid receptor agonists]]

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