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{{Short description|Opioid analgesic}}
{{DISPLAYTITLE:''N''-Methylcarfentanil}}
{{DISPLAYTITLE:''N''-}}
{{drugbox
{{Drugbox
| verifiedrevid = 440000484
| verifiedrevid =
| drug_name = ''N''-Methylcarfentanil
| IUPAC_name = Methyl 1-methyl-4-(N-phenylpropionamido)piperidine-4-carboxylate
| IUPAC_name = 1-methyl-4-(N-)piperidine-4-carboxylate
| image = N-methylcarfentanil_structure.png
| image = N-.
| image2 = N-methylnorcarfentanil.png
| width = 200px

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| CAS_number =
<!--Clinical data-->
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| ATC_prefix =
| ATC_suffix =
| =
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| pregnancy_category =
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| PubChem =
| legal_CA = Schedule I
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| C=17 | H=24 | N=2 | O=3
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| legal_UK
| molecular_weight = 304.384 g/mol
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| routes_of_administration =
| CASNo =

| PubChem =
<!--Pharmacokinetic data-->
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| bioavailability =
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| protein_bound =
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| metabolism =
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| elimination_half-life =
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| excretion =

<!--Identifiers-->
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| CAS_number =
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| ATC_prefix =
| ATC_suffix =
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| PubChem =
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26231037
| ChemSpiderID = 26231037
| UNII = 85WEL251JZ
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

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| StdInChI=1S/C17H24N2O3/c1-4-15(20)19(14-8-6-5-7-9-14)17(16(21)22-3)10-12-18(2)13-11-17/h5-9H,4,10-13H2,1-3H3
<!--Chemical data-->
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| C=17 | H=24 | N=2 | O=3
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| StdInChIKey = KKEVIELPQLXPRR-UHFFFAOYSA-N
| smiles = O=C(OC)C1(N(C2=CC=CC=C2)C(CC)=O)CCN(C)CC1
| smiles = O=C(OC)C1(N(C2=CC=CC=C2)C(CC)=O)CCN(C)CC1
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| bioavailability = ?
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| StdInChI=1S/C17H24N2O3/c1-4-15(20)19(14-8-6-5-7-9-14)17(16(21)22-3)10-12-18(2)13-11-17/h5-9H,4,10-13H2,1-3H3
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| protein_bound = ?
⚫
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
| metabolism = ?
⚫
| StdInChIKey = KKEVIELPQLXPRR-UHFFFAOYSA-N
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| elimination_half-life =
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| excretion = ?
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| legal_UK =
| legal_US =
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| routes_of_administration =
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| pregnancy_category = ?
}}
}}


'''''N''-Methylcarfentanil''' ('''R-32395''') is an [[opioid]] analgesic drug related to the highly potent animal tranquilizer [[carfentanil]], but several thousand times weaker, being only slightly stronger than [[morphine]]. It was first synthesised by a team of chemists at [[Janssen Pharmaceutica]] led by [[Paul Janssen]], who were investigating the [[structure-activity relationship]]s of the [[fentanyl]] family of drugs. They found that replacing the phenethyl group attached to the piperidine nitrogen of fentanyl with a smaller methyl group, made it so much weaker that it was inactive as an analgesic in animals. However the same change made to the more potent analogue carfentanil retained reasonable [[opioid receptor]] activity, reflecting the higher [[Dissociation constant#Protein-ligand binding|binding affinity]] produced by the 4-carbomethoxy group.<ref name="pmid1310142">{{cite journal |author=Cometta-Morini C, Maguire PA, Loew GH |title=Molecular determinants of mu receptor recognition for the fentanyl class of compounds |journal=Molecular Pharmacology |volume=41 |issue=1 |pages=185–96 |year=1992 |month=January |pmid=1310142 |doi= |url=}}</ref><ref>{{Cite doi|10.1016/0014-2999(92)90685-W}}</ref><ref>Dukhovich FS, Darkhovskii MB, Gorbatova EN, Kurochkin VK. Molecular recognition: pharmacological aspects. 2004, Nova Science Publishers, New York. p 81. ISBN 1590338871</ref>
'''''N''-''' ('''R-32395''') is an [[opioid]] analgesic drug related to the highly potent animal tranquilizer [[carfentanil]], but several thousand times weaker, being only slightly stronger than [[morphine]]. It was first synthesised by a team of chemists at [[Janssen Pharmaceutica]] led by [[Paul Janssen]], who were investigating the [[structure-activity relationship]]s of the [[fentanyl]] family of drugs. They found that replacing the phenethyl group attached to the piperidine nitrogen of fentanyl with a smaller methyl group, made it so much weaker that it was inactive as an analgesic in animals. However the same change made to the more potent analogue carfentanil retained reasonable [[opioid receptor]] activity, reflecting the higher [[Dissociation constant#Protein-ligand binding|binding affinity]] produced by the 4-carbomethoxy group.<ref name="pmid1310142">{{cite journal |=Cometta-Morini C, Maguire PA, Loew GH |title=Molecular determinants of mu receptor recognition for the fentanyl class of compounds |journal=Molecular Pharmacology |volume=41 |issue=1 |pages = |=January |pmid=1310142 | url=}}</ref><ref>{{ |10.1016/0014-2999(92)90685-W}}</ref><ref>Dukhovich FS, Darkhovskii MB, Gorbatova EN, Kurochkin VK. Molecular recognition: pharmacological aspects. 2004, Nova Science Publishers, New York. p 81. ISBN</ref>

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 = 626–631 | date = July 2015 | pmid = 25976511 | doi = 10.1016/j.drugpo.2015.04.003 }}</ref>

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==References==
{{reflist}}


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


{{DEFAULTSORT:Methylcarfentanil, N-}}
{{DEFAULTSORT:Methylcarfentanil, N-}}
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[[Category:Propionamides]]
[[Category:Propionamides]]
[[Category:Anilides]]
[[Category:Anilides]]
[[Category:Mu-opioid agonists]]
[[Category:Mu-opioid agonists]]
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