View source for Chemistry:Pethidine intermediate A

{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 412260743
| IUPAC_name = 1-methyl-4-phenylpiperidine-4-carbonitrile
| image = Pethidineintermediate.svg
| width = 160

<!--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 = A1
| legal_CA = <!-- Schedule I -->
| legal_UK = <!-- Class A -->
| legal_US = Schedule II
| legal_UN = N I
| legal_DE = Anlage II
| routes_of_administration = N/A

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

<!--Identifiers-->
| CAS_number = 3627-62-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EL4L2474TY
| ATC_prefix = none
| ATC_suffix =  
| PubChem = 62513
| KEGG = C22687
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank          = 
| ChemSpiderID      = 56289

<!--Chemical data-->
| C=13 | H=16 | N=2 
| synonyms =  
| smiles            = CN1CCC(CC1)(C#N)c2ccccc2
| StdInChI          = 1S/C13H16N2/c1-15-9-7-13(11-14,8-10-15)12-5-3-2-4-6-12/h2-6H,7-10H2,1H3
| StdInChIKey       = ZLFQTZYFXYOGLS-UHFFFAOYSA-N
}}

'''Pethidine intermediate A''' is a 4-phenyl[[Chemistry:Piperidine|piperidine]] derivative that is a [[Biology:Precursor|precursor]] to the [[Chemistry:Opioid|opioid]] [[Biology:Analgesic|analgesic]] drug [[Chemistry:Pethidine|pethidine]] (meperidine). It is not known to have any analgesic activity in its own right, however other derivatives of pethidine with a 4-cyano group in place of the carboxylate ethyl ester have been found to be active,<ref name="pmid15743177">{{cite journal | vauthors = Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML | title = Synthesis and biological evaluation of meperidine analogues at monoamine transporters | journal = Journal of Medicinal Chemistry | volume = 48 | issue = 5 | pages = 1336–43 | date = March 2005 | pmid = 15743177 | doi = 10.1021/jm0401614 }}</ref> so pethidine intermediate A might also show opioid effects. It is scheduled by {{wipe|United Nations}} [[Medicine:Single Convention on Narcotic Drugs|Single Convention on Narcotic Drugs]]. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9232.  The 2014 annual manufacturing quota was 6 grammes (as an end product, presumably for research use).<ref>{{cite web | title = Conversion Factors for Controlled Substances | url = http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice }}</ref>

== See also ==
* [[Chemistry:Moramide intermediate|Moramide intermediate]]
* [[Chemistry:Methadone intermediate|Methadone intermediate]]
* Pethidine intermediate B (norpethidine)
* Pethidine intermediate C (pethidinic acid)

== References ==
{{Reflist|2}}


[[Category:Synthetic opioids]]
[[Category:4-Phenylpiperidines]]
[[Category:Nitriles]]

{{Sourceattribution|Pethidine intermediate A}}