View source for Chemistry:Α-Eucaine

{{Short description|Chemical compound}}
{{lowercasetitle}}
{{Infobox drug
| drug_name         =''alpha''-Eucaine
| INN               =
| type              =<!-- empty -->
| IUPAC_name        = Methyl 4-benzoyloxy-1,2,2,6,6-pentamethylpiperidine-4-carboxylate
| image             = Alpha-Eucaine.svg
| width             = 150
| caption           =
<!-- Clinical data -->
| pronounce         =
| tradename         = Alpha-Eucaine 
| Drugs.com         = 
| MedlinePlus       = 
| pregnancy_AU      = <!-- A/B1/B2/B3/C/D/X -->
| pregnancy_AU_comment = 
| pregnancy_US      = <!-- A/B/C/D/X/N -->
| pregnancy_category= 
| routes_of_administration = 
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU_comment =
| legal_BR =  <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_DE = <!-- Anlage I, II, III -->
| legal_NZ = <!-- Class A, B, C -->
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_US = <!-- OTC/Rx-only/Schedule I, II, III, IV, V -->
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_status      = <!-- Free text -->
<!-- Pharmacokinetic data -->
| bioavailability   = 
| protein_bound     = 
| metabolism        = 
| metabolites       =
| onset             = 
| elimination_half-life = 
| duration_of_action =
| excretion         = 
<!-- Identifiers -->
| CAS_number        = 470-68-8
| class             = 
| ATCvet            = 
| ATC_prefix        = <!-- 'none' if uncategorised -->
| ATC_suffix        = 
| PubChem           = 5282357
| KEGG = C14166
| ChEBI = 35059
| ChemSpiderID = 4445520
| DrugBank          = 
| synonyms          = α-Eucaine; Eucaine A
<!-- Chemical and physical data -->
| C=19|H=27|N=1|O=4
| StdInChI=1S/C19H27NO4/c1-17(2)12-19(16(22)23-6,13-18(3,4)20(17)5)24-15(21)14-10-8-7-9-11-14/h7-11H,12-13H2,1-6H3
| StdInChIKey = MJMZACWQGQGLBI-UHFFFAOYSA-N
| smiles = CC1(CC(CC(N1C)(C)C)(C(=O)OC)OC(=O)C2=CC=CC=C2)C
}}

'''α-Eucaine''' (''alpha''-eucaine) is a drug that was previously used as a [[Medicine:Local anesthetic|local anesthetic]].<ref name="Sneader2005">{{cite book| vauthors = Sneader W |title=Drug Discovery: A History|url=https://books.google.com/books?id=jglFsz5EJR8C&pg=PA127|date=31 October 2005|publisher=John Wiley & Sons|isbn=978-0-470-01552-0|pages=127–9}}</ref> It was designed as an [[Chemistry:Functional analog|analog]] of [[Biology:Cocaine|cocaine]] and was one of the first synthetic chemical compounds to find general use as an anesthetic.<ref name="Manske2014">{{cite book| vauthors = Manske RH |title=The Alkaloids: Chemistry and Physiology|url=https://books.google.com/books?id=DvbJCgAAQBAJ&pg=PA213|date=12 May 2014|publisher=Elsevier|isbn=978-1-4832-2192-2|pages=213–4}}</ref> 

==Synthesis==
[[File:Eucaine (alpha) synthesis.svg|thumb|center|500px|Background:<ref>{{cite journal | vauthors=((Parsons, C. L.)) | journal=Journal of the American Chemical Society | title=THE IDENTIFICATION AND PROPERTIES OF α- AND β-EUCAINE. 1 | volume=23 | issue=12 | pages=885–893 | date= December 1901 | doi=10.1021/ja02038a002| url=https://zenodo.org/record/2044259 }}</ref>]]
The [[Chemistry:Aldol condensation|Aldol condensation]] between two equivalents of acetone gives [[Chemistry:Mesityl oxide|Mesityl oxide]] [141-79-7] ('''1''') ([[Chemistry:Isophorone|isophorone]] is a side-product of this reaction). Ammonolysis of mesityl oxide formed diacetonamine [625-04-7] ('''2'''). The reaction of this product with acetone then gives 2,2,6,6-tetramethyl-4-piperidone [826-36-8] ('''3'''). ''N''-methylation of the secondary amine gives 1,2,2,6,6-pentamethylpiperidin-4-one [5554-54-1] ('''4'''). Cyanohydrin formation gives [https://pubchem.ncbi.nlm.nih.gov/compound/434556 CID:434556] ('''5'''). Esterification of the tertiary alcohol with benzoyl chloride gives ('''6'''). Pinner reaction of the nitrile with EtOH/H+ affords alpha-eucaine ('''7''').

==See also==
* [[Chemistry:Eucaine|Eucaine]], or β-eucaine, a related local anesthetic

==References==
{{reflist}}


[[Category:Piperidines]]
[[Category:Benzoate esters]]
[[Category:Methyl esters]]

{{Sourceattribution|Α-Eucaine}}