Tofenacin

{{Drugbox

| IUPAC_name = N-methyl-2-[(2-methylphenyl)(phenyl)methoxy]ethanamine

| image = Tofenacin.svg

| image_class = skin-invert-image

|tradename= Elamol, Tofacine, Tofalin

|USAN=tofenacin hydrochloride

| CAS_number = 15301-93-6

| CAS_supplemental =
10488-36-5 (HCl)

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

| UNII = C4A112M10H

| ATC_prefix = None

| ATC_suffix =

| PubChem = 25315

| ChemSpiderID = 23647

| C=17 | H=21 | N=1 | O=1

| SMILES = O(CCNC)C(c1ccccc1)c2ccccc2C

| StdInChI = 1S/C17H21NO/c1-14-8-6-7-11-16(14)17(19-13-12-18-2)15-9-4-3-5-10-15/h3-11,17-18H,12-13H2,1-2H3

| StdInChIKey = PNYKGCPSFKLFKA-UHFFFAOYSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = By mouth

}}

Tofenacin is an antidepressant drug with a tricyclic-like structure which was developed and marketed in the United Kingdom and Italy in 1971 and 1981, respectively, by Brocades-Stheeman & Pharmacia (now part of Astellas Pharma).{{cite book | title = Index Nominum 2000: International Drug Directory | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1041 | access-date = 19 May 2012 | year = 2000 | publisher = Taylor & Francis US | isbn = 978-3-88763-075-1 | page = 1041}}{{cite book | vauthors = Buckingham J | title = Dictionary of organic compounds: Chemical Abstracts Service registry number index | url = https://books.google.com/books?id=2Ggj1SncMBEC&pg=PA6074 | access-date = 19 May 2012 | year = 1996 | publisher = CRC Press | isbn = 978-0-412-54090-5 | page = 6074}}{{cite book | title = Pharmaceutical Manufacturing Encyclopedia | edition = 3rd | url = https://books.google.com/books?id=TIu28TH_iAYC&pg=PA3268 | access-date = 19 May 2012 | publisher = Elsevier | isbn = 978-0-8155-1526-5 | page = 3268|date = 2013-01-15}} It acts as a serotonin-norepinephrine reuptake inhibitor,{{cite book | vauthors = van Dijk J, Hartog J, Hillen FC | chapter = Non-Tricyclic Antidepressants| veditors = Ellis GP, West GB | title = Progress in Medicinal Chemistry | chapter-url = https://books.google.com/books?id=YN9YWk4T4fwC&pg=PA284 | access-date = 19 May 2012 | date = 1 January 1978 | publisher = Elsevier | isbn = 978-0-7204-0655-9 | page = 284}} and based on its close relation to orphenadrine, may also possess anticholinergic and antihistamine properties. Tofenacin is also the major active metabolite of orphenadrine and likely plays a role in its beneficial effects against depressive symptoms seen in Parkinson's disease patients.{{cite journal | vauthors = Capstick N, Pudney H | title = A comparative trial of orphenadrine and tofenacin in the control of depression and extrapyramidal side-effects associated with fluphenazine decanoate therapy | journal = The Journal of International Medical Research | volume = 4 | issue = 6 | pages = 435–440 | year = 1976 | pmid = 800383 | doi = 10.1177/030006057600400610 | s2cid = 40083513 }}{{cite journal | vauthors = Altamura AC, Mauri MC, De Novellis F, Percudani M, Vampini V | title = Residual neuroleptic-induced parkinsonian symptoms in schizophrenia. A naturalistic study with orphenadrine | journal = Pharmacopsychiatry | volume = 22 | issue = 6 | pages = 246–249 | date = November 1989 | pmid = 2616635 | doi = 10.1055/s-2007-1014608 | s2cid = 39693625 }}