Last updated
Clinical data
Trade names Elamol, Tofacine, Tofalin
Other namestofenacin hydrochloride (USAN US)
Routes of
By mouth
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
  • N-methyl-2-[(2-methylphenyl)(phenyl)methoxy]ethanamine
CAS Number
PubChem CID
ECHA InfoCard 100.035.746 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H21NO
Molar mass 255.361 g·mol−1
3D model (JSmol)
  • O(CCNC)C(c1ccccc1)c2ccccc2C
  • InChI=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

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). [1] [2] [3] It acts as a serotonin-norepinephrine reuptake inhibitor, [4] 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. [5] [6]



Thieme Patent: Tofenacin synthesis.svg
Thieme Patent:

The ether formation between 2-Methylbenzhydrol [5472-13-9] (1) and 2-chloroethanol [107-07-3] (2) gives CID:90470367 (3). Reaction with methylamine completed the synthesis of Tofenacin (4).

See also

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