Benzhydryl compounds

The benzhydryl compounds are a group of organic compounds whose parent structures include diphenylmethane (which is two benzene rings connected by a single methane), with any number of attached substituents, including bridges. This group typically excludes compounds in which either benzene is fused to another ring (bicyclic, tricyclic, polycyclic)[1] or includes a heteroatom, or where the methane connects to three or four benzenes.

The benzhydryl radical can be abbreviated Ph
2
CH•
or Bzh.[2]

Carboaromatic

Alcohols

  • Acyclic: pridinol
  • Pyrolidino: diphenylprolinol
  • 2-Piperidine: pipradrol
  • 4-Piperidine: terfenadine, fexofenadine
  • Benzilic ester: QNB, JB-336, JB-318, benactyzine

Alkenes

  • Tricycle: amitriptyline, melitracen, cyclobenzaprine, tianeptine, amineptine, clopenthixol, chlorprothixene, flupentixol, thiothixene, zuclopenthixol
  • Tricyclic and piperidine: pimethixene, cyproheptadine
  • Acyclic: gilutensin

Alkyl(amine)s

  • Acyclic: (3-phenylpropylamine), tolpropamine, tolterodine
  • Piperidine: desoxypipradrol, budipine[3]
  • N-alkyl-4-piperidinol: penfluridol
  • N-arylalkyl-piperidine: pimozide
  • Tetrahydronaphthalene: tametraline (4-phenylaminotetralin), sertraline
  • Tetrahydroisoquinoline: nomifensine, diclofensine "tetrahydronaphisoquinoline", dinapsoline (see doxanthrine and dinoxyline)
  • Pyrroloisoquinoline: JNJ-7925476
  • Indanamine: Lu 19-005
  • Tricyclic: 9-Aminomethyl-9,10-dihydroanthracene, phenindamine (see MPTP)
  • Tetracyclic: maprotiline, dihydrexidine, butaclamol, ecopipam
  • Tetrahydrobenzazepine: SKF-83959, SKF-82958, SKF-81297, SKF 38393, fenoldopam, 6-Br-APB, SCH 23390
  • Piperazine: amperozide
  • Triazaspiro: fluspirilene

Alkoxy compounds

  • Acyclic (3 °C): diphenhydramine (c.f deramciclane), orphenadrine, p-methyldiphenhydramine
  • Acyclic (4 °C): moxastine, Clemastine, embramine,
  • Piperazine: GBR-12935, GBR 12909, DBL-583
  • Tropine: benztropine, deptropine, etybenzatropine, difluoropine
  • Piperidine: diphenylpyraline
  • Phthalane: talopram, citalopram
  • Octahedral: nefopam
  • Benzdihydropyran: A-68930 (isochromene)

Amines

  • Piperazine: cyclizine, clocinizine, hydroxyzine, meclozine, cetirizine, dotarizine, cinnarizine
  • Benzazepine: mianserin
  • Tetracyclic: dizocilpine

Other

  • Aromatic alkoxy: bifemelane, phenyltoloxamine
  • Keto: phenadoxone, methadone, dipipanone, etc.
  • Amido: dextromoramide
  • Imino: benzodiazepine, GYKI-52895
  • Sulfinyl: modafinil, adrafinil
  • Pituxate gem-diphenylcyclopropane

Heteroaromatic

These species are not strictly benzhydryl-containing but are analogous.

Heteroaromatic rings

  • Alkene: thiambutene, loratadine
  • Alkylamine: A-86929, amfonelic acid

Benzenes linked by a non-carbon atom

  • Nitrogen: promethazine, imipramine, acepromazine, chlorpromazine, fluphenazine, mesoridazine, levomepromazine, perazine, periciazine, perphenazine, prochlorperazine, sulforidazine, thioridazine, trifluoperazine, triflupromazine, clozapine, thiethylperazine
  • Indolic nitrogen: sertindole
  • Oxygen: loxapine, asenapine, tyrima

Benzene and heterocycle linked through a non-carbon

  • Olanzapine

References

  1. Benzhydryl Compounds at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
  2. "Abbreviations and Symbols". European Journal of Biochemistry. 74 (1): 1–6. 1977. doi:10.1111/j.1432-1033.1977.tb11359.x. ISSN 0014-2956.
  3. U.S. patent 4,022,786
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