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.

Ball-and-stick model of the benzhydryl radical

Ball-and-stick model of diphenylmethane

The benzhydryl radical can be abbreviated Ph
₂CH• 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 (cf. 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