Benzhydryl compounds

Short description: Organic compounds which include diphenylmethane

Ball-and-stick model of diphenylmethane

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

The benzhydryl radical can be abbreviated Ph2CH• or Bzh.[2]

## Contents

* 1 Carboaromatic
* 1.1 Alcohols
* 1.2 Alkenes
* 1.3 Alkyl(amine)s
* 1.4 Alkoxy compounds
* 1.5 Amines
* 1.6 Other
* 2 Heteroaromatic
* 2.1 Heteroaromatic rings
* 2.2 Benzenes linked by a non-carbon atom
* 2.3 Benzene and heterocycle linked through a non-carbon
* 3 References
* 4 External links

## 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 US 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. https://febs.onlinelibrary.wiley.com/doi/10.1111/j.1432-1033.1977.tb11359.x.
3. ↑ U.S. Patent 4,022,786

## External links

* Benzhydryl+Compounds at the US National Library of Medicine Medical Subject Headings (MeSH)
* Bromodiphenylmethane from PubChem, a.k.a. called benzhydryl bromide
* 1-Benzyl-2-bromobenzene from PubChem, not called benzhydryl bromide

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