The benzhydryl compounds are a group of organic compounds whose parent structures include

diphenylmethane Diphenylmethane is an organic compound with the formula (C6H5)2CH2 (often abbreviated ). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid. Diphenylmethane is a common skeleton in or ...

(which is two

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

rings connected by a single

methane Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The relative abundance of methane on Eart ...

), with any number of attached

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...

s, including

bridges A bridge is a structure built to Span (engineering), span a physical obstacle (such as a body of water, valley, road, or rail) without blocking the way underneath. It is constructed for the purpose of providing passage over the obstacle, whic ...

. This group typically excludes compounds in which either benzene is fused to another ring ( bicyclic, tricyclic, polycyclic) or includes a heteroatom, or where the methane connects to three or

four 4 (four) is a number, numeral and digit. It is the natural number following 3 and preceding 5. It is the smallest semiprime and composite number, and is considered unlucky in many East Asian cultures. In mathematics Four is the smallest c ...

benzenes.

The benzhydryl ''

radical Radical may refer to: Politics and ideology Politics *Radical politics, the political intent of fundamental societal change *Radicalism (historical), the Radical Movement that began in late 18th century Britain and spread to continental Europe and ...

'' can be abbreviated or Bzh.

Carboaromatic

Alcohols

*''Acyclic:''

pridinol Pridinol, sold under the brand name Myopridin, is a muscle relaxant that is used as an antiparkinsonian and anticholinergic Anticholinergics (anticholinergic agents) are substances that block the action of the neurotransmitter called acetyl ...

*''Pyrolidino:''

diphenylprolinol Diphenylprolinol (D2PM), or (''R''/''S'')-(±)-diphenyl-2-pyrrolidinyl-methanol, is a norepinephrine-dopamine reuptake inhibitor which is used as a designer drug. Pharmacology The dextrorotary (''R'')-(+)-enantiomer is the more pharmacological ...

*''2-Piperidine:''

pipradrol Pipradrol (Meratran) is a mild central nervous system stimulant ( norepinephrine-dopamine reuptake inhibitor) that is no longer widely used in most countries due to concerns about its abuse potential. Pipradrol is still used in some European cou ...

*''4-Piperidine:''

terfenadine Terfenadine is an antihistamine formerly used for the treatment of allergic conditions. It was brought to market by Hoechst Marion Roussel (now Sanofi-Aventis) and was marketed under various brand names, including Seldane in the United States, Tr ...

, fexofenadine *''Benzilic ester:'' QNB, JB-336, JB-318,

benactyzine Benactyzine is an anticholinergic drug that was used as an antidepressant in the treatment of depression and associated anxiety before it was pulled from the U.S. market by the FDA due to its ineffectiveness. Its use for these indications was ...

Alkenes

*''Tricycle:'' amitriptyline,

melitracen Melitracen (brand names Melixeran) is a tricyclic antidepressant (TCA), for the treatment of depression and anxiety. In addition to single drug preparations, it is also available as Deanxit, marketed by Lundbeck, a combination product containin ...

cyclobenzaprine Cyclobenzaprine (sold under the brand name Flexeril, among others) is a medication used for muscle spasms from musculoskeletal conditions of sudden onset. It is not useful in cerebral palsy. It is taken by mouth. Use is not recommended for mor ...

, tianeptine, amineptine,

clopenthixol Clopenthixol (Sordinol), also known as clopentixol, is a typical antipsychotic drug of the thioxanthene class. It was introduced by Lundbeck in 1961. Clopenthixol is a mixture of ''cis'' and ''trans'' isomers. Zuclopenthixol, the pure ''cis'' is ...

chlorprothixene Chlorprothixene, sold under the brand name Truxal among others, is a typical antipsychotic of the thioxanthene group. Medical uses Chlorprothixene's principal indications are the treatment of psychotic disorders (e.g. schizophrenia) and of acu ...

flupentixol Flupentixol (INN), also known as flupenthixol (former BAN), marketed under brand names such as Depixol and Fluanxol is a typical antipsychotic drug of the thioxanthene class. It was introduced in 1965 by Lundbeck. In addition to single drug prep ...

thiothixene Tiotixene, or thiothixene, sold under the brand name Navane among others, is a typical antipsychotic of the thioxanthene class which is related to chlorprothixene and is used in the treatment of psychoses like schizophrenia and bipolar mania. ...

zuclopenthixol Zuclopenthixol (brand names Cisordinol, Clopixol and others), also known as zuclopentixol, is a medication used to treat schizophrenia and other psychoses. It is classed, pharmacologically, as a typical antipsychotic. Chemically it is a thioxanth ...

*''Tricyclic and piperidine:''

pimethixene Pimethixene is an antihistamine and anticholinergic of the thioxanthene chemical class originally developed to treat hyperactivity, anxiety, sleep disorders, and allergy. It is also used for anesthesia and as a bronchodilator (to dilate the bron ...

, cyproheptadine *''Acyclic:''

gilutensin Etifelmine (INN; also known as gilutensin) is a stimulant drug. It was used for the treatment of hypotension (low blood pressure). Synthesis The base catalyzed reaction between benzophenone 19-61-9(1) and butyronitrile 09-74-0(2) gives 2- y ...

Alkyl(amine)s

*''Acyclic:'' (3-phenylpropylamine), tolpropamine, tolterodine *''Piperidine:''

desoxypipradrol Desoxypipradrol, also known as 2-⁠diphenylmethylpiperidine (2-DPMP), is a drug developed by Ciba in the 1950s which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI). Chemistry Desoxypipradrol is closely related on a structural lev ...

budipine Budipine (brand name Parkinsan) is an antiparkinson agent marketed for the treatment of Parkinson's disease. While its exact mechanism of action is not well characterized, it is believed to be an NMDA receptor antagonist, but also promoting the ...

*''N-alkyl-4-piperidinol:'' penfluridol *''N-arylalkyl-piperidine:'' pimozide *''Tetrahydronaphthalene:''

tametraline Tametraline (CP-24,441) is the parent of a series of chemical compounds investigated at Pfizer that eventually led to the development of sertraline (CP-51,974-1). Sertraline has been called "3,4-dichloro-tametraline". This is correct but it is a ...

(4-phenylaminotetralin),

sertraline Sertraline, sold under the brand name Zoloft among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. The efficacy of sertraline for depression is similar to that of other antidepressants, and the differe ...

*''Tetrahydroisoquinoline:'' nomifensine, diclofensine "tetrahydronaphisoquinoline",

dinapsoline Dinapsoline is a drug developed for the treatment of Parkinson's disease, that acts as a selective full agonist at the dopamine D1 receptor Receptor may refer to: * Sensory receptor, in physiology, any structure which, on receiving environmen ...

(see

doxanthrine Doxanthrine is a synthetic compound which is a potent and selective full agonist for the dopamine D1 receptor. Doxanthrine has been shown to be orally active in producing contralateral rotation in the 6-hydroxydopamine rat model of Parkin ...

and

dinoxyline Dinoxyline is a synthetic compound developed for scientific research, which acts as a potent full agonist at all five dopamine receptor Dopamine receptors are a class of G protein-coupled receptors that are prominent in the vertebrate central ...

) *''Pyrroloisoquinoline:''

JNJ-7925476 JNJ-7925476 is a triple reuptake inhibitor antidepressant discovered by Johnson & Johnson, but never marketed. These molecules were first prepared by Bruce E. Maryanoff and coworkers during the late 1970s–1980s. The structure is a pyrrol ...

*''Indanamine:'' Lu 19-005 *''Tricyclic:'' 9-Aminomethyl-9,10-dihydroanthracene,

phenindamine Phenindamine (Nolahist, Thephorin) is an antihistamine and anticholinergic closely related to cyproheptadine. It was developed by Hoffman-La Roche in the late 1940s. It is used to treat symptoms of the common cold and allergies, such as sneezing, ...

(see MPTP) *''Tetracyclic:'' maprotiline,

dihydrexidine Dihydrexidine (DAR-0100) is a moderately selective full agonist at the dopamine D1 and D5 receptors. It has approximately 10-fold selectivity for D1 and D5 over the D2 receptor. Although dihydrexidine has some affinity for the D2 receptor, ...

butaclamol Butaclamol (AY-23,028) is a typical antipsychotic which was never marketed. Sold as the hydrochloride salt for use in research, the compound acts as a dopamine receptor Dopamine receptors are a class of G protein-coupled receptors that are pro ...

ecopipam Ecopipam (development codes SCH-39166, EBS-101, and PSYRX-101) is a dopamine antagonist which is under development for the treatment of Lesch-Nyhan syndrome, Tourette's syndrome, speech disorders, and restless legs syndrome. It is taken by mouth ...

*''Tetrahydrobenzazepine:''

SKF-83959 SKF-83,959 is a chemical synthesis, synthetic benzazepine chemical derivative, derivative used in scientific research which acts as an agonist at the D1-D2 Dopamine receptor heteromer, D1–D2 dopamine receptor heteromer. It behaves as a full ago ...

SKF-82958 SKF-82,958 is a synthetic compound of the benzazepine class that acts as a D1/ D5 receptor full agonist. SKF-82,958 and similar D1-like-selective full agonists like SKF-81,297 and 6-Br-APB produce characteristic anorectic effects, hyperactivity ...

, SKF-81297, SKF 38393, fenoldopam, 6-Br-APB, SCH 23390 *''Piperazine:''

amperozide Amperozide is an atypical antipsychotic of the diphenylbutylpiperazine class which acts as an antagonist at the 5-HT2A receptor. It does not block dopamine receptors as with most antipsychotic drugs, but does inhibit dopamine release, and alter ...

*''Triazaspiro:'' fluspirilene

Alkoxy compounds

*''Acyclic'' (3 °C):

diphenhydramine Diphenhydramine (DPH) is an antihistamine and sedative mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremor in parkinsonism, and nausea. It is taken by mouth, injected into a vein ...

(c.f

deramciclane Deramciclane (EGIS-3886) is a non-benzodiazepine-type anxiolytic drug to treat various types of anxiety disorders. Deramciclane is a unique alternative to current anxiolytics on the market because it has a novel chemical structure and target. It ...

orphenadrine Orphenadrine (sold under many brand names) is an anticholinergic drug of the ethanolamine antihistamine class; it is closely related to diphenhydramine. It is a muscle relaxant that is used to treat muscle pain and to help with motor control in Pa ...

, p-methyldiphenhydramine *''Acyclic'' (4 °C): moxastine,

Clemastine Clemastine, also known as meclastin, is a first-generation H1 histamine antagonist (antihistamine) with anticholinergic properties (drying) and sedative side effects. Like all first-generation antihistamines, it is sedating. Patented in 1960 ...

embramine Embramine (a.k.a. Mebryl, Bromadryl) is an antihistamine and anticholinergic Anticholinergics (anticholinergic agents) are substances that block the action of the neurotransmitter called acetylcholine (ACh) at synapses in the central and peri ...

, *''Piperazine:''

GBR-12935 GBR-12935 is a piperazine derivative which is a potent and selective dopamine reuptake inhibitor. It was originally developed in its 3H radiolabelled form for the purpose of mapping the distribution of dopaminergic neurons in the brain by selec ...

, GBR 12909,

DBL-583 DBL-583 is a selective dopamine reuptake inhibitor of the piperazine chemical class. It is the decanoate ester of a hydroxy vanoxerine. DBL-583 breaks down very slowly in the body, lasting for up to a month after a single injection. See also * ...

*''Tropine:'' benztropine,

deptropine Deptropine (Brontina) also known as dibenzheptropine, is an antihistamine with anticholinergic properties acting at the H1 receptor. It is usually marketed as the citrate Citric acid is an organic compound with the chemical formula HOC(CO2 ...

, etybenzatropine,

difluoropine Difluoropine (O-620) is a stimulant drug synthesised from tropinone, which acts as a potent and selective dopamine reuptake inhibitor. Difluoropine is unique among the tropane-derived dopamine reuptake inhibitors in that the active stereoisomer ...

*''Piperidine:''

diphenylpyraline Diphenylpyraline (DPP; sold as Allergen, Arbid, Belfene, Diafen, Hispril, Histyn, Lergobine, Lyssipol, Mepiben, Neargal) is a first-generation antihistamine with anticholinergic effects of the diphenylpiperidine class. It is marketed in Europe fo ...

*''Phthalane:''

talopram Talopram (Lu 3-010), also known as phthalapromine, is a selective norepinephrine reuptake inhibitor (NRI) which was researched for the management of depression in the 1960s and 1970s but was never commercialized. Along with talsupram, talopram ...

, citalopram *''Octahedral:''

nefopam Nefopam, sold under the brand name Acupan among others, is a centrally acting, non-opioid painkilling medication, that is primarily used to treat moderate to severe pain. Nefopam acts in the brain and spinal cord to relieve pain via novel mecha ...

*''Benzdihydropyran:''

A-68930 A-68930 is a synthetic compound that acts as a selective dopamine receptor D1 agonist. It is orally active and has antidepressant and anorectic effects in animals, producing wakefulness and tachycardia, but without stimulant effects, instead p ...

( isochromene)

Amines

*''Piperazine:''

cyclizine Cyclizine, sold under a number of brand names, is a medication used to treat and prevent nausea, vomiting and dizziness due to motion sickness or vertigo. It may also be used for nausea after general anaesthesia or that which developed from opio ...

, clocinizine, hydroxyzine,

meclozine Meclizine, sold under the brand name Bonine, among others, is an antihistamine used to treat motion sickness and dizziness (vertigo). It is taken by mouth. Effects generally begin in an hour and last for up to a day. Common side effects incl ...

, cetirizine,

dotarizine Dotarizine is a drug used in the treatment of migraine, which acts as a calcium channel blocker, and also as an antagonist at the 5HT2A receptor, and to a lesser extent at the 5HT1A and 5HT2C receptors. The anti-migraine action is thought to ...

cinnarizine Cinnarizine is an antihistamine and calcium channel blocker of the diphenylmethylpiperazine group. It is prescribed for nausea and vomiting due to motion sickness or other sources such as chemotherapy, vertigo, or Ménière's disease. Cinnarizin ...

*'' Benzazepine:''

mianserin Mianserin, sold under the brand name Tolvon among others, is an atypical antidepressant that is used primarily in the treatment of depression in Europe and elsewhere in the world. It is a tetracyclic antidepressant (TeCA). Mianserin is closely ...

*''Tetracyclic:''

dizocilpine Dizocilpine (INN), also known as MK-801, is a pore blocker of the ''N''-Methyl-D-aspartate (NMDA) receptor, a glutamate receptor, discovered by a team at Merck in 1982. Glutamate is the brain's primary excitatory neurotransmitter. The channel is ...

Other

*''Aromatic alkoxy:''

bifemelane Bifemelane (INN) (Alnert, Celeport), or bifemelane hydrochloride (JAN), also known as 4-(''O''-benzylphenoxy)-''N''-methylbutylamine, is an antidepressant and cerebral activator that is widely used in the treatment of cerebral infarction patient ...

phenyltoloxamine Phenyltoloxamine is an antihistamine with sedative and analgesic effects. It is available in combination with other drugs such as paracetamol (acetominophen). Common use Phenyltoloxamine is widely used in preparations as an enhancing agent f ...

*''Keto:'' phenadoxone, methadone, dipipanone, etc. *''Amido:'' dextromoramide *''Imino:''

benzodiazepine Benzodiazepines (BZD, BDZ, BZs), sometimes called "benzos", are a class of depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed to treat conditions such as anxiety disorders, ...

GYKI-52895 GYKI 52895 is a drug which is a 2,3- benzodiazepine derivative that also shares the 3,4-methylenedioxyphenethylamine pharmacophore. Unlike other similar drugs, GYKI 52895 is a selective dopamine reuptake inhibitor (DARI), which appears to have an ...

*''Sulfinyl:''

modafinil Modafinil, sold under the brand name Provigil among others, is a central nervous system (CNS) stimulant medication used to treat sleepiness due to narcolepsy, shift work sleep disorder, and obstructive sleep apnea. While it has seen off-label ...

adrafinil Adrafinil, sold under the brand name Olmifon, is a wakefulness-promoting medication that was formerly used in France to improve alertness, attention, wakefulness, and mood, particularly in the elderly. It was also used off-label by individuals w ...

* Pituxate gem-diphenylcyclopropane

Heteroaromatic

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

Heteroaromatic rings

*''Alkene:'' thiambutene,

loratadine Loratadine, sold under the brand name Claritin among others, is a medication used to treat allergies. This includes allergic rhinitis (hay fever) and hives. It is also available in combination with pseudoephedrine, a decongestant, known as lora ...

*''Alkylamine:''

A-86929 A-86929 is a synthetic compound that acts as a selective dopamine receptor D1 agonist. It was developed as a possible treatment for Parkinson's disease, as well as for other applications such as treatment of cocaine addiction, but while it had r ...

amfonelic acid Amfonelic acid (AFA; WIN 25,978) is a research chemical and dopaminergic stimulant with antibiotic properties. History The stimulant properties of AFA were discovered serendipitously at Sterling-Winthrop in the midst of research on the antibiot ...

Benzenes linked by a non-carbon atom

*''Nitrogen:'' promethazine,

imipramine Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. The drug is also used to treat bedwetting. ...

acepromazine Acepromazine, acetopromazine, or acetylpromazine (commonly known as ACP, Ace, or by the trade names Atravet or Acezine 2, number depending on mg/ml dose) is a phenothiazine derivative antipsychotic drug. It was used in humans during the 1950s as ...

, chlorpromazine, fluphenazine,

mesoridazine Mesoridazine (Serentil) is a piperidine neuroleptic drug belonging to the class of drugs called phenothiazines, used in the treatment of schizophrenia. It is a metabolite of thioridazine. The drug's name is derived from the methylsulfoxy and pipe ...

, levomepromazine,

perazine Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. It is quite similar to chlorpromazine, and acts as a dopamine antagonist. A 2014 systematic review compared it with other antipsychotic drugs: Synthe ...

periciazine Periciazine (INN), also known as pericyazine ( BAN) or propericiazine, is a drug that belongs to the phenothiazine class of typical antipsychotics. Periciazine is not approved for sale in the United States. It is commonly sold in Canada, Italy ...

perphenazine Perphenazine is a typical antipsychotic drug. Chemically, it is classified as a piperazinyl phenothiazine. Originally marketed in the United States as Trilafon, it has been in clinical use for decades. Perphenazine is roughly ten times as poten ...

prochlorperazine Prochlorperazine, formerly sold under the brand name Compazine among others, is a medication used to treat nausea, migraines, schizophrenia, psychosis and anxiety. It is a less preferred medication for anxiety. It may be taken by mouth, rectally ...

sulforidazine Sulforidazine (Imagotan, Psychoson, Inofal) a typical antipsychotic and a metabolite of thioridazine; it and mesoridazine Mesoridazine (Serentil) is a piperidine neuroleptic drug belonging to the class of drugs called phenothiazines, used in t ...

, thioridazine,

trifluoperazine Trifluoperazine, marketed under the brand name Stelazine among others, is a typical antipsychotic primarily used to treat schizophrenia. It may also be used short term in those with generalized anxiety disorder but is less preferred to benzodiaze ...

triflupromazine Triflupromazine (Vesprin) is an antipsychotic medication of the phenothiazine class. Among different effects of triflupromazine indication for use of this drug is severe emesis and severe Hiccups. Due to its potential side effects (triflupromazine ...

, clozapine,

thiethylperazine Thiethylperazine (Torecan, Norzine) is an antiemetic of the phenothiazine class. It is an antagonist of dopamine receptors (DRD1, DRD2, DRD4) as well as of 5-HT2A, 5-HT2C receptors, mAChRs (1 through 5), α1 adrenergic receptor and H1 recepto ...

*''Indolic nitrogen:''

sertindole Sertindole, sold under the brand name Serdolect among others, is an antipsychotic medication. Sertindole was developed by the Danish pharmaceutical company Lundbeck and marketed under license by Abbott Labs. Like other atypical antipsychotics, i ...

*''Oxygen:''

loxapine Loxapine, sold under the brand names Loxitane and Adasuve (''inhalation'' only) among others, is an antipsychotic medication used primarily in the treatment of schizophrenia. The medicine is a member of the dibenzoxazepine class and structural ...

, asenapine, tyrima

Benzene and heterocycle linked through a non-carbon

* Olanzapine

References

External links

* *, a.k.a. called benzhydryl bromide *{{PubChem, 13061, 1-Benzyl-2-bromobenzene, ''not'' called benzhydryl bromide Aromatic compounds