The benzhydryl compounds are a group of organic compounds whose

parent A parent is a caregiver of the offspring in their own species. In humans, a parent is the caretaker of a child (where "child" refers to offspring, not necessarily age). A ''biological parent'' is a person whose gamete resulted in a child, a male ...

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 ...

(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 ato ...

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 Ear ...

), 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 '' ...

s, including

bridges A bridge is a structure built to 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, which is usually somethi ...

. This group typically excludes compounds in which either benzene is fused to another ring (

bicyclic In chemistry, a bicyclic molecule () is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (a ...

tricyclic Tricyclics are chemical compounds that contain three interconnected rings of atoms. Many compounds have a tricyclic structure, but in pharmacology, the term has traditionally been reserved to describe heterocyclic drugs. Among these are anti ...

, polycyclic) or includes a

heteroatom In chemistry, a heteroatom () is, strictly, any atom that is not carbon or hydrogen. Organic chemistry In practice, the term is usually used more specifically to indicate that non-carbon atoms have replaced carbon in the backbone of the molecul ...

, or where the methane connects to three or four benzenes. Benzhydryl radical ball

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 an ...

'' can be abbreviated or Bzh.

Carboaromatic

Alcohols

*''Acyclic:'' pridinol *''Pyrolidino:'' diphenylprolinol *''2-Piperidine:'' pipradrol *''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, T ...

fexofenadine Fexofenadine, sold under the brand name Allegra among others, is an antihistamine pharmaceutical drug used in the treatment of allergy symptoms, such as hay fever and urticaria. Therapeutically, fexofenadine is a selective peripheral H1 block ...

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

Alkenes

*''Tricycle:''

amitriptyline Amitriptyline, sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat cyclic vomiting syndrome (CVS), major depressive disorder and a variety of pain syndromes from neuropathic pain to fibromyalgia ...

, melitracen,

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 mo ...

tianeptine Tianeptine, sold under the brand names Stablon and Coaxil among others, is an atypical antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel ...

amineptine Amineptine, formerly sold under the brand name Survector among others, is an atypical antidepressant of the tricyclic antidepressant (TCA) family. It acts as a selective and mixed dopamine reuptake inhibitor and releasing agent, and to a lesse ...

, clopenthixol,

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 ...

, flupentixol,

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 *''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 Cyproheptadine, sold under the brand name Periactin among others, is a first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties. It was patented in 1959 and came into medical use in 196 ...

*''Acyclic:'' gilutensin

Alkyl(amine)s

*''Acyclic:'' (3-phenylpropylamine),

tolpropamine Tolpropamine is an antihistamine and anticholinergic used as an antipruritic Antipruritics, abirritants, or anti-itch drugs, are medications that inhibit the itching (Latin: ''pruritus'') often associated with sunburns, allergic reactions, ecze ...

, 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 Penfluridol (Semap, Micefal, Longoperidol) is a highly potent, first generation diphenylbutylpiperidine antipsychotic. It was discovered at Janssen Pharmaceutica in 1968. Related to other diphenylbutylpiperidine antipsychotics, pimozide and flu ...

*''N-arylalkyl-piperidine:''

pimozide Pimozide (sold under the brand name Orap) is an antipsychotic drug of the diphenylbutylpiperidine class. It was discovered at Janssen Pharmaceutica in 1963. It has a high potency compared to chlorpromazine (ratio 50-70:1). On a weight basis ...

*''Tetrahydronaphthalene:'' tametraline (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 differ ...

*''Tetrahydroisoquinoline:'' nomifensine,

diclofensine Diclofensine (Ro 8-4650) was developed by Hoffmann-La Roche in the 1970s in the search for a new antidepressant. It was found that the (''S'')-isomer was responsible for activity. Is a stimulant drug which acts as a triple monoamine reuptake inh ...

"tetrahydronaphisoquinoline", dinapsoline (see doxanthrine and dinoxyline) *''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 pyrrolois ...

*''Indanamine:''

Lu 19-005 Indatraline (Lu 19-005) is a non- selective monoamine transporter inhibitor shown to block the reuptake of dopamine, norepinephrine, and serotonin, with effects similar to those of cocaine. The effects have been shown to have a slower onset a ...

*''Tricyclic:''

9-Aminomethyl-9,10-dihydroanthracene AMDA (9-Aminomethyl-9,10-dihydroanthracene) is an organic compound which acts as a potent and selective antagonist for the 5-HT2A receptor. It has been used to help study the shape of the 5-HT2A protein, and develop a large family of related der ...

, phenindamine (see

MPTP MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) is a prodrug to the neurotoxin MPP+, which causes permanent symptoms of Parkinson's disease by destroying dopaminergic neurons in the substantia nigra of the brain. It has been used to study d ...

) *''Tetracyclic:''

maprotiline Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression. It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary ...

, dihydrexidine,

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 antagonist. Chemistry pKa = 7.15 (uncorrected for ionic strength The ioni ...

, ecopipam *''Tetrahydrobenzazepine:''

SKF-83959 SKF-83,959 is a synthetic benzazepine derivative used in scientific research which acts as an agonist at the D1–D2 dopamine receptor heteromer. It behaves as a full agonist at the D1 protomer and a high- affinity partial agonist at the D ...

, SKF-82958,

SKF-81297 SKF-81,297 is a synthetic drug of the benzazepine chemical class that acts as a selective dopamine D1/ D5 receptor full agonist, and produces a characteristic stimulant-like pattern of anorexia, hyperactivity and self-administration in anima ...

SKF 38393 SKF-38,393 is a synthetic compound of the benzazepine chemical class which acts as a selective D1/ D5 receptor partial agonist. It has stimulant Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overa ...

, fenoldopam,

6-Br-APB 6-Br-APB is a synthetic compound that acts as a selective D1 agonist, with the (''R'')-enantiomer being a potent full agonist, while the (''S'') enantiomer retains its D1 selectivity but is a weak partial agonist. (''R'')-6-Br-APB and similar ...

, 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 alt ...

*''Triazaspiro:''

fluspirilene Fluspirilene (Redeptin, Imap, R6218) is a diphenylbutylpiperidine typical antipsychotic drug, used for the treatment of schizophrenia. It is administered intramuscularly. It was discovered at Janssen Pharmaceutica in 1963.C. Janssen, NV Res. La ...

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 v ...

(c.f deramciclane),

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 P ...

, 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 Vanoxerine is a piperazine derivative which is a potent and selective dopamine reuptake inhibitor (DRI). Vanoxerine binds to the target site on the dopamine transporter (DAT) ~ 50 times more strongly than cocaine, but simultaneously inhibits ...

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 Benzatropine (INN), known as benztropine in the United States and Japan, is a medication used to treat movement disorders like parkinsonism and dystonia, as well as extrapyramidal side effects of antipsychotics, including akathisia. It is not us ...

, deptropine,

etybenzatropine Etybenzatropine (INN), also known as ethybenztropine ( USAN, BAN) and tropethydrylin, is an anticholinergic/antihistamine marketed under the trade names Panolid, Ponalid, and Ponalide, which is used as an antiparkinsonian agent. Like its analog ...

, difluoropine *''Piperidine:'' diphenylpyraline *''Phthalane:'' talopram,

citalopram Citalopram, sold under the brand name Celexa among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used to treat major depressive disorder, obsessive compulsive disorder, panic disorder, and soc ...

*''Octahedral:'' nefopam *''Benzdihydropyran:'' A-68930 (

isochromene Benzopyran is a polycyclic organic compound that results from the fusion of a benzene ring to a heterocyclic pyran ring. According to current IUPAC nomenclature, the name chromene used in previous recommendations is retained; however, systemat ...

)

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 Clocinizine is a first-generation antihistamine of the diphenylmethylpiperazine class. It is marketed in Spain in combination with phenylpropanolamine Phenylpropanolamine (PPA) is a sympathomimetic agent which is used as a decongestant a ...

hydroxyzine Hydroxyzine, sold under the brand names Atarax, Vistaril and others, is an antihistamine medication. It is used in the treatment of itchiness, insomnia, anxiety, and nausea, including that due to motion sickness. It is used either by mouth or ...

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 Cetirizine, sold under the brand name Zyrtec among others, is a second-generation antihistamine used to treat allergic rhinitis (hay fever), dermatitis, and urticaria (hives). It is taken by mouth. Effects generally begin within thirty minutes ...

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 *''

Benzazepine Benzazepines are heterocyclic chemical compounds consisting of a benzene ring fused to an azepine ring. Examples include: File:Benazepril structure.svg, Benazepril File:Fenoldopam.svg, Fenoldopam File:GSK-189,254.svg, GSK-189,254 File:Ivabradi ...

:''

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 close ...

*''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, phenyltoloxamine *''Keto:''

phenadoxone Phenadoxone (trade names Heptalgin, Morphidone, and Heptazone) is an opioid analgesic of the open chain class (methadone and relatives) invented in Germany by Hoechst in 1947. It is one of a handful of useful synthetic analgesics which were used ...

methadone Methadone, sold under the brand names Dolophine and Methadose among others, is a synthetic opioid agonist used for chronic pain and also for opioid dependence. It is used to treat chronic pain, and it is also used to treat addiction to hero ...

dipipanone Dipipanone (Pipadone) is a strong opioid analgesic drug, used for acute pain by mouth (PO) for adults - initially 10 mg every 6 hours, then increased if necessary up to 30 mg every 6 hours, with the dose to be increased gradually. It is often use ...

, etc. *''Amido:''

dextromoramide Dextromoramide (Palfium, Palphium, Jetrium, Dimorlin) is a powerful opioid analgesic approximately three times more potent than morphine but shorter acting. It is subject to drug prohibition regimes, both internationally through UN treaties and b ...

*''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 lor ...

*''Alkylamine:'' A-86929, amfonelic acid

Benzenes linked by a non-carbon atom

*''Nitrogen:''

promethazine Promethazine is a first-generation antihistamine, antipsychotic, sedative, and antiemetic used to treat allergies, insomnia, and nausea. It may also help with some symptoms associated with the common cold and may also be used for sedating pe ...

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 Chlorpromazine (CPZ), marketed under the brand names Thorazine and Largactil among others, is an antipsychotic medication. It is primarily used to treat psychotic disorders such as schizophrenia. Other uses include the treatment of bipolar di ...

fluphenazine Fluphenazine, sold under the brand name Prolixin among others, is a high-potency typical antipsychotic medication. It is used in the treatment of chronic psychoses such as schizophrenia, and appears to be about equal in effectiveness to low-pote ...

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 Levomepromazine, also known as methotrimeprazine, is a phenothiazine neuroleptic drug. Brand names include Nozinan, Levoprome, Detenler, Hirnamin, Levotomin and Neurocil. It is a low-potency antipsychotic (approximately half as potent as chlorpr ...

, perazine,

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 an ...

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 pote ...

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 Thioridazine (Mellaril or Melleril) is a first generation antipsychotic drug belonging to the phenothiazine drug group and was previously widely used in the treatment of schizophrenia and psychosis. The branded product was withdrawn worldwid ...

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,

clozapine Clozapine is a psychiatric medication and is the first atypical antipsychotic (also called second-generation antipsychotic). It is primarily used to treat people with schizophrenia and schizoaffective disorders who have had an inadequate resp ...

, thiethylperazine *''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, ...

*''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 structurall ...

asenapine Asenapine, sold under the brand name Saphris among others, is an atypical antipsychotic medication used to treat schizophrenia and acute mania associated with bipolar disorder. It was chemically derived via altering the chemical structure of the ...

tyrima CX157 (proposed trade name TriRima, formerly Tyrima) is a selective and reversible inhibitor of MAO-A (RIMA). As of 2007 it was in phase II clinical trial Clinical trials are prospective biomedical or behavioral research studies on human ...

Benzene and heterocycle linked through a non-carbon

Olanzapine Olanzapine (sold under the trade name Zyprexa among others) is an atypical antipsychotic primarily used to treat schizophrenia and bipolar disorder. For schizophrenia, it can be used for both new-onset disease and long-term maintenance. It is ta ...

References

External links

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