Tricyclic

Tricyclics are cyclic chemical compounds that contain three fused rings of atoms.

Many compounds have a tricyclic structure, but in pharmacology, the term has traditionally been reserved to describe heterocyclic drugs. They include antidepressants, antipsychotics, anticonvulsants, and antihistamines (as antiallergens, anti-motion sickness drugs, antipruritics, and hypnotics/sedatives) of the dibenzazepine, dibenzocycloheptene, dibenzothiazepine, dibenzothiepin, phenothiazine, and thioxanthene chemical classes, and others.

## Contents

* 1 History
* 2 Gallery
* 3 See also
* 4 References

## History

* Promethazine and other first generation antihistamines with a tricyclic structure were discovered in the 1940s.
* Chlorpromazine, derived from promethazine originally as a sedative, was found to have neuroleptic properties in the early 1950s, and was the first typical antipsychotic.
* Imipramine, originally investigated as an antipsychotic, was discovered in the early 1950s, and was the first tricyclic antidepressant.
* Carbamazepine was discovered in 1953, and was subsequently introduced as an anticonvulsant in 1965.
* Clozapine, a derivative of imipramine, was synthesized in 1958 and entered the European market in 1972 under the name Leponex.
* Antidepressants with a tetracyclic structure such as mianserin and maprotiline were first developed in the 1970s as tetracyclic antidepressants.
* Loratadine was introduced as a non-sedating second generation antihistamine in the 1990s.[1]

## Gallery

Antidepressants

Imipramine

Amitriptyline

Iprindole

Tianeptine

Doxepin

Antipsychotics

Chlorpromazine

Thioridazine

Chlorprothixene

Loxapine

Clozapine

Antihistamines

Promethazine

Cyproheptadine

Latrepirdine

Loratadine

Rupatadine

Others

Carbamazepine

Carvedilol

Cyclobenzaprine

Pizotifen

## See also

* Bisulepin
* Tetracyclic
* Tricyclic tropane analogs
* Heterocyclic
* Tricyclic antidepressant

## References

1. ↑ Kay, G. G.; Harris, A. G. (1999). "Loratadine: a non-sedating antihistamine. Review of its effects on cognition, psychomotor performance, mood and sedation". Clinical and Experimental Allergy 29 Suppl 3: 147–150. doi:10.1046/j.1365-2222.1999.0290s3147.x. PMID 10444229.

* v
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* e

Tricyclics

Classes|

* Acridine
* Anthracene
* Dibenzazepine
* Dibenzocycloheptene
* Dibenzodiazepine
* Dibenzothiazepine
* Dibenzothiepin
* Dibenzoxazepine
* Dibenzoxepin
* Phenothiazine
* Pyridazinobenzoxazine
* Pyridinobenzodiazepine
* Thioxanthene

Antidepressants
(TCAs and TeCAs)|

* 7-OH-Amoxapine
* Amezepine
* Amineptine
* Amitriptyline
* Amitriptylinoxide
* Amoxapine
* Aptazapine
* Azepindole
* Azipramine
* Batelapine
* Butriptyline
* Cianopramine
* Ciclazindol
* Ciclopramine
* Cidoxepin
* Clomipramine
* Cotriptyline
* Cyanodothiepin
* Demexiptiline
* Depramine (balipramine)
* Desipramine (desmethylimipramine)
* Desmethylclomipramine
* Desmethyltrimipramine
* Dibenzepin
* Dimetacrine
* Dosulepin (dothiepin)
* Doxepin
* Enprazepine
* Esmirtazapine
* Fantridone
* Fluotracen
* Hepzidine
* Homopipramol
* Imipramine
* Imipraminoxide
* Intriptyline
* Iprindole
* Ketipramine
* Litracen
* Lofepramine
* Losindole
* Loxapine
* Maprotiline
* Mariptiline
* Mazindol
* Melitracen
* Metapramine
* Mezepine
* Mianserin
* Mirtazapine
* Monometacrine
* Naranol
* Nitroxazepine
* Norbutriptyline
* Nordoxepin
* Northiaden (nordosulepin)
* Nortriptyline (noramitriptyline)
* Noxiptiline
* Octriptyline
* Opipramol
* Oxaprotiline
* Pipofezine
* Pirandamine
* Propizepine
* Protriptyline
* Quinupramine
* Setiptiline (teciptiline)
* Spiroxepin
* Tandamine
* Tampramine
* Tianeptine
* Tienopramine
* Trimipramine

Antihistamines|

* Azatadine
* Bisulepin
* Clobenzepam
* Cyproheptadine
* Dacemazine
* Deptropine
* Desloratadine
* Epinastine
* Etymemazine
* Fenethazine
* Hydroxyethylpromethazine
* Isopromethazine
* Isothipendyl
* Ketotifen
* Latrepirdine
* Loratadine
* Mebhydrolin
* Mequitazine
* Methdilazine
* Olopatadine
* Oxomemazine
* Phenindamine
* Pimethixene
* Promethazine
* Propiomazine
* Rupatadine
* Thiazinamium

Antipsychotics|

* Acetophenazine
* Alimemazine
* Amoxapine
* Asenapine
* Butaclamol
* Butaperazine
* Carfenazine (carphenazine)
* Carpipramine
* Chlorpromazine
* Chlorprothixene
* Ciclindole
* Citatepine
* Clocapramine
* Clomacran
* Clorotepine
* Clotiapine
* Clozapine
* Cyanothepin
* Doclothepin
* Docloxythepin
* Erizepine
* Flucindole
* Flumezapine
* Fluotracen
* Flupentixol
* Fluphenazine
* Gevotroline
* Homopipramol
* Isofloxythepin
* Levomepromazine/Methotrimeprazine
* Loxapine
* Lurasidone
* Maroxepin
* Meperathiepin
* Mesoridazine
* Metiapine
* Metitepine
* Metoxepin
* Mosapramine
* Naranol
* Octomethothepin
* Olanzapine
* Oxyclothepin
* Oxyprothepin
* Pentiapine
* Peradithiepin
* Perathiepin
* Perazine
* Perphenazine
* Periciazine
* Pinoxepin
* Piperacetazine
* Pipotiazine
* Piquindone
* Prochlorperazine
* Promazine
* Prothipendyl
* Quetiapine
* Savoxepin/Cipazoxapine
* Sulforidazine
* Tenilapine
* Thiethylperazine
* Thiopropazate
* Thioridazine
* Thiothixene
* Tilozepine
* Traboxopine
* Trifluoperazine
* Triflupromazine
* Trifluthepin
* Zotepine
* Zuclopenthixol

Anticonvulsants|

* Carbamazepine
* Dizocilpine
* Eslicarbazepine
* Eslicarbazepine acetate
* Etazepine
* Licarbazepine
* Oxcarbazepine
* Oxitriptyline
* Rispenzepine

Others|

* Adosopine
* Aminopromazine
* Atiprosin
* Beloxepin
* Benzoctamine
* Carvedilol
* Cidoxepin
* Cyclobenzaprine
* Damotepine
* Darenzepine
* Elanzepine
* Fluradoline
* Methylene blue
* Monatepil
* Nuvenzepine
* Oxetorone
* Perlapine
* P7C3
* Pinadoline
* Pirenzepine
* Pirolate
* Pitrazepin
* Pizotifen
* Profenamine
* Serazapine
* Siltenzepine
* Telenzepine
* Tipindole
* Tropatepine
* Zolenzepine

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* t
* e

Chemical classes of psychoactive drugs

Stimulants|

* Amphetamine-type/dopamine releasing agents: Alkylamines
* Cycloalkylaminopropanes
* Arylpiperazines
* Benzylpiperazines
* Phenylpiperazines
* Phenethylamines
* Aminorexes/phenyloxazolamines
* Amphetamines/α-methylphenethylamines
* Cathinones/β-ketoamphetamines
* β-Hydroxyamphetamines/cathinols
* Naphthylaminopropanes
* Phentermines
* Phenylisobutylamines/α-ethylphenethylamines
* α-Propylphenethylamines
* Phenylmorpholines/phenmetrazines
* Thiopropamines/thienylaminopropanes

* Cocaine-type/typical dopamine reuptake inhibitors: Phenethylamines
* Phenidates/benzylpiperidines
* Phenylethylpyrrolidines
* Pyrrolidinophenones
* Phenyltropanes/cocaine analogues

* Modafinil-type/atypical dopamine reuptake inhibitors: Modafinil analogues
* Phenylpiracetams

* Caffeine-type/adenosine receptor antagonists: Xanthines/methylxanthines

* Nicotine-type/nicotinic acetylcholine receptor agonists: Nicotine analogues

Depressants|

* GABAA receptor positive allosteric modulators: Alcohols/ethanol analogues
* Barbiturates
* Benzodiazepines
* Pyrrolobenzodiazepines
* Thienobenzodiazepines
* Thienodiazepines
* Thienotriazolodiazepines
* Triazolobenzodiazepines
* Carbamates
* Ethers
* Neuroactive steroids
* Nonbenzodiazepines
* β-Carbolines
* Cyclopyrrolones
* Imidazopyridines
* Pyrazolopyrimidines
* Phenols
* Piperidinediones
* Quinazolinones

* GABAA receptor agonists: Isoxazoles

* GHB receptor agonists: 1,4-Butanediols

* α2δ subunit-containing voltage-gated calcium channel blockers: Gabapentinoids

* Opioids/μ-opioid receptor agonists: Benzimidazoles
* Nitazenes
* Fentanyl analogues/phenylpiperidines
* Mitragyna alkaloids
* Morphinans/phenanthrenes
* Opiates/opium alkaloids
* Utopioids

* Antihistamines/H1 receptor antagonists: Benzimidazoles
* Diarylmethanes
* Ethylenediamines
* Tricyclics
* Dibenzocycloheptenes

Hallucinogens|

* Serotonergic psychedelics/serotonin 5-HT2A receptor agonists: Arylpiperazines
* Phenylpiperazines
* Quinolinylpiperazines
* Cyclized phenethylamines
* 3-Benzazepines
* Cyclized tryptamines
* Azepinoindoles
* Ibogalogs
* Iboga alkaloids
* β-Carbolines
* Harmala alkaloids
* Ergolines
* Lysergamides
* Simplified/partial lysergamides
* Phenethylamines (methoxyphenethylamines)
* 2Cs
* 25-NB/NBOMes
* 2C-Os
* 2C-Ts
* HOT-x
* TWEETIOs
* Amphetamines/α-methylphenethylamines
* 3Cs
* Dimethoxyamphetamines/DMAs
* DOx
* Alephs
* Ethylenedioxyamphetamines/EDxx
* Methylenedioxyamphetamines/MDxx
* Trimethoxyamphetamines/TMAs
* BOx
* FLYs/benzofurans
* Phenylisobutylamines/α-ethylphenethylamines
* 4Cs
* Scalines
* Ψ-PEAs
* Tryptamines
* α-Alkyltryptamines
* α-Alkyl-β-ketotryptamines
* 4-Hydroxytryptamines
* 5-Hydroxytryptamines
* 5-Methoxytryptamines
* Miscellaneous

* Dissociatives/NMDA receptor antagonists: Adamantanes
* Arylcyclohexylamines
* Diarylethylamines
* Morphinans

* κ-Opioid receptor agonists: Benzomorphans
* Salvinorins

* GABAA receptor agonists: Isoxazoles

* Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists: Diarylmethanes
* Tropanes

* Others: Cyclized tryptamines
* Azepinoindoles
* Iboga alkaloids
* (Phyto)cannabinoids

Entactogens|

* Serotonin releasing agents: Phenethylamines
* 2-Aminoindanes
* 2-Aminotetralins
* Amphetamines
* Benzofuranylaminopropanes
* Benzothiophenylaminopropanes
* Ethylenedioxyamphetamines/EDxx
* Indanylaminopropanes
* Indolylaminopropanes
* Methylenedioxyamphetamines/MDxx
* Tetralinylaminopropanes
* Tryptamines
* α-Alkyltryptamines
* Miscellaneous

Psychiatric drugs|

* Anxiolytics: Azapirones
* Benzodiazepines
* Pyrrolobenzodiazepines
* Thienobenzodiazepines
* Thienodiazepines
* Thienotriazolodiazepines
* Triazolobenzodiazepines

* Antidepressants: Tricyclic antidepressants
* Dibenzazepines
* Dibenzocycloheptenes
* Dibenzothiepins
* Dibenzoxazepines
* Dibenzoxepins
* Tetracyclic antidepressants

* Antipsychotics/dopamine D2 receptor antagonists or partial agonists: Benzamides
* Benzimidazoles
* Benzisothiazoles
* Benzisoxazoles
* Butyrophenones
* Diphenylbutylpiperidines
* Phenylpiperazines
* Tricyclics
* Dibenzazepines
* Dibenzodiazepines
* Dibenzothiazepines
* Dibenzothiepins
* Dibenzoxazepines
* Phenothiazines
* Thienobenzodiazepines

* Mood stabilizers/anticonvulsants: Gabapentinoids
* Tricyclics
* Dibenzazepines
* Valproates

Others|

* Nootropics: Racetams
* Phenylpiracetams

* Miscellaneous: 3-Benzazepines
* Adamantanes
* Catecholamines
* Tetrahydroisoquinolines
* Yohimbans

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