Imipramine

From Wikipedia, the free encyclopedia

Imipramine

Systematic (IUPAC) name

3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine
Clinical data

Trade names

Tofranil

AHFS/Drugs.com

monograph

MedlinePlus

a682389

Pregnancy cat.

D(US)
Known risk of damage to fetus.

Legal status

℞ Prescription only

Routes

Oral

Pharmacokinetic data

Bioavailability

?
Metabolism

Hepatic

Main active metabolite desipramine

Half-life

11-25 hours

Excretion

Renal

Identifiers

CAS number
50-49-7

ATC code

N06AA02

PubChem

CID 3696

DrugBank

APRD00672

ChemSpider
3568

UNII

OGG85SX4E4

KEGG

D08070

ChEBI

CHEBI:47499

ChEMBL

CHEMBL11
Chemical data

Formula

C19H24N2

Mol. mass

280.407 g/mol

SMILES

eMolecules & PubChem

InChI[show]

(what is this?) (verify)

Imipramine (sold as Antideprin, Deprimin, Deprinol, Depsol, Depsonil, Dynaprin, Eupramin, Imipramil,
Irmin, Janimine, Melipramin, Surplix, Tofranil), also known as melipramine, is an antidepressant
medication, a tricyclic antidepressant of the dibenzazepine group. Imipramine is mainly used in the
treatment of major depression and enuresis (inability to control urination).

It has also been evaluated for use in panic disorder.[1]

Contents

[hide] 1 Therapeutic uses

2 History

3 Mechanism of action

4 Comparison with other antidepressants

5 Metabolism

6 Side effects

7 Dosage

8 Overdose

9 See also

10 References

11 External links

[edit] Therapeutic uses

Imipramine is used in the treatment of depression, such as depression associated with agitation or
anxiety and has similar efficacy to the antidepressant drug moclobemide.[2]

[edit] History

Imipramine was, in the late 1950s, the first tricyclic antidepressant to be developed (by Ciba). It was first
tried against psychotic disorders, such as schizophrenia, but proved insufficient. As an antidepressant, it
did well in clinical studies and it is known to work well in even the most severe cases of depression.[3] It
is not surprising, therefore, that Imipramine is also known to cause a high rate of manic and hypomanic
reactions, especially in patients with preexisting bipolar disorder. It is estimated that up to 25% of such
patients maintained on Imipramine will switch into mania or hypomania.[4] Such powerful
antidepressant properties have made it favorable in the treatment of treatment-resistant depression.

At the advent of SSRIs, its sometimes intolerable side-effect profile became more tolerable. Therefore, it
became extensively used as a standard antidepressant and later served as a prototypical drug for the
development of the later-released tricyclics. It is not as commonly used today, but is sometimes used to
treat major depression as a second-line treatment. It has also seen limited use in the treatment of
migraines, ADHD, and post concussive syndrome. Imipramine has additional indications for the
treatment of panic attacks, chronic pain, and Kleine-Levin syndrome. In pediatric patients, it is relatively
frequently used to treat pavor nocturnus and nocturnal enuresis.

[edit] Mechanism of action

Imipramine, a tertiary amine, affects numerous neurotransmitter systems known to be involved in the
etiology of depression, anxiety , ADHD, enuresis and numerous other mental and physical conditions.
Imipramine is similar in structure to some muscle relaxants, and has a significant analgesic effect and,
thus, is very useful in some pain conditions.

The mechanisms of Imipramine's medicinal action include, but are not limited to, effects on:

Serotonin (5-HT): Moderate to strong reuptake inhibition. Imipramine's serotonin reuptake inhibition is
almost comparable but still less than its reuptake inhibition of norepinephrine. When compared to other
tricyclic antidepressants (with the exception of Clomipramine) Imipramine's strong serotonin reuptake
inhibition make it more akin to the SSRI class of antidepressants than its metabolite Desipramine, which
has almost purely noradrenergic effects.

Norepinephrine (NE): Strong reuptake inhibition.

Dopamine (DA): Reuptake and release at D1 and D2 receptors. Similar but less potent than
psychostimulants, dopamine agonists, and the atypical antidepressant buproprion on dopaminergic
mechanisms (increase in release and blockade of reuptake inhibition). While this effect is much less than
the primary effects on NE, SER and ACh, it is nonetheless significant and is partially responsible for the
therapeutic benefits of treatment with Imipramine. Enhancement of brain dopamine activity has been
implicated in Imipramine's ability to stimulate motor activity and prolong time spent in escape in mice.
Regarding dopamine uptake, imipramine is far less potent than most other antidepressants (for
example, it has only 5% of the potency of amitryptiline or paroxetine, see the table below).[citation
needed]

Acetylcholine (ACh): Imipramine is an anticholinergic. Thus, it is prescribed with caution to the elderly
and with extreme caution to those with psychosis, as the general brain activity enhancement in
combination with the "dementing" effects of anticholinergics increases the potential of Imipramine to
cause hallucinations, confusion and delirium in this population. Imipramine is an antagonist at M2
muscarinic acetylcholine receptors (see external links). The blockade of cholinergic (muscarine)
receptors is known to cause euphoria, potentially contributing to the mood lifting effects of Imipramine
as well. Antimuscarinic effect is also responsible for rapid heart rate (tachycardia).

Epinephrine: Imipramine antagonizes adreno-receptors (II), thus sometimes causing increased heart
rate (contributed to by other effects as well), orthostatic hypotension, and a general decrease in the
responsiveness of the central nervous system (hence, a contribution to its potent anti-anxiety
properties).

σ receptor and Enkephalinase: Activity on σ receptors is present, but it is very low (Ki of 520 nM on σ
receptors, see references) and it is about half the power of amitryptiline (300 nM).

Histamine: Imipramine is an antagonist at histamine H1 receptors. This contributes to the acute

sedative effect that it has in most people. In turn, its anti-histaminergic and general calming effects take
place immediately, and, thus, Imipramine is sometimes prescribed as a sleep aid in low doses.

BDNF: BDNF is implicated in neurogenesis in the hippocampus, and studies suggest that depressed
patients have decreased levels of BDNF and reduced hippocampal neurogenesis. It is not clear how
neurogenesis restores mood, as ablation of hippocampal neurogenesis in murine models do not show
anxiety related or depression related behaviours. Chronic Imipramine administration results in increased
histone acetylation (which is associated with transcriptional activation and decondensed chromatin) at
the hippocampal BDNF promotor, and also reduced expression of hippocampal HDAC5.[5][6]

μ receptor: Imipramine has been shown to increase the expression of μ-opioid receptors in rat
forebrain.[7]

[edit] Comparison with other antidepressants

The potency (affinity) of imipramine and other antidepressant on various transporters and receptors are
summarized below. Data are from "Pharmacology of antidepressant", Mayo Clin Proc, May 2001, Vol 76.
[8]

Potency (affinity) data are expressed as the inverse of equilibrium dissociation constant multiplied by a
factor of 10−7. So, the higher the number, the higher the blocking power.

Drug
SERT

NET

DAT

α1 blockade

D2 blockade

H1 blockade

muscarinic blockade

5HT2 blockade

imipramine

70

2.7
0.012

1.5

0.05

9.1

1.1

1.2

desipramine (also an imipramine metabolite)

5.7

128

0.024

0.77
0.03

0.91

0.5

0.38

amitriptyline

23

2.9

0.023

3.7

0.1

91

5.6
3.4

clomipramine

360

2.7

0.045

2.6

0.53

3.2

2.7

3.7
paroxetine

800

2.5

0.2

0.025

0.003

0.03

0.93

0.005

citalopram

98

0.035
0.0038

0.053

0.21

0.045

0.34

[edit] Metabolism

Imipramine is converted to desipramine, another TCA, in the body.

[edit] Side effects

Those listed in Italic text below denote common side effects. Those listed in bold text denote life-
threatening side effects.[9]

Central Nervous System: Dizziness, drowsiness, confusion, seizures, headache, anxiety, tremors,
stimulation, weakness, insomnia, nightmares, Extrapyramidal symptoms in geriatric patients, increased
psychiatric symptoms, paresthesia
Cardiovascular: Orthostatic hypotension, EKG changes, tachycardia, hypertension, palpitations,
dysrhythmias

Eyes, Ears, Nose and Throat: Blurred vision, tinnitus, mydriasis

Gastrointestinal: Diarrhea, Dry mouth, nausea, vomiting, paralytic ileus, increased appetite, cramps,
epigastric distress, jaundice, hepatitis, stomatitis, constipation, taste change

Genitourinary: Urinary retention, acute renal failure

Hematological: Agranulocytosis, thrombocytopenia, eosinophilia, leukopenia

Skin: Rash, urticaria, sweating, pruritus, photosensitivity

[edit] Dosage

Hospitalized patients: starting with 3 times 25 mg, increasing to 125 mg. Up to 300 mg may be given in
resistant cases. After remission dose is often reduced to 50 to 100 mg daily.

Ambulatory patients: starting with 25 to 75 mg daily, increasing up to a maximum of 200 mg daily, after
remission dose is often reduced to 50–100 mg daily.

Pediatric patients: starting with 10 mg daily the dose is adjusted according to the severity of the
symptoms to be treated, the side-effects encountered and the weight of the patient.

[edit] Overdose

Main article: Tricyclic antidepressant overdose

The symptoms and the treatment of an imipramine overdose are largely the same as for the other
tricyclic antidepressants. Cardinal symptoms are cardiac (tachycardia, widened QRS complex) and
neurological disturbances. Any ingestion by children should be considered as serious and potentially
fatal.

Antidepressants (N06A)
[hide]

Specific reuptake inhibitors (RIs), enhancers (REs), and releasing agents (RAs)

Selective serotonin reuptake inhibitors (SSRIs)

Alaproclate • Citalopram • Escitalopram • Femoxetine • Fluoxetine# • Fluvoxamine • Indalpine •
Ifoxetine • Litoxetine • Lubazodone • Panuramine • Paroxetine • Pirandamine • Seproxetine •
Sertraline# • Zimelidine‡

Serotonin–norepinephrine reuptake inhibitors (SNRIs)

Bicifadine • Clovoxamine • Desvenlafaxine • Duloxetine • Levomilnacipran • Eclanamine • Milnacipran •

Sibutramine • Venlafaxine

Serotonin–norepinephrine–dopamine reuptake inhibitors (SNDRIs)

Brasofensine • BTS-74,398 • Cocaine • Diclofensine • DOV-21,947 • DOV-102,677 • DOV-216,303 • EXP-
561 • Fezolamine • JNJ-7925476 • NS-2359 • PRC200-SS • Pridefine • SEP-225,289 • SEP-227,162 •
Tesofensine

Norepinephrine reuptake inhibitors (NRIs)

Amedalin • Atomoxetine/Tomoxetine • Binedaline • Ciclazindol • Daledalin • Esreboxetine •

Lortalamine • Mazindol • Nisoxetine • Reboxetine • Talopram • Talsupram • Tandamine • Viloxazine

Dopamine reuptake inhibitors (DRIs)

Medifoxamine • Vanoxerine
Norepinephrine-dopamine reuptake inhibitors (NDRIs)

Amineptine • Bupropion/Amfebutamone# • Cilobamine • Manifaxine • Methylphenidate • Nomifensine

• Radafaxine • Tametraline

Norepinephrine-dopamine releasing agents (NDRAs)

Amphetamine • Befuraline • Lisdexamfetamine • Methamphetamine • Phenethylamine • Piberaline •

Tranylcypromine
Serotonin-norepinephrine-dopamine releasing agents (SNDRAs)

4-Methyl-αMT • αET/Etryptamine • αMT/Metryptamine

Selective serotonin reuptake enhancers (SSREs)

Tianeptine
Others

Indeloxazine • Teniloxazine • Tramadol • Viqualine

[hide]

Receptor antagonists and/or reuptake inhibitors

Serotonin antagonists and reuptake inhibitors (SARIs)

Etoperidone • Nefazodone • Trazodone

Noradrenergic and specific serotonergic antidepressants (NaSSAs)

Aptazapine • Esmirtazapine • Mianserin • Mirtazapine • Setiptiline/Teciptiline

Norepinephrine-dopamine disinhibitors (NDDIs)

Agomelatine

Serotonin modulators and stimulators (SMSs)

Vortioxetine

Others
Tedatioxetine • Vilazodone

[hide]

Heterocyclic antidepressants (bi-, tri-, and tetracyclics)

Bicyclics

Tiazesim

Tricyclics

Amezepine • Amineptine • Amitriptyline# • Amitriptylinoxide • Azepindole • Butriptyline •

Cianopramine • Clomipramine • Cotriptyline • Cyanodothiepin • Demexiptiline •
Depramine/Balipramine • Desipramine • Dibenzepin • Dimetacrine • Dosulepin/Dothiepin • Doxepin •
Enprazepine • Fluotracen • Hepzidine • Homopipramol • Imipramine • Imipraminoxide • Intriptyline •
Iprindole • Ketipramine • Litracen • Lofepramine • Losindole • Mariptiline • Melitracen • Metapramine
• Mezepine • Naranol • Nitroxazepine • Nortriptyline • Noxiptiline • Octriptyline • Opipramol •
Pipofezine • Propizepine • Protriptyline • Quinupramine • Tampramine • Tianeptine • Tienopramine •
Trimipramine;
Tetracyclics

Amoxapine • Aptazapine • Azipramine • Ciclazindol • Ciclopramine • Esmirtazapine • Maprotiline •

Mazindol • Mianserin • Mirtazapine • Oxaprotiline • Setiptiline/Teciptiline

[hide]

Monoamine oxidase inhibitors (MAOIs)

Nonselective

Irreversible: Benmoxin • Echinopsidine • Iproclozide • Iproniazid • Isocarboxazid • Mebanazine •

Metfendrazine • Nialamide • Octamoxin • Phenelzine • Pheniprazine • Phenoxypropazine •
Pivalylbenzhydrazine • Safrazine • Tranylcypromine; Reversible: Caroxazone • Paraxazone;• Quercetin;

MAOA-Selective

Irreversible: Clorgiline; Reversible: Amiflamine • Bazinaprine • Befloxatone • Befol • Berberine •

Brofaromine • Cimoxatone • Esuprone • Harmala Alkaloids (Harmine, Harmaline, Tetrahydroharmine,
Harman, Norharman, etc) • Methylene Blue • Metralindole • Minaprine • Moclobemide • Pirlindole •
Sercloremine • Tetrindole • Toloxatone • Tyrima;

MAOB-Selective

Irreversible: Ladostigil • Mofegiline • Pargyline • Rasagiline • Selegiline; Reversible: Lazabemide •

Milacemide
[hide]

Azapirones and other 5-HT1A receptor agonists

Alnespirone • Aripiprazole • Befiradol • Buspirone • Eptapirone • Flesinoxan • Flibanserin • Gepirone •

Ipsapirone • Oxaflozane • Tandospirone • Vilazodone • Zalospirone

#WHO-EM. ‡Withdrawn from market. Clinical trials: †Phase III. §Never to phase III
M: PSO/PSI

mepr

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc(eval/thrp), drug(N5A/5B/5C/6A/6B/6D)
[hide]

v·

d·

Anxiolytics (N05B)

GABAA PAMs
Benzodiazepine

Adinazolam • Alprazolam • Bretazenil • Bromazepam • Camazepam • Chlordiazepoxide • Clobazam •

Clonazepam • Clorazepate • Clotiazepam • Cloxazolam • Diazepam • Ethyl Loflazepate • Etizolam •
Fludiazepam • Halazepam • Imidazenil • Ketazolam • Lorazepam • Medazepam • Nordazepam •
Oxazepam • Pinazepam • Prazepam

Carbamates

Emylcamate • Mebutamate • Meprobamate (Carisoprodol, Tybamate) • Phenprobamate • Procymate

Nonbenzodiazepines
Abecarnil • Adipiplon • Alpidem • CGS-8216 • CGS-9896 • CGS-13767 • CGS-20625 • Divaplon • ELB-139
• Fasiplon • GBLD-345 • Gedocarnil • L-838,417 • NS-2664 • NS-2710 • Ocinaplon • Pagoclone •
Panadiplon • Pipequaline • RWJ-51204 • SB-205,384 • SL-651,498 • Taniplon • TP-003 • TP-13 • TPA-
023 • Y-23684 • ZK-93423

Pyrazolopyridines

Cartazolate • Etazolate • ICI-190,622 • Tracazolate

Others
Chlormezanone • Ethanol (Alcohol) • Etifoxine • Kavalactones (Kava Kava) • Skullcap • Valerenic Acid
(Valerian)

α2δ VDCC Blockers

Gabapentin • Pregabalin

5-HT1A Agonists

Azapirones: Buspirone • Gepirone • Tandospirone; Others: Flesinoxan • Oxaflozane

H1 Antagonists

Diphenylmethanes: Captodiame • Hydroxyzine; Others: Brompheniramine • Chlorpheniramine •

Pheniramine

CRH1 Antagonists

Antalarmin • CP-154,526 • Pexacerfont • Pivagabine

NK2 Antagonists
GR-159,897 • Saredutant

MCH1 antagonists

ATC-0175 • SNAP-94847

mGluR2/3 Agonists

Eglumegad
mGluR5 NAMs

Fenobam

TSPO agonists

DAA-1097 • DAA-1106 • Emapunil • FGIN-127 • FGIN-143

σ1 agonists
Afobazole • Opipramol

Others

Benzoctamine • Carbetocin • Demoxytocin • Mephenoxalone • Mepiprazole • Oxanamide • Oxytocin •

Promoxolane • Tofisopam • Trimetozine • WAY-267,464

#WHO-EM. ‡Withdrawn from market. Clinical trials: †Phase III. §Never to phase III
M: PSO/PSI

mepr

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc(eval/thrp), drug(N5A/5B/5C/6A/6B/6D)
[hide]

v·

d·

Adrenergics

[hide]

Receptor ligands
α1

Agonists: 5-FNE • 6-FNE • Amidephrine • Anisodamine • Anisodine • Cirazoline • Dipivefrine •

Dopamine • Ephedrine • Epinephrine (Adrenaline) • Etilefrine • Ethylnorepinephrine • Indanidine •
Levonordefrin • Metaraminol • Methoxamine • Methyldopa • Midodrine • Naphazoline •
Norepinephrine (Noradrenaline) • Octopamine • Oxymetazoline • Phenylephrine •
Phenylpropanolamine • Pseudoephedrine • Synephrine • Tetrahydrozoline

Antagonists: Abanoquil • Adimolol • Ajmalicine • Alfuzosin • Amosulalol • Arotinolol • Atiprosin •

Benoxathian • Buflomedil • Bunazosin • Carvedilol • CI-926 • Corynanthine • Dapiprazole • DL-017 •
Domesticine • Doxazosin • Eugenodilol • Fenspiride • GYKI-12,743 • GYKI-16,084 • Indoramin •
Ketanserin • L-765,314 • Labetalol • Mephendioxan • Metazosin • Monatepil • Moxisylyte
(Thymoxamine) • Naftopidil • Nantenine • Neldazosin • Nicergoline • Niguldipine • Pelanserin •
Phendioxan • Phenoxybenzamine • Phentolamine • Piperoxan • Prazosin • Quinazosin • Ritanserin • RS-
97,078 • SGB-1,534 • Silodosin • SL-89.0591 • Spiperone • Talipexole • Tamsulosin • Terazosin •
Tibalosin • Tiodazosin • Tipentosin • Tolazoline • Trimazosin • Upidosin • Urapidil • Zolertine

* Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone,
trazodone, nefazodone, etoperidone, and mepiprazole all antagonize α1-adrenergic receptors as well,
which contributes to their side effects such as orthostatic hypotension.
α2

Agonists: (R)-3-Nitrobiphenyline • 4-NEMD • 6-FNE • Amitraz • Apraclonidine • Brimonidine •

Cannabivarin • Clonidine • Detomidine • Dexmedetomidine • Dihydroergotamine • Dipivefrine •
Dopamine • Ephedrine • Ergotamine • Epinephrine (Adrenaline) • Esproquin • Etilefrine •
Ethylnorepinephrine • Guanabenz • Guanfacine • Guanoxabenz • Levonordefrin • Lofexidine •
Medetomidine • Methyldopa • Mivazerol • Naphazoline • Norepinephrine (Noradrenaline) •
Phenylpropanolamine • Piperoxan • Pseudoephedrine • Rilmenidine • Romifidine • Talipexole •
Tetrahydrozoline • Tizanidine • Tolonidine • Urapidil • Xylazine • Xylometazoline

Antagonists: 1-PP • Adimolol • Aptazapine • Atipamezole • BRL-44408 • Buflomedil • Cirazoline •

Efaroxan • Esmirtazapine • Fenmetozole • Fluparoxan • GYKI-12,743 • GYKI-16,084 • Idazoxan •
Mianserin • Mirtazapine • MK-912 • NAN-190 • Olanzapine • Phentolamine • Phenoxybenzamine •
Piperoxan • Piribedil • Rauwolscine • Rotigotine • SB-269,970 • Setiptiline • Spiroxatrine • Sunepitron •
Tolazoline • Yohimbine

* Note that many atypical antipsychotics and azapirones like buspirone and gepirone (via metabolite 1-
PP) antagonize α2-adrenergic receptors as well.

Agonists: 2-FNE • 5-FNE • Amibegron • Arbutamine • Arformoterol • Arotinolol • BAAM • Bambuterol •

Befunolol • Bitolterol • Broxaterol • Buphenine • Carbuterol • Cimaterol • Clenbuterol • Denopamine •
Deterenol • Dipivefrine • Dobutamine • Dopamine • Dopexamine • Ephedrine • Epinephrine
(Adrenaline) • Etafedrine • Etilefrine • Ethylnorepinephrine • Fenoterol • Formoterol • Hexoprenaline •
Higenamine • Indacaterol • Isoetarine • Isoprenaline (Isoproterenol) • Isoxsuprine • Labetalol •
Levonordefrin • Levosalbutamol • Mabuterol • Methoxyphenamine • Methyldopa • N-
Isopropyloctopamine • Norepinephrine (Noradrenaline) • Orciprenaline • Oxyfedrine •
Phenylpropanolamine • Pirbuterol • Prenalterol • Ractopamine • Procaterol • Pseudoephedrine •
Reproterol • Rimiterol • Ritodrine • Salbutamol (Albuterol) • Salmeterol • Solabegron • Terbutaline •
Tretoquinol • Tulobuterol • Xamoterol • Zilpaterol • Zinterol

Antagonists: Acebutolol • Adaprolol • Adimolol • Afurolol • Alprenolol • Alprenoxime • Amosulalol •

Ancarolol • Arnolol • Arotinolol • Atenolol • Befunolol • Betaxolol • Bevantolol • Bisoprolol • Bopindolol
• Bormetolol • Bornaprolol • Brefonalol • Bucindolol • Bucumolol • Bufetolol • Buftiralol • Bufuralol •
Bunitrolol • Bunolol • Bupranolol • Burocrolol • Butaxamine • Butidrine • Butofilolol • Capsinolol •
Carazolol • Carpindolol • Carteolol • Carvedilol • Celiprolol • Cetamolol • Cicloprolol • Cinamolol •
Cloranolol • Cyanopindolol • Dalbraminol • Dexpropranolol • Diacetolol • Dichloroisoprenaline •
Dihydroalprenolol • Dilevalol • Diprafenone • Draquinolol • Dropranolol • Ecastolol • Epanolol • Ericolol
• Ersentilide • Esatenolol • Esmolol • Esprolol • Eugenodilol • Exaprolol • Falintolol • Flestolol •
Flusoxolol • Hydroxycarteolol • Hydroxytertatolol • ICI-118,551 • Idropranolol • Indenolol • Indopanolol
• Iodocyanopindolol • Iprocrolol • Isoxaprolol • Isamoltane • Labetalol • Landiolol • Levobetaxolol •
Levobunolol • Levocicloprolol • Levomoprolol • Medroxalol • Mepindolol • Metalol • Metipranolol •
Metoprolol • Moprolol • Nadolol • Nadoxolol • Nafetolol • Nebivolol • Neraminol • Nifenalol •
Nipradilol • Oberadilol • Oxprenolol • Pacrinolol • Pafenolol • Pamatolol • Pargolol • Parodilol •
Penbutolol • Penirolol • PhQA-33 • Pindolol • Pirepolol • Practolol • Primidolol • Procinolol •
Pronethalol • Propafenone • Propranolol • Ridazolol • Ronactolol • Soquinolol • Sotalol • Spirendolol •
SR 59230A • Sulfinalol • TA-2005 • Talinolol • Tazolol • Teoprolol • Tertatolol • Terthianolol • Tienoxolol
• Tilisolol • Timolol • Tiprenolol • Tolamolol • Toliprolol • Tribendilol • Trigevolol • Xibenolol •
Xipranolol
[hide]

Reuptake inhibitors

NET

Selective norepinephrine reuptake inhibitors: Amedalin • Atomoxetine (Tomoxetine) • Ciclazindol •

Daledalin • Esreboxetine • Lortalamine • Mazindol • Nisoxetine • Reboxetine • Talopram • Talsupram •
Tandamine • Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine • Bupropion
(Amfebutamone) • Fencamine • Fencamfamine • Lefetamine • Levophacetoperane • LR-5182 •
Manifaxine • Methylphenidate • Nomifensine • O-2172 • Radafaxine; Serotonin-norepinephrine
reuptake inhibitors: Bicifadine • Desvenlafaxine • Duloxetine • Eclanamine • Levomilnacipran •
Milnacipran • Sibutramine • Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors:
Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303 • JNJ-7925476 • JZ-IV-10 •
Methylnaphthidate • Naphyrone • NS-2359 • PRC200-SS • SEP-225,289 • SEP-227,162 • Tesofensine;
Tricyclic antidepressants: Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine •
Dosulepin • Doxepin • Imipramine • Lofepramine • melitracen • Nortriptyline • Protriptyline •
Trimipramine; Tetracyclic antidepressants: Amoxapine • Maprotiline • Mianserin • Oxaprotiline •
Setiptiline; Others: Cocaine • CP-39,332 • EXP-561 • Fezolamine • Ginkgo biloba • Indeloxazine •
Nefazodone • Nefopam • Pridefrine • Tapentadol • Tedatioxetine • Teniloxazine • Tramadol •
Ziprasidone

VMAT

Ibogaine • Reserpine • Tetrabenazine

[hide]

Releasing agents

Morpholines: Fenbutrazate • Morazone • Phendimetrazine • Phenmetrazine; Oxazolines: 4-

Methylaminorex • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline •
Thozalinone; Phenethylamines (also amphetamines, cathinones, phentermines, etc): 2-OH-PEA • 4-CAB
• 4-FA • 4-FMA • 4-MA • 4-MMA • Alfetamine • Amfecloral • Amfepentorex • Amfepramone •
Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • β-Me-PEA • BDB •
Benzphetamine • BOH • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine •
D-Deprenyl • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, metamfepramone) • DMA
• DMMA • EBDB • Ephedrine • Ethcathinone • Ethylamphetamine • Ethylone • Famprofazone •
Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • IAP • IMP • L-
Deprenyl (Selegiline) • Lisdexamfetamine • Lophophine • MBDB • MDA (Tenamfetamine) • MDEA •
MDMA • MDMPEA • MDOH • MDPEA • Mefenorex • Mephedrone • Mephentermine •
Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methcathinone •
Methedrone • Methylone • NAP • Ortetamine • Paredrine • pBA • pCA • Pentorex (Phenpentermine) •
Phenethylamine • Pholedrine • Phenpromethamine • Phentermine • Phenylpropanolamine • pIA •
Prenylamine • Propylamphetamine • Pseudoephedrine • Tiflorex • Tyramine • Xylopropamine •
Zylofuramine; Piperazines: 2C-B-BZP • BZP • MBZP • mCPP • MDBZP • MeOPP • pFPP; Others: 2-Amino-
1,2-dihydronaphthalene • 2-Aminoindane • 2-Aminotetralin • 2-Benzylpiperidine • 4-Benzylpiperidine •
5-IAI • Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin •
Heptaminol • Hexacyclonate • Indanorex • Isometheptene • Methylhexanamine • Octodrine •
Phthalimidopropiophenone • Propylhexedrine (Levopropylhexedrine) • Tuaminoheptane
[hide]

Enzyme inhibitors

Anabolism
PAH

3,4-Dihydroxystyrene

TH

3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone

AAAD

Benserazide • Carbidopa • Genistein • Methyldopa

DBH

Bupicomide • Disulfiram • Dopastin • Fusaric acid • Nepicastat • Phenopicolinic acid • Tropolone

PNMT
CGS-19281A • SKF-64139 • SKF-7698

Catabolism

MAO

Nonselective: Benmoxin • Caroxazone • Echinopsidine • Furazolidone • Hydralazine • Indantadol •

Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine •
Nialamide • Octamoxin • Paraxazone • Phenelzine • Pheniprazine • Phenoxypropazine •
Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A selective: Amiflamine •
Bazinaprine • Befloxatone • Befol • Brofaromine • Cimoxatone • Clorgiline • Esuprone • Harmala
alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene Blue •
Metralindole • Minaprine • Moclobemide • Pirlindole • Sercloremine • Tetrindole • Toloxatone •
Tyrima; MAO-B selective: D-Deprenyl • Selegiline (L-Deprenyl) • Ladostigil • Lazabemide • Milacemide •
Mofegiline • Pargyline • Rasagiline • Safinamide
* Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the
breakdown of their precursor dopamine.

COMT

Entacapone • Tolcapone
[hide]

Others

Precursors

L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine • L-DOPS (Droxidopa)

Cofactors
Ferrous Iron (Fe2+) • S-Adenosyl-L-Methionine • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin
B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate) • Vitamin B9 (Folic acid →
Tetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn2+)

Others

Activity enhancers: BPAP • PPAP; Release blockers: Bethanidine • Bretylium • Guanadrel • Guanazodine
• Guanclofine • Guanethidine • Guanoxan; Toxins: Oxidopamine (6-Hydroxydopamine)

List of adrenergic drugs

[hide]

v·

d·

Cholinergics

[hide]
Receptor ligands

mAChR

Agonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B •

AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034
• CDD-0078 • CDD-0097 • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine •
LY-593,039 • L-689,660 • LY-2,033,298 • McNA343 • Methacholine • Milameline • Muscarine • NGX-
267 • Ocvimeline • Oxotremorine • PD-151,832 • Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 •
Sebacylcholine • Suberylcholine • Talsaclidine • Tazomeline • Thiopilocarpine • Vedaclidine • VU-
0029767 • VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 • WAY-132,983 • Xanomeline • YM-
796

Antagonists: 3-Quinuclidinyl Benzilate • 4-DAMP • Aclidinium Bromide • Anisodamine • Anisodine •

Atropine • Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99
• Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 •
CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate • Darifenacin • DAU-5884 •
Dimethindene • Dexetimide • DIBD • Dicyclomine (Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-
3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine •
HL-031,120 • Ipratropium bromide • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 •
Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl Benzilate • N-
Methyl-3-Piperidyl Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID • PD-102,807 • PD-
0298029 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine •
Profenamine • RU-47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) •
Solifenacin • Telenzepine • Tiotropium bromide • Tolterodine • Trihexyphenidyl • Tripitamine •
Tropatepine • Tropicamide • WIN-2299 • Xanomeline • Zamifenacin; Others: 1st Generation
Antihistamines (Brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate,
diphenhydramine, doxylamine, mepyramine/pyrilamine, phenindamine, pheniramine, tripelennamine,
triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, doxepin, trimipramine, etc) • Tetracyclic
Antidepressants (Amoxapine, maprotiline, etc) • Typical Antipsychotics (Chlorpromazine, thioridazine,
etc) • Atypical Antipsychotics (Clozapine, olanzapine, quetiapine, etc)

nAChR

Agonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 • ABT-418 • ABT-560 •

ABT-894 • Acetylcholine • Altinicline • Anabasine • Anatoxin-a • AR-R17779 • Butyrylcholine •
Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline •
Dimethylphenylpiperazinium • Epibatidine • Epiboxidine • Ethanol • Ethoxysebacylcholine • EVP-4473 •
EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-
1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline •
Sazetidine A • Sebacylcholine • SIB-1508Y • SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-
1734 • TC-1827 • TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 •
Varenicline • WAY-317,538 • XY-4083

Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Amantadine •

Anatruxonium • Atracurium • Bupropion (Amfebutamone) • Chandonium • Chlorisondamine •
Cisatracurium • Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan •
Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine (Metocurine) •
Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine •
Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Isoflurane • Ketamine • Kynurenic acid
• Laudexium (Laudolissin) • Levacetylmethadol • Malouetine • Mecamylamine • Memantine •
Methadone • Methorphan (Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium •
Morphanol (Racemorphanol) • Neramexane • Nitrous Oxide • Pancuronium • Pempidine • Pentamine •
Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin
• Suxamethonium (Succinylcholine) • Thiocolchicoside • Toxiferine • Trimethaphan • Tropeinium •
Tubocurarine • Vecuronium • Xenon

[hide]

Reuptake inhibitors
Plasmalemmal

CHT Inhibitors

Hemicholinium-3 (Hemicholine; HC3) • Triethylcholine

Vesicular
VAChT Inhibitors

Vesamicol

[hide]

Enzyme inhibitors
Anabolism

ChAT inhibitors

1-(-Benzoylethyl)pyridinium • 2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole • 4-(1-

Naphthylvinyl)pyridine • Acetylseco hemicholinium-3 • Acryloylcholine • AF64A • B115 • BETA • CM-
54,903 • N,N-Dimethylaminoethylacrylate • N,N-Dimethylaminoethylchloroacetate
Catabolism

AChE inhibitors

Reversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb • Carbaryl • Carbendazim • Carbetamide •

Carbofuran • Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb • Fenobucarb • Fenoxycarb •
Formetanate • Furadan • Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl • Phenmedipham •
Pinmicarb • Pirimicarb • Propamocarb • Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine •
Phenserine • Physostigmine • Pyridostigmine • Rivastigmine; Others: Acotiamide • Ambenonium •
Donepezil • Edrophonium • Galantamine • Huperzine A • Minaprine • Tacrine • Zanapezil

Irreversible: Organophosphates: Acephate • Azinphos-methyl • Bensulide • Cadusafos • Chlorethoxyfos

• Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl • Coumaphos • Cyclosarin (GF) • Demeton •
Demeton-S-Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl fluorophosphate (Guthion) •
Diisopropylphosphate • Dimethoate • Dioxathion • Disulfoton • EA-3148 • Echothiophate • Ethion •
Ethoprop • Fenamiphos • Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate • Isoxathion •
Malaoxon • Malathion • Methamidophos • Methidathion • Metrifonate • Mevinphos • Monocrotophos
• Naled • Novichok agent • Omethoate • Oxydemeton-Methyl • Paraoxon • Parathion • Parathion-
Methyl • Phorate • Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-Methyl • Sarin (GB) •
Soman (GD) • Tabun (GA) • Temefos • Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE • VG •
VM • VR • VX; Others: Demecarium • Onchidal (Onchidella binneyi)
BChE inhibitors

Cymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase

inhibitors.

[hide]
Others

Precursors

Choline (Lecithin) • Citicoline • Cyprodenate • Dimethylethanolamine (DMAE, deanol) •

Glycerophosphocholine • Meclofenoxate (Centrophenoxine) • Phosphatidylcholine •
Phosphatidylethanolamine • Phosphorylcholine • Pirisudanol

Cofactors
Acetic acid • Acetylcarnitine • Acetyl-coA • Vitamin B5 (Pantethine, Pantetheine, Panthenol)

Others

Acetylcholine releasing agents: α-Latrotoxin • β-Bungarotoxin; Acetylcholine release inhibitors:

Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime • Obidoxime • Pralidoxime

[hide]
v·

d·

Histaminergics

Receptor

ligands

H1

Agonists: 2-Pyridylethylamine • Betahistine • Histamine • HTMT • UR-AK49

Antagonists: "1st generation": 4-Methyldiphenhydramine • Alimemazine • Antazoline • Azatadine •

Bamipine • Benzatropine (Benztropine) • Bepotastine • Bromazine • Brompheniramine • Buclizine •
Captodiame • Carbinoxamine • Chlorcyclizine • Chloropyramine • Chlorothen • Chlorphenamine •
Chlorphenoxamine • Cinnarizine • Clemastine • Clobenzepam • Clocinizine • Cyclizine • Cyproheptadine
• Dacemazine • Deptropine • Dexbrompheniramine • Dexchlorpheniramine • Dimenhydrinate •
Dimetindene • Diphenhydramine • Diphenylpyraline • Doxylamine • Embramine • Etybenzatropine
(Ethylbenztropine) • Etymemazine • Histapyrrodine • Homochlorcyclizine • Hydroxyethylpromethazine
• Hydroxyzine • Isopromethazine • Isothipendyl • Meclozine • Mepyramine (Pyrilamine) • Mequitazine
• Methafurylene • Methapyrilene • Methdilazine • Moxastine • Niaprazine • Orphenadrine •
Oxatomide • Oxomemazine • Phenindamine • Pheniramine • Phenyltoloxamine • Pimethixene •
Piperoxan • Promethazine • Propiomazine • Pyrrobutamine • Talastine • Thenalidine • Thenyldiamine •
Thiazinamium • Thonzylamine • Tolpropamine • Tripelennamine • Triprolidine; "2nd generation":
Acrivastine • Astemizole • Azelastine • Cetirizine • Clemizole • Clobenztropine • Ebastine • Emedastine
• Epinastine • Ketotifen • Latrepirdine • Levocabastine • Loratadine • Mebhydrolin • Mizolastine •
Olopatadine • Rupatadine • Setastine • Terfenadine; "3rd generation": Desloratadine • Fexofenadine •
Levocetirizine; Miscellaneous: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc) •
Tetracyclic antidepressants (Mianserin, Mirtazapine, etc) • Serotonin antagonist and reuptake inhibitors
(Trazodone, Nefazodone) • Typical antipsychotics (Chlorpromazine, Thioridazine, etc) • Atypical
antipsychotics (Clozapine, Olanzapine, Quetiapine, etc)

H2

Agonists: Amthamine • Betazole • Dimaprit • Histamine • HTMT • Impromidine • UR-AK49

Antagonists: Burimamide • Cimetidine • Ebrotidine • Famotidine • Lafutidine • Lavoltidine/Loxtidine •

Lupitidine • Metiamide • Niperotidine • Nizatidine • Oxmetidine • Ranitidine • Roxatidine
H3

Agonists: α-Methylhistamine • Cipralisant • Histamine • Imetit • Immepip • Immethridine • Methimepip

• Proxyfan

Antagonists: A-349,821 • A-423,579 • ABT-239 • Betahistine • Burimamide • Ciproxifan • Clobenpropit

• Conessine • GSK-189,254 • Impentamine • Iodophenpropit • JNJ-5,207,852 • MK-0249 • NNC-38-
1,049 • PF-03654746 • Pitolisant • SCH-79,687 • Thioperamide • VUF-5,681

H4

Agonists: 4-Methylhistamine • Histamine • VUF-8,430

Antagonists: JNJ-7,777,120 • Thioperamide • VUF-6,002

Reuptake

inhibitors

Vesicular

VMAT inhibitors

Ibogaine • Reserpine • Tetrabenazine

Enzyme

inhibitors

Anabolism

HDC inhibitors

Catechin • Meciadanol • Naringenin • Tritoqualine

Catabolism

HNMT inhibitors

Amodiaquine • Diphenhydramine • Harmaline • Metoprine • Quinacrine • SKF-91,488 • Tacrine

DAO inhibitors

Aminoguanidine

Others

Precursors

L-Histidine
Cofactors

Vitamin B6 (pyridoxine, pyridoxamine, pyridoxal → Pyridoxal phosphate)

[hide]

v·

d·

Serotonergics
[hide]

5-HT1 receptor ligands

5-HT1A
Agonists: Azapirones: Alnespirone • Binospirone • Buspirone • Enilospirone • Eptapirone • Gepirone •
Ipsapirone • Perospirone • Revospirone • Tandospirone • Tiospirone • Umespirone • Zalospirone;
Antidepressants: Etoperidone • Nefazodone • Trazodone • Vortioxetine; Antipsychotics: Aripiprazole •
Asenapine • Clozapine • Quetiapine • Ziprasidone; Ergolines: Dihydroergotamine • Ergotamine •
Lisuride • Methysergide • LSD; Tryptamines: 5-CT • 5-MeO-DMT • 5-MT • Bufotenin • DMT •
Indorenate • Psilocin • Psilocybin; Others: 8-OH-DPAT • Adatanserin • Bay R 1531 • Befiradol • BMY-
14802 • Cannabidiol • Dimemebfe • Ebalzotan • Eltoprazine • F-11,461 • F-12,826 • F-13,714 • F-14,679
• F-15,063 • F-15,599 • Flesinoxan • Flibanserin • Lesopitron • LY-293,284 • LY-301,317 • MKC-242 •
NBUMP • Osemozotan • Oxaflozane • Pardoprunox • Piclozotan • Rauwolscine • Repinotan • Roxindole
• RU-24,969 • S 14,506 • S-14,671 • S-15,535 • Sarizotan • SSR-181,507 • Sunepitron • U-92,016-A •
Urapidil • Vilazodone • Xaliproden • Yohimbine

Antagonists: Antipsychotics: Iloperidone • Risperidone • Sertindole; Beta blockers: Alprenolol •

Cyanopindolol • Iodocyanopindolol • Oxprenolol • Pindobind • Pindolol • Propranolol • Tertatolol;
Others: AV965 • BMY-7,378 • CSP-2503 • Dotarizine • Flopropione • GR-46611 • Isamoltane •
Lecozotan • Mefway • Metitepine/Methiothepin • MPPF • NAN-190 • PRX-00023 • Robalzotan • S-
15535 • SB-649,915 • SDZ 216-525 • Spiperone • Spiramide • Spiroxatrine • UH-301 • WAY-100,135 •
WAY-100,635 • Xylamidine

5-HT1B

Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Methysergide; Piperazines: Eltoprazine •

TFMPP; Triptans: Avitriptan • Eletriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT;
Others: CGS-12066A • CP-93,129 • CP-94,253 • CP-135,807 • RU-24,969 • Vortioxetine

Antagonists: Lysergamides: Metergoline; Others: AR-A000002 • Elzasonan • GR-127,935 • Isamoltane •

Metitepine/Methiothepin • SB-216,641 • SB-224,289 • SB-236,057 • Yohimbine
5-HT1D

Agonists: Lysergamides: Dihydroergotamine • Methysergide; Triptans: Almotriptan • Avitriptan •

Eletriptan • Frovatriptan • Naratriptan • Rizatriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT •
5-Ethyl-DMT • 5-MT • 5-(Nonyloxy)tryptamine; Others: CP-135,807 • CP-286,601 • GR-46611 • L-
694,247 • L-772,405 • PNU-109,291 • PNU-142,633

Antagonists: Lysergamides: Metergoline; Others: Alniditan • BRL-15,572 • Elzasonan • GR-127,935 •

Ketanserin • LY-310,762 • LY-367,642 • LY-456,219 • LY-456,220 • Metitepine/Methiothepin •
Ritanserin • Yohimbine • Ziprasidone

5-HT1E
Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: BRL-54443 • Tryptamine

Antagonists: Metitepine/Methiothepin

5-HT1F

Agonists: Triptans: Eletriptan • Naratriptan • Sumatriptan; Tryptamines: 5-MT; Others: BRL-54443 •

Lasmiditan • LY-334,370

Antagonists: Metitepine/Methiothepin
[hide]

5-HT2 receptor ligands

5-HT2A

Agonists: Lysergamides: ALD-52 • Ergometrine • Lisuride • LA-SS-Az • LSD • LSD-Pip • Lysergic acid 2-
butyl amide • Lysergic acid 3-pentyl amide • Methysergide; Phenethylamines: 25I-NBF • 25I-NBMD •
25I-NBOH • 25I-NBOMe • 2C-B • 2C-B-FLY • 2CB-Ind • 2C-C-NBOMe • 2C-E • 2C-I • 2C-TFM-NBOMe •
2C-T-2 • 2C-T-7 • 2C-T-21 • 2CBCB-NBOMe • 2CBFly-NBOMe • Bromo-DragonFLY • DOB • DOC • DOI •
DOM • MDA • MDMA • Mescaline • TCB-2 • TFMFly; Piperazines: BZP • Quipazine • TFMPP;
Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-
DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin •
Psilocybin; Others: AL-34662 • AL-37350A • Dimemebfe • Medifoxamine • Oxaflozane • PNU-22394 •
RH-34
Antagonists: Atypical antipsychotics: Amperozide • Aripiprazole • Carpipramine • Clocapramine •
Clorotepine • Clozapine • Gevotroline • Iloperidone • Melperone • Mosapramine • Olanzapine •
Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical
antipsychotics: Loxapine • Pipamperone; Antidepressants: Amitriptyline • Amoxapine • Aptazapine •
Etoperidone • Mianserin • Mirtazapine • Nefazodone • Teniloxazine • Trazodone; Others: 5-I-R91150 •
5-MeO-NBpBrT • AC-90179 • Adatanserin • Altanserin • AMDA • APD-215 • Blonanserin • Cinanserin •
CSP-2503 • Cyproheptadine • Deramciclane • Dotarizine • Eplivanserin • Esmirtazapine • Fananserin •
Flibanserin • Ketanserin • KML-010 • Lubazodone • Mepiprazole • Metitepine/Methiothepin •
Nantenine • Pimavanserin • Pizotifen • Pruvanserin • Rauwolscine • Ritanserin • S-14,671 •
Sarpogrelate • Setoperone • Spiperone • Spiramide • SR-46349B • Volinanserin • Xylamidine •
Yohimbine

5-HT2B

Agonists: Oxazolines: 4-Methylaminorex • Aminorex; Phenethylamines: Chlorphentermine • Cloforex •

DOB • DOC • DOI • DOM • Fenfluramine • MDA • MDMA • Norfenfluramine; Tryptamines: 5-CT • 5-MT
• α-Methyl-5-HT; Others: BW-723C86 • Cabergoline • mCPP • Pergolide • PNU-22394 • Ro60-0175

Antagonists: Agomelatine • Asenapine • EGIS-7625 • Ketanserin • Lisuride • LY-272,015 •

Metitepine/Methiothepin • PRX-08066 • Rauwolscine • Ritanserin • RS-127,445 • Sarpogrelate • SB-
200,646 • SB-204,741 • SB-206,553 • SB-215,505 • SB-221,284 • SB-228,357 • SDZ SER-082 • Tegaserod
• Yohimbine
5-HT2C

Agonists: Phenethylamines: 2C-B • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • DOB • DOC • DOI • DOM •
MDA • MDMA • Mescaline; Piperazines: Aripiprazole • mCPP • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET
• 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT
• α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: A-372,159 • AL-38022A •
CP-809,101 • Dimemebfe • Lorcaserin• Medifoxamine • MK-212 • Org 12,962 • ORG-37,684 •
Oxaflozane • PNU-22394 • Ro60-0175 • Ro60-0213 • Vabicaserin • WAY-629 • WAY-161,503 • YM-348

Antagonists: Atypical antipsychotics: Clorotepine • Clozapine • Iloperidone • Melperone • Olanzapine •

Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical
antipsychotics: Chlorpromazine • Loxapine • Pipamperone; Antidepressants: Agomelatine •
Amitriptyline • Amoxapine • Aptazapine • Etoperidone • Fluoxetine • Mianserin • Mirtazapine •
Nefazodone • Nortriptyline • Tedatioxetine • Trazodone; Others: Adatanserin • Cinanserin •
Cyproheptadine • Deramciclane • Dotarizine • Eltoprazine • Esmirtazapine • FR-260,010 • Ketanserin •
Ketotifen • Latrepirdine • Metitepine/Methiothepin • Methysergide • Pizotifen • Ritanserin • RS-
102,221 • S-14,671 • SB-200,646 • SB-206,553 • SB-221,284 • SB-228,357 • SB-242,084 • SB-243,213 •
SDZ SER-082 • Xylamidine
[hide]

5-HT3, 5-HT4, 5-HT5, 5-HT6, 5-HT7 ligands

5-HT3

Agonists: Piperazines: BZP • Quipazine; Tryptamines: 2-Methyl-5-HT • 5-CT; Others:

Chlorophenylbiguanide • Butanol • Ethanol • Halothane • Isoflurane • RS-56812 • SR-57,227 • SR-
57,227-A • Toluene • Trichloroethane • Trichloroethanol • Trichloroethylene • YM-31636

Antagonists: Antiemetics: AS-8112 • Alosetron • Azasetron • Batanopride • Bemesetron • Cilansetron •

Dazopride • Dolasetron • Granisetron • Lerisetron • Ondansetron • Palonosetron • Ramosetron •
Renzapride • Tropisetron • Zacopride • Zatosetron; Atypical antipsychotics: Clozapine • Olanzapine •
Quetiapine; Tetracyclic antidepressants: Amoxapine • Mianserin • Mirtazapine; Others: CSP-2503 • ICS-
205,930 • MDL-72,222 • Memantine • Nitrous Oxide • Ricasetron • Sevoflurane • Tedatioxetine •
Thujone • Vortioxetine • Xenon

5-HT4

Agonists: Gastroprokinetic Agents: Cinitapride • Cisapride • Dazopride • Metoclopramide • Mosapride •

Prucalopride • Renzapride • Tegaserod • Velusetrag • Zacopride; Others: 5-MT • BIMU8 • CJ-033,466 •
PRX-03140 • RS-67333 • RS-67506 • SL65.0155 • Antagonists: GR-113,808 • GR-125,487 • L-Lysine •
Piboserod • RS-39604 • RS-67532 • SB-203,186 • SB-204,070

5-HT5A
Agonists: Lysergamides: Ergotamine • LSD; Tryptamines: 5-CT; Others: Valerenic Acid

Antagonists: Asenapine • Latrepirdine • Metitepine/Methiothepin • Ritanserin • SB-699,551

* Note that the 5-HT5B receptor is not functional in humans.

5-HT6

Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Lisuride • LSD • Mesulergine • Metergoline

• Methysergide; Tryptamines: 2-Methyl-5-HT • 5-BT • 5-CT • 5-MT • Bufotenin • E-6801 • E-6837 •
EMD-386,088 • EMDT • LY-586,713 • N-Methyl-5-HT • Tryptamine; Others: WAY-181,187 • WAY-
208,466

Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Doxepin • Mianserin •

Nortriptyline; Atypical antipsychotics: Aripiprazole • Asenapine • Clorotepine • Clozapine • Fluperlapine
• Iloperidone • Olanzapine • Tiospirone; Typical antipsychotics: Chlorpromazine • Loxapine; Others:
BGC20-760 • BVT-5182 • BVT-74316 • Cerlapirdine • EGIS-12,233 • GW-742,457 • Ketanserin •
Latrepirdine • Lu AE58054 • Metitepine/Methiothepin • MS-245 • PRX-07034 • Ritanserin • Ro04-6790
• Ro 63-0563 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885 • SB-742,457
5-HT7

Agonists: Lysergamides: LSD; Tryptamines: 5-CT • 5-MT • Bufotenin; Others: 8-OH-DPAT • AS-19 •
Bifeprunox • E-55888 • LP-12 • LP-44 • RU-24,969 • Sarizotan

Antagonists: Lysergamides: 2-Bromo-LSD • Bromocriptine • Dihydroergotamine • Ergotamine •

Mesulergine • Metergoline • Methysergide; Antidepressants: Amitriptyline • Amoxapine •
Clomipramine • Imipramine • Maprotiline • Mianserin; Atypical antipsychotics: Amisulpride •
Aripiprazole • Clorotepine • Clozapine • Olanzapine • Risperidone • Sertindole • Tiospirone •
Ziprasidone • Zotepine; Typical antipsychotics: Chlorpromazine • Loxapine; Others: Butaclamol • EGIS-
12,233 • Ketanserin • LY-215,840 • Metitepine/Methiothepin • Pimozide • Ritanserin • SB-258,719 • SB-
258,741 • SB-269,970 • SB-656,104 • SB-656,104-A • SB-691,673 • SLV-313 • SLV-314 • Spiperone •
SSR-181,507 • Vortioxetine

[hide]

Reuptake inhibitors
SERT

Selective serotonin reuptake inhibitors (SSRIs): Alaproclate • Citalopram • Dapoxetine •

Desmethylcitalopram • Desmethylsertraline • Escitalopram • Femoxetine • Fluoxetine • Fluvoxamine •
Indalpine • Ifoxetine • Litoxetine • Lubazodone • Panuramine • Paroxetine • Pirandamine • RTI-353 •
Seproxetine • Sertraline • Tedatioxetine • Vilazodone • Vortioxetine • Zimelidine; Serotonin-
norepinephrine reuptake inhibitors (SNRIs): Bicifadine • Desvenlafaxine • Duloxetine • Eclanamine •
Levomilnacipran • Milnacipran • Sibutramine • Venlafaxine; Serotonin-norepinephrine-dopamine
reuptake inhibitors (SNDRIs): Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303
• NS-2359 • SEP-225289 • SEP-227,162 • Tesofensine; Tricyclic antidepressants (TCAs): Amitriptyline •
Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine •
Lofepramine • Nortriptyline • Pipofezine • Protriptyline • Trimipramine; Tetracyclic antidepressants
(TeCAs): Amoxapine; Piperazines: Nefazodone • Trazodone; Antihistamines: Brompheniramine •
Chlorphenamine • Diphenhydramine • Mepyramine/Pyrilamine • Pheniramine • Tripelennamine;
Opioids: Pethidine • Methadone • Propoxyphene; Others: Cocaine • CP-39,332 • Cyclobenzaprine •
Dextromethorphan • Dextrorphan • EXP-561 • Fezolamine • Mesembrine • Nefopam • PIM-35 •
Pridefine • Roxindole • SB-649,915 • Ziprasidone
VMAT

Ibogaine • Reserpine • Tetrabenazine

[hide]

Releasing agents
Aminoindanes: 5-IAI • AMMI • ETAI • MDAI • MDMAI • MMAI • TAI; Aminotetralins: 6-CAT • 8-OH-
DPAT • MDAT • MDMAT; Oxazolines: 4-Methylaminorex • Aminorex • Clominorex • Fluminorex;
Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Methyl-MDA • 4-CAB • 4-FA •
4-FMA • 4-HA • 4-MTA • 5-APDB • 5-Methyl-MDA • 6-APDB • 6-Methyl-MDA • AEMMA • Amiflamine •
BDB • BOH • Brephedrone • Butylone • Chlorphentermine • Cloforex • Amfepramone •
Metamfepramone • DCA • DFMDA • DMA • DMMA • EBDB • EDMA • Ethylone • Etolorex •
Fenfluramine (Dexfenfluramine) • Flephedrone • IAP • IMP • Lophophine • MBDB • MDA • MDEA •
MDHMA • MDMA • MDMPEA • MDOH • MDPEA • Mephedrone • Methedrone • Methylone • MMA •
MMDA • MMDMA • MMMA • NAP • Norfenfluramine • 4-TFMA • pBA • pCA • pIA • PMA • PMEA •
PMMA • TAP; Piperazines: 2C-B-BZP • 2-BZP • 3-MeOPP • BZP • DCPP • MBZP • mCPP • MDBZP •
MeOPP • Mepiprazole • pCPP • pFPP • pTFMPP • TFMPP; Tryptamines: 4-Methyl-αET • 4-Methyl-αMT •
5-CT • 5-MeO-αET • 5-MeO-αMT • 5-MT • αET • αMT • DMT • Tryptamine (itself); Others: Indeloxazine
• Tramadol • Viqualine

[hide]

Enzyme inhibitors
Anabolism

TPH

AGN-2979 • Fenclonine
AAAD

Benserazide • Carbidopa • Genistein • Methyldopa

Catabolism

MAO
Nonselective: Benmoxin • Caroxazone • Echinopsidine • Furazolidone • Hydralazine • Indantadol •
Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine •
Nialamide • Octamoxin • Paraxazone • Phenelzine • Pheniprazine • Phenoxypropazine •
Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Amiflamine •
Bazinaprine • Befloxatone • Befol • Brofaromine • Cimoxatone • Clorgiline • Esuprone • Harmala
alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene Blue •
Metralindole • Minaprine • Moclobemide • Pirlindole • Sercloremine • Tetrindole • Toloxatone •
Tyrima

[hide]

Others
Precursors

L-Tryptophan → 5-HTP

Cofactors

Ferrous iron (Fe2+) • Magnesium (Mg2+) • Tetrahydrobiopterin • Vitamin B3 (Niacin, Nicotinamide →

NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal phosphate) • Vitamin B9 (Folic
Acid → Tetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn2+)
Others

Activity enhancers: BPAP • PPAP; Reuptake enhancers: Tianeptine

[hide]

v·

d·

Tricyclics
Classes

Acridine • Anthracene • Dibenzazepine • Dibenzocycloheptene • Dibenzodiazepine • Dibenzothiazepine

• Dibenzothiepin • Dibenzoxazepine • Dibenzoxepin • Phenothiazine • Pyridazinobenzoxazine •
Pyridinobenzodiazepine • Thioxanthene

Antidepressants

7-OH-Amoxapine • Amezepine • Amineptine • Amitriptyline • Amitriptylinoxide • Amoxapine •

Aptazapine • Azepindole • Azipramine • Butriptyline • Cianopramine • Ciclazindol • Ciclopramine •
Clomipramine • Cotriptyline • Cyanodothiepin • Demexiptiline • Depramine/Balipramine • Desipramine
• Dibenzepin • Dimetacrine • Dosulepin/Dothiepin • Doxepin • Enprazepine • Esmirtazapine •
Fluotracen • Hepzidine • Homopipramol • Imipramine • Imipraminoxide • Intriptyline • Iprindole •
Ketipramine • Litracen • Lofepramine • Losindole • Loxapine • Maprotiline • Mariptiline • Mazindol •
Melitracen • Metapramine • Mezepine • Mianserin • Mirtazapine • Naranol • Nitroxazepine •
Nortriptyline • Noxiptiline • Octriptyline • Opipramol • Oxaprotiline • Pipofezine • Pirandamine •
Propizepine • Protriptyline • Quinupramine • Setiptiline/Teciptiline • Tandamine • Tampramine •
Tianeptine • Tienopramine • Trimipramine

Antihistamines

Alimemazine • Azatadine • Clobenzepam • Cyproheptadine • Dacemazine • Deptropine • Desloratadine

• Epinastine • Etymemazine • Hydroxyethylpromethazine • Isopromethazine • Isothipendyl • Ketotifen
• Latrepirdine • Loratadine • Mebhydrolin • Mequitazine • Methdilazine • Olopatadine • Oxomemazine
• Phenindamine • Pimethixene • Promethazine • Propiomazine • Rupatadine • Thiazinamium

Antipsychotics

Acetophenazine • Amoxapine • Asenapine • Butaclamol • Butaperazine • Carphenazine • Carpipramine

• Chlorpromazine • Chlorprothixene • Ciclindole • Clocapramine • Clomacran • Clorotepin • Clotiapine •
Clozapine • Cyanothepin • Doclothepin • Docloxythepin • Erizepine • Flucindole • Flumezapine •
Fluotracen • Flupentixol • Fluphenazine • Gevotroline • Homopipramol • Isofloxythepin •
Levomepromazine/Methotrimeprazine • Loxapine • Maroxepin • Meperathiepin • Mesoridazine •
Metitepine • Metoxepin • Mosapramine • Naranol • Octomethothepin • Olanzapine • Oxyclothepin •
Oxyprothepin • Peradithiepin • Perathiepin • Perazine • Perphenazine • Periciazine • Piperacetazine •
Pipotiazine • Piquindone • Prochlorperazine • Promazine • Prothipendyl • Quetiapine • Sulforidazine •
Thiethylperazine • Thiopropazate • Thioridazine • Thiothixene • Tilozepine • Trifluoperazine •
Triflupromazine • Trifluthepin • Zotepine • Zuclopenthixol

Others

Atiprosin • Carbamazepine • Carvedilol • Cyclobenzaprine • Darenzepine • Elanzepine • Eslicarbazepine

acetate • Etazepine • Licarbazepine • Methylene Blue • Monatepil • Nuvenzepine • Oxcarbazepine •
Oxitriptyline • Pirenzepine • Pirolate • Pitrazepin • Pizotifen • Profenamine • Rispenzepine • Serazapine
• Siltenzepine • Telenzepine • Zolenzepine

imipramine, Tofranil
 Understanding Depression Slideshow

Can You Recognize Depression? Take the Quiz

Depression Tips Slideshow Pictures

GENERIC NAME: imipramine

BRAND NAME: Tofranil

DRUG CLASS AND MECHANISM: Imipramine is an antidepressant medication of the tricyclic

class. Medications in this class are often referred to as tricyclic antidepressants or TCAs. Depression is
defined as an all-pervasive sense of sadness and gloom. In patients with depression, abnormal levels of
chemicals in the brain (called neurotransmitters) may be the cause of their depression. These
neurotransmitters are what the nerves in the brain use to communicate with each other. Imipramine
elevates mood by raising the level of neurotransmitters in brain tissue. Imipramine also is used for
childhood enuresis (bedwetting), several disorders associated with chronic pain, and attention-deficit
hyperactivity disorder (ADHD. Imipramine was first synthesized in the late 1940s and was approved by
the FDA for depression in 1959 and for enuresis in 1973.

PRESCRIPTION: yes

GENERIC AVAILABLE: yes

PREPARATIONS: Tablets: 10mg, 25mg, 50mg. Sustained- release capsules: 75, 100, 125 or 150
mg.

STORAGE: Imipramine should be stored below 86°F (30°C) in a tight, light resistant container.

PRESCRIBED FOR: Imipramine is used to elevate the mood of patients with depression.
Imipramine also causes sedation. Therefore, it is useful in depressed patients with insomnia,
restlessness, and nervousness.

DOSING: The dose of imipramine is tailored to the patient's needs. Sometimes, physicians will
start with low doses, such as 25mg, three times a day, to reduce the risk of excessive sedation; doses
then will be increased slowly. Other physicians prefer to give imipramine once daily, in which case it is
generally given at bedtime to take advantage of its sedating properties. Elderly persons and patients
with advanced liver disease may need lower doses since they may eliminate imipramine less well from
the body. Mood elevation occurs only in depressed individuals and not in individuals without
depression. It may take 2-3 weeks of therapy before effects are seen.

For the treatment of enuresis, children 6 years or older usually are started on 10-25 mg, at
bedtime. If this dose is not effective after 1 week, the dose may be increased by 25 mg/day.
 For the treatment of attention-deficit hyperactivity disorder (ADHD), children ages 6-12 years
old usually are started on 10-30 mg/day.

DRUG INTERACTIONS: Imipramine interacts with other medications and drugs that slow the
brain's processes, such as alcohol, barbiturates, benzodiazepines, e.g. lorazepam (Ativan), diazepam
(Valium), temazepam (Restoril), oxazepam (Serax), clonazepam (Klonopin), zolpidem (Ambien), and
narcotics. Reserpine, given to patients taking TCAs, can cause agitation and anxiety. Imipramine and
other TCAs should not be used with monoamine oxidase inhibiting drugs, for example, isocarboxazid
(Marplan), phenelzine (Nardil), tranylcypromine (Parnate), and procarbazine (Matulane), since high
fever, convulsions and even death can occur.

Concurrent use of cimetidine (Tagamet) can increase imipramine blood levels by reducing
elimination of imipramine from the body and possibly lead to imipramine- related side effects. Other
drugs which share this effect include propafenone (Rythmol), flecainide (Tonocard), quinidine (Quinidex,
Quinaglute), and fluoxetine (Prozac).

imipramine, Tofranil (cont.)

PREGNANCY: There is very little information about the effects on the fetus of imipramine given
to pregnant women. Physicians may elect to use it if its benefits are deemed to outweigh the potential
but unknown risks.

NURSING MOTHERS: It is not known if imipramine is secreted in breast milk.

SIDE EFFECTS: The most commonly encountered side effects associated with imipramine include
fast heart rate, blurred vision, urinary difficulty urinating, dry mouth, constipation, weight gain or loss,
and low blood pressure when standing. Rash, hives, seizures, and hepatitis are rare side effects.
Imipramine also can cause elevated pressure in the eyes of some patients with glaucoma. Overdose with
imipramine can cause life-threatening abnormal heart rhythms or seizures.
 Following prolonged therapy in high doses, abrupt discontinuation of TCAs, including
imipramine, could lead to certain cholinergic symptoms such as nausea, vomiting, or diarrhea.
Therefore, many experts recommend gradually reducing the dose of drug if the drug is to be
discontinued.