塩酸イミプラミン

関: imipramine、Tofranil

WordNet

a tricyclic antidepressant (trade names Imavate and Tofranil) used to treat clinical depression (同)impramine hydrochloride, Imavate, Tofranil
a complex consisting of an organic base in association with hydrogen chloride

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/05/15 11:22:55」(JST)

wiki en

Imipramine, sold as Tofranil and also known as melipramine, is a tricyclic antidepressant (TCA) of the dibenzazepine group. Imipramine is mainly used in the treatment of major depression and enuresis (inability to control urination).

Imipramine was discovered in 1951.^[3]

Medical uses

Imipramine is used in the treatment of depression, such as depression associated with agitation or anxiety. It is similar in efficacy to the antidepressant drug moclobemide.^[4] It has also been used to treat nocturnal enuresis because of its ability to shorten the time of delta wave stage sleep, where wetting occurs. In veterinary medicine, imipramine is used with xylazine to induce pharmacologic ejaculation in stallions.

Side effects

Those listed in italic text below denote common side effects.^[5]

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, ECG changes, tachycardia, hypertension, palpitations, dysrhythmias
Eyes, ears, nose and throat: blurred vision, tinnitus, mydriasis
Gastrointestinal: dry mouth, nausea, vomiting, paralytic ileus, increased appetite, cramps, epigastric distress, jaundice, hepatitis, stomatitis, constipation, taste change
Genitourinary: urinary retention
Hematological: agranulocytosis, thrombocytopenia, eosinophilia, leukopenia
Skin: rash, urticaria, diaphoresis, pruritus, photosensitivity

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): very strong reuptake inhibition.
Norepinephrine (NE): strong reuptake inhibition. Desipramine has more affinity to NET than imipramine.
Dopamine (DA): Imipramine blocks D₂ receptors.^[6] Imipramine, and its metabolite desipramine, have no appreciable affinity for the dopamine transporter (8,500 and >10,000 K_inM respectively).^[7]
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).
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).^{[citation needed]}
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).^{[citation needed]}
Histamine: imipramine is an antagonist at histamine H₁ receptors.
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.^[8]^[9]
μ Receptor: imipramine has been shown to increase the expression of μ-opioid receptors in rat forebrain.^[10]

Within the body, imipramine is converted to desipramine, another TCA.

History

In the late 1950s, imipramine was the first tricyclic antidepressant to be developed (by Ciba). At the first international congress of neuro-pharmacology in Rome, September 1958 Dr Freyhan from the University of Pennsylvania discussed as one of the first clinicians the effects of imipramine in a group of 46 patients, most of them diagnosed as "depressive psychosis". The patients were selected for this study based on symptoms such as depressive apathy, kinetic retardation and feelings of hopelessness and despair. In 30% of all patients, he reported optimal results, and in around 20%, failure. The side effects noted were atropine-like, and most patients suffered from dizziness. Imipramine 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.^[11] It is not surprising, therefore, that imipramine may cause a high rate of manic and hypomanic reactions in hospitalized patients with pre-existing bipolar disorder, with one study showing that up to 25% of such patients maintained on Imipramine switched into mania or hypomania.^[12] Such powerful antidepressant properties have made it favorable in the treatment of treatment-resistant depression.

Before the advent of SSRIs, its sometimes intolerable side-effect profile was considered 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. Today it is no longer used as commonly, but is sometimes still prescribed as a second-line treatment for treating major depression . 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.

Comparison with other antidepressants

Binding Profile of popular TCAs towards their cloned human (unless otherwise specified) molecular targets (K_i in nM)^[13]^[14]

Drug	SERT	NET	DAT	α₁	α_2A	D₂	H₁	M₁	M₃	5-HT_1A	5-HT_2A	5-HT_2C	5-HT₆	5-HT₇
imipramine	10.4	51.7	8,500	-	3,100 (Human, Brain)	726	11.0	42	60	>10,000	120 (Rat, Cloned)	120 (Rat, Cloned)	190 (Rat, Cloned)	1,000 (Rat, Cloned)
desipramine	179	2.27	>10,000	130	1,380 (Human, Brain)	1,560	45.6	110	210	>10,000	114 (Rat, Cloned)	496 (Rat, Cloned)	-	1,000 (Rat, Cloned)
amitriptyline	3.13	22.4	4,440	24 (Human, Brain)	690 (Human, Brain)	1,460 (Human, Brain)	0.5	14.7	12.8	450 (Human, Brain)	5.60 (Rat, Cortex)	6.15 (Rat, Cloned)	103	114 (Rat, Cloned)
clomipramine	0.21	45.9	2,610	3.2	525	120	31.2	-	-	>10,000	35.5	64.6	53.8 (Rat, Cloned)	127 (Rat, Cloned)

References

^ "Bioavailability of imipramine tablets relative to a stable isotope-labelled internal standard: increasing the power of bioavailability tests". Journal of Pharmacokinetics and Biopharmaceutics. 7 (3): 233–248. June 1979. doi:10.1007/bf01060015. PMID 480146.
^ ^a ^b ^c ^d "PRODUCT INFORMATION TOLERADE® (imipramine hydrochloride)". TGA eBusiness Services. PMIP Pty Ltd. 4 June 2013. Retrieved 16 October 2013.
^ Walker, S. R. (2012). Trends and Changes in Drug Research and Development. Springer Science & Business Media. p. 109. ISBN 9789400926592.
^ Delini-Stula, A; Mikkelsen, H; Angst, J (October 1995). "Therapeutic efficacy of antidepressants in agitated anxious depression--a meta-analysis of moclobemide studies". Journal of Affective Disorders. 35 (1–2): 21–30. doi:10.1016/0165-0327(95)00034-K. PMID 8557884.
^ Skidmore-Roth, L., ed. (2010). Mosby's Nursing Drug Reference (23rd ed.). St. Louis, MO: Mosby Elsevier.
^ Smiałowski, A. (1991-05-01). "Dopamine D2 receptor blocking effect of imipramine in the rat hippocampus". Pharmacology, Biochemistry, and Behavior. 39 (1): 105–108. ISSN 0091-3057. PMID 1924491.
^ Schulze, David R.; Carroll, F. Ivy; McMahon, Lance R. (2012-08-01). "Interactions between dopamine transporter and cannabinoid receptor ligands in rhesus monkeys". Psychopharmacology. 222 (3): 425–438. doi:10.1007/s00213-012-2661-9. ISSN 0033-3158. PMC 3620032 . PMID 22374253.
^ Tsankova, N. M.; Berton, O; Renthal, W; Kumar, A; Neve, R. L.; Nestler, E. J. (April 2006). "Sustained hippocampal chromatin regulation in a mouse model of depression and antidepressant action". Nature Neuroscience. 9 (4): 519–25. doi:10.1038/nn1659. PMID 16501568.
^ Krishnan, V; Nestler, E. J. (October 2008). "The molecular neurobiology of depression". Nature. 455 (7215): 894–902. Bibcode:2008Natur.455..894K. doi:10.1038/nature07455. PMC 2721780 . PMID 18923511.
^ De Gandarias, J. M.; Echevarria, E; Acebes, I; Silio, M; Casis, L (July 1998). "Effects of imipramine administration on mu-opioid receptor immunostaining in the rat forebrain". Arzneimittel-Forschung. 48 (7): 717–9. PMID 9706370.
^ Healy, David (1997). The Antidepressant Era. Harvard University Press. p. 211.
^ Bottlender, R; Rudolf, D; Strauss, A; Möller, H. J. (1998). "Antidepressant-associated maniform states in acute treatment of patients with bipolar-I depression". European Archives of Psychiatry and Clinical Neuroscience. 248 (6): 296–300. doi:10.1007/s004060050053. PMID 9928908.
^ National Institute of Mental Health. PDSD Ki Database (Internet) [cited 2013 Jul 28]. Chapel Hill (NC): University of North Carolina. 1998–2013. Available from: "Archived copy". Archived from the original on November 8, 2013. Retrieved July 5, 2013.
^ Brunton L, Chabner B, Knollman B, Goodman and Gilman’s (2010). The Pharmacological Basis of Therapeutics (Twelfth ed.). McGraw Hill Professional.

External links

Imipramine – Medicinenet.com
Neurotransmitter – Neurotransmitter.net
Imipramine bound to proteins in the PDB

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Related Pictures

★リンクテーブル★

リンク元	「イミプラミン」「Tofranil」
関連記事	「hydrochloride」「imipramine」

「イミプラミン」

Imipramine
Clinical data
Trade names	Tofranil, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682389
Pregnancy; category	AU: C; US: N (Not classified yet); ;
Routes of; administration	Oral
ATC code	N06AA02 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	94-96%
Protein binding	86%
Metabolism	Hepatic (CYP1A2, CYP2C19, CYP2D6); Main active metabolite desipramine
Biological half-life	20 hours
Excretion	Renal (80%), Faecal (20%) (mostly as inactive metabolites)
Identifiers
	IUPAC name 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine;
Synonyms	G 22355
CAS Number	50-49-7 ;
PubChem CID	3696;
IUPHAR/BPS	357;
DrugBank	DB00458 ;
ChemSpider	3568 ;
UNII	OGG85SX4E4;
KEGG	D08070 ;
ChEBI	CHEBI:47499 ;
ChEMBL	CHEMBL11 ;
ECHA InfoCard	100.000.039
Chemical and physical data
Formula	C19H24N2
Molar mass	280.407 g/mol
3D model (Jmol)	Interactive image;
	SMILES c1cc3c(cc1)CCc2c(cccc2)N3CCCN(C)C ;
	InChI InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3 ; Key:BCGWQEUPMDMJNV-UHFFFAOYSA-N ;
(verify)

　　[★]

英: imipramine
化: 塩酸イミプラミン imipramine hydrochloride
商: イミドール、トフラニール Tofranil

分類

抗うつ薬

三環系抗うつ薬

作用機序

脳内のセロトニン、ノルエピネフリンの神経終末への取り込み阻害による受容体刺激の増進
代謝物のデシプラミンのノルエピネフリン取り込み阻害はイミプラミンより強い

重大な副作用

イミドール糖衣錠(10)／イミドール糖衣錠(25)

1. 悪性症候群（Syndrome malin）（頻度不明）

無動緘黙，強度の筋強剛，嚥下困難，頻脈，血圧の変動，発汗等が発現し，それに引き続き発熱がみられる場合は，投与を中止し，体冷却，水分補給等の全身管理とともに適切な処置を行う．

本症発症時には，白血球の増加や血清CK（CPK）の上昇がみられることが多く，またミオグロビン尿を伴う腎機能の低下がみられることがある．なお，高熱が持続し，意識障害，呼吸困難，循環虚脱，脱水症状，急性腎不全へと移行し，死亡した例が報告されている．

2. セロトニン症候群（頻度不明）

不安，焦燥，せん妄，興奮，発熱，発汗，頻脈，振戦，ミオクロヌス，反射亢進，下痢等を主症状とするセロトニン症候群があらわれることがあるので，これらの症状が出現した場合には投与を中止し，水分補給等の全身管理とともに適切な処置を行うこと．

3. てんかん発作（頻度不明）

てんかん発作があらわれることがあるので，観察を十分に行い，異常が認められた場合には投与を中止し，適切な処置を行うこと．

4. 無顆粒球症（頻度不明）

無顆粒球症（前駆症状として，発熱，咽頭痛，インフルエンザ様症状等）があらわれることがあるので，定期的に血液検査を実施するなど観察を十分に行い，異常が認められた場合には投与を中止し，適切な処置を行うこと．

5. 麻痺性イレウス（頻度不明）

腸管麻痺（食欲不振，悪心・嘔吐，著しい便秘，腹部の膨満あるいは弛緩及び腸内容物のうっ滞等の症状）を来し，麻痺性イレウスに移行することがあるので，腸管麻痺があらわれた場合には投与を中止すること．なお，この悪心・嘔吐は，本剤の制吐作用により不顕性化することもあるので注意すること．

6. 間質性肺炎，好酸球性肺炎（頻度不明）

発熱，咳嗽，呼吸困難，肺音の異常（捻髪音）等が認められた場合には投与を中止し，速やかに胸部X線等の検査を実施し，副腎皮質ホルモン剤の投与等の適切な処置を行うこと．

7. 心不全（頻度不明）

心不全があらわれることがあるので，観察を十分に行い，異常が認められた場合には投与を中止し，適切な処置を行うこと．

8. QT延長，心室頻拍（Torsades de pointesを含む）（頻度不明）

定期的に心電図検査を行うなど観察を十分に行い，異常が認められた場合には投与を中止し，適切な処置を行うこと．

9. 抗利尿ホルモン不適合分泌症候群（SIADH）（頻度不明）

症状として低ナトリウム血症，低浸透圧血症，尿中ナトリウム排泄量の増加，高張尿，痙攣，意識障害等があらわれることがあるので，このような場合には投与を中止し，水分摂取の制限等適切な処置を行うこと1）．

10. 肝機能障害，黄疸（頻度不明）

AST（GOT），ALT（GPT），γ-GTPの上昇等を伴う肝機能障害，黄疸があらわれることがあるので，観察を十分に行い，異常が認められた場合には投与を中止し，適切な処置を行うこと．

禁忌

イミドール糖衣錠(10)／イミドール糖衣錠(25)

1. 緑内障の患者〔抗コリン作用により眼圧を上昇させるおそれがある．〕
2. 本剤の成分又は三環系抗うつ剤に対し過敏症の既往歴のある患者
3. 心筋梗塞の回復初期の患者〔症状を悪化させるおそれがある．〕
4. 尿閉（前立腺疾患等）のある患者〔抗コリン作用により症状が悪化することがある．〕
5. モノアミン酸化酵素阻害剤（セレギリン）を投与中あるいは投与中止後2週間以内の患者〔発汗，不穏，全身痙攣，異常高熱，昏睡等があらわれるおそれがある．〕（「相互作用」の項参照）
6. QT延長症候群のある患者〔心室性不整脈を起こすおそれがある．〕

効能又は効果

イミドール糖衣錠(10)／イミドール糖衣錠(25)

精神科領域におけるうつ病・うつ状態
遺尿症（昼，夜）

薬効薬理

イミドール糖衣錠(10)／イミドール糖衣錠(25)

動物での作用

(1) ラットを用いたin vivo の実験で，脳内ノルアドレナリン及びセロトニンの再取り込みを抑制する4）．
(2) ラットを用いた実験で，レセルピンによる眼瞼下垂及び下痢に対して拮抗作用が認められている5）．またラットのテトラベナジンによるカタレプシーに対しても拮抗作用が認められている5）．
(3) マウスを用いた実験で，メタンフェタミン投与による運動亢進作用を有意に増強する6）．
(4) ラットの脳を用いたin vitro の実験で，脳内のイミプラミン特異的結合部位に対して親和性を示す6）．

添付文書

イミドール糖衣錠(10)／イミドール糖衣錠(25)

http://www.info.pmda.go.jp/go/pack/1174006F1027_4_10/1174006F1027_4_10?view=body

「Tofranil」

　　[★]

トフラニール

関: imipramine、imipramine hydrochloride

「hydrochloride」

　　[★] 塩酸塩、ハイドロクロライド　

「imipramine」

　　[★] イミプラミン

同: Tofranil

[Pharm-1] "Bioavailability of imipramine tablets relative to a stable isotope-labelled internal standard: increasing the power of bioavailability tests". Journal of Pharmacokinetics and Biopharmaceutics. 7 (3): 233–248. June 1979. doi:10.1007/bf01060015. PMID 480146.

[TOLERADE-2] "PRODUCT INFORMATION TOLERADE® (imipramine hydrochloride)". TGA eBusiness Services. PMIP Pty Ltd. 4 June 2013. Retrieved 16 October 2013.

[Wal2012-3] Walker, S. R. (2012). Trends and Changes in Drug Research and Development. Springer Science & Business Media. p. 109. ISBN 9789400926592.

[pmid8557884-4] Delini-Stula, A; Mikkelsen, H; Angst, J (October 1995). "Therapeutic efficacy of antidepressants in agitated anxious depression--a meta-analysis of moclobemide studies". Journal of Affective Disorders. 35 (1–2): 21–30. doi:10.1016/0165-0327(95)00034-K. PMID 8557884.

[5] Skidmore-Roth, L., ed. (2010). Mosby's Nursing Drug Reference (23rd ed.). St. Louis, MO: Mosby Elsevier.

[6] Smiałowski, A. (1991-05-01). "Dopamine D2 receptor blocking effect of imipramine in the rat hippocampus". Pharmacology, Biochemistry, and Behavior. 39 (1): 105–108. ISSN 0091-3057. PMID 1924491.

[7] Schulze, David R.; Carroll, F. Ivy; McMahon, Lance R. (2012-08-01). "Interactions between dopamine transporter and cannabinoid receptor ligands in rhesus monkeys". Psychopharmacology. 222 (3): 425–438. doi:10.1007/s00213-012-2661-9. ISSN 0033-3158. PMC 3620032 . PMID 22374253.

[8] Tsankova, N. M.; Berton, O; Renthal, W; Kumar, A; Neve, R. L.; Nestler, E. J. (April 2006). "Sustained hippocampal chromatin regulation in a mouse model of depression and antidepressant action". Nature Neuroscience. 9 (4): 519–25. doi:10.1038/nn1659. PMID 16501568.

[9] Krishnan, V; Nestler, E. J. (October 2008). "The molecular neurobiology of depression". Nature. 455 (7215): 894–902. Bibcode:2008Natur.455..894K. doi:10.1038/nature07455. PMC 2721780 . PMID 18923511.

[pmid9706370-10] De Gandarias, J. M.; Echevarria, E; Acebes, I; Silio, M; Casis, L (July 1998). "Effects of imipramine administration on mu-opioid receptor immunostaining in the rat forebrain". Arzneimittel-Forschung. 48 (7): 717–9. PMID 9706370.

[11] Healy, David (1997). The Antidepressant Era. Harvard University Press. p. 211.

[urlSpringerLink_.E2.80.93_Journal_Article-12] Bottlender, R; Rudolf, D; Strauss, A; Möller, H. J. (1998). "Antidepressant-associated maniform states in acute treatment of patients with bipolar-I depression". European Archives of Psychiatry and Clinical Neuroscience. 248 (6): 296–300. doi:10.1007/s004060050053. PMID 9928908.

[13] National Institute of Mental Health. PDSD Ki Database (Internet) [cited 2013 Jul 28]. Chapel Hill (NC): University of North Carolina. 1998–2013. Available from: "Archived copy". Archived from the original on November 8, 2013. Retrieved July 5, 2013.

[14] Brunton L, Chabner B, Knollman B, Goodman and Gilman’s (2010). The Pharmacological Basis of Therapeutics (Twelfth ed.). McGraw Hill Professional.

v t e Histamine receptor modulators

H₁	Agonists: 2-Pyridylethylamine Betahistine Histamine HTMT L-Histidine UR-AK49 Antagonists: First-generation: 4-Methyldiphenhydramine Alimemazine Antazoline Azatadine Bamipine Benzatropine (benztropine) Bepotastine Bromazine Brompheniramine Buclizine Captodiame Carbinoxamine Chlorcyclizine Chloropyramine Chlorothen Chlorphenamine Chlorphenoxamine Cinnarizine Clemastine Clobenzepam Clocinizine Cloperastine Cyclizine Cyproheptadine Dacemazine Decloxizine Deptropine Dexbrompheniramine Dexchlorpheniramine Dimenhydrinate Dimetindene Diphenhydramine Diphenylpyraline Doxylamine Embramine Etodroxizine Etybenzatropine (ethylbenztropine) Etymemazine Fenethazine Flunarizine Histapyrrodine Homochlorcyclizine Hydroxyethylpromethazine Hydroxyzine Isopromethazine Isothipendyl Meclozine Medrylamine Mepyramine (pyrilamine) Mequitazine Methafurylene Methapyrilene Methdilazine Moxastine Orphenadrine Oxatomide Oxomemazine Phenindamine Pheniramine Phenyltoloxamine Pimethixene Piperoxan Pipoxizine Promethazine Propiomazine Pyrrobutamine Talastine Thenalidine Thenyldiamine Thiazinamium Thonzylamine Tolpropamine Tripelennamine Triprolidine Second/third-generation: Acrivastine Alinastine Astemizole Azelastine Bamirastine Barmastine Bepiastine Bepotastine Bilastine Cabastinen Carebastine Cetirizine Clemastine Clemizole Clobenztropine Desloratadine Dorastine Ebastine Efletirizine Emedastine Epinastine Fexofenadine Flezelastine Ketotifen Latrepirdine Levocabastine Levocetirizine Linetastine Loratadine Mapinastine Mebhydrolin Mizolastine Moxastine Noberastine Octastine Olopatadine Perastine Pibaxizine Piclopastine Quifenadine (phencarol) Rocastine Rupatadine Setastine Sequifenadine (bicarphen) Talastine Temelastine Terfenadine Vapitadine Zepastine Non-generational: Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, RP-5063, ziprasidone, zotepine) Tetracyclic antidepressants (e.g., amoxapine, loxapine, maprotiline, mianserin, mirtazapine, oxaprotiline) Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, iprindole, lofepramine, nortriptyline, protriptyline, trimipramine) Typical antipsychotics (e.g., chlorpromazine, flupenthixol, fluphenazine, loxapine, perphenazine, prochlorperazine, thioridazine, thiothixene) Unknown/unsorted: Belarizine Elbanizine Flotrenizine Napactadine Tagorizine Trelnarizine Trenizine

H₂	Agonists: Amthamine Betazole Dimaprit Histamine HTMT Impromidine L-Histidine UR-AK49 Antagonists: Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine Lamtidine Lavoltidine (loxtidine) Lupitidine Metiamide Mifentidine Niperotidine Nizatidine Osutidine Oxmetidine Pibutidine Quisultazine (quisultidine) Ramixotidine Ranitidine Roxatidine Sufotidine Tiotidine Tuvatidine Venritidine Xaltidine Zolantidine

H₃	Agonists: α-Methylhistamine Cipralisant Histamine Imetit Immepip Immethridine L-Histidine Methimepip Proxyfan Antagonists: A-349,821 A-423,579 ABT-239 ABT-652 AZD5213 Betahistine Burimamide Ciproxifan Clobenpropit Conessine Enerisant GSK-189,254 Impentamine Iodophenpropit Irdabisant JNJ-5207852 MK-0249 NNC 38-1049 PF-03654746 Pitolisant SCH-79687 Thioperamide VUF-5681

H₄	Agonists: 4-Methylhistamine α-Methylhistamine Histamine L-Histidine OUP-16 VUF-8430 Antagonists: JNJ-7777120 Mianserin Thioperamide Toreforant VUF-6002

See also: Receptor/signaling modulators • Monoamine metabolism modulators • Monoamine reuptake and release modulators

v t e Sigma receptor modulators

σR	Agonists: 3-MeO-PCE 3-MeO-PCP 3-PPP 4-MeO-PCP 4-IBP 4-PPBP Afobazole Alazocine Amantadine Amitriptyline Arketamine BD-1008 BD1031 BD1052 Berberine Buprenorphine Captodiame Citalopram Clorgiline Cocaine Cutamesine Cyclazocine DHEA DHEA-S Desipramine Dextrallorphan Dextromethorphan Dextrorphan Dimemorfan DMT Donepezil DTG Escitalopram Fluoxetine Fluvoxamine Heroin Ibogaine Igmesine Imipramine JO-1784 Ketamine L-687,384 Lamotrigine Lu 28-179 MDMA Memantine Metaphit Methamphetamine Methoxetamine Methylphenidate Morphine Naluzotan Noscapine OPC-14523 Opipramol PB-28 PD-144,415 Pentazocine Pentoxyverine Phencyclidine PRE-084 Pregnenolone Pregnenolone sulfate Quetiapine RTI-55 SA-4503 Siramesine Tapentadol Tenocyclidine Tramadol UMB23 UMB82 Venlafaxine Antagonists: AC927 AHD1 AZ66 BD1008 BD1047 BD1060 BD1063 BD1067 BMY-14802 CM156 E-5842 Haloperidol Lamotrigine LR132 LR172 MIN-101 MS-377 Naloxone Naltrexone NE-100 Panamesine PD-144418 Progesterone Quingestrone Rimcazole S1RA (E-52862) Sertraline SM-21 SR-31742A UMB100 UMB101 UMB103 UMB116 YZ-011 YZ-069 YZ-185 Unknown/unsorted: 4C-T-2 5-MeO-DiPT 18-MC β-Endopsychosin Chlorpromazine Clemastine Clocapramine Cloperastine D-Deprenyl DiPT DPT Gevotroline Nepinalone Selegiline TMA; Allosteric modulators: SKF-83959

See also: Receptor/signaling modulators

v t 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 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 Nortriptyline Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline/Teciptiline Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine

Antihistamines	Azatadine 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 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 Methylene blue Monatepil Nuvenzepine Oxetorone Perlapine P7C3 Pinadoline Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Serazapine Siltenzepine Telenzepine Tipindole Tropatepine Zolenzepine

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