Medication for slow heart rate
Pharmaceutical compound
Isoprenaline Clinical data Trade names Isuprel, others[ 1] [ 2] Other names Isoproterenol; Isopropylnorepinephrine; Isopropylnoradrenaline; Isopropydine; WIN-5162 AHFS /Drugs.com Monograph MedlinePlus a601236 Pregnancy Routes of Intravenous ,intramuscular ,subcutaneous ,intracardiac ,inhalation ,sublingual ,rectal [ 3] [ 4] ATC code Legal status Legal status AU: S4 (Prescription only)In general: ℞ (Prescription only) Pharmacokinetic dataBioavailability Oral : Very low[ 5] [ 6] Protein binding 69% (mostly toalbumin )[ 3] Metabolism Methylation (COMT Tooltip Catechol O-methyltransferase ),conjugation (sulfation )[ 7] [ 3] Metabolites • 3-O -Methylisoprenaline[ 3] Sulfate conjugates [ 7] Onset of action Inhalation : 2–5 min[ 8] Eliminationhalf-life IV Tooltip Intravenous infusion : 2.5–5 min[ 3] Oral : 40 min[ 3] Duration of action Inhalation : 0.5–2 hours[ 8] Excretion Urine : 59–107%[ 3] Feces : 12–27%[ 3] Identifiers CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEMBL CompTox Dashboard (EPA) ECHA InfoCard 100.028.807 Chemical and physical data Formula C 11 H 17 N O 3 Molar mass −1 3D model (JSmol ) InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3
Y Key:JWZZKOKVBUJMES-UHFFFAOYSA-N
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Isoprenaline , also known asisoproterenol and sold under the brand nameIsuprel among others, is asympathomimetic medication which is used in the treatment of acutebradycardia (slow heart rate),heart block , and rarely forasthma , among other indications.[ 9] injection into a vein ,muscle ,fat , or theheart , byinhalation , and in the pastunder the tongue orinto the rectum .[ 3] [ 4]
Side effects of isoprenaline includerapid heart beat ,heart palpitations , andarrhythmias , among others.[ 9] selective agonist of theβ-adrenergic receptors , including both theβ1 - andβ2 -adrenergic receptors .[ 9] receptors , it increasesheart rate and theforce of heart contractions .[ 10] synthetic catecholamine and is theN -isopropyl analogue ofnorepinephrine (noradrenaline) andepinephrine (adrenaline).[ 11] [ 3] [ 12] [ 13]
Isoprenaline was one of the firstsynthetic sympathomimetic amines and was the firstselective β-adrenergic receptor agonist.[ 7] [ 14] [ 5] [ 15]
Isoprenaline is used to treatheart block and episodes ofAdams–Stokes syndrome that are not caused byventricular tachycardia orfibrillation , in emergencies forcardiac arrest untilelectric shock can be administered, forbronchospasm occurring duringanesthesia , and as anadjunct in the treatment ofhypovolemic shock ,septic shock , lowcardiac output (hypoperfusion ) states,congestive heart failure , andcardiogenic shock .[ 9] Torsades de Pointes in patients withlong QT refractory tomagnesium and to treat patients with intermittent Torsades de Pointes refractory to treatment withmagnesium .[ 16] [ 17]
Historically, it was used to treatasthma via metered aerosol or nebulizing devices; it was also available in sublingual, oral, intravenous, and intramuscular formulations.[ 15] bronchoconstriction .[ 18]
Many formulations of isoprenaline appear to have been discontinued in theUnited States and many other countries.[ 4] [ 1] [ 2] [ 3] injectable solution .[ 4] aerosol , powder, or disc forinhalation and as atablet forsublingual andrectal administration , but these formulations were discontinued.[ 4]
It should not be used in people withtachyarrhythmias (except in special circumstances),[ 19] tachycardia orheart block caused bydigitalis poisoning,ventricular arrhythmias which requireinotropic therapy, or withangina .[ 9]
Side effects of isoprenaline may includenervousness ,headache ,dizziness ,nausea ,blurred vision ,tachycardia ,palpitations ,angina ,Adams-Stokes attacks ,pulmonary edema ,hypertension ,hypotension ,ventricular arrhythmias ,tachyarrhythmias ,difficulty breathing ,sweating , mildtremors ,weakness ,flushing , andpallor .[ 9] insulin resistance leading todiabetic ketoacidosis .[ 20]
Overdose of isoprenaline may produce effects includingtachycardia ,arrhythmias ,palpitations ,angina ,hypotension ,hypertension , andmyocardial necrosis .[ 3] [ 9]
Isoprenaline is aβ1 - andβ2 -adrenergic receptor full agonist and has almost noactivity at theα-adrenergic receptors at lower concentrations.[ 15] [ 21] affinity for the β1 - and β2 -adrenergic receptors.[ 21] [ 8] [ 8] [ 22] [ 23] trace amine-associated receptor 1 (TAAR1) additionally provide it withpharmacodynamic effects that resemble those of the endogenoustrace amines , liketyramine .[ 24]
Isoprenaline's effects on thecardiovascular system (non-selective) relate to its actions oncardiac β1 -adrenergic receptors and β2 -adrenergic receptors onsmooth muscle within thetunica media ofarterioles . Isoprenaline haspositive inotropic andchronotropic effects on the heart. β2 -Adrenergic receptor stimulation inarteriolar smooth muscle inducesvasodilation . Its inotropic and chronotropic effects elevatesystolic blood pressure , while its vasodilatory effects tend to lowerdiastolic blood pressure. The overall effect is to decreasemean arterial pressure due to the vasodilation caused by β2 -adrenergic receptor activation.[ 25]
Theisopropylamine group in isoprenaline makes it selective for β-adrenergic receptors.[ 26]
The adverse effects of isoprenaline are also related to the drug'scardiovascular effects. Isoprenaline can producetachycardia (an elevatedheart rate ), which predisposes people who take it tocardiac arrhythmias .[ 15]
Data on theabsorption of isoprenaline are limited.[ 3] Oral isoprenaline iswell-absorbed but is subject to strongfirst-pass metabolism [ 27] times lesspotent thanintravenous administration .[ 6] bioavailability is very low.[ 5] [ 6] pharmacodynamic activity via different routes, was slightly less than 4%.[ 27] [ 28]
Isoprenaline is minimally able to cross theblood–brain barrier and hence is aperipherally selective drug .[ 29] [ 30] hydrophilicity .[ 29] intravenous injection in humans was 3.8%, the extraction of propranolol, which is a morelipophilic compound and is readily able to cross into the brain, was 63.0%.[ 29]
Theplasma protein binding of isoprenaline is 68.8 ± 1.2%.[ 3] albumin .[ 3]
Isoprenaline ismetabolized bycatecholO -methyltransferase (COMT) andconjugation bysulfation .[ 7] [ 31] [ 32] [ 3] glucuronidated .[ 7] interindividual variability in the sulfation of isoprenaline.[ 7] catechol hydroxyl groups keep it susceptible to enzymatic metabolism.[ 26] substrate formonoamine oxidase (MAO) and is not metabolized by this enzyme.[ 7] [ 9] epinephrine andnorepinephrine .[ 7] [ 6] metabolite 3-O -methylisoprenaline, formed by COMT, isactive as a weakβ-adrenergic receptor antagonist .[ 7]
Isoprenaline isexcreted primarily in theurine , assulfate conjugates .[ 7] [ 31] [ 32] [ 3] feces .[ 3] [ 3] [ 6]
Theelimination half-life of isoprenaline byintravenous administration is approximately 2.5 to 5 minutes.[ 3] oral administration is approximately 40 minutes.[ 3] [ 6]
Isoprenaline, also known asN -isopropyl-3,4,β-trihydroxyphenethylamine or asN -isopropylnorepinephrine, is asubstituted phenethylamine andsynthetic catecholamine derivative .[ 11] [ 3] [ 12] [ 9] N -isopropyl analogue ofnorepinephrine (3,4,β-trihydroxyphenethylamine) andepinephrine (3,4,β-trihydroxy-N -methylphenethylamine).[ 11] [ 13]
Isoprenaline is asmall-molecule compound with themolecular formula C11 H17 NO3 and amolecular weight of 211.26 g/mol.[ 11] [ 3] [ 12] [ 9] hydrophilic compound[ 29] log P of -0.6 to 0.25.[ 11] [ 3] [ 12] [ 33] [ 34]
Isoprenaline is used pharmaceutically as thehydrochloride andsulfate salts .[ 1] free base .[ 1]
Isoprenaline is aracemic mixture oflevorotatory anddextrorotatory enantiomers .[ 11] [ 3] [ 12] R )-enantiomer of isoprenaline is known as levisoprenaline (INN Tooltip International Nonproprietary Name ) but was never marketed.[ 35] [ 36] [ 37]
Synthetic analogues closely related to isoprenaline includearbutamine ,dichloroisoprenaline (dichloroisoproterenol),hexoprenaline ,isoetharine (α-ethylisoprenaline),orciprenaline (metaproterenol; apositional isomer of isoprenaline),prenalterol , andsoterenol (3-methanesulfonamidylisoprenaline), among others.[ 5]
Isoprenaline was discovered in 1940[ 5] [ 7] [ 15] synthetic sympathomimetic amines , was the firstselective β-adrenergic receptor agonist , and was the first major sympathomimetic agent devoid ofpressor effects.[ 7] [ 14]
Between 1963 and 1968 in England, Wales, Scotland, Ireland, Australia, and New Zealand there was an increase in deaths among people using isoprenaline to treat asthma. This was attributed to unintentionaloverdose : the inhalers produced in that area were dispensing five times the dosage dispensed by inhalers produced in the United States and Canada, where the deaths were not observed.[ 38] [ 39]
The shortduration of action and poororal activity of isoprenaline led to the development of the much longer-acting and orally activeorciprenaline (metaproterenol).[ 40] [ 7]
Society and culture [ edit ] Isoprenaline is the majorgeneric name of the drug and itsINN Tooltip International Nonproprietary Name ,BAN Tooltip British Approved Name , andDCF Tooltip Dénomination Commune Française .[ 35] [ 1] [ 36] [ 2] Isoprenalina is itsItalian generic name and itsDCIT Tooltip Denominazione Comune Italiana .[ 1] [ 2] Isoprenaline hydrochloride andisoprenaline sulfate are itsBANM Tooltip British Approved Name in the case of thehydrochloride andsulfate salts , respectively.[ 1] Isoproterenol is another important synonym of the drug.[ 35] [ 1] [ 2] Isoproterenol hydrochloride is itsUSAN Tooltip United States Adopted Name andJAN Tooltip Japanese Accepted Name in the case of the hydrochloride salt andisoproterenol sulfate is itsUSAN and JAN in the case of the sulfate salt.[ 35] [ 1] [ 36] [ 2] isopropylnorepinephrine ,isopropylnoradrenaline , andisopropydine .[ 35] [ 1] [ 36] [ 2] WIN-5162 .[ 1] [ 2]
Isoprenaline has been marketed under many brand names worldwide.[ 1] [ 2] [ 1] [ 2] combination drug withcromoglicic acid as Frenal Compositum, in combination withpronase as Isopal P, and in combination withatropine as Stmerin D.[ 2]
^a b c d e f g h i j k l m Schweizerischer Apotheker-Verein (2004).Index Nominum: International Drug Directory ISBN 978-3-88763-101-7 . Retrieved1 August 2024 . ^a b c d e f g h i j k "Isoprenaline" .drugs.com . 6 August 2017. Archived fromthe original on 26 June 2019. Retrieved1 August 2024 .^a b c d e f g h i j k l m n o p q r s t u v w x y "Isoprenaline: Uses, Interactions, Mechanism of Action" .DrugBank Online . 19 February 1948. Retrieved31 July 2024 .^a b c d e "Drugs@FDA: FDA-Approved Drugs" .accessdata.fda.gov . Archived fromthe original on November 4, 2016. Retrieved31 July 2024 .^a b c d e Waldeck B (June 2002). "Beta-adrenoceptor agonists and asthma--100 years of development".Eur J Pharmacol .445 (1– 2):1– 12.doi :10.1016/s0014-2999(02)01728-4 .PMID 12065188 . ^a b c d e f Conolly ME, Davies DS, Dollery CT, Morgan CD, Paterson JW, Sandler M (November 1972)."Metabolism of isoprenaline in dog and man" .Br J Pharmacol .46 (3):458– 472.doi :10.1111/j.1476-5381.1972.tb08143.x .PMC 1666503 PMID 4656607 . ^a b c d e f g h i j k l m Morgan DJ (April 1990). "Clinical pharmacokinetics of beta-agonists".Clin Pharmacokinet .18 (4):270– 294.doi :10.2165/00003088-199018040-00002 .PMID 1969785 . ^a b c d Sterling LP (May 1995). "Beta adrenergic agonists".AACN Clin Issues .6 (2):271– 278.doi :10.1097/00044067-199505000-00010 .PMID 7743429 . ^a b c d e f g h i j "Label: Isoproterenol hydrochloride injection, solution" . NIH DailyMed. September 10, 2013. RetrievedJune 21, 2017 .^ Motwani SK, Saunders H (2024). "Inotropes".Anaesthesia & Intensive Care Medicine .25 (3):185– 191.doi :10.1016/j.mpaic.2023.11.019 . ^a b c d e f "Isoproterenol" .PubChem . Retrieved31 July 2024 .^a b c d e "Isoprenaline" .ChemSpider . 21 July 2022. Retrieved31 July 2024 .^a b Konzett H (1981). "On the discovery of isoprenaline".Trends in Pharmacological Sciences .2 :47– 49.doi :10.1016/0165-6147(81)90259-5 . ^a b Ružena Č, Jindra V, Renáta H (18 June 2020)."Chirality of β2-agonists. An overview of pharmacological activity, stereoselective analysis, and synthesis" .Open Chemistry .18 (1):628– 647.doi :10.1515/chem-2020-0056 ISSN 2391-5420 . ^a b c d e Mozayani A, Raymon L (2003).Handbook of Drug Interactions: A Clinical and Forensic Guide 541– 542.ISBN 978-1-59259-654-6 ^ Cohagan B, Brandis D (August 2022). "Torsade de Pointes".StatPearls . Treasure Island (FL): StatPearls Publishing.PMID 29083738 .NBK459388 . ^ Kusumoto FM, Schoenfeld MH, Barrett C, Edgerton JR, Ellenbogen KA, Gold MR, et al. (August 2019). "2018 ACC/AHA/HRS Guideline on the Evaluation and Management of Patients With Bradycardia and Cardiac Conduction Delay: A Report of the American College of Cardiology/American Heart Association Task Force on Clinical Practice Guidelines and the Heart Rhythm Society".Circulation .140 (8):e382 – e482 .doi :10.1161/CIR.0000000000000628 .PMID 30586772 . ^ National Asthma Education and Prevention Program Expert Panel (August 28, 2007)."Expert Panel Report 3: Guidelines for the Diagnosis and Management of Asthma" (PDF) . NIH National Heart, Lung, and Blood Institute. Archived fromthe original (PDF) on November 27, 2014. ^ Jongman JK, Jepkes-Bruin N, Ramdat Misier AR, Beukema WP, Delnoy PP, Oude Lutttikhuis H, et al. (April 2007)."Electrical storms in Brugada syndrome successfully treated with isoproterenol infusion and quinidine orally" .Netherlands Heart Journal .15 (4):151– 155.doi :10.1007/BF03085972 .PMC 1847769 PMID 17612676 . ^ Hoff R, Koh CK (2018)."Isoproterenol Induced Insulin Resistance Leading to Diabetic Ketoacidosis in Type 1 Diabetes Mellitus" .Case Reports in Endocrinology .2018 4328954.doi :10.1155/2018/4328954 PMC 6311779 PMID 30647979 . ^a b Emilien G, Maloteaux JM (February 1998). "Current therapeutic uses and potential of beta-adrenoceptor agonists and antagonists".Eur J Clin Pharmacol .53 (6):389– 404.doi :10.1007/s002280050399 .PMID 9551698 . ^ Furchgott RF, Bhadrakom S (June 1953)."Reactions of strips of rabbit aorta to epinephrine, isopropylarterenol, sodium nitrite and other drugs" The Journal of Pharmacology and Experimental Therapeutics .108 (2):129– 143.doi :10.1016/S0022-3565(25)05163-8 .PMID 13062084 . ^ Copik AJ, Baldys A, Nguyen K, Sahdeo S, Ho H, Kosaka A, et al. (21 January 2015)."Isoproterenol acts as a biased agonist of the alpha-1A-adrenoceptor that selectively activates the MAPK/ERK pathway" .PLOS ONE .10 (1) e0115701.Bibcode :2015PLoSO..1015701C .doi :10.1371/journal.pone.0115701 PMC 4301629 PMID 25606852 . ^ Kleinau G, Pratzka J, Nürnberg D, Grüters A, Führer-Sakel D, Krude H, et al. (October 2011)."Differential modulation of Beta-adrenergic receptor signaling by trace amine-associated receptor 1 agonists" .PLOS ONE .6 (10) e27073.Bibcode :2011PLoSO...627073K .doi :10.1371/journal.pone.0027073 PMC 3205048 PMID 22073124 .Table 1. EC50 values of different agonists at hTAAR1, hADRB1 and hADRB2 ^ Korbut R (2017).Farmakologia (in Polish). Wydawnictwo Lekarskie PZWL. p. 36.ISBN 978-83-200-5368-5 ^a b Mehta A (January 27, 2011)."Notes - Medicinal Chemistry of the Peripheral Nervous System - Adrenergics and Cholinergic" . Pharmaxchange. Archived fromthe original on 4 November 2010. RetrievedJune 21, 2017 . ^a b George CF (1981). "Drug metabolism by the gastrointestinal mucosa".Clin Pharmacokinet .6 (4):259– 274.doi :10.2165/00003088-198106040-00002 .PMID 6113909 . ^ Redwood D (January 1969)."Conservative treatment of chronic heart block" .Br Med J .1 (5635):26– 29.doi :10.1136/bmj.1.5635.26 .PMC 1981820 PMID 5761891 . ^a b c d Olesen J, Hougård K, Hertz M (1978). "Isoproterenol and propranolol: ability to cross the blood-brain barrier and effects on cerebral circulation in man".Stroke .9 (4):344– 349.doi :10.1161/01.str.9.4.344 .PMID 209581 .Mean extraction of isoproterenol in a single passage of the brain circulation was 3.8% and the calculated PS product was 2.0 ml/100g/min. The mean extraction of propranolol was 63.0% and the mean PS product 46.7 ml/100 g/min. [...] Passage of Isoproterenol and Propranolol Across Blood–Brain Barrier: No data are available in the literature concerning the ability of isoproterenol to cross the blood-brain barrier. From the hydrophilic nature of the molecule one might expect diffusion to be very slow, but the possibility of active uptake mechanisms still existed. The extraction of 3.8% found in the present study corresponds to that of sodium or other hydrophilic molecules.12 It is likely that a significant part of this extraction stems from areas known to be devoid of a blood-brain barrier. The extraction is clearly much smaller than that seen for amino acids and other substances that pass the barrier by facilitated diffusion.14 ^ Crystal GJ, Salem MR (October 2002). "Beta-adrenergic stimulation restores oxygen extraction reserve during acute normovolemic hemodilution".Anesth Analg .95 (4):851– 857, table of contents.doi :10.1097/00000539-200210000-00011 .PMID 12351256 .The lack of effect of blood-borne catecholamines, including isoproterenol, on cerebral blood flow has been attributed to their inability to cross the blood-brain barrier (26). ^a b Procaccini DE, Sawyer JE, Watt KM (2019). "Pharmacology of Cardiovascular Drugs".Critical Heart Disease in Infants and Children . pp. 192–212.e6.doi :10.1016/B978-1-4557-0760-7.00019-X .ISBN 978-1-4557-0760-7 S2CID 81053428 . ^a b Szymanski MW, Singh DP (2023). "Isoproterenol".StatPearls . StatPearls Publishing.PMID 30252298 .NBK526042 . ^ "Epinephrine" .PubChem . Retrieved1 August 2024 .^ "Norepinephrine" .PubChem . Retrieved1 August 2024 .^a b c d e Elks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 . Retrieved1 August 2024 . ^a b c d Morton IK, Hall JM (2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms ISBN 978-94-011-4439-1 . Retrieved1 August 2024 . ^ Morton IK, Hall JM (2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms ISBN 978-94-011-4439-1 . Retrieved2024-08-01 . ^ Pearce N, Hensley MJ (1998)."Epidemiologic studies of beta agonists and asthma deaths" .Epidemiologic Reviews .20 (2):173– 186.doi :10.1093/oxfordjournals.epirev.a017979 PMID 9919437 . ^ Jalba MS (2008). "Three generations of ongoing controversies concerning the use of short acting beta-agonist therapy in asthma: a review".The Journal of Asthma .45 (1):9– 18.doi :10.1080/02770900701495512 .PMID 18259990 .S2CID 31732029 . ^ Dserendorf H (1995).Drug Actions: Basic Principles and Theraputic Aspects ISBN 978-0-8493-7774-7 . Retrieved1 August 2024 .
α1
Agonists Antagonists Abanoquil ADRIANA Ajmalicine Alfuzosin Anisodamine Anisodine Atiprosin Atypical antipsychotics (e.g.,brexpiprazole ,clozapine ,olanzapine ,quetiapine ,risperidone )Benoxathian Beta blockers (e.g.,adimolol ,amosulalol ,arotinolol ,carvedilol ,eugenodilol ,labetalol )Buflomedil Bunazosin Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g.,acetergamine ,ergotamine ,dihydroergotamine ,lisuride ,nicergoline ,terguride )Etoperidone Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Niaprazine Niguldipine Pardoprunox Pelanserin Perlapine Phendioxan Phenoxybenzamine Phentolamine Phenylpiperazine antidepressants (e.g.,hydroxynefazodone ,nefazodone ,trazodone ,triazoledione )Piperoxan Prazosin Quinazosin Quinidine Silodosin Spegatrine Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,doxepin ,imipramine ,trimipramine )Trimazosin Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,loxapine ,thioridazine )Urapidil WB-4101 Zolertine
α2
Agonists Antagonists 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g.,asenapine ,brexpiprazole ,clozapine ,lurasidone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,zotepine )Azapirones (e.g.,buspirone ,gepirone ,ipsapirone ,tandospirone )BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan Ketanserin Lisuride mCPP Mianserin Mirtazapine NAN-190 Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine Setiptiline Spegatrine Spiroxatrine Sunepitron Terguride Tolazoline Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,loxapine ,thioridazine )Yohimbine
β
TAAR1 Tooltip Trace amine-associated receptor 1
TAAR5 Tooltip Trace amine-associated receptor 5
Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the
List of trace amines ,
TAAR , and
TAAR1 pages.
See also: Receptor/signaling modulators
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted 1-Aminomethylindanes (e.g.,2CB-Ind ,AMMI ,bromojimscaline ,jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam ,lorcaserin ,7-chlorolorcaserin ,SCHEMBL5334361 )3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine ,3-PPP ,OSU-6162 (PNU-96391) ,LPH-5 ,LPH-48 ,Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g.,adrenochrome ,adrenolutin )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,bromotomscaline ,S33005 ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI ,RU-27849 ,DEIMDHPCA ,DEMPDHPCA ,DEMPDHPCA-2C-D ,RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA ,TMT ,tranylcypromine )Phenylpiracetams (e.g.,phenylpiracetam ,MRZ-9547 ,RGPU-95 )Pyridopyrroloquinoxalines (e.g.,lumateperone ,deulumateperone ,IHCH-7079 ,IHCH-7086 ,IHCH-7113 ,ITI-1549 )Tetrahydrobenzopyranylamines (e.g.,CT-5126 )Tolazoline Tricyclics (e.g.,AMDA ,AMDH ,benzoctamine ,dizocilpine ,SpAMDA )ZC-B
Related compounds 2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g.,1,3-DMBA Tooltip 1,3-dimethylbutylamine ,1,4-DMAA Tooltip 1,4-dimethylamylamine ,heptaminol ,iproheptine ,isometheptene ,methylhexanamine/ 1,3-DMAA ,octodrine ,oenethyl ,tuaminoheptane )Benzylamines (e.g.,benzylamine ,α-methylbenzylamine ,MDM1EA ,ALPHA ,M-ALPHA ,pargyline )Benzylpiperazines (e.g.,benzylpiperazine ,MDBZP ,fipexide )Cyclohexylaminopropanes (e.g.,propylhexedrine ,norpropylhexedrine )Cyclopentylaminopropanes (e.g.,isocyclamine ,cyclopentamine )Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine ,CT-4719 ,ORG-37684 )Phenylalkenylamines (e.g.,phenylbutenamine )Phenylalkynylamines (e.g.,phenylbutynamine )Phenylpiperazines (e.g.,1-phenylpiperazine ,mCPP Tooltip meta-chlorophenylpiperazine ,TFMPP Tooltip trifluoromethylphenylpiperazine ,oMPP Tooltip ortho-methylphenylpiperazine ,pFPP Tooltip para-fluorophenylpiperazine ,pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g.,phenylpropylamine ,homo-MDA ,homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine ,methiopropamine ,thiothinone )
