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Pharmaceutical compound
Nolomirole Other names CHF-1035; CHF1035; 5,6-Diisobutyryloxy-N -methyl-2-aminotetralin; 5,6-Diisobutyryloxy-2-(methylamino)-1,2,3,4-tetrahydronaphthalene; 5,6,7,8-Tetrahydro-6-(methylamino)-1,2-naphthylene diisobutyrate; N -Methyl-2-aminotetralin Routes of Oral [ 1] [ 2] Drug class Dopamine D2 receptor agonist ; α2 -Adrenergic receptor agonist
[6-(methylamino)-1-(2-methylpropanoyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl] 2-methylpropanoate
CAS Number PubChem CID ChemSpider UNII ChEMBL Formula C 19 H 27 N O 4 Molar mass −1 3D model (JSmol )
CC(C)C(=O)OC1=C(C2=C(CC(CC2)NC)C=C1)OC(=O)C(C)C
InChI=1S/C19H27NO4/c1-11(2)18(21)23-16-9-6-13-10-14(20-5)7-8-15(13)17(16)24-19(22)12(3)4/h6,9,11-12,14,20H,7-8,10H2,1-5H3
Key:OMMYLOLVPCCZQZ-UHFFFAOYSA-N
Nolomirole (INN Tooltip International Nonproprietary Name ; developmental code name CHF-1035 ), also known as 5,6-diisobutyryloxy-N -methyl-2-aminotetralin , is a dual dopamine D2 and α2 -adrenergic receptor agonist which was under development for the treatment of heart failure but was never marketed.[ 1] [ 2] [ 3] [ 4] orally .[ 1] [ 2]
The drug acts as an agonist of the dopamine D2 receptor, with an affinity (Ki ) of 120 nM for the (–)- enantiomer and 2,400 nM for the (+)- enantiomer, and as an agonist of the α2 -adrenergic receptor, with an affinity (Ki ) of 130 nM for the (–)- enantiomer and 1,600 nM for the (+)- enantiomer.[ 1] [ 2] prodrug of CHF-1024 (5,6-dihydroxy-N -methyl-2-aminotetralin), to which it is rapidly hydrolyzed by circulating esterase enzymes .[ 1] elimination half-life of nolomirole is said to be 3 hours and its log P is 1.97.[ 3] cyclized phenethylamines and 2-aminotetralin analogues of the catecholamine neurotransmitter dopamine and its N -methyl derivative epinine (deoxyepinephrine, N -methyldopamine).[ 1] [ 2]
Nolomirole was first described in the scientific literature by 1992.[ 1] [ 5] pharmaceutical company Chiesi in the 1990s and 2000s.[ 1] [ 4] phase 3 clinical trials prior to the discontinuation of its development.[ 1] [ 4]
^ a b c d e f g h i Mealy, N.E.; Leeson, P.A.; Bayes, M.; Castaner, J. (2001). "Nolomirole Hydrochloride" . Drugs of the Future . 26 (11): 1046. doi :10.1358/dof.2001.026.11.642071 . Retrieved 19 June 2025 . ^ a b c d e Tang WH, Francis GS (November 2003). "Novel pharmacological treatments for heart failure". Expert Opin Investig Drugs . 12 (11): 1791– 1801. doi :10.1517/13543784.12.11.1791 . PMID 14585055 . ^ a b Dörwald, Florencio Zaragoza (4 February 2013). Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds ISBN 978-3-527-64565-7 . Retrieved 19 June 2025 . ^ a b c "Nolomirole hydrochloride" . AdisInsight . 9 January 2002. Retrieved 19 June 2025 .^ Redenti, Enrico; Fronza, Giovanni; Bovis, Giovanni; Ventura, Paolo (1992). "Application of γ‐cyclodextrin to enantiomeric purity determination of a new 2‐amino‐tetralin derivative by 1 H‐NMR spectroscopy" . Chirality . 4 (6): 404– 405. doi :10.1002/chir.530040613 . ISSN 0899-0042 . Retrieved 19 June 2025 .
α1
Agonists Antagonists
Abanoquil 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
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 , jimscaline )2-ADN 2-Benzhydrylpyrrolidine 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 )6-AB AL-1095 Aminochromes (e.g., adrenochrome , adrenolutin )Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , S33005 , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )Butyltolylquinuclidine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g., LSD )GYKI-52895 HDMP-29 Ivabradine Lumateperone and analogues (e.g., IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )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 )Tetrahydrobenzopyranylamines (e.g., CT-5126 )Tricyclics (e.g., benzoctamine , dizocilpine )Z3517967757 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 )
