Chemistry:Adimolol

Adimolol
Clinical data
ATC code	none;
Identifiers
	IUPAC name 3-[3-[[2-hydroxy-3-(1-naphthyloxy)propyl]amino]-3-methyl-butyl]-1H-benzimidazol-2-one;
CAS Number	78459-19-5 ;
PubChem CID	71227;
ChemSpider	64362 ;
UNII	B6CJY5K2ST;
ChEMBL	ChEMBL1742448 ;
Chemical and physical data
Formula	C25H29N3O3
Molar mass	419.525 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2Nc1ccccc1N2CCC(NCC(O)COc4c3ccccc3ccc4)(C)C;
	InChI InChI=1S/C25H29N3O3/c1-25(2,14-15-28-22-12-6-5-11-21(22)27-24(28)30)26-16-19(29)17-31-23-13-7-9-18-8-3-4-10-20(18)23/h3-13,19,26,29H,14-17H2,1-2H3,(H,27,30) ; Key:YWRIUGFSIQMHJK-UHFFFAOYSA-N ;
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Short description: Chemical compound

Adimolol (developmental code name MEN-935) is antihypertensive agent which acts as a non-selective α₁-, α₂-, and β-adrenergic receptor antagonist.^[1]

Synthesis

The reaction between 1-Naphthyl glycidyl ether [2461-42-9] (1) and 3-(3-amino-3-methylbutyl)-1H-benzimidazol-2-one [64928-58-1] (2) gives adimolol (3).

References

↑ "Interactions of MEN 935 (adimolol), a long acting beta- and alpha-adrenolytic antihypertensive agent, with postsynaptic alpha-adrenoceptors in different isolated blood vessels--influence of angiotensin II". Naunyn-Schmiedeberg's Archives of Pharmacology 333 (3): 277–83. July 1986. doi:10.1007/bf00512941. PMID 3020439.
↑ "Adimolol Hydrochloride Hydrate.". Drugs of the Future 11: 9. 1986. doi:10.1358/dof.1986.011.01.62036.
↑ Koppe H, Mentrup A, Renth EO, Schromm K, Hoefke W, Muacevic G, US patent 4255430, issued 1981, assigned to Boehringer Ingelheim Gmbh.

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[pmid3020439-1] "Interactions of MEN 935 (adimolol), a long acting beta- and alpha-adrenolytic antihypertensive agent, with postsynaptic alpha-adrenoceptors in different isolated blood vessels--influence of angiotensin II". Naunyn-Schmiedeberg's Archives of Pharmacology 333 (3): 277–83. July 1986. doi:10.1007/bf00512941. PMID 3020439.

[2] "Adimolol Hydrochloride Hydrate.". Drugs of the Future 11: 9. 1986. doi:10.1358/dof.1986.011.01.62036.

[3] Koppe H, Mentrup A, Renth EO, Schromm K, Hoefke W, Muacevic G, US patent 4255430, issued 1981, assigned to Boehringer Ingelheim Gmbh.

[1]

[2]

[3]

v t e Adrenergic receptor modulators
α₁	Agonists: 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Desglymidodrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline Antagonists: Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., brexpiprazole, clozapine,Chemistry:Olanzapine
α₂	Agonists: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rezatomidine Rilmenidine Romifidine Talipexole Tasipimidine Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil Vatinoxan XP21279 Xylazine Xylometazoline Antagonists: 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, Chemistry:Brexpiprazole
β	Agonists: Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Colterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

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Clinical data

ATC code	none
Identifiers
IUPAC name 3-[3-[[2-hydroxy-3-(1-naphthyloxy)propyl]amino]-3-methyl-butyl]-1H-benzimidazol-2-one
CAS Number	78459-19-5^N
PubChem CID	71227
ChemSpider	64362^Y
UNII	B6CJY5K2ST
ChEMBL	ChEMBL1742448^N
Chemical and physical data
Formula	C₂₅H₂₉N₃O₃
Molar mass	419.525 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C2Nc1ccccc1N2CCC(NCC(O)COc4c3ccccc3ccc4)(C)C
InChI InChI=1S/C25H29N3O3/c1-25(2,14-15-28-22-12-6-5-11-21(22)27-24(28)30)26-16-19(29)17-31-23-13-7-9-18-8-3-4-10-20(18)23/h3-13,19,26,29H,14-17H2,1-2H3,(H,27,30)^Y Key:YWRIUGFSIQMHJK-UHFFFAOYSA-N^Y
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