Ciclafrine

Ciclafrine
Clinical data

ATC code	None
Identifiers
IUPAC name 3-(1-Oxa-4-azaspiro[4.6]undec-2-yl)phenol
CAS Number	55694-98-9
PubChem CID	193971
ChemSpider	168322
Chemical and physical data
Formula	C₁₅H₂₁NO₂
Molar mass	247.333 g/mol
3D model (JSmol)	Interactive image
SMILES c1cc(cc(c1)O)C2CNC3(O2)CCCCCC3
InChI InChI=1S/C15H21NO2/c17-13-7-5-6-12(10-13)14-11-16-15(18-14)8-3-1-2-4-9-15/h5-7,10,14,16-17H,1-4,8-9,11H2 Key:AJNAKEPPGKJNKU-UHFFFAOYSA-N

Ciclafrine (INN) is a sympathomimetic phenethylamine and antihypertensive which does not appear to have ever been marketed.^[1]^[2]

Synthesis

Ciclafrine synthesis: Satzinger and Herrmann, DE 2336746 (1975).

References

↑ C.R. Ganellin; David J. Triggle (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 586–. ISBN 978-0-412-46630-4.
↑ Andrejus Korolkovas (1988). Essentials of medicinal chemistry. John Wiley & Sons, Incorporated. p. 405. ISBN 978-0-471-88356-2.

Sympatholytic (and closely related) antihypertensives (C02)

Sympatholytics
(antagonize α-adrenergic
vasoconstriction)

Central

α₂ agonist	Clonidine Guanabenz Guanfacine Methyldopa^# Tiamenidine^‡
Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guanethidine Guanoclor Guanazodine Guanoxabenz Guanoxan
Imidazoline receptor agonist	Moxonidine Rilmenidine Tolonidine
Ganglion-blocking/nicotinic antagonist	Hexamethonium^‡ Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

MAOI	Pargyline^‡
Adrenergic uptake inhibitor	Bietaserpine Deserpidine Methoserpidine Rescinnamine Reserpine Syrosingopine
Tyrosine hydroxylase inhibitor	Metirosine

Direct

α₁ blockers	Prazosin Indoramin Trimazosin Doxazosin Urapidil
Non-selective α blocker	Phentolamine

Other antagonists

Serotonin antagonist	Ketanserin Lidanserin
Endothelin antagonist (for PH)	dual (Bosentan, Macitentan) selective (Ambrisentan, Sitaxentan)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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., clozapine, olanzapine, quetiapine, risperidone); Benoxathian; Buflomedil; Bunazosin; Carvedilol; Corynanthine; Dapiprazole; Domesticine; Doxazosin; Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride); Etoperidone; Eugenodilol; Fenspiride; Hydroxyzine; Indoramin; Ketanserin; L-765,314; Labetalol; mCPP; Mepiprazole; Metazosin; Monatepil; Moxisylyte; Naftopidil; Nantenine; Nefazodone; Neldazosin; Niaprazine; Nicergoline; Niguldipine; Pardoprunox; Pelanserin; Phendioxan; Phenoxybenzamine; Phentolamine; Piperoxan; Prazosin; Quinazosin; Ritanserin; Silodosin; Spiperone; Talipexole; Tamsulosin; Terazosin; Tiodazosin; Tolazoline; Trazodone; 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: (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; Tetrahydrozoline; Tiamenidine; Tizanidine; Tolonidine; Urapidil; XP21279; Xylazine; Xylometazoline

Antagonists: 1-PP; Adimolol; Aptazapine; Atipamezole; Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine); Azapirones (e.g., buspirone, tandospirone); BRL-44408; Buflomedil; Cirazoline; Efaroxan; Esmirtazapine; Fenmetozole; Fluparoxan; Idazoxan; mCPP; Mianserin; Mirtazapine; NAN-190; Olanzapine; Pardoprunox; Phentolamine; Phenoxybenzamine; Piperoxan; Piribedil; Rauwolscine; Rotigotine; SB-269970; Setiptiline; Spiroxatrine; Sunepitron; Tolazoline; Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine); Yohimbine

Agonists: Abediterol; Alifedrine; Amibegron; Arbutamine; Arformoterol; Arotinolol; BAAM; Bambuterol; Befunolol; Bitolterol; Broxaterol; Buphenine; Carbuterol; Carmoterol; Cimaterol; Clenbuterol; 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

See also: Receptor/signaling modulators

Dopaminergics

Serotonergics

Monoamine reuptake inhibitors

Monoamine releasing agents

Monoamine metabolism modulators

Monoamine neurotoxins

Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-N 2C-P 2C-SE 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-21 2C-TFM 2C-YN Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA MDEA MDHMA MDMA MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Theodrenaline Thiamphenicol UWA-101

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