Ciclafrine

Ciclafrine
Clinical data
Other names	Go 3026A; W-43026A
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;
UNII	76HZX0GVCD;
ChEMBL	ChEMBL2110798;
CompTox Dashboard (EPA)	DTXSID60971060 ;
Chemical and physical data
Formula	C15H21NO2
Molar mass	247.338 g·mol−1
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 (INNTooltip International Nonproprietary Name; developmental code names Go 3026A, W-43026A) is a sympathomimetic and antihypotensive agent of the phenethylamine family that was never marketed.^[1]^[2]^[3]^[4]

Chemistry

Ciclafrine is a substituted phenethylamine and belongs to the class of hemiaminal ethers.

Synthesis

Ciclafrine can be prepared by the reaction of norfenefrine with cycloheptanone.^[5]

References

^ Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 271. ISBN 978-1-4757-2085-3. Retrieved 2024-08-31.
^ Ganellin CR, Triggle DJ (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 586–. ISBN 978-0-412-46630-4.
^ Milne, G.W.A. (2018). Drugs: Synonyms and Properties. Routledge Revivals. Taylor & Francis. p. 325. ISBN 978-1-351-78990-5. Retrieved 31 August 2024.
^ Korolkovas A (1988). Essentials of medicinal chemistry. John Wiley & Sons, Incorporated. p. 405. ISBN 978-0-471-88356-2.
^ DE 2336746, Satzinger, Gerhard & Herrmann, Manfred, "2-Hydroxyphenyl-1-oxa-4-azaspiro-alkan-Derivate [2-Hydroxyphenyl-1-oxa-4-azaspiro-alkane derivatives]", published 1975-02-13, assigned to Gödecke AG

[Elks2014-1] Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 271. ISBN 978-1-4757-2085-3. Retrieved 2024-08-31.

[GanellinTriggle1996-2] Ganellin CR, Triggle DJ (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 586–. ISBN 978-0-412-46630-4.

[Milne2018-3] Milne, G.W.A. (2018). Drugs: Synonyms and Properties. Routledge Revivals. Taylor & Francis. p. 325. ISBN 978-1-351-78990-5. Retrieved 31 August 2024.

[Korolkovas1988-4] Korolkovas A (1988). Essentials of medicinal chemistry. John Wiley & Sons, Incorporated. p. 405. ISBN 978-0-471-88356-2.

[5] DE 2336746, Satzinger, Gerhard & Herrmann, Manfred, "2-Hydroxyphenyl-1-oxa-4-azaspiro-alkan-Derivate [2-Hydroxyphenyl-1-oxa-4-azaspiro-alkane derivatives]", published 1975-02-13, assigned to Gödecke AG

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[2]

[3]

[4]

[5]

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 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 ZDCM-04 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 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 (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) 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 N-Ethylhexedrone N-Ethylpentedrone 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) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

Ciclafrine

Chemistry

Synthesis

See also

References