Ciladopa

Ciladopa
Clinical data
Other names	AY-27,110
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 2-{4-[(2S)-2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]piperazin-1-yl}cyclohepta-2,4,6-trien-1-one;
CAS Number	80109-27-9;
PubChem CID	133371;
ChemSpider	117659;
UNII	D09L486R3J;
ChEMBL	ChEMBL2110793;
CompTox Dashboard (EPA)	DTXSID101024642 ;
Chemical and physical data
Formula	C21H26N2O4
Molar mass	370.449 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C3/C=C\C=C/C=C3/N2CCN(C[C@@H](O)c1ccc(OC)c(OC)c1)CC2;

Ciladopa (developmental code name AY-27,110) is a dopamine agonist with a similar chemical structure to dopamine.^[1] It was under investigation as an antiparkinsonian agent but was discontinued due to concerns of tumorogenesis in rodents.^[2]^[3]^[4]^[5]

References

^ Voith K (1985). "The comparative long-term effects of ciladopa (AY-27,110), a chemically novel dopaminergic agonist, in 6-OHDA-lesioned and intact rats". Psychopharmacology. 85 (4): 405–9. doi:10.1007/BF00429654. PMID 3927334. S2CID 1573473.
^ Koller WC, Fields JZ, Gordon JH, Perlow MJ (September 1986). "Evaluation of ciladopa hydrochloride as a potential anti-Parkinson drug". Neuropharmacology. 25 (9): 973–9. doi:10.1016/0028-3908(86)90190-5. PMID 3774130. S2CID 19175441.
^ Weiner WJ, Factor SA, Sanchez-Ramos J, Berger J (1987). "A double-blind evaluation of ciladopa in Parkinson's disease". Movement Disorders. 2 (3): 211–7. doi:10.1002/mds.870020308. PMID 3332914. S2CID 31784301.
^ Lieberman A, Gopinathan G, Neophytides A, Pasternack P, Goldstein M (May 1987). "Advanced Parkinson's disease: use of partial dopamine agonist, ciladopa". Neurology. 37 (5): 863–5. doi:10.1212/wnl.37.5.863. PMID 3574692. S2CID 25273606.
^ Lang AE (August 1987). "Update on dopamine agonists in Parkinson's disease: "beyond bromocriptine"". The Canadian Journal of Neurological Sciences. 14 (3 Suppl): 474–82. doi:10.1017/s031716710003794x. PMID 3315148.

[pmid3927334-1] Voith K (1985). "The comparative long-term effects of ciladopa (AY-27,110), a chemically novel dopaminergic agonist, in 6-OHDA-lesioned and intact rats". Psychopharmacology. 85 (4): 405–9. doi:10.1007/BF00429654. PMID 3927334. S2CID 1573473.

[pmid3774130-2] Koller WC, Fields JZ, Gordon JH, Perlow MJ (September 1986). "Evaluation of ciladopa hydrochloride as a potential anti-Parkinson drug". Neuropharmacology. 25 (9): 973–9. doi:10.1016/0028-3908(86)90190-5. PMID 3774130. S2CID 19175441.

[pmid3332914-3] Weiner WJ, Factor SA, Sanchez-Ramos J, Berger J (1987). "A double-blind evaluation of ciladopa in Parkinson's disease". Movement Disorders. 2 (3): 211–7. doi:10.1002/mds.870020308. PMID 3332914. S2CID 31784301.

[pmid3574692-4] Lieberman A, Gopinathan G, Neophytides A, Pasternack P, Goldstein M (May 1987). "Advanced Parkinson's disease: use of partial dopamine agonist, ciladopa". Neurology. 37 (5): 863–5. doi:10.1212/wnl.37.5.863. PMID 3574692. S2CID 25273606.

[pmid3315148-5] Lang AE (August 1987). "Update on dopamine agonists in Parkinson's disease: "beyond bromocriptine"". The Canadian Journal of Neurological Sciences. 14 (3 Suppl): 474–82. doi:10.1017/s031716710003794x. PMID 3315148.

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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