Chemistry:Dinapsoline

Dinapsoline
Clinical data
ATC code	none;
Identifiers
	IUPAC name 8,9-dihydroxy-2,3,7,11b-tetrahydro-1H-naph[1,2,3-de]isoquinoline;
CAS Number	458563-40-1 ;
PubChem CID	9816455;
ChemSpider	7992205 ;
UNII	GZ9XC6C5P9;
Chemical and physical data
Formula	C16H15NO2
Molar mass	253.301 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc1c3c(ccc1O)[C@H]4c2c(cccc2C3)CNC4;
	InChI InChI=1S/C16H15NO2/c18-14-5-4-11-12(16(14)19)6-9-2-1-3-10-7-17-8-13(11)15(9)10/h1-5,13,17-19H,6-8H2/t13-/m0/s1 ; Key:ZQTSNGJHMUKLOM-ZDUSSCGKSA-N ;
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Short description: Chemical compound

Dinapsoline is a drug developed for the treatment of Parkinson's disease,^[1] that acts as a selective full agonist at the dopamine D₁ receptor.^[2]^[3]^[4]^[5]

References

↑ "Dinapsoline: characterization of a D1 dopamine receptor agonist in a rat model of Parkinson's disease". The Journal of Pharmacology and Experimental Therapeutics 296 (2): 338–44. February 2001. PMID 11160615.
↑ "9-Dihydroxy-2,3,7,11b-tetrahydro-1H-naph[1,2,3-de]isoquinoline: a potent full dopamine D1 agonist containing a rigid-beta-phenyldopamine pharmacophore". Journal of Medicinal Chemistry 39 (2): 549–55. January 1996. doi:10.1021/jm950707+. PMID 8558526.
↑ "(+)-Dinapsoline: an efficient synthesis and pharmacological profile of a novel dopamine agonist". Journal of Medicinal Chemistry 45 (17): 3660–8. August 2002. doi:10.1021/jm0101545. PMID 12166939.
↑ "Synthesis and SAR exploration of dinapsoline analogues". Bioorg. Med. Chem. 12 (4): 715–34. February 2004. doi:10.1016/j.bmc.2003.11.015. PMID 14759732.
↑ "Effects of dopamine D1 receptor agonists in rats trained to discriminate dihydrexidine". Psychopharmacology 186 (1): 25–31. May 2006. doi:10.1007/s00213-006-0342-2. PMID 16575553.

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Original source: https://en.wikipedia.org/wiki/Dinapsoline. Read more

[pmid11160615-1] "Dinapsoline: characterization of a D1 dopamine receptor agonist in a rat model of Parkinson's disease". The Journal of Pharmacology and Experimental Therapeutics 296 (2): 338–44. February 2001. PMID 11160615.

[pmid8558526-2] "9-Dihydroxy-2,3,7,11b-tetrahydro-1H-naph[1,2,3-de]isoquinoline: a potent full dopamine D1 agonist containing a rigid-beta-phenyldopamine pharmacophore". Journal of Medicinal Chemistry 39 (2): 549–55. January 1996. doi:10.1021/jm950707+. PMID 8558526.

[pmid12166939-3] "(+)-Dinapsoline: an efficient synthesis and pharmacological profile of a novel dopamine agonist". Journal of Medicinal Chemistry 45 (17): 3660–8. August 2002. doi:10.1021/jm0101545. PMID 12166939.

[pmid14759732-4] "Synthesis and SAR exploration of dinapsoline analogues". Bioorg. Med. Chem. 12 (4): 715–34. February 2004. doi:10.1016/j.bmc.2003.11.015. PMID 14759732.

[pmid16575553-5] "Effects of dopamine D1 receptor agonists in rats trained to discriminate dihydrexidine". Psychopharmacology 186 (1): 25–31. May 2006. doi:10.1007/s00213-006-0342-2. PMID 16575553.

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[5]

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Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
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Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 5-DBFPV α-PPP α-PBP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
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ATC code: N06B

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Clinical data

ATC code	none
Identifiers
IUPAC name 8,9-dihydroxy-2,3,7,11b-tetrahydro-1H-naph[1,2,3-de]isoquinoline
CAS Number	458563-40-1^Y
PubChem CID	9816455
ChemSpider	7992205^N
UNII	GZ9XC6C5P9
Chemical and physical data
Formula	C₁₆H₁₅NO₂
Molar mass	253.301 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Oc1c3c(ccc1O)[C@H]4c2c(cccc2C3)CNC4
InChI InChI=1S/C16H15NO2/c18-14-5-4-11-12(16(14)19)6-9-2-1-3-10-7-17-8-13(11)15(9)10/h1-5,13,17-19H,6-8H2/t13-/m0/s1^N Key:ZQTSNGJHMUKLOM-ZDUSSCGKSA-N^N
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