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Fosopamine

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Pharmaceutical compound

Fosopamine
Clinical data

Other names	Fosfenamine;N-Methyldopamine 4-O-phosphate; Epinine 4-O-phosphate; SIM-2055; Z-2055
Routes of administration	Oral^[1]
Drug class	Dopamine receptor agonist^[1]
Identifiers
IUPAC name [2-hydroxy-4-[2-(methylamino)ethyl]phenyl] dihydrogen phosphate
CAS Number	103878-96-2
PubChemCID	65878
ChemSpider	59287
UNII	50Q2Q042YR
ChEMBL	ChEMBL2104671
CompTox Dashboard(EPA)	DTXSID70869409
Chemical and physical data
Formula	C₉H₁₄NO₅P
Molar mass	247.187 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CNCCC1=CC(=C(C=C1)OP(=O)(O)O)O
InChI InChI=1S/C9H14NO5P/c1-10-5-4-7-2-3-9(8(11)6-7)15-16(12,13)14/h2-3,6,10-11H,4-5H2,1H3,(H2,12,13,14) Key:WHEGQKBWPSOMHG-UHFFFAOYSA-N

Fosopamine (INNTooltip International Nonproprietary Name; developmental code namesSIM-2055,Z-2055; also known asfosfenamine orN-methyldopamine 4-O-phosphate) is adopamine receptor agonist of thephenethylamine andcatecholamine families which was under development for the treatment ofhypertension but was never marketed.^[1]^[2] It is takenorally.^[1] Fosopamine is aprodrug ofepinine (N-methyldopaine) and is said to beselectively metabolized into epinine in thekidneys.^[3] The drug was being developed byAstraZeneca and Zambon Group SpA.^[1] It reachedphase 2 clinical trials prior to the discontinuation of its development.^[1]

References

[edit]

^^a ^b ^c ^d ^e ^f"Fosopamine".AdisInsight. 7 April 1999. Retrieved27 February 2025.
^Negwer M (1994).Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag.ISBN 978-3-05-500156-7. Retrieved27 February 2025.
^Supuran C, Angeli A, Tanini D (2024).Advances in Prodrugs: Design and Therapeutic Applications. Elsevier. p. 296.ISBN 978-0-443-15634-2. Retrieved27 February 2025.

Adrenergic receptor modulators

α₁

Agonists

Antagonists

α₂

Agonists

Antagonists

Agonists

Antagonists

See also:Receptor/signaling modulators
Dopaminergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

Dopamine receptor modulators

D₁-like

Agonists	Benzazepines:6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines:Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride Dihydrexidine derivatives:A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine Phenethylamines:BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Melevodopa L-Phenylalanine L-Tyrosine XP21279 Others:A-68930 Apomorphine Isocorypalmine Nuciferine PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine SKF-89,145 SKF-89,626 Stepholidine Tavapadon Tetrahydropalmatine
PAMs	Tetrahydroisoquinolines:DETQ DPTQ Mevidalen
Antagonists	Typical antipsychotics:Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol Atypical antipsychotics:Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (+fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Zicronapine Ziprasidone Zotepine Others:Berupipam Ecopipam EEDQ Metitepine (methiothepin) Odapipam Perlapine SCH-23390

D₂-like

Agonists

Phenethylamines:Deoxyepinephrine (N-methyldopamine, epinine)
Dopexamine
Etilevodopa
Ibopamine
L-DOPA (levodopa)
L-Phenylalanine
L-Tyrosine
Melevodopa
XP21279

Atypical antipsychotics:Alentemol (U-66444B)
Aripiprazole (+sertraline)
Aripiprazole lauroxil
Bifeprunox
Brexpiprazole
Brilaroxazine
Cariprazine
F-15063
Lumateperone
Norclozapine

Antagonists

Antiemetics/gastroprokinetics/sedatives:Aceprometazine
AS-8112
Alimemazine
Alizapride
Benzquinamide
Bromopride
Clebopride
Deudomperidone
Domperidone
Eticlopride
Hydroxyzine
Itopride
Metoclopramide
Metopimazine
Promethazine
Thiethylperazine
Trazpiroben
Trimethobenzamide

See also:Receptor/signaling modulators
Adrenergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

Phenethylamines

Entactogens:Lophophine
MDPEA
MDMPEA

Amphetamines

Phentermines

Entactogens:MDPH
MDMPH

Others:Cericlamine

Cathinones

Phenylisobutylamines
(and further-extended)

Stimulants:α-Propylphenethylamine
Hexapradol
Phenylisobutylamine (α-ethylphenethylamine)

Catecholamines
(and close relatives)

Cyclized
phenethylamines

Phenylalkylpyrrolidines	α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP Fluorolintane MOPPP MOPVP MPBP MPEP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
2-Benzylpiperidines (phenidates)	2-Benzylpiperidine 3-Bromomethylphenidate 3-Chloromethylphenidate 3-Methylmethylphenidate 3,4-Dichloro-2-benzylpiperidine 3,4-Dichloroethylphenidate 3,4-Dichloromethylphenidate 4-Bromoethylphenidate 4-Bromomethylphenidate 4-Chloromethylphenidate 4-Fluoroethylphenidate 4-Fluoroisopropylphenidate 4-Fluoromethylphenidate 4-Methyl-2-benzylpiperidine 4-Methylisopropylphenidate 4-Methylmethylphenidate 4-Nitromethylphenidate α-Acetyl-2-benzylpiperidine α-Keto-2-benzylpiperidine CPMBP Desoxypipradrol (2-DPMP) Difemetorex Ethylnaphthidate (HDEP-28) Ethylphenidate Isopropylnaphthidate Isopropylphenidate MDMPH Methylnaphthidate (HDMP-28) Methylphenidate Phacetoperane Pipradrol Propylphenidate Rimiterol Ritalinamide Ritalinic acid SCH-5472 Serdexmethylphenidate
Phenylmorpholines (phenmetrazines)	(2R,3R)-Hydroxybupropion 2-(2,5-Dimethoxy-4-bromophenyl)morpholine 2-Fluorophenmetrazine 2-Methylphenmetrazine 2-Phenylmorpholine 2-Phenyl-3,6-dimethylmorpholine 3-Chlorophenmetrazine (PAL-594) 3-Fluorophenetrazine 3-Fluorophenmetrazine (PAL-593) 3-Methoxyphenmetrazine 3-Methylphenmetrazine (PAL-773) 4-Fluorophenmetrazine (PAL-748) 4-Methylphendimetrazine 4-Methylphenmetrazine (PAL-747) 2C-B-morpholine Fenbutrazate Fenmetramide Flumexadol G-130 Isophenmetrazine Manifaxine Methylenedioxyphenmetrazine Morazone N-Ethylphenmetrazol Naphthylmetrazine (PAL-704) Naphthylmorpholine (PAL-678) Oxaflozane PDM-35 PF-219,061) Phendimetrazine Phenetrazine Phenmetetrazine Phenmetrazine Phenmetrazol Pseudophenmetrazine Radafaxine ((2S,3S)-hydroxybupropion)
Phenyloxazolamines (aminorexes)	3-Methylaminorex 4-Ethylaminorex (4-EAR) 4'-Fluoroaminorex 4-Methylaminorex (4-MAR) 4,4'-Dimethylaminorex (4,4'-DMAR) 2C-B-aminorex 2F-MAR 4B-MAR 4C-MAR 4F-MAR Aminorex Clominorex Cyclazodone Ephedroxane Fenozolone Fluminorex MDMAR Methylenedioxyaminorex (MDAR) N-Methylcyclazodone N,N-Dimethylaminorex Pemoline Thozalinone
Isoquinolines and tetrahydroisoquinolines	Anhalamine Anhalidine Anhalinine Anhalonidine Anhalonine Anhalotine Arizonine Calycotomine Carnegine (pectenine) Corypalline Debrisoquine Deglucopterocereine Deutetrabenazine Diclofensine DOB-CR DOM-CR Esproquin Gigantine Hedycarine Heliamine Hydrastinine Hydrocotarnine Hydrohydrastinine (MDMTHIQ; MDMA-CR) Isoanhalamine Isoanhalidine Isoanhalonidine Isocorypalline Isopellotine Isosalsoline Lemaireocereine Longimammamine Longimammatine Longimammidine Longimammosine Lophocerine Lophophorine Lophotine MDMA-CR Mescalotam N-Methylanhalinine N-Methylheliamine N-Methylisosalsoline N-Methyl-DOM-CR (Beatrice-CR) N-Methyl-THIQ (METH-CR) Nomifensine Norsalsolinol Nortehaunine Norweberine O-Methylanhalonidine O-Methylpellotine Pachycereine Pellotine Perafensine Peyoglutam Peyophorine Peyotine PMMA-CR Quinisocaine Reticuline Salsolidine Salsoline Salsolinol TDIQ (MDTHIQ, MDA-CR) Tehaunine TehaunineN-oxide Tepenine Tetrabenazine Tetrahydroisoquinoline (THIQ; AMPH-CR) Tetrahydropapaveroline Tilisolol Tretoquinol Uberine Valbenazine Weberidine Weberine Zelandopam
2-Aminoindanes	2-Aminoindane (2-AI) 5-IAI Aprindine BFAI BFMAI DHAI DOM-AI ETAI Indantadol MDAI MDMAI MEAI (5-MeO-AI) MMAI NM-2-AI PNU-99,194 Pyr-AI TAI
2-Aminotetralins	2-Aminotetralin (2-AT) 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 CHF-1024 DOM-AT MDAT MDMAT Nolomirole UH-232
Others / unsorted	1-Aminomethylindanes (e.g.,2CB-Ind,AMMI,bromojimscaline,jimscaline) 2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam,lorcaserin,7-chlorolorcaserin,SCHEMBL5334361) 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine,3-PPP,OSU-6162 (PNU-96391),LPH-5,LPH-48,Z3517967757 (Z7757)) 6-AB AL-1095 Aminochromes (e.g.,adrenochrome,adrenolutin) Benzocyclobutenes (e.g.,2CBCB-NBOMe,bromotomscaline,S33005,TCB-2,tomscaline) Benzoxepins (e.g.,BBOX,IBOX,TFMBOX) Butyltolylquinuclidine Camfetamine Cypenamine (trans-2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD) Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI,RU-27849,DEIMDHPCA,DEMPDHPCA,DEMPDHPCA-2C-D,RU-27251) PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA,TMT,tranylcypromine) Phenylpiracetams (e.g.,phenylpiracetam,MRZ-9547,RGPU-95) Pyridopyrroloquinoxalines (e.g.,lumateperone,deulumateperone,IHCH-7079,IHCH-7086,IHCH-7113,ITI-1549) Tetrahydrobenzopyranylamines (e.g.,CT-5126) Tolazoline Tricyclics (e.g.,AMDA,AMDH,benzoctamine,dizocilpine,SpAMDA) ZC-B

Related compounds

2-Furylethylamine
2-Pyrrolylethylamine
3-Pyrrolylethylamine
3-Pyrrolylpropylamine
2-Tetrahydrofurylethylamine
4-Benzylpiperidine
7-AB
Alkylamines (e.g.,1,3-DMBATooltip 1,3-dimethylbutylamine,1,4-DMAATooltip 1,4-dimethylamylamine,heptaminol,iproheptine,isometheptene,methylhexanamine/1,3-DMAA,octodrine,oenethyl,tuaminoheptane)
Benzylamines (e.g.,benzylamine,α-methylbenzylamine,MDM1EA,ALPHA,M-ALPHA,pargyline)
Benzylpiperazines (e.g.,benzylpiperazine,MDBZP,fipexide)
Cyclohexylaminopropanes (e.g.,propylhexedrine,norpropylhexedrine)
Cyclopentylaminopropanes (e.g.,isocyclamine,cyclopentamine)
Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine,CT-4719,ORG-37684)
Phenylalkenylamines (e.g.,phenylbutenamine)
Phenylalkynylamines (e.g.,phenylbutynamine)
Phenylpiperazines (e.g.,1-phenylpiperazine,mCPPTooltip meta-chlorophenylpiperazine,TFMPPTooltip trifluoromethylphenylpiperazine,oMPPTooltip ortho-methylphenylpiperazine,pFPPTooltip para-fluorophenylpiperazine,pMeOPPTooltip para-methoxyphenylpiperazine)
Phenylpropylamines (e.g.,phenylpropylamine,homo-MDA,homo-MDMA)
Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine,methiopropamine,thiothinone)

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