From Wikipedia, the free encyclopedia
Neuroleptic
Pharmaceutical compound
Mefeclorazine
1-(2-chlorophenyl)-4-[2-(3,4-dimethoxyphenyl)ethyl]piperazine
CAS Number PubChem CID ChemSpider UNII ChEMBL CompTox Dashboard (EPA ) Formula C 20 H 25 Cl N 2 O 2 Molar mass −1 3D model (JSmol )
COC1=C(C=C(C=C1)CCN2CCN(CC2)C3=CC=CC=C3Cl)OC
InChI=1S/C20H25ClN2O2/c1-24-19-8-7-16(15-20(19)25-2)9-10-22-11-13-23(14-12-22)18-6-4-3-5-17(18)21/h3-8,15H,9-14H2,1-2H3
Key:PJDRMPCBIWKBJA-UHFFFAOYSA-N
Mefeclorazine (INN Tooltip International Nonproprietary Name ) is a neuroleptic (antipsychotic) of the phenethylamine and arylpiperazine groups.[ 1] [ 2] [ 3]
Part of mefeclorazine's chemical structure is based on 3,4-dimethoxyphenethylamine (DMPEA or homoveratrylamine), which has structural similarity to the neurotransmitter dopamine .[ 1] Eli Lilly in 1958.[ 4] [ 1]
The ortho -chlorophenylpiperazinemoiety forms part of the molecular structure.[ 1] precursor finds dual use in the synthesis of the arylpiperazines enpiprazole and KMUP-1 .[citation needed
^ a b c d Elks J, Ganellin CR (1990). Dictionary of drugs: Chemical Data, Structures, and Bibliographies ISBN 978-1-4757-2085-3 Mefeclorazine, INN 1-(2-Chlorophenyl)-4-(3,4-dimethoxyphenethyl)-piperazine. SD 218-06 [1243-33-0] [...] C20H25ClN202 M 360.883 M-00061 Neuroleptic agent. [...] ^ Ratouis R, Boissier JR, Dumont C (January 1965). "Synthesis and Pharmacological Study of New Piperazine Derivatives. II. Phenethylpiperazines". Journal of Medicinal Chemistry . 8 (1): 104– 107. doi :10.1021/jm00325a021 . PMID 14287237 . ^ Boissier JR (1963). "A new class of neuroleptics: N, N'-disubstituted piperazines". Psychopharmacol. Methods . Proc. Symp. 1961 . Prague: 92– 100. ^ US 2927924 , Mills J, "Phenethyl substituted piperazines", issued 8 March 1960, assigned to Eli Lilly & Co.
Phenylpiperazines
1-Phenylpiperazine (1-PP; PP) 3,4-CFP 2C-B-PP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-7625 EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635 Benzylpiperazines Naphthylpiperazines Quinolinylpiperazines Diphenylalkylpiperazines Pyrimidinylpiperazines Pyridinylpiperazines Benzo(iso)thiazolyl piperazines Tricyclic -linked piperazinesOthers/uncategorized
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted
1-Aminomethylindanes (e.g., 2CB-Ind , AMMI , jimscaline )2-ADN 2-Benzhydrylpyrrolidine 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 )6-AB AL-1095 Aminochromes (e.g., adrenochrome , adrenolutin )Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , S33005 , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )Butyltolylquinuclidine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g., LSD )GYKI-52895 HDMP-29 Ivabradine Lumateperone and analogues (e.g., IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )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 )Tetrahydrobenzopyranylamines (e.g., CT-5126 )Tricyclics (e.g., benzoctamine , dizocilpine )Z3517967757 ZC-B
Related compounds
2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 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 , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )
