Desmethylclozapine
File:N-Desmethylclozapine.png | |
Systematic (IUPAC) name | |
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8-chloro-11-piperazin-1-yl-5H-dibenzo[b,e][1,4]diazepine | |
Clinical data | |
Routes of administration | Oral |
Legal status | |
Legal status |
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Identifiers | |
CAS Number | 6104-71-8 |
ATC code | none |
PubChem | CID 2820 |
ChemSpider | 14126465 |
Chemical data | |
Formula | C17H17ClN4 |
Molar mass | 312.80 g/mol[[Script error: No such module "String".]] |
Script error: No such module "collapsible list". | |
N-Desmethylclozapine (NDMC), or norclozapine, is a major active metabolite of the atypical antipsychotic drug clozapine.[1][2] Interestingly, unlike clozapine, it possesses intrinsic activity at the D2/D3 receptors, and acts as a weak partial agonist at these sites similarly to aripiprazole and bifeprunox.[3] Notably, NDMC has also been shown to act as a potent and efficacious agonist at the M1 and δ-opioid receptors, unlike clozapine as well. Therefore, NDMC is considered a delta-opioid agonist.[4][5][6] It was hypothesized that on account of these unique actions, NDMC might underlie the clinical superiority of clozapine over other antipsychotics. However, clinical trials found NMDC itself ineffective in the treatment of schizophrenia.[7][8] This may be due to the fact that it possesses relatively low D2/D3 occupancy compared to 5-HT2 (<15% versus 64-79% at a dose of 10-60 mg/kg s.c. in animal studies).[9] In any case, though not useful in the treatment of positive symptoms on its own, it cannot be ruled out that NDMC may contribute to the improvement of cognitive and/or negative symptoms with clozapine.[7]
See also
References
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Receptor ligands |
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Reuptake inhibitors |
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Enzyme inhibitors |
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Others |
Opium and Poppy straw derivatives |
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Morphinans |
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Benzomorphans | 5,9-DEHB · Alazocine · Anazocine · Bremazocine · Cogazocine · Cyclazocine · Dezocine · Eptazocine · Etazocine · Ethylketocyclazocine · Fluorophen · Ketazocine · Metazocine · Pentazocine · Phenazocine · Quadazocine · Thiazocine · Tonazocine · Volazocine · Zenazocine | ||||||||||||||||||||||||||||||||
4-Phenylpiperidines |
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Open Chain Opioids |
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Anilidopiperidines | 3-Allylfentanyl · 3-Methylfentanyl · 3-Methylthiofentanyl · 4-Phenylfentanyl · Alfentanil · α-methylacetylfentanyl · α-methylfentanyl · α-methylthiofentanyl · Benzylfentanyl · β-hydroxyfentanyl · β-hydroxythiofentanyl · β-methylfentanyl · Brifentanil · Carfentanil · Fentanyl · Lofentanil · Mirfentanil · Ocfentanil · Ohmefentanyl · Parafluorofentanyl · Phenaridine · Remifentanil · Sufentanil · Thenylfentanyl · Thiofentanyl · Trefentanil | ||||||||||||||||||||||||||||||||
Oripavine derivatives | 6,14-Endoethenotetrahydrooripavine · 7-PET · Acetorphine · Alletorphine · BU-48 · Buprenorphine · Butorphine · Cyprenorphine · Dihydroetorphine · Diprenorphine (M5050) · Etorphine · 18,19-Dehydrobuprenorphine (HS-599) · N-cyclopropylmethyl-noretorphine · Nepenthone · Norbuprenorphine · Thevinone · Thienorphine | ||||||||||||||||||||||||||||||||
Phenazepanes | |||||||||||||||||||||||||||||||||
Pirinitramides | |||||||||||||||||||||||||||||||||
Benzimidazoles | |||||||||||||||||||||||||||||||||
Indoles | |||||||||||||||||||||||||||||||||
Diphenylmethylpiperazines | |||||||||||||||||||||||||||||||||
Opioid peptides see also: The Opioid Peptides | Adrenorphin · Amidorphin · Casomorphin · DADLE · DALDA · DAMGO · Dermenkephalin · Dermorphin · Deltorphin · DPDPE · Dynorphin · Endomorphin · Endorphin · Enkephalin · Gliadorphin · Morphiceptin · Nociceptin · Octreotide · Opiorphin · Rubiscolin · TRIMU 5 | ||||||||||||||||||||||||||||||||
Others | 3-(3-Methoxyphenyl)-3-ethoxycarbonyltropane · AH-7921 • Azaprocin · BDPC · Bisnortilidine · BRL-52537 · Bromadoline • C-8813 · Ciramadol · Doxpicomine • Enadoline · Esketamine · Faxeladol · GR-89696 · Herkinorin · ICI-199,441 · ICI-204,448 · J-113,397 · JTC-801 · Ketamine · LPK-26 · Methopholine · Methoxetamine · N-Desmethylclozapine · NNC 63-0532 · Nortilidine · O-Desmethyltramadol · Phenadone · Phencyclidine · Prodilidine · Profadol · Ro64-6198 · Salvinorin A · SB-612,111 · SC-17599 · RWJ-394,674 · TAN-67 · Tapentadol · Tecodine · Tifluadom · Tilidine · Tramadol · Trimebutine · U-50,488 · U-69,593 · Viminol · W-18 · | ||||||||||||||||||||||||||||||||
Opioid Antagonists & Inverse-Agonists | 5'-Guanidinonaltrindole · β-Funaltrexamine · 6β-Naltrexol · Alvimopan · Amiphenazole · Binaltorphimine · Chlornaltrexamine · Clocinnamox · Cyclazocine · Cyprodime · Diprenorphine (M5050) · Fedotozine · JDTic · Levallorphan · Methocinnamox · Methylnaltrexone · Nalfurafine · Nalmefene · Nalmexone · Naloxazone · Naloxonazine · Naloxone · Naloxone benzoylhydrazone · Nalorphine · Naltrexone · Naltriben · Naltrindole · Norbinaltorphimine · Oxilorphan · S-allyl-3-hydroxy-17-thioniamorphinan (SAHTM) |
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Simple piperazines (no additional rings) | |
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Phenylpiperazines | Acaprazine • Antrafenine • Aripiprazole • Batoprazine • Bifeprunox • BRL-15,572 • Ciprofloxacin • CSP-2503 • Dapiprazole • DCPP • DMPP • Dropropizine • EGIS-12,233 • Elopiprazole • Eltoprazine • Enpiprazole • Ensaculin • Etoperidone • Flesinoxan • Flibanserin • Fluprazine • Itraconazole • Ketoconazole • Levodropropizine • Lorpiprazole • mCPP • MeOPP • Mepiprazole • Naftopidil • Naphthylpiperazine • Nefazodone • Niaprazine • Oxypertine • Pardoprunox • pCPP • pFPP • Posaconazole • PRX-00023 • 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 • WAY-100,135 • WAY-100,635 |
Benzylpiperazines | 2C-B-BZP • Befuraline • Bifeprunox • Buclizine • BZP • Chlorbenzoxamine • DBZP • Fipexide • Imatinib • MBZP • MDBZP • Meclozine • Piberaline • Piribedil • Trimetazidine • Vesnarinone |
Diphenylalkylpiperazines (benzhydrylalkylpiperazines) | Almitrine • Amperozide • BRL-15,572 • Buclizine • BW373U86 • Cetirizine • Chlorbenzoxamine • Chlorcyclizine • Cinnarizine • Clocinizine • Cyclizine • DBL-583 • Diphenylmethylpiperazine • Dotarizine • DPI-221 • DPI-287 • DPI-3290 • GBR-12,783 • GBR-12,935 • GBR-13,069 • GBR-13,098 • GBR-13,119 • Hydroxyzine • Lidoflazine • Manidipine • Meclozine • Oxatomide • SNC-80 • Vanoxerine |
Pyrimidinylpiperazines | Buspirone • Dasatinib • Eptapirone • Gepirone • Ipsapirone • Piribedil • Pyrimidinylpiperazine • Revospirone • Tandospirone • Tirilazad • Trimazosin • Umespirone • Zalospirone |
Pyridinylpiperazines | |
Benzo(iso)thiazolylpiperazines | |
Tricyclics (piperazine attached via side chain) | |
Others | 6-Nitroquipazine • Azimilide • Cinepazet • Cyclohexylpiperazine • Hexocyclium • Indinavir • JNJ-7777120 • Lodenafil • Mirodenafil • PB-28 • Quipazine • Ranolazine • SA-4503 • Sildenafil • Tadalafil • Vardenafil • VUF-6002 • Zipeprol |
Classes | |
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Antidepressants | 7-OH-Amoxapine • Amezepine • Amineptine • Amitriptyline • Amitriptylinoxide • Amoxapine • Aptazapine • Azepindole • Azipramine • Butriptyline • Cianopramine • Ciclazindol • Ciclopramine • Clomipramine • Cotriptyline • Cyanodothiepin • Demexiptiline • Depramine/Balipramine • Desipramine • Dibenzepine • Dimetacrine • Dosulepin/Dothiepin • Doxepin • Enprazepine • Esmirtazapine • Fluotracen • Hepzidine • Homopipramol • Imipramine • Imipraminoxide • Intriptyline • Iprindole • Ketipramine • Litracen • Lofepramine • Losindole • Loxapine • Maprotiline • Mariptiline • Mazindol • Melitracen • Metapramine • Mezepine • Mianserin • Mirtazapine • Naranol • Nitroxazepine • Nortriptyline • Noxiptiline • Octriptyline • Opipramol • Oxaprotiline • Pipofezine • Pirandamine • Propizepine • Protriptyline • Quinupramine • Setiptiline/Teciptiline • Tandamine • Tampramine • Tianeptine • Tienopramine • Trimipramine |
Antihistamines | Alimemazine • Azatadine • Clobenzepam • Cyproheptadine • Dacemazine • Deptropine • Desloratadine • Epinastine • Etymemazine • Hydroxyethylpromethazine • Isopromethazine • Isothipendyl • Ketotifen • Latrepirdine • Loratadine • Mebhydrolin • Mequitazine • Methdilazine • Olopatadine • Oxomemazine • Phenindamine • Pimethixene • Promethazine • Propiomazine • Rupatadine • Thiazinamium |
Antipsychotics | Acetophenazine • Amoxapine • Asenapine • Butaclamol • Butaperazine • Carphenazine • Carpipramine • Chlorpromazine • Chlorprothixene • Ciclindole • Clocapramine • Clomacran • Clotiapine • Clozapine • Flucindole • Fluotracen • Flupentixol • Fluphenazine • Gevotroline • Homopipramol • Levomepromazine/Methotrimeprazine • Loxapine • Maroxepin • Mesoridazine • Metitepine/Methiothepin • Metoxepin • Mosapramine • Naranol • Olanzapine • Perazine • Perphenazine • Periciazine • Piperacetazine • Pipotiazine • Piquindone • Prochlorperazine • Promazine • Prothipendyl • Quetiapine • Sulforidazine • Thiethylperazine • Thiopropazate • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Zotepine • Zuclopenthixol |
Others |
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- Jump up ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Jump up to: 7.0 7.1 Bishara D, Taylor D (2008). "Upcoming agents for the treatment of schizophrenia: mechanism of action, efficacy and tolerability". Drugs. 68 (16): 2269–92. PMID 18973393.
- Jump up ↑ Mendoza MC, Lindenmayer JP (2009). "N-desmethylclozapine: is there evidence for its antipsychotic potential?". Clinical Neuropharmacology. 32 (3): 154–7. doi:10.1097/WNF.0b013e31818d46f5. PMID 19483482.
- Jump up ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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