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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 432335310 |
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| verifiedrevid = 449580729 |
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| IUPAC_name = (''S'')-2-amino-3-(4-chlorophenyl)propanoic acid |
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| IUPAC_name = (''S'')-2-Amino-3-(4-chlorophenyl)propanoic acid |
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| image = Fenclonine.png |
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| image = Fenclonine.svg |
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| width = 150 |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| IUPHAR_ligand = 5240 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 7424-00-2 |
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| CAS_number = 7424-00-2 |
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| ATC_prefix = none |
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| ATC_prefix = None |
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| PubChem = 4652 |
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| PubChem = 4652 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D04143 |
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| KEGG = D04143 |
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| synonyms = CP-10188; Fenclonina; Fencloninum; NSC-77370; Parachlorophenylalanine<ref>"Fenclonine" entry in Martindale – The Complete Drug Reference. Maintained in Martindale purely for archival purposes, and is no longer subject to revision and update. (Last reviewed: 2008-08-01; last modified: 2011-09-12). The Royal Pharmaceutical Society of Great Britain 2014</ref> |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=9 | H=10 | Cl=1 | N=1 | O=1 |
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| C=9 | H=10 | Cl=1 | N=1 | O=2 |
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| solubility = |
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| molecular_weight = 199.634 g/mol |
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| melting_point = 240 |
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| boiling_point = 339.5 |
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| density = 1.336 |
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| smiles = Clc1ccc(cc1)CC(C(=O)O)N |
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| smiles = Clc1ccc(cc1)CC(C(=O)O)N |
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| InChI = 1/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13) |
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| InChIKey = NIGWMJHCCYYCSF-UHFFFAOYAR |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13) |
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| StdInChI = 1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13) |
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'''Fenclonine''', also known as '''''para''-chlorophenylalanine''' ('''PCPA'''), is a synthetic ] which acts as a selective and irreversible inhibitor of ], which is a rate-limiting enzyme in the biosynthesis of ].<ref>Jéquier E, Lovenberg W, Sjoerdsma A. Tryptophan hydroxylase inhibition: the mechanism by which p-chlorophenylalanine depletes rat brain serotonin. ''Molecular Pharmacology''. 1967 May;3(3):274-8. PMID 6037686</ref> Fenclonine consequently depletes serotonin in the body and reduces its actions, acting as an indirect ]. It is used in scientific research to investigate the effects of serotonin depletion on behaviour.<ref>O'Leary OF, Bechtholt AJ, Crowley JJ, Hill TE, Page ME, Lucki I. Depletion of serotonin and catecholamines block the acute behavioral response to different classes of antidepressant drugs in the mouse tail suspension test. ''Psychopharmacology (Berlin)''. 2007 Jun;192(3):357-71. PMID 17318507</ref> |
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'''Fenclonine''', also known as '''''para''-chlorophenylalanine''' ('''PCPA'''), acts as a selective and irreversible inhibitor of ], which is a rate-limiting enzyme in the biosynthesis of ].<ref name=Jouvet>{{cite journal | vauthors = Jouvet M | title = Sleep and serotonin: an unfinished story | journal = Neuropsychopharmacology | volume = 21 | issue = 2 Suppl | pages = 24S–27S | date = August 1999 | pmid = 10432485 | doi = 10.1016/S0893-133X(99)00009-3 | doi-access = free }}</ref> |
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It has been used experimentally to treat ], but the side effects, mostly hypersensitivity reactions and psychiatric disturbances, have prevented development for this use.<ref>{{cite journal | vauthors = Kvols LK | title = Metastatic carcinoid tumors and the carcinoid syndrome. A selective review of chemotherapy and hormonal therapy | journal = The American Journal of Medicine | volume = 81 | issue = 6B | pages = 49–55 | date = December 1986 | pmid = 2432781 | doi = 10.1016/0002-9343(86)90584-x }}</ref> |
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==See also== |
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* ] (AMPT) |
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The effects of serotonin depletion from fenclonine are so drastic that serotonin cannot even be detected ] within the first day after administration of a control dose. Tryptophan hydroxylase activity can be detected neither in cell bodies or nerve terminals. After one week 10% of control values (the baseline extrapolated for the study) had replenished in the ], and after two weeks from initial treatment as much was again detected in the hypothalamus region. ] (AADC) levels were at no time affected.<ref>{{cite journal | vauthors = Park DH, Stone DM, Baker H, Kim KS, Joh TH | title = Early induction of rat brain tryptophan hydroxylase (TPH) mRNA following parachlorophenylalanine (PCPA) treatment | journal = Brain Research. Molecular Brain Research | volume = 22 | issue = 1–4 | pages = 20–8 | date = March 1994 | pmid = 8015380 | doi = 10.1016/0169-328x(94)90028-0 }}</ref> |
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It is used in scientific research in humans<ref>{{cite journal | vauthors = Ruhé HG, Mason NS, Schene AH | title = Mood is indirectly related to serotonin, norepinephrine and dopamine levels in humans: a meta-analysis of monoamine depletion studies | journal = Molecular Psychiatry | volume = 12 | issue = 4 | pages = 331–59 | date = April 2007 | pmid = 17389902 | doi = 10.1038/sj.mp.4001949 | doi-access = }}</ref> and animals<ref name=Jouvet /> to investigate the effects of serotonin depletion. |
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== See also == |
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* ] (AMPT, metirosine) |
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* ] (PCA) |
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* ] (PCA) |
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* ] (Xermelo) |
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* ] |
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==References== |
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== References == |
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{{Reflist|2}} |
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{{Reflist|30em}} |
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{{Monoamine metabolism modulators}} |
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{{Serotonergics}} |
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{{Phenethylamines}} |
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{{Phenethylamines}} |
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{{nervous-system-drug-stub}} |
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