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Fenclonine

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Title: Fenclonine  
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Subject: Serotonin antagonist, Serotonin–norepinephrine–dopamine reuptake inhibitor, DMMDA, EDMA, 2-Methyl-MDA
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Fenclonine

Fenclonine
Systematic (IUPAC) name
(S)-2-amino-3-(4-chlorophenyl)propanoic acid
Identifiers
CAS Registry Number  YesY
ATC code None
PubChem CID:
IUPHAR/BPS
ChemSpider  YesY
UNII  YesY
KEGG  YesY
Synonyms CP-10188; Fenclonina; Fencloninum; NSC-77370; Parachlorophenylalanine[1]
Chemical data
Formula C9H10ClNO
Molecular mass 199.634 g/mol
Physical data
Density 1.336 g/cm3
Melting point 240 °C (464 °F)
Boiling point 339.5 °C (643.1 °F)
 YesY   

Fenclonine, also known as para-chlorophenylalanine (PCPA), acts as a selective and irreversible inhibitor of tryptophan hydroxylase, which is a rate-limiting enzyme in the biosynthesis of serotonin.[2]

It has been used experimentally to treat carcinoid syndrome, but the side effects, mostly hypersensitivity reactions and psychiatric disturbances, have prevented development for this use.[3]

It is used in scientific research in humans[4] and animals[2] to investigate the effects of serotonin depletion.

See also

References

  1. ^ "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
  2. ^ a b Jouvet M Sleep and serotonin: an unfinished story. Neuropsychopharmacology. 1999 Aug;21(2 Suppl):24S-27S. PMID 10432485
  3. ^ Kvols LK. Metastatic carcinoid tumors and the carcinoid syndrome. A selective review of chemotherapy and hormonal therapy. (Am J Med. 1986 Dec 22;81(6B):49-55. PMID 2432781
  4. ^ Ruhé HG, Mason NS, Schene AH. Mood is indirectly related to serotonin, norepinephrine and dopamine levels in humans: a meta-analysis of monoamine depletion studies. Mol Psychiatry. 2007 Apr;12(4):331-59. PMID 17389902


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