Fenclonine

Fenclonine
Systematic (IUPAC) name
	(S)-2-amino-3-(4-chlorophenyl)propanoic acid
Identifiers
CAS Number	7424-00-2
ATC code	none
PubChem	CID: 4652
IUPHAR/BPS	5240
ChemSpider	4491
UNII	R5J7E3L9SP
KEGG	D04143
Synonyms	CP-10188; Fenclonina; Fencloninum; NSC-77370; Parachlorophenylalanine
Chemical data
Formula	C9H10ClNO
Molecular mass	199.634 g/mol
	SMILES Clc1ccc(cc1)CC(C(=O)O)N ;
	InChI InChI=1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13) ; Key:NIGWMJHCCYYCSF-UHFFFAOYSA-N ;
Physical data
Density	1.336 g/cm3
Melting point	240 °C (464 °F)
Boiling point	339.5 °C (643.1 °F)
(verify)

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.

References

↑ "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
↑ ^2.0 ^2.1 Jouvet M Sleep and serotonin: an unfinished story. Neuropsychopharmacology. 1999 Aug;21(2 Suppl):24S-27S. PMID 10432485
↑ 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
↑ 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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[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

[Jouvet-2] 2.0 ^2.1 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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Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-N 2C-P 2C-SE 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-21 2C-TFM 2C-YN Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
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Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
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Fenclonine

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