FENCLONINE

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H10ClNO2
Molecular Weight	199.634
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(CC1=CC=C(Cl)C=C1)C(O)=O

InChI

InChIKey=NIGWMJHCCYYCSF-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C9H10ClNO2
Molecular Weight	199.634
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/131950 | https://www.ncbi.nlm.nih.gov/pubmed/5311687

Fenclonine, also known as p-chlorophenylalanine, is an inhibitor of tryptophan hydroxylase, the enzyme that plays a rate-limiting role in the biosynthesis of serotonin. Fenclonine was studied for the treatment of carcinoid syndrome, but the psychological side effects, prevented for the further development for this use.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
CHEMBL3831287: Tryptophan 5-hydroxylase 2 Target ID: CHEMBL3831287: Tryptophan 5-hydroxylase Sources: https://www.ncbi.nlm.nih.gov/pubmed/11900855 \| https://www.ncbi.nlm.nih.gov/pubmed/5311687	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Carcinoid syndrome 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4254559	Primary		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Sex differences in the regulation of serotonergic transmission and behavior in 5-HT receptor knockout mice.	2005-06	15688089
The role of 5-HT in the impairment of thermoregulation observed in rats administered MDMA ('ecstasy') when housed at high ambient temperature.	2005-06	15650843
Differential involvement of serotonin and dopamine systems in cost-benefit decisions about delay or effort.	2005-05	15864561
Involvement of serotonin in the hypoglycemic response to 2 Hz electroacupuncture of zusanli acupoint (ST36) in rats.	2005-04-29	15814202
Serotonin refines the locomotor-related alternations in the in vitro neonatal rat spinal cord.	2005-03	15813943
Analysis of serotonin in brain microdialysates using capillary electrophoresis and native laser-induced fluorescence detection.	2005-03	15706576
A reassessment of the role of serotonergic system in the control of feeding behavior.	2005-03	15692681
Long-lasting effects of serotonin deficiency on differentiating peptidergic neurons in the rat suprachiasmatic nucleus.	2005-02	15730890
Serotonin modulates the suppressive effects of corticosterone on proliferating progenitor cells in the dentate gyrus of the hippocampus in the adult rat.	2005-02	15536491
Dissociating barrel development and lesion-induced plasticity in the mouse somatosensory cortex.	2005-01-19	15659608
GABAB receptor antagonist-mediated antidepressant-like behavior is serotonin-dependent.	2005-01	15333677
Tetrandrine, a bisbenzylisoquinoline alkaloid from Chinese herb Radix, augmented the hypnotic effect of pentobarbital through serotonergic system.	2004-12-15	15588729
Serotonin and stress: protective or malevolent actions in the biobehavioral response to repeated trauma?	2004-12	15677425
5-HT1A receptors are differentially involved in the anxiolytic- and antidepressant-like effects of 8-OH-DPAT and fluoxetine in the rat.	2004-12	15589388
Serotonin involvement in the electroacupuncture- and moxibustion-induced gastric emptying in rats.	2004-10-15	15451650
Elevated serotonin is involved in hyperactivity but not in the paradoxical effect of amphetamine in mice neonatally lesioned with 6-hydroxydopamine.	2004-10-15	15378510
Evidence for serotonin receptor subtypes involvement in agmatine antidepressant like-effect in the mouse forced swimming test.	2004-10-15	15374751
5-HT-mediated inhibition of cardiovagal baroreceptor reflex response during defense reaction in the rat.	2004-10	15165987
Loss of flight and associated neuronal rhythmicity in inositol 1,4,5-trisphosphate receptor mutants of Drosophila.	2004-09-08	15356199
Effects of autacoid inhibitors and of an antagonist on malaria infection in mice.	2004-08	15273821
Increased CRE-binding activity and tryptophan hydroxylase mRNA expression induced by 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") in the rat frontal cortex but not in the hippocampus.	2004-07-26	15249142
Immediate plasticity in the motor pathways after spinal cord hemisection: implications for transcranial magnetic motor-evoked potentials.	2004-06	15144873
NMDA receptor subunit and CaMKII changes in rat hippocampus induced by acute MDMA treatment: a mechanism for learning impairment.	2004-05	14985918
Brain serotonin depletion enhances the sodium appetite induced by sodium depletion or beta-adrenergic stimulation.	2004-03	15048197
Evidence of melatonin synthesis by human lymphocytes and its physiological significance: possible role as intracrine, autocrine, and/or paracrine substance.	2004-03	14715696
Serotonin regulates mammary gland development via an autocrine-paracrine loop.	2004-02	14960274
5-HT1A and beta-adrenergic receptors regulate proliferation of rat blood lymphocytes.	2004	15316241
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L.	2004	15270248
Endogenous 5-HT inhibits firing activity of hippocampal CA1 pyramidal neurons during conditioned fear stress-induced freezing behavior through stimulating 5-HT1A receptors.	2004	15098719
Decreased serotonin level during pregnancy alters morphological and functional characteristics of tonic nociceptive system in juvenile offspring of the rat.	2003-11-13	14614772
Serotonin synthesis inhibition in olivo-cerebellar system attenuates harmaline-induced tremor in Swiss albino mice.	2003-10-17	14529803
Elimination of serotonergic cells induces a marked increase in generation of dopaminergic neurons from mesencephalic precursors.	2003-10	14622177
Orienting and defensive behaviors elicited by superior colliculus stimulation in rats: effects of 5-HT depletion, uptake inhibition, and direct midbrain or frontal cortex application.	2003-09-15	12946599
The effects of serotonin on the differentiation of neurons producing vasoactive intestinal polypeptide in the suprachiasmatic nucleus of the rat.	2003-09	14552543
Effect of the inhibition of serotonin biosynthesis on the antinociception induced by nonsteroidal anti-inflammatory drugs.	2003-08-30	12909285
Prenatal serotonin depletion changes the behavioral response in the nociceptive formalin test in rats.	2003-08-28	12940142
Is the Ecstasy-induced ipsilateral rotation in 6-hydroxydopamine unilaterally lesioned rats dopamine independent?	2003-07	12811632
Evidence for a monoamine mediated, opioid-independent, antihyperalgesic effect of venlafaxine, a non-tricyclic antidepressant, in a neurogenic pain model in rats.	2003-06	12791429
Influence of serotonin on the development and migration of gonadotropin-releasing hormone neurones in rat foetuses.	2003-06	12716405
[Osmoregulating reactions following serotonin metabolism inhibition or activation].	2003-04	12966722
Serotonin depletion enhances the intracerebroventricularly administered MK-801-induced plasma interleukin-6 levels in mice.	2003-04	12673041
Increases in avoidance responding produced by REM sleep deprivation or serotonin depletion are reversed by administration of 5-hydroxytryptophan.	2003-03-18	12644281
Serotonin depletion increases respiratory variability in freely moving rats: implications for panic disorder.	2003-03	12899736
Serotonin-GABA interactions in the modulation of mu- and kappa-opioid analgesia.	2003-03	12604090
Short-term effects of 3,4-methylenedioximethamphetamine on noradrenergic activity in locus coeruleus and hippocampus of the rat.	2003-02-13	12536039
5-HT1 and 5-HT2 receptor activation reduces N-methyl-D-aspartate (NMDA)-stimulated LH secretion in prepubertal male and female rats.	2003-01	12534365
Depletion of endogenous serotonin synthesis with p-CPA attenuates upregulation of constitutive isoform of heme oxygenase-2 expression, edema formation and cell injury following a focal trauma to the rat spinal cord.	2003	14753474
Synaptic loss following depletion of noradrenaline and/or serotonin in the rat visual cortex: a quantitative electron microscopic study.	2003	14622906
Pharmacological blockage of serotonin biosynthesis and circadian changes in oxaliplatin toxicity in rats.	2002-11	12511030
The effects of DL-p-chlorophenylalanine and DL-alpha-methyl-p-tyrosine on the brain catecholamine, serotonin and free amino acid contents in rat.	1975-12-31	129787

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:49:10 GMT 2025` Edited by `admin` on `Mon Mar 31 18:49:10 GMT 2025`
Record UNII	R5J7E3L9SP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CP-10,188

Preferred Name

English

FENCLONINE

Official Name

English

CP-10188

Code

English

NSC-77370

Code

English

fenclonine [INN]

Common Name

English

FENCLONINE [HSDB]

Common Name

English

DL-3-(P-CHLOROPHENYL)ALANINE

Systematic Name

English

P-CHLOROPHENYLALANINE, DL-

Common Name

English

ALANINE, 3-(4-CHLOROPHENYL)-, DL-

Systematic Name

English

FENCLONINE [USAN]

Common Name

English

FENCLONINE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471