Chemistry:Para-Chlorophenethylamine

*para*-Chlorophenethylamine
Clinical data
Drug class	serotonergic agent; serotonin-releasing agent; monoaminergic neurotoxin
ATC code	none;
Identifiers
	IUPAC name 2-(4-chlorophenyl)ethanamine;
CAS Number	156-41-2;
PubChem CID	67430;
ChemSpider	60755;
ChEMBL	ChEMBL477764;
CompTox Dashboard (EPA)	40166018;
Chemical and physical data
Formula	C8H10ClN
Molar mass	155.63 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC(=CC=C1CCN)Cl;
	InChI InChI=1S/C8H10ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5-6,10H2; Key:SRXFXCKTIGELTI-UHFFFAOYSA-N;

Short description: Chemical compound

para-Chlorophenethylamine (pCPE) also known as 4-chlorophenylethylamine, is a potent serotonergic drug that is a structural analog of para-chloroamphetamine, lacking a methyl group at the α-position.

Pharmacology

Pharmacodynamics

para-Chlorophenethylamine acts primarily as a serotonin-releasing agent with an EC₅₀ value of 430 nM for the serotonin transporter, approximately the dose required to induce serotonin syndrome with seizures, tremor, and hyperthermia in mice, is quite low compared to other derivatives (such as ortho-chlorophenethylamine and meta-chlorophenethylamine)^[1]^[2] In mice with serotonin syndrome induced by para-chlorophenethylamine, the following symptoms were observed: lateral head bobbing, a Straub tail reaction, abduction of the hind limbs, tremors, hyperactivity, mutual pawing with the front paws, salivation, and piloerection.^[3] It acts as a full, weak agonist of TAAR with an EC₅₀ value of 2,900 ± 1,000 nM.^[4]

In vitro, it inhibited the activity of the enzyme phenylethanolamine N-methyltransferase.^[5] Para-chlorophenelethylamine stimulated 5-HT receptors.^[3]^[6]

Pharmacokinetics

para-Chlorophenethylamine is a known metabolite of the para-chlorophenylalanine (fenclonine); it rapidly accumulated in the brain following administration of fenclonine.^[7]

Drug control

Para-chlorophenylethylamine is a controlled substance in Hungary, classified under the category “New Psychoactive Substances”^[8]

References

↑ "Comparative effects of substituted phenylethylamines on brain serotonergic mechanisms". The Journal of Pharmacology and Experimental Therapeutics 213 (2): 254–260. May 1980. doi:10.1016/S0022-3565(25)32053-7. PMID 6965983.
↑ "Comparative effects of various serotonin releasing agents in mice". Biochemical Pharmacology 29 (23): 3163–3167. December 1980. doi:10.1016/0006-2952(80)90580-8. PMID 6449931.
↑ ^3.0 ^3.1 "Behavioral and biochemical actions of p-chlorophenylethylamine (p-CPEA) in mice". Life Sciences 24 (7): 595–601. February 1979. doi:10.1016/0024-3205(79)90155-3. PMID 155767.
↑ "Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1". Bioorganic & Medicinal Chemistry 16 (15): 7415–7423. August 2008. doi:10.1016/j.bmc.2008.06.009. PMID 18602830.
↑ "Possible resolution of a paradox concerning the use of p-chlorophenylalanine and 5-hydroxytryptophan: evidence for a mode of action involving adrenaline in manipulating the surge of luteinizing hormone in rats". Neuroscience 8 (3): 583–591. March 1983. doi:10.1016/0306-4522(83)90200-2. PMID 6222267.
↑ "Para-halogenated phenethylamines: similar serotonergic effects in rats by different mechanisms". Pharmacology, Biochemistry, and Behavior 13 (2): 283–286. August 1980. doi:10.1016/0091-3057(80)90084-2. PMID 6447879.
↑ "Para-chlorophenylethylamine in brains of rats treated with a monoamine oxidase inhibitor and p-chlorophenylalanine". Progress in Neuro-Psychopharmacology & Biological Psychiatry 6 (4–6): 343–346. 1982. doi:10.1016/s0278-5846(82)80103-6. PMID 6219431.
↑ "78/2022. (XII. 28.) BM rendelet - Nemzeti Jogszabálytár". https://njt.hu/jogszabaly/2022-78-20-0A.

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[1] "Comparative effects of substituted phenylethylamines on brain serotonergic mechanisms". The Journal of Pharmacology and Experimental Therapeutics 213 (2): 254–260. May 1980. doi:10.1016/S0022-3565(25)32053-7. PMID 6965983.

[2] "Comparative effects of various serotonin releasing agents in mice". Biochemical Pharmacology 29 (23): 3163–3167. December 1980. doi:10.1016/0006-2952(80)90580-8. PMID 6449931.

[:0-3] 3.0 ^3.1 "Behavioral and biochemical actions of p-chlorophenylethylamine (p-CPEA) in mice". Life Sciences 24 (7): 595–601. February 1979. doi:10.1016/0024-3205(79)90155-3. PMID 155767.

[4] "Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1". Bioorganic & Medicinal Chemistry 16 (15): 7415–7423. August 2008. doi:10.1016/j.bmc.2008.06.009. PMID 18602830.

[5] "Possible resolution of a paradox concerning the use of p-chlorophenylalanine and 5-hydroxytryptophan: evidence for a mode of action involving adrenaline in manipulating the surge of luteinizing hormone in rats". Neuroscience 8 (3): 583–591. March 1983. doi:10.1016/0306-4522(83)90200-2. PMID 6222267.

[6] "Para-halogenated phenethylamines: similar serotonergic effects in rats by different mechanisms". Pharmacology, Biochemistry, and Behavior 13 (2): 283–286. August 1980. doi:10.1016/0091-3057(80)90084-2. PMID 6447879.

[7] "Para-chlorophenylethylamine in brains of rats treated with a monoamine oxidase inhibitor and p-chlorophenylalanine". Progress in Neuro-Psychopharmacology & Biological Psychiatry 6 (4–6): 343–346. 1982. doi:10.1016/s0278-5846(82)80103-6. PMID 6219431.

[8] "78/2022. (XII. 28.) BM rendelet - Nemzeti Jogszabálytár". https://njt.hu/jogszabaly/2022-78-20-0A.

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V 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 Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
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 N-Ethylhexedrone N-Ethylpentedrone 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
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101

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