Chemistry:Para-Chloroamphetamine

*para*-Chloroamphetamine
Clinical data
Other names	PCA; 4-Chloroamphetamine; 4-CA
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) ; UK: Class A ;
Identifiers
	IUPAC name 1-(4-Chlorophenyl)propan-2-amine;
CAS Number	64-12-0 ;
PubChem CID	3127;
IUPHAR/BPS	4592;
ChemSpider	3015 ;
UNII	897NVD4A52;
ChEMBL	ChEMBL358967 ;
Chemical and physical data
Formula	C9H12ClN
Molar mass	169.65 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1)CC(N)C;
	InChI InChI=1S/C9H12ClN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3 ; Key:WWPITPSIWMXDPE-UHFFFAOYSA-N ;
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Short description: Chemical compound

para-Chloroamphetamine (PCA), also known as 4-chloroamphetamine (4-CA), is a substituted amphetamine and monoamine releaser similar to MDMA, but with substantially higher neurotoxicity, thought to be due to the unrestrained release of both serotonin and dopamine by a metabolite.^[1] It is used as a neurotoxin by neurobiologists to selectively kill serotonergic neurons for research purposes, in the same way that 6-hydroxydopamine is used to kill dopaminergic neurons.^[2]^[3]^[4]^[5]

para-Chloroamphetamine has been detected as an apparent designer drug,^[6] along with the related 3-chloroamphetamine, which is even more potent as a releaser of dopamine and serotonin but slightly less neurotoxic.^[7]^[8]^[9]^[10]^[11]

The closely related N-methylated derivative, para-chloromethamphetamine (CMA), which is metabolized to para-chloroamphetamine in vivo, has neurotoxic properties as well.

Legal status

China

As of October 2015, 4-CA is a controlled substance in China.^[12]

References

↑ "Metabolic activation of the serotonergic neurotoxin para-chloroamphetamine to chemically reactive intermediates by hepatic and brain microsomal preparations". Biochemical Pharmacology 35 (10): 1737–1742. May 1986. doi:10.1016/0006-2952(86)90332-1. PMID 3707603.
↑ "Effect of p-chloroamphetamine on cerebral tryptophan-5-hydroxylase in vivo: a reexamination". Neuropharmacology 14 (1): 31–39. January 1975. doi:10.1016/0028-3908(75)90063-5. PMID 125387.
↑ "5-Hydroxytryptamine: the effects of impaired synthesis on its metabolism and release in rat". British Journal of Pharmacology 63 (4): 627–634. August 1978. doi:10.1111/j.1476-5381.1978.tb17275.x. PMID 80243.
↑ "5-HT loss in rat brain following 3,4-methylenedioxymethamphetamine (MDMA), p-chloroamphetamine and fenfluramine administration and effects of chlormethiazole and dizocilpine". British Journal of Pharmacology 108 (3): 583–589. March 1993. doi:10.1111/j.1476-5381.1993.tb12846.x. PMID 7682129.
↑ "Cerebral metabolic responses to clomipramine are greatly reduced following pretreatment with the specific serotonin neurotoxin para-chloroamphetamine (PCA). A 2-deoxyglucose study in rats". Neuropsychopharmacology 13 (3): 215–222. November 1995. doi:10.1016/0893-133X(95)00053-G. PMID 8602894.
↑ "Detection of p-chloroamphetamine in urine samples with mass spectrometry". Journal of Analytical Toxicology 35 (4): 205–210. May 2011. doi:10.1093/anatox/35.4.205. PMID 21513613.
↑ "Drug disposition as a factor in the lowering of brain serotonin by chloroamphetamines in the rat". Biochemical Pharmacology 21 (10): 1413–1417. May 1972. doi:10.1016/0006-2952(72)90365-6. PMID 5029422.
↑ "Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones". Acta Pharmacologica et Toxicologica 41 (4): 353–368. October 1977. doi:10.1111/j.1600-0773.1977.tb02674.x. PMID 303437.
↑ "Inhibition of 3H-dopamine accumulation in reserpinized and normal rat striatum". Acta Pharmacologica et Toxicologica 44 (5): 329–335. May 1979. doi:10.1111/j.1600-0773.1979.tb02339.x. PMID 474143.
↑ "Long-lasting reduction of brain 5-hydroxytryptamine concentration by 3-chloramphetamine and 4-chloroamphetamine in iprindole-treated rats". The Journal of Pharmacy and Pharmacology 26 (11): 912–914. November 1974. doi:10.1111/j.2042-7158.1974.tb09206.x. PMID 4156568.
↑ "Substituted amphetamine derivatives. I. Effect on uptake and release of biogenic monoamines and on monoamine oxidase in the mouse brain". Acta Pharmacologica et Toxicologica 41 (4): 337–352. October 1977. doi:10.1111/j.1600-0773.1977.tb02673.x. PMID 579062.
↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html.

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[1] "Metabolic activation of the serotonergic neurotoxin para-chloroamphetamine to chemically reactive intermediates by hepatic and brain microsomal preparations". Biochemical Pharmacology 35 (10): 1737–1742. May 1986. doi:10.1016/0006-2952(86)90332-1. PMID 3707603.

[2] "Effect of p-chloroamphetamine on cerebral tryptophan-5-hydroxylase in vivo: a reexamination". Neuropharmacology 14 (1): 31–39. January 1975. doi:10.1016/0028-3908(75)90063-5. PMID 125387.

[3] "5-Hydroxytryptamine: the effects of impaired synthesis on its metabolism and release in rat". British Journal of Pharmacology 63 (4): 627–634. August 1978. doi:10.1111/j.1476-5381.1978.tb17275.x. PMID 80243.

[4] "5-HT loss in rat brain following 3,4-methylenedioxymethamphetamine (MDMA), p-chloroamphetamine and fenfluramine administration and effects of chlormethiazole and dizocilpine". British Journal of Pharmacology 108 (3): 583–589. March 1993. doi:10.1111/j.1476-5381.1993.tb12846.x. PMID 7682129.

[5] "Cerebral metabolic responses to clomipramine are greatly reduced following pretreatment with the specific serotonin neurotoxin para-chloroamphetamine (PCA). A 2-deoxyglucose study in rats". Neuropsychopharmacology 13 (3): 215–222. November 1995. doi:10.1016/0893-133X(95)00053-G. PMID 8602894.

[6] "Detection of p-chloroamphetamine in urine samples with mass spectrometry". Journal of Analytical Toxicology 35 (4): 205–210. May 2011. doi:10.1093/anatox/35.4.205. PMID 21513613.

[7] "Drug disposition as a factor in the lowering of brain serotonin by chloroamphetamines in the rat". Biochemical Pharmacology 21 (10): 1413–1417. May 1972. doi:10.1016/0006-2952(72)90365-6. PMID 5029422.

[8] "Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones". Acta Pharmacologica et Toxicologica 41 (4): 353–368. October 1977. doi:10.1111/j.1600-0773.1977.tb02674.x. PMID 303437.

[9] "Inhibition of 3H-dopamine accumulation in reserpinized and normal rat striatum". Acta Pharmacologica et Toxicologica 44 (5): 329–335. May 1979. doi:10.1111/j.1600-0773.1979.tb02339.x. PMID 474143.

[10] "Long-lasting reduction of brain 5-hydroxytryptamine concentration by 3-chloramphetamine and 4-chloroamphetamine in iprindole-treated rats". The Journal of Pharmacy and Pharmacology 26 (11): 912–914. November 1974. doi:10.1111/j.2042-7158.1974.tb09206.x. PMID 4156568.

[11] "Substituted amphetamine derivatives. I. Effect on uptake and release of biogenic monoamines and on monoamine oxidase in the mouse brain". Acta Pharmacologica et Toxicologica 41 (4): 337–352. October 1977. doi:10.1111/j.1600-0773.1977.tb02673.x. PMID 579062.

[12] "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html.

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v t e Monoamine neurotoxins
Adrenergic	DSP-4 Oxidopamine (6-OHDA)
Dopaminergic	Fenpropathrin Methamphetamine MPP⁺ MPTP Norsalsolinol Oxidopamine (6-OHDA) Rotenone
Serotonergic	3-CA 4-CAB 5,7-DHT α-Me-DA (3,4-DHA) αET αMT DCA MDA (tenamfetamine) MDMA (midomafetamine) PBA PCA PIA
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators

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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