Exploring 4-Chloroamphetamine. To explore a different substance…

Names:
PCA
4-CA
4-Cl-AMP
4-Chloroamphetamine
p-Chloroamphetamine
IUPAC name:
1-(4-Chlorophenyl)propan-2-amine
2140 · C9H12ClN · 169.651
Neurotoxin
InChI=1S/C9H12ClN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3
WWPITPSIWMXDPE-UHFFFAOYSA-N This stereoisomer Any stereoisomer

Fuller, RW. Structure-activity relationships among the halogenated amphetamines. Ann. N. Y. Acad. Sci., 1 Jan 1978, 305, 147–159. 730 kB. https://doi.org/10.1111/j.1749-6632.1978.tb31518.x

Johnson, MP; Frescas, SP; Oberlender, R; Nichols, DE. Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: Similarities to 3,4-(methylenedioxy)methamphetamine (MDMA). J. Med. Chem., 1 Jan 1991, 34 (5), 1662–1668. 975 kB. https://doi.org/10.1021/jm00109a020

Johnson, MP; Nuang, X; Oberlender, R; Nash, JF; Nichols, DE. Behavioral, biochemical and neurotoxicological actions of the α-ethyl homologue of p-chloroamphetamine. Eur. J. Pharmacol., 1 Jan 1990, 191 (1), 1–10. 1.2 MB. https://doi.org/10.1016/0014-2999(90)94090-K

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10), 1100–1111. 1.2 MB. https://doi.org/10.1021/jm00256a016

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. https://doi.org/10.1016/S0006-2952(97)00405-X #9 PCA

Sprague, JE; Johnson, MP; Schmidt, CJ; Nichols, DE. Studies on the mechanism of p-chloroamphetamine neurotoxicity. Biochem. Pharmacol., 25 Oct 1996, 52 (8), 1271–1277. 859 kB. https://doi.org/10.1016/0006-2952(96)00482-0

Baumgarten, HG; Lachenmayer, L. Serotonin neurotoxins—past and present. Neurotox. Res., 1 Jan 2004, 6 (7–8), 589–614. 402 kB. https://doi.org/10.1007/BF03033455

McKenna, DJ; Guan, AM; Shulgin, AT. 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 505–12. 783 kB. https://doi.org/10.1016/0091-3057(91)90005-M

Johnson, MP; Conarty, PF; Nichols, DE. [3H]Monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues. Eur. J. Pharmacol., 1 Jan 1991, 200 (1), 9–16. 1.1 MB. https://doi.org/10.1016/0014-2999(91)90659-E

Ögren, S; Ross, SB. Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones. Acta Pharmacol. Toxicol., 1 Oct 1977, 41 (4), 353–368. 1.3 MB. https://doi.org/10.1111/j.1600-0773.1977.tb02674.x

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. https://doi.org/10.1124/jpet.106.103622

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. https://doi.org/10.1021/jm00325a020

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1978; Vol. 11, pp 243–333. 2.6 MB. https://doi.org/10.1007/978-1-4757-0510-2_6 Rhodium.

Fuller, RW; Perry, KW; Wong, DT; Molloy, BB. Effects of some homologues of 4-chloroamphetamine on brain serotonin metabolism. Neuropharmacology, 1 Jul 1974, 13 (7), 609–614. 490 kB. https://doi.org/10.1016/0028-3908(74)90050-1

Fuller, RW; Baker, JC; Perry, KW; Molloy, BB. Comparison of 4-chloro-, 4-bromo- and 4-fluoroamphetamine in rats: Drug levels in brain and effects on brain serotonin metabolism. Neuropharmacology, 1 Oct 1975, 14 (10), 739–746. 799 kB. https://doi.org/10.1016/0028-3908(75)90099-4

Owen, MLS; Baker, GB; Coutts, RT; Dewhurst, WG. Analysis of p-chloroamphetamine and a side-chain monofluorinated analogue in rat brain. J. Pharmacol. Methods, 1 Apr 1991, 25 (2), 147–155. 497 kB. https://doi.org/10.1016/0160-5402(91)90005-P

Fuller, RW. Effects of p-chloroamphetamine on brain serotonin neurons. Neurochem. Res., 1 May 1992, 17 (5), 449–456. 906 kB. https://doi.org/10.1007/BF00969891

Glennon, RA. Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention. Advances in Pharmacology, 2014, 69, 581–620. 564 kB. https://doi.org/10.1016/B978-0-12-420118-7.00015-9

Segawa, H; Iwata, YT; Yamamuro, T; Kuwayama, K; Tsujikawa, K; Kanamori, T; Inoue, H. Differentiation of ring-substituted regioisomers of amphetamine and methamphetamine by supercritical fluid chromatography: Differentiation of ring-substituted regioisomers by supercritical fluid chromatography. Drug Test. Analysis, 1 Jan 2016, 9 (3), 389-398. 1.3 MB. https://doi.org/10.1002/dta.2040

Anon. New drugs in Europe, 2012, European Monitoring Centre for Drugs and Drug Addiction, 1 May 2013. 773 kB. #65

Ogino, M; Naiki, T; Orui, H; Kosone, K; Yamazaki, M. Study of method for identifying phenethylamine drugs. JCCL, , 50, 63-82. 627 kB. Retrieved from http://www.customs.go.jp/ccl_search/e_info_search/drugs/r_50_08_e.pdf

Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB.

Baker, LE. Hallucinogens in drug discrimination. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 201-219. 342 kB. https://doi.org/10.1007/7854_2017_476

van Praag, HM; Schut, T; Bosma, E; van den Bergh, R. A comparative study of the therapeutic effects of some 4-chlorinated amphetamine derivatives in depressive patients. Psychopharmacologia, 1 Mar 1971, 20 (1), 66-76. 645 kB. https://doi.org/10.1007/BF00404060

Patrick, TM; McBee, ET; Hass, HB. Synthesis of arylpropylamines. I. From allyl chloride. J. Am. Chem. Soc., 1946, 68 (6), 1009-1011. 373 kB. https://doi.org/10.1021/ja01210a032

Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 652 kB. https://doi.org/10.1007/7854_2016_466

King, LA. New phenethylamines in Europe. Drug Test. Analysis, 1 Jul 2014, 6 (7-8), 808-818. 472 kB. https://doi.org/10.1002/dta.1570

Sloviter, RS; Connor, JD; Dimaano, BP; Drust, EG. Para-halogenated phenethylamines: Similar serotonergic effects in rats by different mechanisms. Pharmacol. Biochem. Behav., 1 Aug 1980, 13 (2), 283-286. 373 kB. https://doi.org/10.1016/0091-3057(80)90084-2

Nichols, DE. Medicinal chemistry and structure-activity relationships. In Amphetamine and its Analogs; Cho, AK; Segal, DS, Eds., Academic Press, San Diego, CA, 1994; pp 3–41. 6.9 MB. #11

Nichols, DE; Oberlender, R. Structure-activity relationships of MDMA-like substances. In Pharmacology and Toxicology of Amphetamine and Related Designer Drugs. NIDA Research Monograph 94; Asghar, K; De Souza, E, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1989; pp 12–40. 282 kB.

Biel, JH; Bopp, BA. Amphetamines: Structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1978; Vol. 11, pp 1–39. 1.0 MB. https://doi.org/10.1007/978-1-4757-0510-2_1

2-Cl-AMP
3-CA · 3-Chloroamphetamine
β-Me-4-Cl-PEA
N-Me-2-Cl-PEA
N-Me-3-Cl-PEA
N-Me-4-Cl-PEA
21 July 2018 · Creative Commons BY-NC-SA ·