2-Chloroamphetamine
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| drug_name =
| image = 2-Chloroamphetamine.svg
| width = 175px
| caption =
| pronounce =
| tradename =
| Drugs.com =
| MedlinePlus =
| licence_CA =
| licence_EU =
| DailyMedID =
| licence_US =
| pregnancy_AU =
| pregnancy_category =
| dependency_liability =
| addiction_liability =
| routes_of_administration =
| class = Monoamine releasing agent
| ATC_prefix =
| ATC_suffix =
| legal_status =
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action =
| excretion =
| CAS_number = 21193-23-7
| CAS_supplemental =
| PubChem = 152331
| PubChemSubstance =
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID = 134269
| UNII = 00Q9Z0HNOQ
| KEGG =
| ChEBI = 180535
| ChEMBL =
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = 2-CA; ortho-Chloroamphetamine; o-Chloroamphetamine; OCA; o-CA
| IUPAC_name = 1-(2-chlorophenyl)propan-2-amine
| C=9 | H=12 | Cl=1 | N=1
| SMILES = CC(CC1=CC=CC=C1Cl)N
| StdInChI = 1S/C9H12ClN/c1-7(11)6-8-4-2-3-5-9(8)10/h2-5,7H,6,11H2,1H3
| StdInChIKey = IQHHOHJDIZRBGM-UHFFFAOYSA-N
}}
2-Chloroamphetamine (2-CA), also known as ortho-chloroamphetamine (OCA), is a monoamine releasing agent (MRA) of the amphetamine family related to 2-fluoroamphetamine (2-FA).{{cite book | vauthors = Blough B | chapter = Dopamine-releasing agents | veditors = Trudell ML, Izenwasser S | title = Dopamine Transporters: Chemistry, Biology and Pharmacology | pages = 305–320 | date = July 2008 | isbn = 978-0-470-11790-3 | oclc = 181862653 | ol = OL18589888W | publisher = Wiley | location = Hoboken [NJ] | doi = | url = https://books.google.com/books?id=QCagLAAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }}
Pharmacology
=Pharmacodynamics=
It has been found to induce the release of norepinephrine and dopamine in rat brain synaptosomes with {{Abbrlink|EC50|half-maximal effective concentration}} values of 19.1 and 62.4{{nbsp}}nM, respectively, whereas serotonin was not reported. It has been found to also induce the release of serotonin in mouse brain slices to some degree,{{cite journal | vauthors = Ross SB, Ogren SO, Renyi AL | title = Substituted amphetamine derivatives. I. Effect on uptake and release of biogenic monoamines and on monoamine oxidase in the mouse brain | journal = Acta Pharmacol Toxicol (Copenh) | volume = 41 | issue = 4 | pages = 337–352 | date = October 1977 | pmid = 579062 | doi = 10.1111/j.1600-0773.1977.tb02673.x | url = }} whereas it did not induce the release of serotonin in the brain in rats in vivo.
In contrast to amphetamine and para-chloroamphetamine (PCA; 4-chloroamphetamine), 2-CA does not appear to produce hyperlocomotion in mice, and instead has been found to decrease locomotor activity.{{cite journal | vauthors = Ogren SO, Ross SB | title = Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones | journal = Acta Pharmacol Toxicol (Copenh) | volume = 41 | issue = 4 | pages = 353–368 | date = October 1977 | pmid = 303437 | doi = 10.1111/j.1600-0773.1977.tb02674.x | url = }} However, it did potentiate the effects of levodopa similarly to amphetamine and PCA. On the other hand, like amphetamine but in contrast to PCA and 4-methylamphetamine (4-MA), 2-CA did not potentiate the effects of 5-hydroxytryptophan (5-HTP). Unlike PCA, 2-CA did not produce the head-twitch response, a behavioral proxy of psychedelic-like effects, in mice.
In contrast to PCA, but similarly to amphetamine, 2-CA does not appear to produce serotonergic neurotoxicity in rats or guinea pigs.{{cite journal | vauthors = Fuller RW | title = Effects of p-chloroamphetamine on brain serotonin neurons | journal = Neurochem Res | volume = 17 | issue = 5 | pages = 449–456 | date = May 1992 | pmid = 1528354 | doi = 10.1007/BF00969891 | url = }}{{cite journal | vauthors = Fuller RW | title = Structure-activity relationships among the halogenated amphetamines | journal = Ann N Y Acad Sci | volume = 305 | issue = 1| pages = 147–159 | date = June 1978 | pmid = 152079 | doi = 10.1111/j.1749-6632.1978.tb31518.x | bibcode = 1978NYASA.305..147F | url = }}{{cite journal | vauthors = Fuller RW, Schaffer RJ, Roush BW, Molloy BB | title = Drug disposition as a factor in the lowering of brain serotonin by chloroamphetamines in the rat | journal = Biochem Pharmacol | volume = 21 | issue = 10 | pages = 1413–1417 | date = May 1972 | pmid = 5029422 | doi = 10.1016/0006-2952(72)90365-6 | url = }}{{cite journal | vauthors = Fuller RW, Snoddy HD, Roush BW, Molloy BB | title = Further structure-activity studies on the lowering of brain 5-hydroxyindoles by 4-chloramphetamine | journal = Neuropharmacology | volume = 12 | issue = 1 | pages = 33–42 | date = January 1973 | pmid = 4687274 | doi = 10.1016/0028-3908(73)90129-9 | url = }} While this could be attributed to rapid metabolism in the case of 3-chloroamphetamine (3-CA), 2-CA continued to lack serotonergic neurotoxicity even when its metabolism was inhibited by desipramine.
References
{{Reflist}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
{{DEFAULTSORT:Chloroamphetamine, 2-}}
Category:2-Chlorophenyl compounds