| Revision as of 18:10, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{drugbox}} taken from revid 451560514 of page 4-Chlorophenylisobutylamine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 19:32, 10 November 2024 edit 76.174.0.57 (talk) Cat. |
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{{short description|Entactogen and stimulant drug of the phenethylamine class}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 445988449 |
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| verifiedrevid = 477221385 |
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| IUPAC_name = 1-(4-chlorophenyl)butan-2-amine |
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| IUPAC_name = 1-(4-chlorophenyl)butan-2-amine |
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| image = 4-Chlorophenylisobutylamine.png |
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| image = 4-Chlorophenylisobutylamine.png |
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| tradename = |
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| tradename = |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_status = Uncontrolled <small>(but may be covered under the ] in the ] and under similar bills in other countries)</small> |
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| legal_status = Uncontrolled (but may be covered under the ] in the ] and under similar bills in other countries) |
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| routes_of_administration = ] |
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| routes_of_administration = ] |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|CAS}} |
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| CAS_number = <!-- blanked - oldvalue: 2275-64-1 --> |
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| CAS_number = 2275-64-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = LJ4HK7485X |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_suffix = |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=10 | H=14 | Cl=1 | N=1 |
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| C=10 | H=14 | Cl=1 | N=1 |
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| molecular_weight = 183.68 g/mol |
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| smiles = Clc1ccc(cc1)CC(N)CC |
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| smiles = Clc1ccc(cc1)CC(N)CC |
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| InChI = 1/C10H14ClN/c1-2-10(12)7-8-3-5-9(11)6-4-8/h3-6,10H,2,7,12H2,1H3 |
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| InChIKey = BDZUAWTZJXBMLX-UHFFFAOYAL |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H14ClN/c1-2-10(12)7-8-3-5-9(11)6-4-8/h3-6,10H,2,7,12H2,1H3 |
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| StdInChI = 1S/C10H14ClN/c1-2-10(12)7-8-3-5-9(11)6-4-8/h3-6,10H,2,7,12H2,1H3 |
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| StdInChIKey = BDZUAWTZJXBMLX-UHFFFAOYSA-N |
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| StdInChIKey = BDZUAWTZJXBMLX-UHFFFAOYSA-N |
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}} |
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}} |
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'''4-Chlorophenylisobutylamine''' ('''4-CAB''', '''AEPCA'''), also known as '''4-chloro-α-ethylphenethylamine''', is an ] and ] ] of the ], ], and ] families.<ref name="pmid1982656">{{cite journal | vauthors = Johnson MP, Huang XM, Oberlender R, Nash JF, Nichols DE | title = Behavioral, biochemical and neurotoxicological actions of the alpha-ethyl homologue of p-chloroamphetamine | journal = European Journal of Pharmacology | volume = 191 | issue = 1 | pages = 1–10 | date = November 1990 | pmid = 1982656 | doi = 10.1016/0014-2999(90)94090-K }}</ref> It is an ] of ] (PCA) where the ] ] has been replaced with an ] ].<ref name="pmid1982656"/> |
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In comparison to PCA, 4-CAB is approximately 2- and 5-fold less ] at ] the ] of ] (] = 330 nM) and ] (IC<sub>50</sub> = 2,343 nM), respectively, and is about 3-fold less potent in substituting for ] in animals in drug discrimination assays.<ref name="pmid1982656"/> Though its ] activity is significantly attenuated compared to PCA, unlike the case of ], it is not abolished{{clarify|date=October 2022}}, and is actually similar to that of MDMA.<ref name="pmid1982656"/> |
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Relative to PCA, 4-CAB is also substantially less effective as a ] ].<ref name="pmid1982656"/> A single 10 mg/kg administration of PCA to rats produces an approximate 80% decrease in serotonin markers as observed 1 week later.<ref name="pmid1982656"/> In contrast, 11 mg/kg and 22 mg/kg doses of 4-CAB result in only 20% and 50% decreases, respectively.<ref name="pmid1982656"/> This is once again similar to MDMA which causes a 40-60% reduction with a single 20 mg/kg dose.<ref name="pmid10619665">{{cite journal | vauthors = Aguirre N, Barrionuevo M, Ramírez MJ, Del Río J, Lasheras B | title = Alpha-lipoic acid prevents 3,4-methylenedioxy-methamphetamine (MDMA)-induced neurotoxicity | journal = NeuroReport | volume = 10 | issue = 17 | pages = 3675–80 | date = November 1999 | pmid = 10619665 | doi = 10.1097/00001756-199911260-00039 }}</ref> |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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{{Entactogens}} |
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{{Stimulants}} |
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{{Monoamine releasing agents}} |
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{{Monoamine neurotoxins}} |
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{{Phenethylamines}} |
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{{DEFAULTSORT:Chlorophenylisobutylamine, 4-}} |
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] |
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] |
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] |
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] |