4-Chlorophenylisobutylamine

4-Chlorophenylisobutylamine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Identifiers
IUPAC name
  • 1-(4-chlorophenyl)butan-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H14ClN
Molar mass183.68 g·mol−1
3D model (JSmol)
SMILES
  • Clc1ccc(cc1)CC(N)CC
InChI
  • InChI=1S/C10H14ClN/c1-2-10(12)7-8-3-5-9(11)6-4-8/h3-6,10H,2,7,12H2,1H3 checkY
  • Key:BDZUAWTZJXBMLX-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

4-Chlorophenylisobutylamine (4-CAB, AEPCA), also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine class.[1] It is an analogue of para-chloroamphetamine (PCA) where the alpha position methyl has been replaced with an ethyl group.[1]

In comparison to PCA, 4-CAB is approximately 2- and 5-fold less potent at inhibiting the reuptake of serotonin (IC50 = 330 nM) and dopamine (IC50 = 2,343 nM), respectively, and is about 3-fold less potent in substituting for MDMA in animals in drug discrimination assays.[1] Though its dopaminergic activity is significantly attenuated compared to PCA, unlike the case of MBDB, it is not abolished, and is actually similar to that of MDMA.[1]

Relative to PCA, 4-CAB is also substantially less effective as a serotonergic neurotoxin.[1] A single 10 mg/kg administration of PCA to rats produces an approximate 80% decrease in serotonin markers as observed 1 week later.[1] In contrast, 11 mg/kg and 22 mg/kg doses of 4-CAB result in only 20% and 50% decreases, respectively.[1] This is once again similar to MDMA which causes a 40-60% reduction with a single 20 mg/kg dose.[2]

See also

References

  1. 1 2 3 4 5 6 7 Johnson MP, Huang XM, Oberlender R, Nash JF, Nichols DE (November 1990). "Behavioral, biochemical and neurotoxicological actions of the alpha-ethyl homologue of p-chloroamphetamine". European Journal of Pharmacology. 191 (1): 1–10. doi:10.1016/0014-2999(90)94090-K. PMID 1982656.
  2. ↑ Aguirre N, Barrionuevo M, Ramírez MJ, Del Río J, Lasheras B (November 1999). "Alpha-lipoic acid prevents 3,4-methylenedioxy-methamphetamine (MDMA)-induced neurotoxicity". NeuroReport. 10 (17): 3675–80. doi:10.1097/00001756-199911260-00039. PMID 10619665.
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