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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	2275-64-1
PubChem CID	150989
ChemSpider	133083
UNII	LJ4HK7485X
CompTox Dashboard (EPA)	DTXSID30945430
Chemical and physical data
Formula	C10H14ClN
Molar mass	183.68 g·mol
3D model (JSmol)	Interactive image
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 Key:BDZUAWTZJXBMLX-UHFFFAOYSA-N
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4-Chlorophenylisobutylamine (4-CAB, AEPCA), also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine, amphetamine, and phenylisobutylamine families. It is an analogue of para-chloroamphetamine (PCA) where the alpha position methyl has been replaced with an ethyl group.

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. 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.

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

See also

• Phenylisobutylamine
• 4-Methylphenylisobutylamine

References

1. ^ 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.

• Drugs not assigned an ATC code
• Entactogens and empathogens
• Monoaminergic neurotoxins
• Phenylisobutylamines
• Serotonin-norepinephrine-dopamine releasing agents