4-Chlorophenylisobutylamine
- none
- Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
- 1-(4-chlorophenyl)butan-2-amine
- 2275-64-1 N
- 150989
- 133083 Y
- LJ4HK7485X
- DTXSID30945430
- Interactive image
- Clc1ccc(cc1)CC(N)CC
- InChI=1S/C10H14ClN/c1-2-10(12)7-8-3-5-9(11)6-4-8/h3-6,10H,2,7,12H2,1H3 Y
- Key:BDZUAWTZJXBMLX-UHFFFAOYSA-N Y
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[clarification needed], 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
- ^ a b c d e f g 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.
- ^ 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.
- v
- t
- e
amines
(other than
cathinones)
- Unfused benzene ring: 3-CMA
- 4-CAB
- 4-FA
- 4-MA
- 4-MMA
- 4-FMA
- 4-MTA
- 4,4'-DMAR
- Ariadne
- Metaescaline
- MMA
- PMA
- PMEA
- PMMA
- mMMA
Benzodioxine: EDMA
Benzodioxoles: Phenethylamine: { Lophophine } - Amphetamines: { 2-Methyl-MDA
- 2,3-MDA
- 3,4-MDA (tenamfetamine)
- 5-Methyl-MDA
- 6-Methyl-MDA
- DFMDA
- DMMDA
- DMMDA-2
- EIDA
- Lys-MDA
- MDEA
- MDMA (midomafetamine)
- MDMOH
- MDOH
- MMDA
- MMDA-2
- MMDMA
- N-t-BOC-MDMA }
- 1-Phenylbutan-2-amines: { BDB
- EBDB
- MBDB }
- Phentermines: { MDMP
- MDPH }
Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB - 5-APB
- 5-APDB
- 5-EAPB
- 5-MAPB
- 5-MAPDB
- 5-MAPBT
- 5-MBPB
- 6-APB
- 6-APDB
- 6-EAPB
- 6-MAPB
- 6-MAPDB
- IBF5MAP
Indanes: 5-APDI - 5-MAPDI
Indoles: 5-IT - 6-API
Naphthalenes: Methamnetamine - Naphthylaminopropane
Tetralin: 6-APT
alkylamines