4-Chlorophenylisobutylamine
Encyclopedia
4-Chlorophenylisobutylamine (4-CAB, AEPCA), also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant
drug
of the phenethylamine
class. 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.
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
of the phenethylamine
Substituted phenethylamine
The substituted phenethylamines are chemical compounds with the 2-phenethylamine chemical structure modified at the phenyl ring, sidechain, and/or amino group. Some of them are psychoactive drugs, including stimulants, psychedelics, opioids, and entactogens, which exert their effects primarily...
class. It is an analogue of para-chloroamphetamine
Para-Chloroamphetamine
para-Chloroamphetamine , also known as 4-chloroamphetamine , is an amphetamine derivative and monoamine releaser similar to MDMA, but with substantially higher neurotoxicity, thought to be due to the unrestrained release of both serotonin and dopamine as with MDMA itself...
(PCA) where the alpha position
Alpha carbon
The alpha carbon in organic chemistry refers to the first carbon that attaches to a functional group . By extension, the second carbon is the beta carbon, and so on....
methyl has been replaced with an ethyl
Ethyl group
In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....
group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
.
In comparison to PCA, 4-CAB is approximately 2- and 5-fold less potent
Potency (pharmacology)
In the field of pharmacology, potency is a measure of drug activity expressed in terms of the amount required to produce an effect of given intensity. A highly potent drug evokes a larger response at low concentrations, while a drug of lower potency evokes a small response at low concentrations...
at inhibiting
Reuptake inhibitor
A reuptake inhibitor , also known as a transporter blocker, is a drug that inhibits the plasmalemmal transporter-mediated reuptake of a neurotransmitter from the synapse into the pre-synaptic neuron, leading to an increase in the extracellular concentrations of the neurotransmitter and therefore an...
the reuptake
Reuptake
Reuptake, or re-uptake, is the reabsorption of a neurotransmitter by a neurotransmitter transporter of a pre-synaptic neuron after it has performed its function of transmitting a neural impulse....
of serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
(IC50
IC50
The half maximal inhibitory concentration is a measure of the effectiveness of a compound in inhibiting biological or biochemical function. This quantitative measure indicates how much of a particular drug or other substance is needed to inhibit a given biological process by half...
= 330 nM) and dopamine
Dopamine
Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...
(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
Dopaminergic
Dopaminergic means related to the neurotransmitter dopamine. For example, certain proteins such as the dopamine transporter , vesicular monoamine transporter 2 , and dopamine receptors can be classified as dopaminergic, and neurons which synthesize or contain dopamine and synapses with dopamine...
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
Serotonergic
Serotonergic or serotoninergic means "related to the neurotransmitter serotonin". A synapse is serotonergic if it uses serotonin as its neurotransmitter...
neurotoxin
Neurotoxin
A neurotoxin is a toxin that acts specifically on nerve cells , usually by interacting with membrane proteins such as ion channels. Some sources are more general, and define the effect of neurotoxins as occurring at nerve tissue...
. 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
- PhenylisobutylaminePhenylisobutylaminePhenylisobutylamine, also known as α-ethylphenethylamine or AEPEA, is a stimulant drug of the phenethylamine class. It is a higher homologue of amphetamine, differing from amphetamine's molecular structure only by the substitution of the methyl group at the alpha position of the side chain with an...
- 4-Methylphenylisobutylamine4-Methylphenylisobutylamine4-Methylphenylisobutylamine , also known as 4-methyl-α-ethylphenethylamine, is a stimulant drug of the phenethylamine class.- References :...
- para-ChloroamphetaminePara-Chloroamphetaminepara-Chloroamphetamine , also known as 4-chloroamphetamine , is an amphetamine derivative and monoamine releaser similar to MDMA, but with substantially higher neurotoxicity, thought to be due to the unrestrained release of both serotonin and dopamine as with MDMA itself...