6-APB
Encyclopedia
6-benzofuran or 1-benzofuran-6-ylpropan-2-amine (6-APB) is thought to be a stimulant
and entactogen drug
although to date, no authoritative source can say even whether or not it is psychoactive. Chemically, it is of the phenethylamine
and substituted amphetamine
classes. It is similar to MDA
in that the 3,4-methylenedioxy
phenyl ring
system has been replaced with a benzofuran
ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB
. There is currently no toxicology data available.
action
, but based on its chemical similarity to other amphetamines and methylenedioxy compounds, it likely acts as a releasing agent
and reuptake inhibitor
of serotonin
, norepinephrine
, and dopamine
. Though its effects on monoamine release have not been validated, 6-APB has been claimed to act as an agonist
of the 5-HT2C receptor
. It may also act as an agonist of the 5-HT2A
and 5-HT2B receptor
s, the former likely explaining its reputed psychedelic
effects.
in the United States. However, this chemical may be covered under the Federal Analogue Act in the United States
.
Certain countries contain a "substantially similar" catch-all clause in their drug law, such as New Zealand and Australia. This includes 6-APB as it is in some respects similar in chemical structure to the class A drug MDA, meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions.
6-APB is unscheduled under the Controlled Drugs and Substances Act (CDSA) in Canada, although there is a Schedule III amphetamine analogue clause. Due to 6-APB's structure, it may be considered an analogue of MDA, but these types of offenses are rarely prosecuted.
Canada's CDSA defines an analogue as any substance that, in relation to a controlled substance, has a substantially similar chemical structure.
6-APB is currently legal in the UK.
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...
and entactogen 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...
although to date, no authoritative source can say even whether or not it is psychoactive. Chemically, it is 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...
and substituted amphetamine
Substituted amphetamine
Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...
classes. It is similar to MDA
3,4-Methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...
in that the 3,4-methylenedioxy
Methylenedioxy
Methylenedioxy in the field of chemistry, particularly in organic chemistry, is the name for a functional group with the structural formula R-O-CH2-O-R' which is connected to the rest of a molecule by two chemical bonds. The methylenedioxy group consists of two oxygen atoms connected to a methylene...
phenyl ring
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...
system has been replaced with a benzofuran
Benzofuran
Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the "parent" of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several...
ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB
6-APDB
6--2,3-dihydrobenzofuran is a stimulant and entactogen drug of the phenethylamine and amphetamine classes. It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3,4-methylenedioxy ring has been replaced with a methylene group...
. There is currently no toxicology data available.
Pharmacology
6-APB has not been properly assessed in terms of pharmacologicalPharmacology
Pharmacology is the branch of medicine and biology concerned with the study of drug action. More specifically, it is the study of the interactions that occur between a living organism and chemicals that affect normal or abnormal biochemical function...
action
Mechanism of action
In pharmacology, the term mechanism of action refers to the specific biochemical interaction through which a drug substance produces its pharmacological effect...
, but based on its chemical similarity to other amphetamines and methylenedioxy compounds, it likely acts as a releasing agent
Releasing agent
A releasing agent , or simply releaser, is a drug that induces the release of a neurotransmitter from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitter. Many drugs use neurotransmitter release to exert their psychological and...
and reuptake inhibitor
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...
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...
, norepinephrine
Norepinephrine
Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter...
, 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...
. Though its effects on monoamine release have not been validated, 6-APB has been claimed to act as an agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
of the 5-HT2C receptor
5-HT2C receptor
The 5-HT2C receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor that is coupled to Gq/G11 and mediates excitatory neurotransmission. HTR2C denotes the human gene encoding for the receptor, that in humans is located at the...
. It may also act as an agonist of the 5-HT2A
5-HT2A receptor
The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...
and 5-HT2B receptor
5-HT2B receptor
5-hydroxytryptamine receptor 2B, also known as HTR2B, is a 5-HT2 receptor, but also denotes the human gene encoding it.-Function:...
s, the former likely explaining its reputed psychedelic
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
effects.
Law
6-APB is unscheduledControlled Substances Act
The Controlled Substances Act was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. The CSA is the federal U.S. drug policy under which the manufacture, importation, possession, use and distribution of certain...
in the United States. However, this chemical may be covered under the Federal Analogue Act in the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
.
Certain countries contain a "substantially similar" catch-all clause in their drug law, such as New Zealand and Australia. This includes 6-APB as it is in some respects similar in chemical structure to the class A drug MDA, meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions.
6-APB is unscheduled under the Controlled Drugs and Substances Act (CDSA) in Canada, although there is a Schedule III amphetamine analogue clause. Due to 6-APB's structure, it may be considered an analogue of MDA, but these types of offenses are rarely prosecuted.
Canada's CDSA defines an analogue as any substance that, in relation to a controlled substance, has a substantially similar chemical structure.
6-APB is currently legal in the UK.
See also
- 5-APB5-APB5-benzofuran or 1-benzofuran-5-ylpropan-2-amine is a drug claimed to act as an agonist of the 5-HT2C receptor, which has been sold as a designer drug...
- 5-APDB
- 6-APDB6-APDB6--2,3-dihydrobenzofuran is a stimulant and entactogen drug of the phenethylamine and amphetamine classes. It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3,4-methylenedioxy ring has been replaced with a methylene group...
- 5-(2-Aminopropyl)indole5-(2-Aminopropyl)indole5-indole is an indole derivative which is mentioned in TIHKAL as a fairly potent and long-lasting stimulant drug. It is related to several well known drugs, and can be viewed both as a structural isomer of α-MT , and as a ring-substituted derivative of amphetamine...
- EthylenedioxymethamphetamineEDMA3,4-Ethylenedioxy-N-methylamphetamine is an entactogen drug of the amphetamine class. It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring. EDMA was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage is listed as 150–250 mg,...
- IndanylaminopropaneIndanylaminopropaneIndanylaminopropane , sometimes incorrectly referred to as indanylamphetamine, is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes...
- Naphthylaminopropane
- TetralinylaminopropaneTetralinylaminopropaneTetralinylaminopropane is an entactogen drug of the amphetamine class which acts as a selective serotonin releasing agent . It has IC50 values of 121 nM, 6,436 nM, and 3,371 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively...