5-APB

5-APB (abbreviation of "5-(2-aminopropyl)benzofuran") is an empathogenic psychoactive compound of the phenethylamine, amphetamine, and benzofuran families. The drug and other compounds have sometimes been informally called "Benzofury". 5-APB has been sold as a designer drug since 2010.^[2]

5-APB

Clinical data
Other names	1-Benzofuran-5-ylpropan-2-amine
Routes of administration	Oral
Drug class	Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Stimulant; Psychedelic
ATC code	None
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)[1] DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B UN: Unscheduled.
Identifiers
IUPAC name 1-(1-benzofuran-5-yl)propan-2-amine
CAS Number	286834-81-9 Y
PubChem CID	9837232
ChemSpider	8012953 Y
UNII	2M3825704H
CompTox Dashboard (EPA)	DTXSID101010106
Chemical and physical data
Formula	C11H13NO
Molar mass	175.231 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(N)CC1=CC(C=CO2)=C2C=C1
InChI InChI=1S/C11H13NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8H,6,12H2,1H3 Y Key:VKUMKUZDZWHMQU-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Effects

Users describe the effects of 5-APB as including euphoria among others.^[3] Largely, its effects reported were similar to those of the drug MDMA but not as strong.^{[citation needed]} The drug has been reported to produce visual disturbances and is said to have mild psychedelic effects.^[3][4]

Recreational use of 5-APB has been associated with death in combination with other drugs^[5][6] and solely as the result of 5-APB.^[7]

Pharmacology

5-APB acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC₅₀Tooltip half-maximal effective concentration values for monoamine release of 19 nM for serotonin, 21 nM for norepinephrine, and 31 nM for dopamine in rat brain synaptosomes.^[8][9] It is also a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).^[8]

5-APB is a potent agonist of the serotonin 5-HT_2A and 5-HT_2B receptors.^[8][9] Its EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy) values were 6,300 nM (54%) at the serotonin 5-HT_2A receptor and 280 nM (61–92%) at the serotonin 5-HT_2B receptor.^[8][9] It also shows affinity for the serotonin 5-HT_2C receptor (K_i = 880 nM) and the serotonin 5-HT_1A receptor (K_i = 3,300 nM).^[8][9] It has been reported to act as an agonist of the serotonin 5-HT_2C receptor similarly to the serotonin 5-HT_2A and 5-HT_2B receptors.^[3][10] The drug's potent agonism of the serotonin 5-HT_2B receptor makes it likely that 5-APB would be cardiotoxic with long-term use, as seen with other serotonin 5-HT_2B receptor agonists such as fenfluramine and MDMA.^{[citation needed]}

5-APB also shows high affinity for the mouse and rat trace amine-associated receptor 1 (TAAR1).^[8]

In animal studies, 5-APB produces robust hyperlocomotion, robust conditioned place preference (CPP) but limited self-administration, fully substitutes for MDMA in drug discrimination tests, and partially substitutes for DOM, cocaine, and methamphetamine in drug discrimination tests.^[11]

Chemistry

5-APB is commonly found as the succinate and hydrochloride salt. The hydrochloride salt is 10% more potent by mass and doses should be adjusted accordingly.

Detection

A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.^[12] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.^[13]

Society and culture

Legal status

United Kingdom

On March 5, 2014 the UK Home Office announced that 5-APB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.^[14]

See also

• Borax combo
• 6-APB
• 5-APBT
• 5-API
• 5-APDB