5-MAPB

5-MAPB, also known as 5-(N-methyl-2-aminopropyl)benzofuran, is an entactogen and designer drug of the amphetamine family that is similar to MDMA in its structure and effects.^[1]

5-MAPB

Clinical data
Other names	5-(N-Methyl-2-aminopropyl)benzofuran
Routes of administration	Oral, Insufflated, Rectal
Legal status
Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class B Illegal in China
Identifiers
IUPAC name 1-(Benzofuran-5-yl)-N-methylpropan-2-amine
CAS Number	1354631-77-8
PubChem CID	102336592
ChemSpider	32078887
UNII	XW34GUY2OY
CompTox Dashboard (EPA)	DTXSID801017189 DTXSID301010102, DTXSID801017189
Chemical and physical data
Formula	C12H15NO
Molar mass	189.25 g/mol (freebase) 225.7 g/mol (HCl salt) g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(NC)CC1=CC(C=CO2)=C2C=C1
InChI InChI=1S/C12H15NO/c1-9(13-2)7-10-3-4-12-11(8-10)5-6-14-12/h3-6,8-9,13H,7H2,1-2H3 Key:ZOVRTIPCNFERHY-UHFFFAOYSA-N

It has been patented by Tactogen as an entactogen for potential use as a medicine.^[2]

Pharmacology

Pharmacodynamics

5-MAPB acts as a serotonin–norepinephrine–dopamine releasing agent with EC₅₀Tooltip half-maximal effective concentration values for induction of monoamine release of 64 nM for serotonin, 24 nM for norepinephrine, and 41 nM for dopamine using rat brain synaptosomes.^[3][4][5][6] It is also a partial agonist of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[3][4][7]

Monoamine release of 5-MAPB and its enantiomers^[2]

Compound	SERTTooltip Serotonin transporter	NETTooltip Norepinephrine transporter	DATTooltip Dopamine transporter	DAT/SERT ratio
(S)-5-MAPB	67	ND	258	0.26
75% (S)-5-MAPB	80	ND	632	0.13
(RS)-5-MAPB	90	ND	459	0.20
75% (R)-5-MAPB	122	ND	794	0.15
(R)-5-MAPB	184	ND	1951	0.09
Note: This assay used Chinese hamster ovary (CHO) cells expressing human monoamine transporters rather than the more typical rat brain synaptosomes assay.[2]

5-MAPB has been described by Matthew Baggott as the MDMA analogue so far known that has the closest effects and so-called "magic" to MDMA itself.^[8][9] Other analogues that lack the full quality of MDMA include MBDB, methylone, 6-APDB, 5-APDB, 6-APB, 5-APB, MDAT, and MDAI, among others.^[8][9]

5-MAPB has been marketed as a less- or non-neurotoxic alternative to MDMA.^[10] However, 5-MAPB has been found to be a dose-dependent serotonergic neurotoxin in rodents similarly to MDMA, and might also be a dopaminergic neurotoxin.^[10]

Pharmacokinetics

Little formal knowledge exists on 5-MAPB. It does not form the α-methyldopamine metabolite that contributes to the neurotoxicity of MDMA or MDA.^{[11][12][13][14]} A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.^[15]

Legal Status

Canada

5-MAPB is not listed itself in the CDSA but since it is structurally related to MDMA it may be considered illegal in Canada, although this has not been tested in court.^[16]

China

As of October 2015 5-MAPB is a controlled substance in China.^[17]

Luxembourg

As of July 2021, 5-MAPB is not cited in the list of prohibited substances.^[18] Therefore, it is still a legal substance.

United Kingdom

5-MAPB was originally banned in the UK in June 2013 under a Temporary class drug order.^[19] On March 5, 2014, the UK Home Office announced that 5-MAPB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.^[20]

See also

• Borax combo