5-MAPB

5-MAPB (1-(benzofuran-5-yl)-N-methylpropan-2-amine) is an entactogenic designer drug similar to MDMA in its structure and effects.^[1]

5-MAPB

Clinical data
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

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.^[2]

China

As of October 2015 5-MAPB is a controlled substance in China.^[3]

Luxembourg

As of July 2021, 5-MAPB is not cited in the list of prohibited substances.^[4] 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.^[5] 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.^[6]

Pharmacokinetics

5-MAPB is a triple reuptake inhibitor of serotonin, dopamine and norepinephrine and an agonist for the 5-HT_2A and 5-HT_2B receptors ^[7]

Metabolism and toxicity

Little formal knowledge exists on 5-MAPB. It does not form the alpha-methyldopamine metabolite that contributes to the neurotoxicity of MDMA or MDA.^{[8][9][10][11]} A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.^[12]

Pharmacodynamics

5-MAPB binds to the dopamine transporter in rat brain cells with a lower affinity than cocaine. In silico data suggests that the primary action on dopamine is through reversal of the transporter to release dopamine. This is consistent with the effects and it is possible that it exerts a similar action on serotonin and norepinephrine transporters.^[13]

References

1. "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 June 2013. Retrieved 2013-07-10.
2. "Schedule I". Government Of Canada. 2014-12-12. Archived from the original on 2013-11-22. Retrieved 2014-12-13.
3. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
4. "Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie" [Law of February 19, 1973 concerning the sale of medicinal substances and the fight against drug addiction.]. Journal officiel du Grand-Duché de Luxembourg (in French).
5. "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. Retrieved 10 April 2014.
6. UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.
7. Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL (January 2013). "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology. 700 (1–3): 147–151. doi:10.1016/j.ejphar.2012.12.006. PMID 23261499.
8. Shimshoni JA, Winkler I, Golan E, Nutt D (January 2017). "Neurochemical binding profiles of novel indole and benzofuran MDMA analogues". Naunyn-Schmiedeberg's Archives of Pharmacology. 390 (1): 15–24. doi:10.1007/s00210-016-1297-4. PMID 27650729.
9. McCann UD, Ricaurte GA (April 1991). "Major metabolites of (+/-)3,4-methylenedioxyamphetamine (MDA) do not mediate its toxic effects on brain serotonin neurons". Brain Research. 545 (1–2): 279–282. doi:10.1016/0006-8993(91)91297-E. PMID 1860050. S2CID 2574803.
10. Miller RT, Lau SS, Monks TJ (April 1997). "2,5-Bis-(glutathion-S-yl)-alpha-methyldopamine, a putative metabolite of (+/-)-3,4-methylenedioxyamphetamine, decreases brain serotonin concentrations". European Journal of Pharmacology. 323 (2–3): 173–180. doi:10.1016/S0014-2999(97)00044-7. PMID 9128836.
11. Conway EL, Louis WJ, Jarrott B (December 1978). "Acute and chronic administration of alpha-methyldopa: regional levels of endogenous and alpha-methylated catecholamines in rat brain". European Journal of Pharmacology. 52 (3–4): 271–280. doi:10.1016/0014-2999(78)90279-0. PMID 729639.
12. Welter J, Kavanagh P, Meyer MR, Maurer HH (February 2015). "Benzofuran analogues of amphetamine and methamphetamine: studies on the metabolism and toxicological analysis of 5-APB and 5-MAPB in urine and plasma using GC-MS and LC-(HR)-MS(n) techniques". Analytical and Bioanalytical Chemistry. 407 (5): 1371–1388. doi:10.1007/s00216-014-8360-0. PMID 25471293. S2CID 20653012.
13. Sahai MA, Davidson C, Khelashvili G, Barrese V, Dutta N, Weinstein H, et al. (April 2017). "Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances - The case of the benzofuran 5-MAPB" (PDF). Progress in Neuro-Psychopharmacology & Biological Psychiatry. 75: 1–9. doi:10.1016/j.pnpbp.2016.11.004. PMID 27890676. S2CID 30943496.