2-MAPB

2-MAPB
Identifiers
	IUPAC name 1-(1-benzofuran-2-yl)-N-methylpropan-2-amine;
CAS Number	806596-15-6 ;
PubChem CID	547092;
ChemSpider	476194;
UNII	W5G20WN7CL;
CompTox Dashboard (EPA)	DTXSID901016908 ;
Chemical and physical data
Formula	C12H15NO
Molar mass	189.258 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC2=CC=CC=C2O1)NC;
	InChI InChI=1S/C12H15NO/c1-9(13-2)7-11-8-10-5-3-4-6-12(10)14-11/h3-6,8-9,13H,7H2,1-2H3; Key:ANJIDHKQUCZNQY-UHFFFAOYSA-N;

2-MAPB is a recreational designer drug with empathogenic effects. As with other related substituted benzofuran derivatives such as 6-APB and 5-MAPB, 2-MAPB is a monoamine releaser with some selectivity for serotonin release, generally similar in pharmacological profile to MDMA but with greater activity as a directly acting agonist of 5-HT₂ receptor subtypes and somewhat greater toxicity.^[1] 2-MAPB has been isolated from post-mortem toxicology screens in several drug-related fatal adverse reactions but generally only as a component of combinations of drugs, making it difficult to determine how much it contributed to the deaths.^[2]^[3] It is illegal in Japan.^[4]

References

^ Fuwa T, Suzuki J, Tanaka T, Inomata A, Honda Y, Kodama T (2016). "Novel psychoactive benzofurans strongly increase extracellular serotonin level in mouse corpus striatum". The Journal of Toxicological Sciences. 41 (3): 329–337. doi:10.2131/jts.41.329. PMID 27193726.
^ Staeheli SN, Boxler MI, Oestreich A, Marti M, Gascho D, Bolliger SA, et al. (October 2017). "Postmortem distribution and redistribution of MDAI and 2-MAPB in blood and alternative matrices" (PDF). Forensic Science International. 279: 83–87. doi:10.1016/j.forsciint.2017.08.007. PMID 28850871. S2CID 31183795.
^ Theofel N, Budach D, Vejmelka E, Scholtis S, Tsokos M (June 2021). "Toxicological investigations in a death involving 2-MAPB". Forensic Science, Medicine, and Pathology. 17 (2): 317–321. doi:10.1007/s12024-021-00366-0. ISSN 1547-769X. PMID 33877515. S2CID 233309570.
^ "指定薬物名称・構造式一覧（平成27年9月16日現在）" (PDF) (in Japanese). 厚生労働省. 16 September 2015. Retrieved 23 August 2016.

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[1] Fuwa T, Suzuki J, Tanaka T, Inomata A, Honda Y, Kodama T (2016). "Novel psychoactive benzofurans strongly increase extracellular serotonin level in mouse corpus striatum". The Journal of Toxicological Sciences. 41 (3): 329–337. doi:10.2131/jts.41.329. PMID 27193726.

[2] Staeheli SN, Boxler MI, Oestreich A, Marti M, Gascho D, Bolliger SA, et al. (October 2017). "Postmortem distribution and redistribution of MDAI and 2-MAPB in blood and alternative matrices" (PDF). Forensic Science International. 279: 83–87. doi:10.1016/j.forsciint.2017.08.007. PMID 28850871. S2CID 31183795.

[3] Theofel N, Budach D, Vejmelka E, Scholtis S, Tsokos M (June 2021). "Toxicological investigations in a death involving 2-MAPB". Forensic Science, Medicine, and Pathology. 17 (2): 317–321. doi:10.1007/s12024-021-00366-0. ISSN 1547-769X. PMID 33877515. S2CID 233309570.

[4] "指定薬物名称・構造式一覧（平成27年9月16日現在）" (PDF) (in Japanese). 厚生労働省. 16 September 2015. Retrieved 23 August 2016.

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v t e Empathogens/entactogens
Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 3-CMA 4-CAB 4-FA 4-MA 4-MMA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA mMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA DMMDA DMMDA-2 EIDA Lys-MDA MDEA MDMA (midomafetamine) (R)-MDMA MDMOH MDOH MMDA MMDA-2 MMDMA N-t-BOC-MDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MAPBT 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB IBF5MAP Indanes: 5-APDI 5-MAPDI Indoles: 5-IT 6-API Naphthalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI BFAI ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-CMC 3-MMC 4-EMC BK-5-MAPB Brephedrone Butylone Dimethylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

See also

References