Chemistry:5-MAPB

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;
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;

Short description: Chemical compound

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

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

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.^[7]^[8]^[9] A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.^[10]

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.^[11]

References

↑ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds.
↑ "Schedule I". Government Of Canada. 2014-12-12. http://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-24.html#h-28.
↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html.
↑ Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie. | http://legilux.public.lu/eli/etat/leg/loi/1973/02/19/n1/jo
↑ "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned.
↑ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. http://www.legislation.gov.uk/ukdsi/2014/9780111110904.
↑ "Major metabolites of (+/-)3,4-methylenedioxyamphetamine (MDA) do not mediate its toxic effects on brain serotonin neurons". Brain Research 545 (1–2): 279–82. April 1991. doi:10.1016/0006-8993(91)91297-E. PMID 1860050.
↑ "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): 173–80. April 1997. doi:10.1016/S0014-2999(97)00044-7. PMID 9128836.
↑ "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): 271–80. December 1978. doi:10.1016/0014-2999(78)90279-0. PMID 729639.
↑ "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): 1371–88. February 2015. doi:10.1007/s00216-014-8360-0. PMID 25471293.
↑ "Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances - The case of the benzofuran 5-MAPB". Progress in Neuro-Psychopharmacology & Biological Psychiatry 75: 1–9. April 2017. doi:10.1016/j.pnpbp.2016.11.004. PMID 27890676. http://clok.uclan.ac.uk/16476/1/Davidson%205MAPB.pdf.

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Original source: https://en.wikipedia.org/wiki/5-MAPB. Read more

[ACMD_report-1] "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds.

[Schedule_1_of_the_CDSA-2] "Schedule I". Government Of Canada. 2014-12-12. http://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-24.html#h-28.

[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" (in Chinese). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html.

[4] Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie. | http://legilux.public.lu/eli/etat/leg/loi/1973/02/19/n1/jo

[HO_press_release-5] "'NBOMe' and 'Benzofury' banned". UK Home Office. 2013-06-04. https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned.

[6] UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. http://www.legislation.gov.uk/ukdsi/2014/9780111110904.

[7] "Major metabolites of (+/-)3,4-methylenedioxyamphetamine (MDA) do not mediate its toxic effects on brain serotonin neurons". Brain Research 545 (1–2): 279–82. April 1991. doi:10.1016/0006-8993(91)91297-E. PMID 1860050.

[8] "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): 173–80. April 1997. doi:10.1016/S0014-2999(97)00044-7. PMID 9128836.

[9] "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): 271–80. December 1978. doi:10.1016/0014-2999(78)90279-0. PMID 729639.

[10] "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): 1371–88. February 2015. doi:10.1007/s00216-014-8360-0. PMID 25471293.

[11] "Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances - The case of the benzofuran 5-MAPB". Progress in Neuro-Psychopharmacology & Biological Psychiatry 75: 1–9. April 2017. doi:10.1016/j.pnpbp.2016.11.004. PMID 27890676. http://clok.uclan.ac.uk/16476/1/Davidson%205MAPB.pdf.

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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 DiFMDA DMMDA DMMDA-2 EIDA MDEA MDMA (midomafetamine) MDMOH MDOH MMDA MMDA-2 MMDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans and dihydrobenzofurans: 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 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 ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-MMC 4-EMC Brephedrone Butylone 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

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101

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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
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

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