| 词条 | 5-MAPB |
| 释义 |
| IUPAC_name = 1-(Benzofuran-5-yl)-N-methylpropan-2-amine | image = 5-MAPB.svg | image2 = 5-MAPB molecule ball.png | alt2 = Ball-and-stick model of 5-MAPB molecule | legal_AU = | legal_CA = Schedule I | legal_UK = Class B | legal_US = | legal_status = Illegal in China | dependency_liability = | routes_of_administration = Oral, Insufflated, Rectal | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number = 1354631-77-8 | CAS_supplemental = | ATCvet = | PubChem = 102336592 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 32078887 | UNII = XW34GUY2OY | KEGG = | ChEBI = | ChEMBL = | synonyms = | chemical_formula = |C=12 | H=15 | N=1 | O=1 | molecular_weight = 189.25 g/mol (freebase) 225.7 g/mol (HCl salt) | smiles = CC(NC)CC1=CC(C=CO2)=C2C=C1 | StdInChI = 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 | StdInChIKey = ZOVRTIPCNFERHY-UHFFFAOYSA-N | density = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | specific_rotation = | sec_combustion = }}5-MAPB (1-(benzofuran-5-yl)-N-methylpropan-2-amine) is an entactogenic designer drug similar to MDMA on its structure and effects.[1] Legal StatusCanada5-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] ChinaAs of October 2015 5-MAPB is a controlled substance in China.[3] United Kingdom5-MAPB was originally banned in the UK in June 2013 under a Temporary class drug order.[4] 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.[5] PharmacokineticsMetabolism and toxicityLittle formal knowledge exists on 5-MAPB. It does not share the neurotoxicity of MDA caused by the alpha-methyldopamine metabolite.[6][7][8] A study in rats indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine.[9] Pharmacodynamics5-MAPB binds to the dopamine transporter in rat brain cells with a lower potency 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 likely that it exerts a similar action on serotonin and norepinephrine transporters.[10] References1. ^{{cite web | url = https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds | title = Temporary class drug order report on 5-6APB and NBOMe compounds | accessdate = 2013-07-10 | date = 4 Jun 2013 | publisher = UK Home Office}} {{Entactogens|state=expanded}}{{Serotonergics}}{{Phenethylamines}}2. ^{{cite web | url=http://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-24.html#h-28 | title='Schedule I' | publisher=Government Of Canada | date=2014-12-12 | access-date=2014-12-13 | archive-url=https://web.archive.org/web/20131122143804/http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-24.html#h-28 | archive-date=2013-11-22 | dead-url=yes | df= }} 3. ^{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}} 4. ^{{cite web | url=https://www.gov.uk/government/news/nbome-and-benzofury-to-be-banned | title='NBOMe' and 'Benzofury' banned | publisher=UK Home Office | date=2013-06-04 | accessdate=10 April 2014}} 5. ^{{cite web | url = http://www.legislation.gov.uk/ukdsi/2014/9780111110904 | title = The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | accessdate = 2014-03-11 | author = UK Home Office | date = 2014-03-05 | publisher = UK Government}} 6. ^{{cite journal | author = McCann UD | author2 = Ricaurte GA | title = Major metabolites of (±)3,4-methylenedioxyamphetamine (MDA) do not mediate its toxic effects on brain serotonin neurons | journal = Brain Research | volume = 545 | issue = 1–2 | pages = 279–282 | year = 1991 | pmid = 1860050 | doi = 10.1016/0006-8993(91)91297-E }} 7. ^{{cite journal | author = Miller RT | author2 = Lau SS | author3 = Monks TJ | title = 2,5-Bis-(glutathion-S-yl)-alpha-methyldopamine, a putative metabolite of (+/-)-3,4-methylenedioxyamphetamine, decreases brain serotonin concentrations | journal = Eur J Pharmacol | volume = 323 | issue = 2–3 | pages = 173–80 | year = 1997 | pmid = 9128836 | doi = 10.1016/S0014-2999(97)00044-7 }} 8. ^{{cite journal | author = Conway EL | author2 = Louis WJ | author3 = Jarrott B | title = Acute and chronic administration of alpha-methyldopa: regional levels of endogenous and alpha-methylated catecholamines in rat brain | journal = Eur J Pharmacol | volume = 52 | issue = 3–4 | pages = 271–80 | year = 1978 | pmid = 729639 | doi = 10.1016/0014-2999(78)90279-0 }} 9. ^{{Cite journal | doi=10.1007/s00216-014-8360-0| pmid=25471293| title=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)-MSn techniques| journal=Analytical and Bioanalytical Chemistry| volume=407| issue=5| pages=1371–88| year=2014| last1=Welter| first1=Jessica| last2=Kavanagh| first2=Pierce| last3=Meyer| first3=Markus R.| last4=Maurer| first4=Hans H.}} 10. ^{{Cite journal |last=Sahai |first=Michelle A |last2=Davidson |first2=Colin |last3=Khelashvili |first3=George |year=2016 |title=Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances – The case of the benzofuran 5-MAPB |url=http://www.sciencedirect.com/science/article/pii/S0278584616303979 |journal=Progress in Neuro-Psychopharmacology and Biological Psychiatry |volume=75 |pages=1–9 |doi=10.1016/j.pnpbp.2016.11.004}} 4 : Methamphetamines|Benzofurans|Designer drugs|Entactogens and empathogens |
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