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5-APDB

5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative entactogen drug of the phenethylamine and amphetamine classes.[2] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.[2] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.[2] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues of MDMA.[2]

5-APDB
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine
CAS Number
  • 152624-03-8 N
PubChem CID
  • 192601
ChemSpider
  • 167143 N
UNII
  • UI10BAJ8SH
CompTox Dashboard (EPA)
  • DTXSID70934560
Chemical and physical data
FormulaC11H15NO
Molar mass177.247 g·mol−1
3D model (JSmol)
  • Interactive image
  • Cl.CC(N)Cc1cc2CCOc2cc1
  • InChI=1S/C11H15NO.ClH/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11;/h2-3,7-8H,4-6,12H2,1H3;1H Y
  • Key:BZKLFXQUBIRXAK-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

In animal studies, 5-APDB's effects generalize most closely to non-stimulant MDMA analogues such as MBDB and MMAI, while producing no substitution for LSD or amphetamine.[2] In vitro studies show that 5-APDB acts as a highly selective serotonin releasing agent (SSRA), with IC50 values of 130 nM, 7,089 nM, and 3,238 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively.[2] In contrast, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.[2]

Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for DOM in animal tests, although they were around one tenth as potent as DOM.[3][4]

Legal status edit

China edit

As of October 2015 5-APDB is a controlled substance in China.[5]

UK edit

On June 10, 2013, 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.[6] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.[7]

References edit

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ a b c d e f g Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE (November 1993). "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine". Journal of Medicinal Chemistry. 36 (23): 3700–3706. doi:10.1021/jm00075a027. PMID 8246240.
  3. ^ Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM (February 1986). "Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats". Journal of Medicinal Chemistry. 29 (2): 302–304. doi:10.1021/jm00152a022. PMID 3950910.
  4. ^ Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". Journal of Medicinal Chemistry. 34 (1): 276–281. doi:10.1021/jm00105a043. PMID 1992127.
  5. ^ [Notice on Printing and Distributing the "Measures for the Scheduling of Non-Pharmaceutical Narcotic Drugs and Psychotropic Substances"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  6. ^ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-06-13.
  7. ^ "'NBOMe' and 'Benzofury' banned". UK Home Office. 4 Jun 2013. Retrieved 2013-06-13.

apdb, aminopropyl, dihydrobenzofuran, desoxy, putative, entactogen, drug, phenethylamine, amphetamine, classes, analogue, where, heterocyclic, position, oxygen, from, methylenedioxy, ring, been, replaced, methylene, bridge, apdb, analogue, where, position, oxy. 5 2 Aminopropyl 2 3 dihydrobenzofuran 5 APDB 3 Desoxy MDA EMA 4 is a putative entactogen drug of the phenethylamine and amphetamine classes 2 It is an analogue of MDA where the heterocyclic 3 position oxygen from the 3 4 methylenedioxy ring has been replaced by a methylene bridge 2 6 APDB is an analogue of 5 APDB where the 4 position oxygen has been replaced by a methylene bridge instead 2 5 APDB was developed by a team led by David E Nichols at Purdue University as part of their research into non neurotoxic analogues of MDMA 2 5 APDBClinical dataRoutes ofadministrationOralATC codenoneLegal statusLegal statusBR Class F2 Prohibited psychotropics 1 CA Schedule I DE NpSG Industrial and scientific use only UK Class BIdentifiersIUPAC name 1 2 3 Dihydro 1 benzofuran 5 yl propan 2 amineCAS Number152624 03 8 NPubChem CID192601ChemSpider167143 NUNIIUI10BAJ8SHCompTox Dashboard EPA DTXSID70934560Chemical and physical dataFormulaC 11H 15N OMolar mass177 247 g mol 13D model JSmol Interactive imageSMILES Cl CC N Cc1cc2CCOc2cc1InChI InChI 1S C11H15NO ClH c1 8 12 6 9 2 3 11 10 7 9 4 5 13 11 h2 3 7 8H 4 6 12H2 1H3 1H YKey BZKLFXQUBIRXAK UHFFFAOYSA N Y N Y what is this verify In animal studies 5 APDB s effects generalize most closely to non stimulant MDMA analogues such as MBDB and MMAI while producing no substitution for LSD or amphetamine 2 In vitro studies show that 5 APDB acts as a highly selective serotonin releasing agent SSRA with IC50 values of 130 nM 7 089 nM and 3 238 nM for inhibiting the reuptake of serotonin dopamine and norepinephrine respectively 2 In contrast 6 APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA 2 Methoxy substituted analogues of 5 APDB and 6 APDB have also been made and substituted for DOM in animal tests although they were around one tenth as potent as DOM 3 4 Contents 1 Legal status 1 1 China 1 2 UK 2 ReferencesLegal status editChina edit As of October 2015 5 APDB is a controlled substance in China 5 UK edit On June 10 2013 5 APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation 6 This means that sale and import of the named substances are criminal offences and are treated as for class B drugs 7 References edit Anvisa 2023 07 24 RDC Nº 804 Listas de Substancias Entorpecentes Psicotropicas Precursoras e Outras sob Controle Especial Collegiate Board Resolution No 804 Lists of Narcotic Psychotropic Precursor and Other Substances under Special Control in Brazilian Portuguese Diario Oficial da Uniao published 2023 07 25 Archived from the original on 2023 08 27 Retrieved 2023 08 27 a b c d e f g Monte AP Marona Lewicka D Cozzi NV Nichols DE November 1993 Synthesis and pharmacological examination of benzofuran indan and tetralin analogues of 3 4 methylenedioxy amphetamine Journal of Medicinal Chemistry 36 23 3700 3706 doi 10 1021 jm00075a027 PMID 8246240 Nichols DE Hoffman AJ Oberlender RA Riggs RM February 1986 Synthesis and evaluation of 2 3 dihydrobenzofuran analogues of the hallucinogen 1 2 5 dimethoxy 4 methylphenyl 2 aminopropane drug discrimination studies in rats Journal of Medicinal Chemistry 29 2 302 304 doi 10 1021 jm00152a022 PMID 3950910 Nichols DE Snyder SE Oberlender R Johnson MP Huang XM January 1991 2 3 Dihydrobenzofuran analogues of hallucinogenic phenethylamines Journal of Medicinal Chemistry 34 1 276 281 doi 10 1021 jm00105a043 PMID 1992127 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 Printing and Distributing the Measures for the Scheduling of Non Pharmaceutical Narcotic Drugs and Psychotropic Substances in Chinese China Food and Drug Administration 27 September 2015 Archived from the original on 1 October 2015 Retrieved 1 October 2015 Temporary class drug order report on 5 6APB and NBOMe compounds UK Home Office 4 Jun 2013 Retrieved 2013 06 13 NBOMe and Benzofury banned UK Home Office 4 Jun 2013 Retrieved 2013 06 13 Retrieved from https en wikipedia org w index php title 5 APDB amp oldid 1172595436, wikipedia, wiki, book, books, library,

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