5-APDB

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5-APDB
File:3-desoxy-MDA.svg
Systematic (IUPAC) name
1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-amine
Clinical data
Pregnancy
category
  •  ?
Routes of
administration		 Oral
Legal status
Legal status
Identifiers
CAS Number 152623-94-4
ATC code none
PubChem CID 192601
ChemSpider 21073073
Chemical data
Formula C11H15NO
Molar mass 177.242 g/mol[[Script error: No such module "String".]]
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5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative entactogen drug of the phenethylamine and amphetamine classes.[1] It is an analogue of the MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene group.[1] 6-APDB is an anlogue of 5-APDB where the 4-position oxygen has been replaced by a methylene instead.[1] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues of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.[1]

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.[1] 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.[1] In contrast, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.[1] Anecdotal reports from human users suggest that 5-APDB produces mild empathy but with relatively little euphoria and is accompanied by sedation.[citation needed]

Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for DOM in animal tests, although they were around 10x less potent than DOM.[2][3]

See also

References

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Aminoindanes
5-IAI • ETAI • MDAI • MDMAI • MMAI • TAI
Aminotetralins
6-CAT • MDAT • MDMAT
Phenethylamines
(and amphetamines,
cathinones, etc)
2-Methyl-MDA • 4-CAB • 4-FA • 4-FMA • 4-MTA • 5-APDB • 5-Methyl-MDA • 6-APDB • 6-Methyl-MDA • Ariadne • BDB • BOH • Brephedrone • Butylone • DMMDA • DMMDA-2 • EBDB • EBDP • EDMA • Ethylone • Eutylone • Fenfluramine (also dexfenfluramine) • Flephedrone • IAP • IMP • Lophophine • MBDB • MBDP • MDA • MDDM • MDEA • MDIP • MDMA • MDMOH • MDMP • MDMPEA • MDOH • MDPEA • MDPH • MDPR • Mephedrone • Methedrone • Methylone • MMA • MMDA • MMDMA • NAP • Norfenfluramine • Pentylone • PMA • PMEA • PMMA • TAP
Tryptamines
Psychedelics
5-HT2AR agonists
Lysergamides: AL-LAD • ALD-52 • BU-LAD • CYP-LAD • DAM-57 • Diallyllysergamide • Ergometrine (Ergonovine, Ergobasine) • ETH-LAD • LAE-32 • LSA (Ergine, Lysergamide) • LSD • LSH • LPD-824 • LSM-775 • Lysergic Acid 2-Butyl Amide • Lysergic Acid 2,4-Dimethylazetidide • Methylergometrine • Methylisopropyllysergamide • Methysergide • MLD-41 • PARGY-LAD • PRO-LAD;
Phenethylamines: Aleph • 2C-B • 2C-B-FLY • 2CBFly-NBOMe • 2C-C • 2C-D • 2CD-5EtO • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • 2CBCB-NBOMe • 25B-NBOMe • 25I-NBMD • 25I-NBOH • 25I-NBOMe • 3C-E • 3C-P • Br-DFLY • DESOXY • DMMDA • DMMDA-2 • DOB • DOC • DOEF • DOET • DOF • DOI • DOM • DON • DOPR • DOTFM • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • IAP • Isoproscaline • Jimscaline • Lophophine • MDA • MDEA • MDMA • MMA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Methallylescaline • Proscaline • TCB-2 • TFMFly • TMA;
Piperazines: pFPP • TMFPP;
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine • 2,N,N-TMT • 4,N,N-TMT • 4-HO-5-MeO-DMT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-Acetoxy-DPT • 4-Acetoxy-MiPT • 4-HO-DPT • 4-HO-MET • 4-Propionyloxy-DMT • 4-Hydroxy-N-Methyl-(α,N-trimethylene)tryptamine • 5-Me-MIPT • 5-N,N-TMT • 5-AcO-DMT • 5-MeO-2,N,N-TMT • 5-MeO-4,N,N-TMT • 5-MeO-α,N,N-TMT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-EiPT • 5-MeO-MET • 5-MeO-MIPT • 5-Methoxy-N-methyl-(α,N-trimethylene)tryptamine • 7,N,N-TMT • α,N,N-TMT • α-ET • α-MT • AL-37350A • Baeocystin • Bufotenin • DALT • DBT • DET • DIPT • DMT • DPT • EiPT • Ethocin • Ethocybin • Iprocin • MET • Miprocin • MIPT • Norbaeocystin • PiPT • Psilocin • Psilocybin;
Others: AL-38022A • Ibogaine • Noribogaine • Voacangine
Dissociatives
NMDAR antagonists
Deliriants
mAChR antagonists
3-Quinuclidinyl benzilate • Atropine • Benactyzine • Benzatropine • Benzydamine • Biperiden • Brompheniramine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • Chlorpheniramine • Chloropyramine • Clemastine • CS-27349 • Cyclizine • Cyproheptadine • Dicyclomine (Dicycloverine) • Dimenhydrinate • Diphenhydramine • Ditran • Doxylamine • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Flavoxate • Hydroxyzine • Hyoscyamine • Meclizine • Myristicin • N-Ethyl-3-piperidyl benzilate • N-Methyl-3-piperidyl benzilate • Pyrilamine • Orphenadrine • Oxybutynin • Pheniramine • Phenyltoloxamine • Procyclidine • Promethazine • Scopolamine (Hyoscine) • Tolterodine • Trihexyphenidyl • Tripelennamine • Triprolidine • WIN-2299
Miscellaneous
Cannabinol • CP-47,497 • CP-55,244 • CP-55,940 • DMHP • HU-210 • JWH-018 • JWH-030 • JWH-073 • JWH-081 • JWH-200 • JWH-250 • Nabilone • Nabitan • Nantradol • Parahexyl • THC (Dronabinol) • WIN-55,212-2
Butane • Chloroform • Diethyl Ether (Ether) • Enflurane • Freon • Gasoline (Petrol) • Kerosene (Paraffin) • Propane
Others
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
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: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • D-Deprenyl • L-Deprenyl (Selegiline)
Phentermines
Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous
  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  2. ↑ Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM. 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. 1986 Feb;29(2):302-4. PMID 3950910
  3. ↑ Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. Journal of Medicinal Chemistry. 1991 Jan;34(1):276-81. PMID 1992127
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