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1-Aminomethyl-5-methoxyindane

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

AMMI
Clinical data

Other names	AMMI
ATC code	None
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name (5-Methoxy-2,3-dihydro-1H-inden-1-yl)methanamine
CAS Number	1415750-28-5^N
PubChemCID	45091234
ChemSpider	24205063^Y
UNII	585V6BDH9X
CompTox Dashboard(EPA)	DTXSID801029881
Chemical and physical data
Formula	C₁₁H₁₅NO
Molar mass	177.247 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES NCC1CCc2c1ccc(OC)c2
InChI InChI=1S/C11H15NO/c1-13-10-4-5-11-8(6-10)2-3-9(11)7-12/h4-6,9H,2-3,7,12H2,1H3^Y Key:WPBKCMLYKMDWRD-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

1-Aminomethyl-5-methoxyindane (AMMI), is adrug developed by a team led byDavid E. Nichols atPurdue University, which acts as aselective serotonin releasing agent (SSRA) and binds to theserotonin transporter (SERT) with similaraffinity relative toDFMDA.^[1]^[2]

References

[edit]

^Roman DL, Saldaña SN, Nichols DE, Carroll FI, Barker EL (February 2004). "Distinct molecular recognition of psychostimulants by human and Drosophila serotonin transporters".The Journal of Pharmacology and Experimental Therapeutics.308 (2):679–87.doi:10.1124/jpet.103.057836.PMID 14593087.S2CID 6439942.
^Walline CC, Nichols DE, Carroll FI, Barker EL (June 2008)."Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition".The Journal of Pharmacology and Experimental Therapeutics.325 (3):791–800.doi:10.1124/jpet.108.136200.PMC 2637348.PMID 18354055.

External links

[edit]

AMMI - Isomer Design

Entactogens

Phenethylamines

Non-ring-extended	Amphetamines:3-CMA 4-FA (PAL-303) 4-FMA 4-MA (PAL-313; Aptrol; normephedrine) 4-MMA (mephedrine) 4-MTA 4-MTMA (NMMTA; PAL-1063) MMA MMMA PMA PMEA PMMA Phenylisobutylamines:4-CAB (AEPCA) Cathinones:3-CMC (clophedrone; βk-3-CMA) 3-MMC (metaphedrone; βk-3-MMA) 4-EMC (βk-4-EMA) Brephedrone (4-BMC; βk-4-BMA) Flephedrone (4-FMC; βk-4-FMA) Mephedrone (4-MMC; 4-methylephedrone; βk-4-MMA) Methedrone (PMMC; βk-PMMA)
Benzodioxoles (methylenedioxy- or MDxx)	Phenethylamines:Lophophine (MMDPEA) Amphetamines:2-Methyl-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA EIDA Lys-MDA MDEA (MDE) MDMA (midomafetamine; ecstasy) (R)-MDMA (EMP-01; MM-402) MDMA/citalopram MDMOH (FLEA; MDHMA) MDOH (MDH) MMDA (5-methoxy-MDA) MMDMA (5-methoxy-MDMA) N-t-BOC-MDMA Phenylisobutylamines:BDB (J) EBDB (Ethyl-J) MBDB (Methyl-J) Phentermines:MDMP MDPH Cathinones:5-Methoxymethylone (2-A1MP; βk-MMDMA) 5-Methylethylone (5-methyl-βk-MDEA) Butylone (βk-MBDB) Dimethylone (βk-MDDMA) Ethylone (MDEC; βk-MDEA) Eutylone (βk-EBDB) Methylenedioxycathinone (MDC; βk-MDA) Methylone (MDMC; βk-MDMA) Putylone (βk-PBDB)
Benzodioxines (ethylenedioxy-)	Amphetamines:EDA EDMA Cathinones:EDMC
Benzofurans	Amphetamines:4-APB 5-APB 5-EAPB 5-MAPB 6-APB 6-EAPB 6-MAPB 7-APB Phenylisobutylamines:5-MBPB (5-MABB) 6-MBPB (6-MABB) Cathinones:BK-5-MAPB BK-6-MAPB
Dihydrobenzofurans	Amphetamines:5-APDB (EMA-4) 5-MAPDB 6-APDB (EMA-3) 6-MAPDB IBF5MAP (5-MAPP)
Benzothiophenes	Amphetamines:4-APBT 5-APBT 5-MAPBT(MY400) 6-APBT 6-MAPBT (MY300) 7-APBT Cathinones:BK-5-MAPBT
Benzothiazoles	Amphetamines:5-BZT-MDA 5-BZT-MDMA 6-BZT-MDA 6-BZT-MDMA
Benzoxathioles	Amphetamines:MY100 MY101 MY200
Indanes	Amphetamines:5-APDI (IAP) 5-MAPDI (IMP)
Indoles	Amphetamines:5-API (5-IT; PAL-571) 6-API (6-IT)
Naphthalenes	Amphetamines:Ethylnaphthylaminopropane (ENAP; PAL-1045) Methamnetamine (MNAP; PAL-1046; MY-10) Naphthylaminopropane (NAP; PAL-287)
Tetralins	Amphetamines:6-APT (TAP) Cathinones:TH-PVP
Others	Amphetamines:ODMA SeDMA TDMA Unknown:MYCO-002 MYCO-006 MYCO-007

Cyclized
phenethylamines

2-Aminoindanes	5-IAI BFAI ETAI MDAI MDMAI MEAI (5-MeO-AI; CMND-100) MMAI TAI
1-Aminomethylindanes	AMMI
2-Aminotetralins	6-CAT MDAT MDMAT
Aminorexes	4,4'-DMAR MDMAR

Tryptamines

α-Alkyltryptamines	4-Methyl-αET 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212, PAL-544) αET (etryptamine; Monase; PAL-125) αMT (Indopan; PAL-17; 3-API; 3-IT) β-Ketotryptamines:BK-NM-AMT BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT

Others

Benzofurans	2-APB 2-MAPB 3-APB
Benzothiophenes	2-APBT 3-APBT (SKF-6678)
Indolizines	1Z2MAP1O
Isotryptamines	isoAMT (PAL-569; 1-API; 1-IT)
Others	Borax combo (Blue Bliss, Pink Star) MDM1EA (α,N-DMMDBA) UnknownTACT411 TACT833 Atypical:2C-B 5-MeO-DiPT 5-MeO-MiPT

Monoamine releasing agents

DRAsTooltip Dopamine releasing agents

Morpholines:Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines:4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines:2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines:2C-B-BZP BZP MBZP MDBZP MeOPP oMPP
Others:2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine

NRAsTooltip Norepinephrine releasing agents

Morpholines:Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines:4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines:2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) Iofetamine (123I) Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine Selegiline (alsoD-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines:2C-B-BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP
Others:2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine Tuaminoheptane

SRAsTooltip Serotonin releasing agents

Aminoindanes:5-IAI AMMI ETAI MDAI MDMAI MMAI TAI
Aminotetralins:6-CAT 8-OH-DPAT MDAT MDMAT
Oxazolines:4-Methylaminorex Aminorex Clominorex Fluminorex
Phenethylamines:2-Methyl-MDA 4-CAB 4-FA 4-FMA 4-HA 4-MTA 5-APDB 5-Methyl-MDA 6-APDB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP Iofetamine Levofenfluramine Lophophine MBDB MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDA-3b MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA TAP
Piperazines:2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP
Tryptamines:4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine
Others:Indeloxazine Viqualine

Others

DAT modulators:Agonist-like:SoRI-9804
SoRI-20040;Antagonist-like:SoRI-20041

Adrenergic release blockers:Bethanidine
Bretylium
Guanadrel
Guanazodine
Guanethidine
Guanoxan

See also:Receptor/signaling modulators •Monoamine reuptake inhibitors •Adrenergics •Dopaminergics •Serotonergics •Monoamine metabolism modulators •Monoamine neurotoxins

Phenethylamines

Entactogens:Lophophine
MDPEA
MDMPEA

Amphetamines

Phentermines

Entactogens:MDPH
MDMPH

Others:Cericlamine

Cathinones

Phenylisobutylamines
(and further-extended)

Stimulants:α-Propylphenethylamine
Hexapradol
Phenylisobutylamine (α-ethylphenethylamine)

Catecholamines
(and close relatives)

Cyclized
phenethylamines

Phenylalkylpyrrolidines	α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP Fluorolintane MOPPP MOPVP MPBP MPEP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
2-Benzylpiperidines (phenidates)	2-Benzylpiperidine 3-Bromomethylphenidate 3-Chloromethylphenidate 3-Methylmethylphenidate 3,4-Dichloro-2-benzylpiperidine 3,4-Dichloroethylphenidate 3,4-Dichloromethylphenidate 4-Bromoethylphenidate 4-Bromomethylphenidate 4-Chloromethylphenidate 4-Fluoroethylphenidate 4-Fluoroisopropylphenidate 4-Fluoromethylphenidate 4-Methyl-2-benzylpiperidine 4-Methylisopropylphenidate 4-Methylmethylphenidate 4-Nitromethylphenidate α-Acetyl-2-benzylpiperidine α-Keto-2-benzylpiperidine CPMBP Desoxypipradrol (2-DPMP) Difemetorex Ethylnaphthidate (HDEP-28) Ethylphenidate Isopropylnaphthidate Isopropylphenidate MDMPH Methylnaphthidate (HDMP-28) Methylphenidate Phacetoperane Pipradrol Propylphenidate Rimiterol Ritalinamide Ritalinic acid SCH-5472 Serdexmethylphenidate
Phenylmorpholines (phenmetrazines)	(2R,3R)-Hydroxybupropion 2-(2,5-Dimethoxy-4-bromophenyl)morpholine 2-Fluorophenmetrazine 2-Methylphenmetrazine 2-Phenylmorpholine 2-Phenyl-3,6-dimethylmorpholine 3-Chlorophenmetrazine (PAL-594) 3-Fluorophenetrazine 3-Fluorophenmetrazine (PAL-593) 3-Methoxyphenmetrazine 3-Methylphenmetrazine (PAL-773) 4-Fluorophenmetrazine (PAL-748) 4-Methylphendimetrazine 4-Methylphenmetrazine (PAL-747) 2C-B-morpholine Fenbutrazate Fenmetramide Flumexadol G-130 Isophenmetrazine Manifaxine Methylenedioxyphenmetrazine Morazone N-Ethylphenmetrazol Naphthylmetrazine (PAL-704) Naphthylmorpholine (PAL-678) Oxaflozane PDM-35 PF-219,061) Phendimetrazine Phenetrazine Phenmetetrazine Phenmetrazine Phenmetrazol Pseudophenmetrazine Radafaxine ((2S,3S)-hydroxybupropion)
Phenyloxazolamines (aminorexes)	3-Methylaminorex 4-Ethylaminorex (4-EAR) 4'-Fluoroaminorex 4-Methylaminorex (4-MAR) 4,4'-Dimethylaminorex (4,4'-DMAR) 2C-B-aminorex 2F-MAR 4B-MAR 4C-MAR 4F-MAR Aminorex Clominorex Cyclazodone Ephedroxane Fenozolone Fluminorex MDMAR Methylenedioxyaminorex (MDAR) N-Methylcyclazodone N,N-Dimethylaminorex Pemoline Thozalinone
Isoquinolines and tetrahydroisoquinolines	Anhalamine Anhalidine Anhalinine Anhalonidine Anhalonine Anhalotine Arizonine Calycotomine Carnegine (pectenine) Corypalline Debrisoquine Deglucopterocereine Deutetrabenazine Diclofensine DOB-CR DOM-CR Esproquin Gigantine Hedycarine Heliamine Hydrastinine Hydrocotarnine Hydrohydrastinine (MDMTHIQ; MDMA-CR) Isoanhalamine Isoanhalidine Isoanhalonidine Isocorypalline Isopellotine Isosalsoline Lemaireocereine Longimammamine Longimammatine Longimammidine Longimammosine Lophocerine Lophophorine Lophotine MDMA-CR Mescalotam N-Methylanhalinine N-Methylheliamine N-Methylisosalsoline N-Methyl-DOM-CR (Beatrice-CR) N-Methyl-THIQ (METH-CR) Nomifensine Norsalsolinol Nortehaunine Norweberine O-Methylanhalonidine O-Methylpellotine Pachycereine Pellotine Perafensine Peyoglutam Peyophorine Peyotine PMMA-CR Quinisocaine Reticuline Salsolidine Salsoline Salsolinol TDIQ (MDTHIQ, MDA-CR) Tehaunine TehaunineN-oxide Tepenine Tetrabenazine Tetrahydroisoquinoline (THIQ; AMPH-CR) Tetrahydropapaveroline Tilisolol Tretoquinol Uberine Valbenazine Weberidine Weberine Zelandopam
2-Aminoindanes	2-Aminoindane (2-AI) 5-IAI Aprindine BFAI BFMAI DHAI DOM-AI ETAI Indantadol MDAI MDMAI MEAI (5-MeO-AI) MMAI NM-2-AI PNU-99,194 Pyr-AI TAI
2-Aminotetralins	2-Aminotetralin (2-AT) 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 CHF-1024 DOM-AT MDAT MDMAT Nolomirole UH-232
Others / unsorted	1-Aminomethylindanes (e.g.,2CB-Ind,AMMI,bromojimscaline,jimscaline) 2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam,lorcaserin,7-chlorolorcaserin,SCHEMBL5334361) 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine,3-PPP,OSU-6162 (PNU-96391),LPH-5,LPH-48,Z3517967757 (Z7757)) 6-AB AL-1095 Aminochromes (e.g.,adrenochrome,adrenolutin) Benzocyclobutenes (e.g.,2CBCB-NBOMe,bromotomscaline,S33005,TCB-2,tomscaline) Benzoxepins (e.g.,BBOX,IBOX,TFMBOX) Butyltolylquinuclidine Camfetamine Cypenamine (trans-2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD) Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI,RU-27849,DEIMDHPCA,DEMPDHPCA,DEMPDHPCA-2C-D,RU-27251) PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA,TMT,tranylcypromine) Phenylpiracetams (e.g.,phenylpiracetam,MRZ-9547,RGPU-95) Pyridopyrroloquinoxalines (e.g.,lumateperone,deulumateperone,IHCH-7079,IHCH-7086,IHCH-7113,ITI-1549) Tetrahydrobenzopyranylamines (e.g.,CT-5126) Tolazoline Tricyclics (e.g.,AMDA,AMDH,benzoctamine,dizocilpine,SpAMDA) ZC-B

Related compounds

2-Furylethylamine
2-Pyrrolylethylamine
3-Pyrrolylethylamine
3-Pyrrolylpropylamine
2-Tetrahydrofurylethylamine
4-Benzylpiperidine
7-AB
Alkylamines (e.g.,1,3-DMBATooltip 1,3-dimethylbutylamine,1,4-DMAATooltip 1,4-dimethylamylamine,heptaminol,iproheptine,isometheptene,methylhexanamine/1,3-DMAA,octodrine,oenethyl,tuaminoheptane)
Benzylamines (e.g.,benzylamine,α-methylbenzylamine,MDM1EA,ALPHA,M-ALPHA,pargyline)
Benzylpiperazines (e.g.,benzylpiperazine,MDBZP,fipexide)
Cyclohexylaminopropanes (e.g.,propylhexedrine,norpropylhexedrine)
Cyclopentylaminopropanes (e.g.,isocyclamine,cyclopentamine)
Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine,CT-4719,ORG-37684)
Phenylalkenylamines (e.g.,phenylbutenamine)
Phenylalkynylamines (e.g.,phenylbutynamine)
Phenylpiperazines (e.g.,1-phenylpiperazine,mCPPTooltip meta-chlorophenylpiperazine,TFMPPTooltip trifluoromethylphenylpiperazine,oMPPTooltip ortho-methylphenylpiperazine,pFPPTooltip para-fluorophenylpiperazine,pMeOPPTooltip para-methoxyphenylpiperazine)
Phenylpropylamines (e.g.,phenylpropylamine,homo-MDA,homo-MDMA)
Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine,methiopropamine,thiothinone)

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