Chemistry:2CD-5EtO

2CD-5EtO
Identifiers
	IUPAC name 1-(5-Ethoxy-2-methoxy-4-methylphenyl)-ethan-1-amine;
CAS Number	1354634-32-4 ;
PubChem CID	57458864;
ChemSpider	26234937 ;
Chemical and physical data
Formula	C12H19NO2
Molar mass	209.289 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC1=CC(=C(C=C1C)OC)CCN;
	InChI InChI=1S/C12H19NO2/c1-4-15-11-8-10(5-6-13)12(14-3)7-9(11)2/h7-8H,4-6,13H2,1-3H3 ; Key:ZMQDQUPRBYFPSO-UHFFFAOYSA-N ;
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Short description: Chemical compound

2CD-5EtO is a homologue of the psychedelic phenethylamine 2C-D, where the 5-methoxy group of 2C-D has been lengthened to an ethoxy group. 2CD-5EtO is a representative example of the so-called "tweetio" compounds discovered by Alexander Shulgin and briefly mentioned in his book PiHKAL. They are homologues of the 2C family of drugs, where either one or both of the methoxy groups at the 2,5-positions of the aromatic ring have been replaced by ethoxy. The term tweetio was derived phonetically from the sound of the "2-ETO" derivatives.

Many tweetio derivatives of various 2C drugs have been synthesized and tested, including the 2-ethoxy homologues 2CD-2EtO, 2CB-2EtO, 2CI-2EtO, 2CT-2EtO, 2CT2-2EtO, 2CT4-2EtO and 2CT7-2EtO, the 5-ethoxy homologues 2CD-5EtO, 2CE-5EtO, 2CB-5EtO, 2CT-5EtO and 2CT2-5EtO, and the 2,5-diethoxy homologues 2CD-diEtO, 2CB-diEtO and 2CT2-diEtO,^[1] as well as 2CE-5iPrO.^[2] In general, the 2-ethoxy homologues were all several times less potent and somewhat shorter acting than the parent compounds, while the 2,5-diethoxy homologues were far less potent and qualitatively milder even at high doses.^[3] The 5-ethoxy homologues however were of a similar potency to the parent compounds and much longer-lasting, with both 2CE-5EtO and 2CT2-5EtO lasting 24 hours or more.

Structures of 2CD-2EtO, 2CE-5EtO and 2CT2-5EtO

References

↑ Laing, Richard R. (2003). Hallucinogens: a forensic drug handbook. Academic Press. pp. 85–86. ISBN 978-0-12-433951-4.
↑ Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD. Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore. ACS Pharmacol Transl Sci. 2020 Aug 13;4(2):488-502. doi:10.1021/acsptsci.0c00063 PMID 33860179
↑ "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Research Monograph 146: 74–91. 1994. PMID 8742795. http://www.erowid.org/psychoactives/journals/psychoactives_journal8.shtml.

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Original source: https://en.wikipedia.org/wiki/2CD-5EtO. Read more

[1] Laing, Richard R. (2003). Hallucinogens: a forensic drug handbook. Academic Press. pp. 85–86. ISBN 978-0-12-433951-4.

[2] Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD. Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore. ACS Pharmacol Transl Sci. 2020 Aug 13;4(2):488-502. doi:10.1021/acsptsci.0c00063 PMID 33860179

[3] "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Research Monograph 146: 74–91. 1994. PMID 8742795. http://www.erowid.org/psychoactives/journals/psychoactives_journal8.shtml.

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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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Identifiers

IUPAC name 1-(5-Ethoxy-2-methoxy-4-methylphenyl)-ethan-1-amine
CAS Number	1354634-32-4^N
PubChem CID	57458864
ChemSpider	26234937^Y
Chemical and physical data
Formula	C₁₂H₁₉NO₂
Molar mass	209.289 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCOC1=CC(=C(C=C1C)OC)CCN
InChI InChI=1S/C12H19NO2/c1-4-15-11-8-10(5-6-13)12(14-3)7-9(11)2/h7-8H,4-6,13H2,1-3H3^Y Key:ZMQDQUPRBYFPSO-UHFFFAOYSA-N^Y
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