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PiHKAL#73 EEE
73
Variant: R2 R4 R5 isomers all
Analogues: 1 3 1 8 13

IUPAC: 1-(2,4,5-Triethoxyphenyl)propan-2-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: PVOHHXSVHWUAMS-UHFFFAOYSA-N

InChI=1S/C15H25NO3/c1-5-17-13-10-15(19-7-3)14(18-6-2)9-12(13)8-11(4)16/h9-11H,5-8,16H2,1-4H3

PubChem CID: 44719557; ChemSpider: 21106296; Wikipedia: EEE (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 346 Row: 29

See also PiHKAL: #121 MEE #122 MEM    

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

One R2 analogue:
121
Analogue 1: Substituting Methoxy for Ethoxy at R2

MEE
2-Methoxy-4,5-diethoxyamphetamine
4,5-Diethoxy-2-methoxyamphetamine

IUPAC: 1-(4,5-Diethoxy-2-methoxyphenyl)propan-2-amine

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: LKJRFMXILZHUHU-UHFFFAOYSA-N

InChI=1S/C14H23NO3/c1-5-17-13-8-11(7-10(3)15)12(16-4)9-14(13)18-6-2/h8-10H,5-7,15H2,1-4H3

PubChem CID: 44719591; ChemSpider: 21106337; Wikipedia: MEE (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 346 Row: 28

See also PiHKAL: #73 EEE #122 MEM    

See also Transcripts: 1.79

See also Pharmacology notes I: p. 79, MEE: Subacute evaluation

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Three R4 analogues:
75
Analogue 1: Substituting Methoxy for Ethoxy at R4

EME
2,5-Diethoxy-4-methoxyamphetamine

IUPAC: 1-(2,5-Diethoxy-4-methoxyphenyl)propan-2-amine

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: IVHFHHXLFFHTTA-UHFFFAOYSA-N

InChI=1S/C14H23NO3/c1-5-17-12-9-13(16-4)14(18-6-2)8-11(12)7-10(3)15/h8-10H,5-7,15H2,1-4H3

PubChem CID: 44719562; ChemSpider: 21106298; Wikipedia: EME (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 346 Row: 27

See also PiHKAL: #73 EEE #122 MEM #136 MME  

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

7424
Analogue 2: Substituting Methyl for Ethoxy at R4

DOM-2,5-DIEtO

IUPAC: 1-(2,5-Diethoxy-4-methylphenyl)propan-2-amine

Formula: C14H23NO2 Molecular weight: 237.33792 g/mol InChI Key: IFOVMAYZCWAFKA-UHFFFAOYSA-N

InChI=1S/C14H23NO2/c1-5-16-13-9-12(8-11(4)15)14(17-6-2)7-10(13)3/h7,9,11H,5-6,8,15H2,1-4H3

Shulgin Index: See #60 DOM; Table: 5 Page: 346 Row: 24

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

528
Analogue 3: Substituting Ethyl for Ethoxy at R4

2,5-Diethoxy-4-ethylamphetamine

IUPAC: 1-(2,5-Diethoxy-4-ethylphenyl)propan-2-amine

Formula: C15H25NO2 Molecular weight: 251.3645 g/mol InChI Key: FHDPGMLAWFPOTM-UHFFFAOYSA-N

InChI=1S/C15H25NO2/c1-5-12-9-15(18-7-3)13(8-11(4)16)10-14(12)17-6-2/h9-11H,5-8,16H2,1-4H3

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

One R5 analogue:
74
Analogue 1: Substituting Methoxy for Ethoxy at R5

EEM
2,4-Diethoxy-5-methoxyamphetamine

IUPAC: 1-(2,4-Diethoxy-5-methoxyphenyl)propan-2-amine

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: SAFDWWQYGOOGMX-UHFFFAOYSA-N

InChI=1S/C14H23NO3/c1-5-17-12-9-14(18-6-2)13(16-4)8-11(12)7-10(3)15/h8-10H,5-7,15H2,1-4H3

PubChem CID: 44719558; ChemSpider: 21106297; Wikipedia: EEM (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 34

See also PiHKAL: #73 EEE #122 MEM    

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Eight isomers:
181
Isomer 1

ABM
α-Butylmescaline
α-n-Butyl-3,4,5-trimethoxyphenethylamine

IUPAC: 1-(3,4,5-Trimethoxyphenyl)hexan-2-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: MSVLOLMKUPHDNN-UHFFFAOYSA-N

InChI=1S/C15H25NO3/c1-5-6-7-12(16)8-11-9-13(17-2)15(19-4)14(10-11)18-3/h9-10,12H,5-8,16H2,1-4H3

PubChem CID: 204173; ChemSpider: 176854

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 13

See also PiHKAL: #1 AEM      

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

303
Isomer 2

MBM
4-n-Butoxy-2,5-dimethoxyamphetamine

IUPAC: 1-(4-Butoxy-2,5-dimethoxyphenyl)propan-2-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: QKAUNHGCSPPQBX-UHFFFAOYSA-N

InChI=1S/C15H25NO3/c1-5-6-7-19-15-10-13(17-3)12(8-11(2)16)9-14(15)18-4/h9-11H,5-8,16H2,1-4H3

PubChem CID: 69456028

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 9

See also PiHKAL: #35 2C-O-4 #138 MPM    

See also Transcripts: 1.86

See also Pharmacology notes I: p. 86, MBM: Subacute evaluation
319
Isomer 3

A
4-n-Amyloxy-3,5-dimethoxyphenethylamine

IUPAC: 2-[3,5-Dimethoxy-4-(pentyloxy)phenyl]ethan-1-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: XXJMQLZVSYOWQC-UHFFFAOYSA-N

InChI=1S/C15H25NO3/c1-4-5-6-9-19-15-13(17-2)10-12(7-8-16)11-14(15)18-3/h10-11H,4-9,16H2,1-3H3

PubChem CID: 54930597

Shulgin Index: Table: 2 Page: 318 Row: 15

See also PiHKAL: #10 B      

Galloway, G; Shulgin, AT; Kornfeld, H; Frederick, SL. Amphetamine, not MDMA, is associated with intracranial hemorrhage. J. Accid Emerg Med., 1 Jan 1995, 12 (3), 231–2. 428 kB. doi:10.1136/emj.12.3.231 The target of Sasha’s critique: Intracranial haemorrhage associated with ingestion of ‘Ecstasy’.

2051
Isomer 4

3C-B
4-n-Butoxy-3,5-dimethoxyamphetamine

IUPAC: 1-(4-Butoxy-3,5-dimethoxyphenyl)propan-2-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: CRELLSBHEKVHPI-UHFFFAOYSA-N

InChI=1S/C15H25NO3/c1-5-6-7-19-15-13(17-3)9-12(8-11(2)16)10-14(15)18-4/h9-11H,5-8,16H2,1-4H3

PubChem CID: 54929093

See also PiHKAL: #10 B      
2064
Isomer 5

Butaxamine
N-tert-Butyl-β-hydroxy-2,5-dimethoxyamphetamine

IUPAC: 2-(tert-Butylamino)-1-(2,5-dimethoxyphenyl)propan-1-ol

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: TWUSDDMONZULSC-UHFFFAOYSA-N

InChI=1S/C15H25NO3/c1-10(16-15(2,3)4)14(17)12-9-11(18-5)7-8-13(12)19-6/h7-10,14,16-17H,1-6H3

PubChem CID: 18026; ChemSpider: 17030; Wikipedia: Butaxamine

See also PiHKAL: #16 BOHD      
2194
Isomer 6

3C-IB
4-Isobutoxy-3,5-dimethoxyamphetamine

IUPAC: 1-[3,5-Dimethoxy-4-(2-methylpropoxy)phenyl]propan-2-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: UZJHKELXUNBJNA-UHFFFAOYSA-N

InChI=1S/C15H25NO3/c1-10(2)9-19-15-13(17-4)7-12(6-11(3)16)8-14(15)18-5/h7-8,10-11H,6,9,16H2,1-5H3

PubChem CID: 54929094

Shulgin Index: See #117 TMA; Table: 5 Page: 351 Row: 21

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 1. Mescalin derivatives. Helv. Chim. Acta, 21 Jun 2002, 85 (9), 3019–3026. 98 kB. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4 In German.

335
Isomer 7

4C-PrO
1-(2,5-Dimethoxyphenyl-4-propoxy)-2-aminobutane
α-Ethyl-2,5-dimethoxy-4-propoxyphenethylamine

IUPAC: 1-(2,5-Dimethoxy-4-propoxyphenyl)butan-2-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: NMDBQRGHZUWCJF-LBPRGKRZSA-N

InChI=1S/C15H25NO3/c1-5-7-19-15-10-13(17-3)11(8-12(16)6-2)9-14(15)18-4/h9-10,12H,5-8,16H2,1-4H3/t12-/m0/s1

ChemSpider: 25051967

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 2

Standridge, RT; Howell, HG; Tilson, HA; Chamberlain, JH; Holava, HM; Gylys, JA; Partyka, RA; Shulgin, AT. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem., 1 Jan 1980, 23 (2), 154–162. 1125 kB. doi:10.1021/jm00176a010

336
Isomer 8

4C-iPrO
1-(4-Isopropoxy-2,5-dimethoxyphenyl)-2-aminobutane
α-Ethyl-4-isopropoxy-2,5-dimethoxyphenethylamine

IUPAC: 1-[2,5-Dimethoxy-4-(propan-2-yloxy)phenyl]butan-2-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: KKDGVJJZQGSVHK-LBPRGKRZSA-N

InChI=1S/C15H25NO3/c1-6-12(16)7-11-8-14(18-5)15(19-10(2)3)9-13(11)17-4/h8-10,12H,6-7,16H2,1-5H3/t12-/m0/s1

ChemSpider: 25040478

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 7

Standridge, RT; Howell, HG; Tilson, HA; Chamberlain, JH; Holava, HM; Gylys, JA; Partyka, RA; Shulgin, AT. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem., 1 Jan 1980, 23 (2), 154–162. 1125 kB. doi:10.1021/jm00176a010

Show all 13 analogues and isomers Show only the one R2 analogues Show only the three R4 analogues Show only the one R5 analogues
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