Pihkal
Page 64
This short index to the phenethylamines lists the 179 entries that follow in alphebetical order. The abbreviation PEA is for phenethylamine, and A is for amphetamine. The long index includes all synonyms and is in Appendix A.
1 AEM; a-ETHYLMESCALINE; 2-AMINO-1-(3,4,5-TRIMETHOXYPHENYL)BUTANE; 1-(3,4,5-TRIMETHOXYPHENYL)-2-AMINOBUTANE
2 AL; 4-ALLYLOXY-3,5-DIMETHOXYPHENETHYLAMINE; 3,5-DIMETHOXY-4-ALLYLOXYPHENETHYLAMINE
3 ALEPH; DOT; PARA-DOT; 2,5-DIMETHOXY-4-METHYLTHIOAMPHETAMINE
4 ALEPH-2; 2,5-DIMETHOXY-4-ETHYLTHIOAMPHETAMINE
5 ALEPH-4; 2,5-DIMETHOXY-4-(i)-PROPYLTHIOAMPHETAMINE
6 ALEPH-6 2,5-DIMETHOXY-4-PHENYLTHIOAMPHETAMINE
7 ALEPH-7; 2,5-DIMETHOXY-4-(n)-PROPYLTHIOAMPHETAMINE
8 ARIADNE; 4C-DOM; BL-3912; DIMOXAMINE; 1-(2,5-DIMETHOXY-4-METHYLPHENYL)-2-AMINOBUTANE; 2,5-DIMETHOXY-a-ETHYL-4-METHYLPHENETHYLAMINE
9 ASB; ASYMBESCALINE; 3,4-DIETHOXY-5-METHOXYPHENETHYLAMINE
10 B; BUSCALINE; 4-(n)-BUTOXY-3,5-DIMETHOXYPHENETHYLAMINE
11 BEATRICE; N-METHYL-DOM; 2,5-DIMETHOXY-4,N-DIMETHYLAMPHETAMINE
12 BIS-TOM; 4-METHYL-2,5-bis-(METHYLTHIO)AMPHETAMINE
13 BOB; '-METHOXY-2C-B; 4-BROMO-2,5-'-TRIMETHOXYPHENETHYLAMINE
14 BOD; '-METHOXY-2C-D; 4-METHYL-2,5,'-TRIMETHOXYPHENETHYLAMINE
15 BOH; '-METHOXY-3,4-METHYLENEDIOXYPHENETHYLAMINE
16 BOHD; 2,5-DIMETHOXY-'-HYDROXY-4-METHYLPHENETHYLAMINE
17 BOM; '-METHOXYMESCALINE; 3,4,5,'-TETRAMETHOXYPHENETHYLAMINE
18 4-BR-3,5-DMA; 3,5-DIMETHOXY-4-BROMOAMPHETAMINE
19 2-BR-4,5-MDA; 6-BR-MDA; 2-BROMO-4,5-METHYLENEDIOXYAMPHETAMINE
20 2C-B; 4-BROMO-2,5-DIMETHOXYPHENETHYLAMINE
21 3C-BZ; 4-BENZYLOXY-3,5-DIMETHOXYAMPHETAMINE
22 2C-C; 2,5-DIMETHOXY-4-CHLOROPHENETHYLAMINE
23 2C-D; LE-25; 2,5-DIMETHOXY-4-METHYLPHENETHYLAMINE
24 2C-E; 2,5-DIMETHOXY-4-ETHYLPHENETHYLAMINE
25 3C-E; 3,5-DIMETHOXY-4-ETHOXYAMPHETAMINE
26 2C-F; 2,5-DIMETHOXY-4-FLUOROPHENETHYLAMINE
27 2C-G; 2,5-DIMETHOXY-3,4-DIMETHYLPHENETHYLAMINE
28 2C-G-3; 2,5-DIMETHOXY-3,4-(TRIMETHYLENE)PHENETHYLAMINE; 5-(2-AMINOETHYL)-4,7-DIMETHOXYINDANE) SYNTHESIS: To a solution of 22 g of KOH in 250 mL of hot EtOH, there was added 50 g of 4-indanol and 75 g methyl iodide. The mixture was held at reflux for 12 h. There was then added an additional 22 g KOH
29 2C-G-4; 2,5-DIMETHOXY-3,4-(TETRAMETHYLENE)PHENETHYLAMINE; 6-(2-AMINOETHYL)-5,8-DIMETHOXY-TETRALIN
30 2C-G-5; 3,6-DIMETHOXY-4-(2-AMINOETHYL)BENZONORBORNANE
31 2C-G-N; 1,4-DIMETHOXYNAPHTHYL-2-ETHYLAMINE
32 2C-H; 2,5-DIMETHOXYPHENETHYLAMINE
33 2C-I; 2,5-DIMETHOXY-4-IODOPHENETHYLAMINE
34 2C-N; 2,5-DIMETHOXY-4-NITROPHENETHYLAMINE
35 2C-O-4; 2,5-DIMETHOXY-4-(i)-PROPOXYPHENETHYLAMINE
36 2C-P; 2,5-DIMETHOXY-4-(n)-PROPYLPHENETHYLAMINE
37 CPM; CYCLOPROPYLMESCALINE;
38 2C-SE; 2,5-DIMETHOXY-4-METHYLSELENEOPHENETHYLAMINE
39 2C-T ; 2,5-DIMETHOXY-4-METHYLTHIOPHENETHYLAMINE
40 2C-T-2; 2,5-DIMETHOXY-4-ETHYLTHIOPHENETHYLAMINE
41 2C-T-4; 2,5-DIMETHOXY-4-(i)-PROPYLTHIOPHENETHYLAMINE
42 Y-2C-T-4; 2,6-DIMETHOXY-4-(i)-PROPYLTHIOPHENETHYLAMINE) SYNTHESIS: A stirred solution of 8.3 g 3,5-dimethoxy-1-chlorobenzene and 7.2 g isopropylsulfide in 100 mL anhydrous Et2O was cooled with an external ice bath, and then treated with 67 mL 1.5 M lithium diisopropylamide in hexane which was added over the course of 10 min.
43 2C-T-7; 2,5-DIMETHOXY-4-(n)-PROPYLTHIOPHENETHYLAMINE
44 2C-T-8; 2,5-DIMETHOXY-4-CYCLOPROPYLMETHYLTHIOPHENETHYLAMINE
45 2C-T-9; 2,5-DIMETHOXY-4-(t)-BUTYLTHIOPHENETHYLAMINE
46 2C-T-13; 2,5-DIMETHOXY-4-(2-METHOXYETHYLTHIO)PHENETHYLAMINE
47 2C-T-15; SESQUI; 2,5-DIMETHOXY-4-CYCLOPROPYLTHIOPHENETHYLAMINE
48 2C-T-17; NIMITZ; 2,5-DIMETHOXY-4-(s)-BUTYLTHIOPHENETHYLAMINE
49 2C-T-21; 2,5-DIMETHOXY-4-(2-FLUOROETHYLTHIO)PHENETHYLAMINE
50 4-D; 3,5-DIMETHOXY-4-TRIDEUTEROMETHOXY-PHENETHYLAMINE
51 '-D; 3,4,5-TRIMETHOXY-','-DIDEUTEROPHENETHYLAMINE
52 DESOXY; 3,5-DIMETHOXY-4-METHYLPHENETHYLAMINE
53 2,4-DMA; 2,4-DIMETHOXYAMPHETAMINE
54 2,5-DMA; DMA; 2,5-DIMETHOXYAMPHETAMINE
55 3,4-DMA; 3,4-DIMETHOXYAMPHETAMINE
56 DMCPA; 2-(2,5-DIMETHOXY-4-METHYLPHENYL)CYCLOPROPYLAMINE
57 DME; 3,4-DIMETHOXY-'-HYDROXYPHENETHYLAMINE
58 DMMDA; 2,5-DIMETHOXY-3,4-METHYLENEDIOXYAMPHETAMINE
59 DMMDA-2; 2,3-DIMETHOXY-4,5-METHYLENEDIOXYAMPHETAMINE
60 DMPEA; 3,4-DIMETHOXYPHENETHYLAMINE
61 DOAM; 2,5-DIMETHOXY-4-(n)-AMYLAMPHETAMINE
62 DOB; 2,5-DIMETHOXY-4-BROMOAMPHETAMINE
63 DOBU; 2,5-DIMETHOXY-4-(n)-BUTYLAMPHETAMINE
64 DOC; 2,5-DIMETHOXY-4-CHLOROAMPHETAMINE
65 DOEF; 2,5-DIMETHOXY-4-(2-FLUOROETHYL)-
66 DOET; HECATE; 2,5-DIMETHOXY-4-ETHYLAMPHETAMINE
67 DOI; 2,5-DIMETHOXY-4-IODOAMPHETAMINE
68 DOM; STP; 2,5-DIMETHOXY-4-METHYLAMPHETAMINE
69 Y-DOM; Z-7; 2,6-DIMETHOXY-4-METHYLAMPHETAMINE
70 DON; 2,5-DIMETHOXY-4-NITROAMPHETAMINE
71 DOPR; 2,5-DIMETHOXY-4-(n)-PROPYLAMPHETAMINE
72 E; ESCALINE; 3,5-DIMETHOXY-4-ETHOXYPHENETHYLAMINE
73 EEE; 2,4,5-TRIETHOXYAMPHETAMINE
74 EEM; 2,4-DIETHOXY-5-METHOXYAMPHETAMINE
75 EME; 2,5-DIETHOXY-4-METHOXYAMPHETAMINE
76 EMM; 4,5-DIMETHOXY-2-ETHOXYAMPHETAMINE
77 ETHYL-J; 2-ETHYLAMINO-1-(3,4-METHYLENEDIOXYPHENYL)BUTANE; N-ETHYL-1-(1,3-BENZODIOXOL-5-YL)-2-BUTANAMINE
78 ETHYL-K; 2-ETHYLAMINO-1-(3,4-METHYLENEDIOXYPHENYL)PENTANE; N-ETHYL-1-(1,3-BENZODIOXOL-5-YL)-2-PENTYLAMINE
79 F-2; 2-M;
80 F-22;
81 FLEA; N-HYDROXY-N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE
82 G-3; 2,5-DIMETHOXY-3,4-(TRIMETHYLENE)AMPHETAMINE; 5-(2-AMINOPROPYL)-4,7-DIMETHOXYINDANE
83 G-4; 2,5-DIMETHOXY-3,4-(TETRAMETHYLENE)AMPHETAMINE; 6-(2-AMINOPROPYL)-5,8-DIMETHOXYTETRALIN
84 G-5; 3,6-DIMETHOXY-4-(2-AMINOPROPYL)BENZONORBORNANE
85 GANESHA; G; 2,5-DIMETHOXY-3,4-DIMETHYLAMPHETAMINE
86 G-N; 1,4-DIMETHOXYNAPHTHYL-2-ISOPROPYLAMINE
87 HOT-2; 2,5-DIMETHOXY-4-ETHYLTHIO-N-HYDROXYPHENETHYLAMINE
88 HOT-7; 2,5-DIMETHOXY-N-HYDROXY-4-(n)-PROPYLTHIOPHENETHYLAMINE
89 HOT-17; 2,5-DIMETHOXY-4-(s)-BUTYLTHIO-N-HYDROXYPHENETHYLAMINE
90 IDNNA; 2,5-DIMETHOXY-N,N-DIMETHYL-4-IODOAMPHETAMINE
91 IM; ISOMESCALINE; 2,3,4-TRIMETHOXYPHENETHYLAMINE
92 IP; ISOPROSCALINE; 3,5-DIMETHOXY-4-(i)-PROPOXYPHENETHYLAMINE
93 IRIS; 5-ETHOXY-2-METHOXY-4-METHYLAMPHETAMINE
94 J; BDB; 2-AMINO-1-(3,4-METHYLENEDIOXYPHENYL)BUTANE; 1-(1,3-BENZODIOXOL-5-YL)-2-BUTANAMINE
95 LOPHOPHINE; 3-METHOXY-4,5-METHYLENEDIOXYPHENETHYLAMINE
96 M; MESCALINE; 3,4,5-TRIMETHOXYPHENETHYLAMINE
97 4-MA; PMA; 4-METHOXYAMPHETAMINE
98 MADAM-6; 2,N-DIMETHYL-4,5-METHYLENEDIOXYAMPHETAMINE
99 MAL; METHALLYLESCALINE;
100 MDA; 3,4-METHYLENEDIOXYAMPHETAMINE
101 MDAL; N-ALLYL-MDA; 3,4-METHYLENEDIOXY-N- ALLYLAMPHETAMINE
102 MDBU; N-BUTYL-MDA; 3,4-METHYLENEDIOXY-N-BUTYLAMPHETAMINE
103 MDBZ; N-BENZYL-MDA; 3,4-METHYLENEDIOXY-N-BENZYLAMPHETAMINE
104 MDCPM; CYCLOPROPYLMETHYL-MDA;
105 MDDM; N,N-DIMETHYL-MDA;
106 MDE; MDEA; EVE; N-ETHYL-MDA;
107 MDHOET; HYDROXYETHYL-MDA;
108 MDIP; N-ISOPROPYL-MDA;
109 MDMA; MDM; ADAM; ECSTASY; 3,4-METHYLENEDIOXY-N-METHYLAMPHETAMINE
110 MDMC; EDMA; 3,4-ETHYLENEDIOXY-N-METHYLAMPHETAMINE
111 MDMEO; N-METHOXY-MDA; 3,4-METHYLENEDIOXY-N-METHYOXYAMPHETAMINE
112 MDMEOET; N-METHOXYETHYL-MDA;
113 MDMP; a,a,N-TRIMETHYL-3,4-METHYLENEDIOXY-PHENETHYLAMINE; METHYLENEDIOXYMEPHENTERM
INE
114 MDOH; N-HYDROXY-MDA; 3,4-METHYLENEDIOXY-N-HYDROXYAMPHETAMINE
115 MDPEA; 3,4-METHYLENEDIOXYPHENETHYLAMINE; HOMOPIPERONYLAMINE
116 MDPH; a,a-DIMETHYL-3,4-METHYLENEDIOXY-
117 MDPL; N-PROPARGYL-MDA; N-PROPYNYL-MDA; 3,4-METHYLENEDIOXY-N-PROPARGYLAMPHETAMINE) SYNTHESIS: A solution of 10.5 g propargylamine hydrochloride in 40 mL
118 MDPR; N-PROPYL-MDA; 3,4-METHYLENEDIOXY-N-PROPYLAMPHETAMINE
119 ME; METAESCALINE; 3,4-DIMETHOXY-5-ETHOXYPHENETHYLAMINE
120 MEDA; 3-METHOXY-4,5-ETHYLENEDIOXYAMPHETAMINE
121 MEE; 4,5-DIETHOXY-2-METHOXYAMPHETAMINE
122 MEM; 2,5-DIMETHOXY-4-ETHOXYAMPHETAMINE
123 MEPEA; 3-METHOXY-4-ETHOXYPHENETHYLAMINE
124 META-DOB; 5-BROMO-2,4-DIMETHOXYAMPHETAMINE
125 META-DOT; 2,4-DIMETHOXY-5-METHYLTHIOAMPHETAMINE
126 METHYL-DMA; DMMA; 2,5-DIMETHOXY-N-METHYLAMPHETAMINE
127 METHYL-DOB; 4-BROMO-2,5-DIMETHOXY-N-METHYLAMPHETAMINE
128 METHYL-J; MBDB; EDEN;
129 METHYL-K; 2-METHYLAMINO-1-(3,4-METHYLENEDIOXYPHENYL)PENTANE; N-METHYL-1-(1,3-BENZODIOXOL-5-YL)-2-PENTYLAMINE
130 METHYL-MA; PMMA; DOONE; 4-MMA; 4-METHOXY-N-METHYLAMPHETAMINE
131 METHYL-MMDA-2; 2-METHOXY-N-METHYL-4,5-METHYLENEDIOXYAMPHETAMINE
132 MMDA; 3-METHOXY-4,5-METHYLENEDIOXYAMPHETAMINE
133 MMDA-2; 2-METHOXY-4,5-METHYLENEDIOXYAMPHETAMINE
134 MMDA-3a; 2-METHOXY-3,4-METHYLENEDIOXYAMPHETAMINE
135 MMDA-3b; 4-METHOXY-2,3-METHYLENEDIOXYAMPHETAMINE
136 MME; 2,4-DIMETHOXY-5-ETHOXYAMPHETAMINE
137 MP; METAPROSCALINE; 3,4-DIMETHOXY-5-(n)-PROPOXYPHENETHYLAMINE
138 MPM; 2,5-DIMETHOXY-4-(n)-PROPOXYAMPHETAMINE
139 ORTHO-DOT; 4,5-DIMETHOXY-2-METHYLTHIOAMPHETAMINE
140 P; PROSCALINE; 3,5-DIMETHOXY-4-(n)-PROPOXYPHENETHYLAMINE
141 PE; PHENESCALINE; 3,5-DIMETHOXY-4-PHENETHYLOXYPHENETHYLAMINE
142 PEA; PHENETHYLAMINE
143 PROPYNYL; 3,5-DIMETHOXY-4-(2-PROPYNYLOXY)PHENETHYLAMINE
144 SB; SYMBESCALINE; 3,5-DIETHOXY-4-METHOXYPHENETHYLAMINE
145 TA; 2,3,4,5-TETRAMETHOXYAMPHETAMINE
146 3-TASB; 3-THIOASYMBESCALINE;
147 4-TASB; 4-THIOASYMBESCALINE;
148 5-TASB; 5-THIOASYMBESCALINE;
149 TB; 4-THIOBUSCALINE; 3,5-DIMETHOXY-4-(n)-BUTYLTHIOPHENETHYLAMINE
150 3-TE; 3-THIOESCALINE;
151 TE; 4-TE; 4-THIOESCALINE; 3,5-DIMETHOXY-4-ETHYLTHIOPHENETHYLAMINE
152 2-TIM; 2-THIOISOMESCALINE; 3,4-DIMETHOXY-2-
153 3-TIM; 3-THIOMESCALINE; 2,4-DIMETHOXY-3-METHYLTHIOPHENETHYLAMINE
154 4-TIM; 4-THIOISOMESCALINE;
155 3-TM; 3-THIOMESCALINE; 3,4-DIMETHOXY-5-METHYLTHIOPHENETHYLAMINE
156 TM; 4-TM; 4-THIOMESCALINE;
157 TMA; 3,4,5-TRIMETHOXYAMPHETAMINE
158 TMA-2; 2,4,5-TRIMETHOXYAMPHETAMINE
159 TMA-3; 2,3,4-TRIMETHOXYAMPHETAMINE
160 TMA-4; 2,3,5-TRIMETHOXYAMPHETAMINE
161 TMA-5; 2,3,6-TRIMETHOXYAMPHETAMINE
162 TMA-6; 2,4,6-TRIMETHOXYAMPHETAMINE
163 3-TME; 3-THIOMETAESCALINE;
164 4-TME; 4-THIOMETAESCALINE;
165 5-TME; 5-THIOMETAESCALINE;
166 2T-MMDA-3a; 3,4-METHYLENEDIOXY-2-METHYLTHIOAMPHETAMINE
167 4T-MMDA-2; 6-(2-AMINOPROPYL)-5-METHOXY-1,3-BENZOXATHIOL; 2-METHOXY-4,5-METHYLENETHIOOXYAMPHETAMINE
168 TMPEA; 2,4,5-TRIMETHOXYPHENETHYLAMINE
169 2-TOET; 4-ETHYL-5-METHOXY-2-METHYLTHIOAMPHETAMINE
170 5-TOET; 4-ETHYL-2-METHOXY-5-METHYLTHIOAMPHETAMINE
171 2-TOM; 5-METHOXY-4-METHYL-2-METHYLTHIOAMPHETAMINE
172 5-TOM; 2-METHOXY-4-METHYL-5-METHYLTHIOAMPHETAMINE
173 TOMSO; 2-METHOXY-4-METHYL-5-METHYLSULFINYLAMPHETAMINE
174 TP; THIOPROSCALINE; 3,5-DIMETHOXY-4-(n)-PROPYLTHIOPHENETHYLAMINE
175 TRIS; TRESCALINE; TRISESCALINE; 3,4,5-TRIETHOXYPHENETHYLAMINE
176 3-TSB; 3-THIOSYMBESCALINE;
177 4-TSB; 4-THIOSYMBESCALINE;
178 3-T-TRIS; 3-THIOTRESCALINE; 3-THIOTRISESCALINE; 3,4-DIETHOXY-5-ETHYLTHIOPHENETHYLAMINE
179 4-T-TRIS; 4-THIOTRESCALINE; 4-THIOTRISESCALINE; 3,5-DIETHOXY-4-ETHYLTHIOPHENETHYLAMINE
1 AEM; a-ETHYLMESCALINE; 2-AMINO-1-(3,4,5-TRIMETHOXYPHENYL)BUTANE; 1-(3,4,5-TRIMETHOXYPHENYL)-2-AMINOBUTANE
SYNTHESIS: To a solution of 45 g 3,4,5-trimethoxybenzaldehyde in 1.2 L
IPA, there was added 125 g nitropropane and 67.5 g t-butylammonium acetate and the reaction mixture was held at reflux for 16 h. This was poured into 6 L H2O, and extracted with 2x250 mL hexane. The pooled extracts were stripped of solvent under vacuum giving a residue that slowly set to a crystalline mass. On filtering, there was obtained 9.4 g of a crude yellow product which, on recrystallization from hexane provided 8.7 g of slightly sticky bright yellow crystals of 2-nitro-1-(3,4,5-trimethoxyphenyl)butene-1, with a mp of 71-73 !C.
A second recrystallization from hexane gave fine yellow crystals with a mp of 72-73 !C. Attempts at the preparation of this nitrostyrene by the more conventional methods with ammonium acetate in acetic acid led either to the formation of a white product C23H30N2O8 which was composed of a molecule of the nitrostyrene, one of the benzaldehyde itself, and a molecule of ammonia, or to 3,4,5-trimethoxybenzonitrile, from reaction with the decomposition products of nitropropane.
A stirred suspension of 5.9 g LAH in 310 mL anhydrous Et2O was held at a gentle reflux in an inert atmosphere. A solution of 8.5 g 2-nitro-1-(3,4,5-trimethoxyphenyl)butene-1 in 125 mL Et2O is added drop-wise over the course of 0.5 h. The reaction was maintained at reflux for 6 h, then cooled, and the excess hydride destroyed by the cautious addition of 300 mL 1.8 N H2SO4. The phases were separated, and the aqueous phase brought to a pH of 6 by the addition of a saturated Na2CO3 solution. The neutral solution was brought to a boil, and clarified by filtration through paper. To the hot filtrate there was added a solution of 8.9 g picric acid in 100 mL boiling EtOH. The mixture was stirred and cooled, with the formation of a heavy yellow crystalline mass. After standing in the ice tub for several hours the mixture was filtered, providing 8.0 g of the picrate salt with a mp of 176-181 !C from H2O. A solution of this salt in 300
mL boiling H2O was treated with 60 mL concentrated HCl. On cooling, there was a deposition of picric acid, which was removed by filtration. The aqueous filtrate was washed with 3x50 mL
nitrobenzene, then with 3x50 mL Et2O. The pH was brought above 9 by the addition of aqueous NaOH, and the filtrate was extracted with 3x100 mL CH2Cl2. Removal of the solvent from the pooled extracts gave a nearly colorless oil, which was dissolved in 300 mL anhydrous Et2O
and saturated with hydrogen chloride gas. The white crystals of 2-amino-1-(3,4,5-trimethoxyphenyl)butane hydrochloride (AEM) were removed by filtration, Et2Owashed, and air dried. They weighed 4.72
g.
DOSAGE: greater than 220 mg.
DURATION: unknown.
EXTENSIONS AND COMMENTARY: The extension of the two-carbon chain of mescaline by alpha-methylation to the three carbon chain of TMA approximately doubled the potency of the compound. And it was felt to be a completely logical possibility that, by extending it one more carbon atom, to the four carbon chain of alpha-ethyl-mescaline, it might double again. And following that logical progression, the doubling of potency with each additional carbon atom, the factor would be 2 to the 7th power by the alpha-octyl (or 256x that of mescaline, or a milligram as active dose) and with a side chain of a 70-carbon alkyl group (alpha-heptacontylmescaline) it would take just a single molecule to be intoxicating. This was rich fantasy stuff. As an active compound, just where would it go in the brain? With an 80-carbon side-chain, would one-thousandth of a single molecule be enough for a person? Or might a single molecule intoxicate a thousand people? And how long a chain on the alpha-position might be sufficient that, by merely writing down the structure on a piece of paper, you would get high? Maybe just conceiving the structure in your
mind would do it. That is, after all, the way of homeopathy.
Maybe it was just as well that this added two-carbon side-chain with lowered activity was already enough to disprove the doubling pattern.
But by the time this non-activity had been learned, the alpha series had already been pushed out quite aways. The machinery of making the appropriate nitroalkane was straightforward, by reaction of the alkyl halide with nitrous acid, and separating the unwanted nitrite ester from the wanted nitroalkane by fractional distillation. The nitrostyrenes all formed reasonably although often in terrible yields, and reduced reasonably, and all formed crystalline picrates for isolation and crystalline hydrochloride salts for pharmacological manipulation. But since the first of these, AEM, was not active, there was no enthusiasm for tasting anything higher. This family was never published; why publish presumably inactive and thus uninteresting material? The Table presents the properties of the precursor nitrostyrenes, and the product picrate and hydrochloride salts, at least whatever information I can still find after thirty years:
TABLE. Physical Properties of the a-Alkylmescaline Homologues and their Precursor Nitrostyrenes
Code Name NS mp !C picrate mp !C HCl mp !C
APM Alpha-propylmescaline 82-83 214-218
ABM Alpha-butylmescaline 73-74 169-174 182-184
AAM Alpha-amylmescaline 54-55 162-163 155-158
AHM Alpha-hexylmescaline 51-52
ASM* Alpha-heptylmescaline 43-44
AOM Alpha-octylmescaline
ANM Alpha-nonylmescaline 46-47 *
AUM Alpha-undecylmescaline *
* S is for septyl, to distinguish heptyl from hexyl. **Never made, as no nonylbromide could be located to make the needed nitrononane. ***The synthesis got as far as the nitrostyrene stage when the inactivity of AEM was determined, and the project was dropped.
2 AL; 4-ALLYLOXY-3,5-DIMETHOXYPHENETHYLAMINE; 3,5-DIMETHOXY-4-ALLYLOXYPHENETHYLAMINE
SYNTHESIS: A solution of 5.8 g of homosyringonitrile (see under E for its preparation), 100 mg decyltriethylammonium iodide, and 13.6 g allyl iodide in 50 mL anhydrous acetone was treated with 6.9 g finely powdered anhydrous K2CO3 and held at reflux for 16 h. The color changed from a near-black to a light yellow. The mixture was filtered, the solids washed with acetone, and the solvent from the combined filtrate and washes removed under vacuum. The residue was suspended in acidified H2O, and extracted with 3x100 mL CH2Cl2. The pooled extracts were washed with 2x50 mL 5% NaOH, once with dilute HCl (which lightened the color of the extract) and then stripped of solvent under vacuum giving 12.4 g of an amber-colored oil. This was distilled at 125-137 !C at 0.1 mm/Hg to yield 5.7 g of 3,5-dimethoxy-4-allyloxyphenylacetonitrile as a yellow oil. Anal.