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This is the second half of PiHKAL: A Chemical Love Story, by Alexander
Shulgin and Ann Shulgin. Please forgive any typos or misprints in this
file; further, because of ASCII limitations, many of the typographical
symbols in the original book could not be properly represented in this file.
If you are seriously interested in the chemistry contained in these
files, you should order a copy of the book PiHKAL. The book may be
purchased for $22.95 ($18.95 + $4.00 postage and handling) from
Transform Press, Box 13675, Berkeley, CA 94701. California residents
please add $1.38 State sales tax.
At the present time, restrictive laws are in force in the United
States and it is very difficult for researchers to abide by the
regulations which govern efforts to obtain legal approval to do work
with these compounds in human beings.... No one who is lacking legal
authorization should attempt the synthesis of any of the compounds
described in these files, with the intent to give them to man. To do
so is to risk legal action which might lead to the tragic ruination of
a life. It should also be noted that any person anywhere who
experiments on himself, or on another human being, with any of the
drugs described herin, without being familiar with that drug's action
and aware of the physical and/or mental disturbance or harm it might
cause, is acting irresponsibly and immorally, whether or not he is
doing so within the bounds of the law.
A SHORT INDEX TO THE PHENETHYLAMINES
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.
Code Compact chemical name
1 AEM a-Ethyl-3,4,5-trimethoxy-PEA
2 AL 4-Allyloxy-3,5-dimethoxy-PEA
3 ALEPH 4-Methylthio-2,5-dimethoxy-A
4 ALEPH-2 4-Ethylthio-2,5-dimethoxy-A
5 ALEPH-4 4-Isopropylthio-2,5-dimethoxy-A
6 ALEPH-6 4-Phenylthio-2,5-dimethoxy-A
7 ALEPH-7 4-Propylthio-2,5-dimethoxy-A
8 ARIADNE 2,5-Dimethoxy-a-ethyl-4-methyl-PEA
9 ASB 3,4-Diethoxy-5-methoxy-PEA
10 B 4-Butoxy-3,5-dimethoxy-PEA
11 BEATRICE 2,5-Dimethoxy-4,N-dimethyl-A
12 BIS-TOM 2,5-Bismethylthio-4-methyl-A
13 BOB 4-Bromo-2,5,beta-trimethoxy-PEA
14 BOD 2,5,beta-Trimethoxy-4-methyl-PEA
15 BOH beta-Methoxy-3,4-methylenedioxy-PEA
16 BOHD 2,5-Dimethoxy-beta-hydroxy-4-methyl-PEA
17 BOM 3,4,5,beta-Tetramethoxy-PEA
18 4-Br-3,5-DMA 4-Bromo-3,5-dimethoxy-A
19 2-Br-4,5-MDA 2-Bromo-4,5-methylenedioxy-A
20 2C-B 4-Bromo-2,5-dimethoxy-PEA
21 3C-BZ 4-Benzyloxy-3,5-dimethoxy-A
22 2C-C 4-Chloro-2,5-dimethoxy-PEA
23 2C-D 4-Methyl-2,5-dimethoxy-PEA
24 2C-E 4-Ethyl-2,5-dimethoxy-PEA
25 3C-E 4-Ethoxy-3,5-dimethoxy-A
26 2C-F 4-Fluoro-2,5-dimethoxy-PEA
27 2C-G 3,4-Dimethyl-2,5-dimethoxy-PEA
28 2C-G-3 3,4-Trimethylene-2,5-dimethoxy-PEA
29 2C-G-4 3,4-Tetramethylene-2,5-dimethoxy-PEA
30 2C-G-5 3,4-Norbornyl-2,5-dimethoxy-PEA
31 2C-G-N 1,4-Dimethoxynaphthyl-2-ethylamine
32 2C-H 2,5-Dimethoxy-PEA
33 2C-I 4-Iodo-2,5-dimethoxy-PEA
34 2C-N 4-Nitro-2,5-dimethoxy-PEA
35 2C-O-4 4-Isopropoxy-2,5-dimethoxy-PEA
36 2C-P 4-Propyl-2,5-dimethoxy-PEA
37 CPM 4-Cyclopropylmethoxy-3,5-dimethoxy-PEA
38 2C-SE 4-Methylseleno-2,5-dimethoxy-PEA
39 2C-T 4-Methylthio-2,5-dimethoxy-PEA
40 2C-T-2 4-Ethylthio-2,5-dimethoxy-PEA
41 2C-T-4 4-Isopropylthio-2,5-dimethoxy-PEA
42 gamma-2C-T-4 4-Isopropylthio-2,6-dimethoxy-PEA
43 2C-T-7 4-Propylthio-2,5-dimethoxy-PEA
44 2C-T-8 4-Cyclopropylmethylthio-2,5-dimethoxy-PEA
45 2C-T-9 4-(t)-Butylthio-2,5-dimethoxy-PEA
46 2C-T-13 4-(2-Methoxyethylthio-2,5-dimethoxy-PEA
47 2C-T-15 4-Cyclopropylthio-2,5-dimethoxy-PEA
48 2C-T-17 4-(s)-Butylthio-2,5-dimethoxy-PEA
49 2C-T-21 4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA
50 4-D 4-Trideuteromethyl-3,5-dimethoxy-PEA
51 beta-D beta,beta-Dideutero-3,4,5-trimethoxy-PEA
52 DESOXY 4-Me-3,5-Dimethoxy-PEA
53 2,4-DMA 2,4-Dimethoxy-A
54 2,5-DMA o-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 deg C picrate mp deg C HCl mp deg 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 deg C at 0.1 mm/Hg to yield