Buscaline · 4-n-Butoxy-3,5-dimethoxyphenethylamine
#10 B SYNTHESIS: A solution of 5.8 g of homosyringonitrile (see under for preparation), 100 mg decyltriethylammonium iodide, and 11 g n-butyl bromide in 50 mL anhydrous acetone was treated with 6.9 g finely powdered anhydrous K2CO3 and held at reflux for 10 h. An additional 6 g of n-butyl bromide was added to the mixture, and the refluxing continued for another 48 h. 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 3×175 mL CH2Cl2. The pooled extracts were washed with 2×50 mL 5% NaOH, once with dilute HCl, and then stripped of solvent under vacuum giving 13.2 g of a deep yellow oil. This was distilled at 132–145 °C at 0.2 mm/Hg to yield 5.0 g of 4-n-butyloxy-3,5-dimethoxyphenylacetonitrile as a pale yellow oil which set up to crystals spontaneously. The mp was 42–43 °C. Anal. (C14H19NO3) C H N.
A solution of AH was prepared by the cautious addition of 0.67 mL of 100% H2SO4 to 25 mL of 1.0 M LAH in THF, which was being vigorously stirred under He at ice bath temperature. A total of 4.9 g of 4-n-butyloxy-3,5-dimethoxyphenylacetonitrile was added as a solid over the course of 10 min. Stirring was continued for another 5 min, then the reaction mixture was brought to reflux on the steam bath for another 45 min. After cooling again to room temperature, IPA was added to destroy the excess hydride (about 5 mL) followed by 10 mL of 15% NaOH which was sufficient to make the aluminum salts loose, white, and filterable. The reaction mixture was filtered, the filter cake washed with IPA, and the mother liquor and washes combined and the solvent removed under vacuum to yield an amber oil. This residue was treated with dilute H2SO4 which generated copious solids. Heating this suspension effected solution, and after cooling, all was washed with 3×50 mL CH2Cl2. The aqueous phase was made basic with aqueous NaOH, and the product extracted with 2×100 mL CH2Cl2. The extracts were evaporated to a residue under vacuum, and this was distilled at 128–138 °C at 0.5 mm/Hg yielding 3.8 g of a colorless oil. This was dissolved in 40 mL IPA, neutralized with concentrated HCl (about 55 drops required) and, with vigorous stirring, 80 mL of anhydrous Et2O was added which produced fine white plates. After standing for several h, the product was filtered, washed with 20% IPA in Et2O, and finally with Et2O. Air drying yielded 3.9 g of 4-n-butyloxy-3,5-dimethoxyphenethylamine hydrochloride (B) with a mp of 152–153 °C. An analytical sample melted at 155–157 °C. Anal. (C14H24ClNO3) C,H,N.
DOSAGE: greater than 150 mg.
DURATION: several hours.
QUALITATIVE COMMENTS: (with 120 mg) “There is a strange taste, not really bitter, it does not linger. The slight change of baseline has certainly disappeared by the eighth hour. No noticeable changes in either the visual or the auditory area.”
(with 150 mg) “Throughout the experiment it was my impression that whatever effects were being felt, they were more in body than mind. The body load never mellowed out, as it would have with , after the first hour or two. Mental effects didn’t develop in any interesting way. I was aware of brief heart arrhythmia. Tummy was uncomfortable, off and on, and there was light diarrhea. Even as late as the fifth hour, my feet were cold, and the whole thing left me with a slightly uncomfortable, ‘Why did I bother?’ feeling.”
EXTENSIONS AND COMMENTARY: There is a jingle heard occasionally in chemical circles, concerning the homologues of methyl. It goes, “There’s ethyl and propyl, but butyl is futile.” And to a large measure this is true with the 4-position homologues of . This butyl compound, B or Buscaline, had originally been patented in England in 1930 without any physical or pharmacological description, and the few physical studies that had involved it (lipophilic this and that) suggested that it was less active than .
In principle, the 5-, the 6-, the 7- and the on-up homologues might be called amylescaline (possibly pentescaline?), hexescaline, heptescaline (possibly septescaline), and God-knows-what-scaline. They would certainly be easily makeable, but there would be little value that could be anticipated from nibbling them. In keeping with the name B (for butoxy), these would be known as (for amyloxy, as the use of a P could confuse pentoxy with propoxy), as (for hexyloxy, but careful; this letter has been used occasionally for DMPEA MDPEA, which is ), and as (the H for heptyloxy has been consumed by the hexyloxy, so let’s shift from the Greek hepta to the Latin septum for the number seven). It seems most likely that the toxic symptoms that might well come along with these phenethylamines would discourage the use of the dosage needed to affect the higher centers of the brain. The same generally negative feeling applies to the amphetamine counterparts , , and .
A brief reiteration of the 2C-3C nomenclature, to avoid a possible misunderstanding. The drug is so named in that it is the two-carbon chain analogue of the three-carbon chain compound . The drug is so named because it is the three-carbon chain analogue of the two-carbon chain compound Buscaline, or more simply, B. There is no logical connection whatsoever, either structural or pharmacological, between 2C-B and 3C-B.
13 May 2016 · Creative Commons BY-NC-SA ·

About PiHKAL · info

This version of Book II of PiHKAL is based on the Erowid online version, originally transcribed by Simson Garfinkle and converted into HTML by Lamont Granquist. I drew also on “Tyrone Slothrop’s” (Unfinished) Review of PIHKAL to enumerate the many analogues mentioned in PiHKAL but not described at length. Many, many others have since been added.
I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore the typographic niceties found in the printed edition. I’ve also made minor changes to some chemical names in line with current nomenclature practice. Typically the change is little more than expanding a prefix or setting it in italics. The history page has further details.

Cautionary note

“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 herein, 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.”
Alexander T. Shulgin

Copyright notice

The copyright for Book I of PiHKAL has been reserved in all forms and it may not be distributed. Book II of PiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.

Ordering information

PiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of phenethylamines. This book belongs in the library of anyone seeking a rational, enlightened and candid perspective on psychedelic drugs.
Though Sasha and Ann have put Book II of PiHKAL in the public domain, available to anyone, I strongly encourage you to buy a copy. We owe them — and there’s still nothing quite like holding a real book in your hands.
PiHKAL (ISBN 0-9630096-0-5) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.
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