Go to PiHKAL • info home
Browse the short index of PiHKAL phenethylamines. Read book II of PiHKAL
Search for phenethylamines and related structures Beyond PiHKAL—Selected writings by Sasha and others. Explore phenethylamine structures and analogues
The essential oils and their amphetamine analogues How PiHKAL • info differs from the printed version
Go to TiHKAL • info home
Book II of PiHKAL: A Chemical Love Story, by Alexander & Ann Shulgin #34: 2C-N
#34 2C-N: 2,5-Dimethoxy-4-nitrophenethylamine

#34 2C-N SYNTHESIS: A cooled, stirred solution of 1.0 g 2,5-dimethoxyphenethylamine (see the recipe for 2C-H for its preparation) in 20 mL glacial acetic acid was treated with 3.3 mL 70% HNO3 in small portions, with the reaction temperature kept down with periodic cooling. After the addition was completed, the stirring was continued until there was the spontaneous separation of a yellow solid. This was 2,5-dimethoxy-4-nitrophenethylamine nitrate (2C-N) which was obtained after removal by filtration, washing with Et2O and air drying, as a fluffy yellow solid. This weighed 1.04 g and melted, with decomposition, in the area of 170–180 °C, depending on the rate of heating. A solution of 0.8 g of this nitrate salt in 50 mL H2O was made basic with aqueous NaOH. Extraction with 3×50 mL CH2Cl2, and removal of the solvent under vacuum gave the free base as a residue. This was distilled at 130–150 °C at 0.35 mm/Hg to give an orange-red oil that weighed 0.5 g and set up as crystals. This was dissolved in 3 mL IPA, neutralized with 7 drops of concentrated HCl (the color lightened considerably at the titration end point) and diluted with 5 mL anhydrous Et2O. There was the formation of the hydrochloride salt which was a pumpkin-colored crystalline mass. After removal by filtration, Et2O washing and air drying, these crystals weighed 0.44 g. The mp, 193–195 °C, was not improved by recrystallization from any of several solvents (MeOH, IPA, CH3CN). The perchlorate salt was a yellow solid from MeOH, with a mp of 211 °C, with decomposition. Nitration of 2C-H in a mixture of acetic acid and acetic anhydride produced the acetamide derivative of 2C-N as yellow crystals with a mp 142.5–143 °C. For the nitrate salt: Anal. (C10H15N3O7) C,H. This was the form used for all human titrations.

DOSAGE: 100–150 mg.

DURATION: 4–6 h.

QUALITATIVE COMMENTS: (with 120 mg) “This came on very fast—I was aware of it within a half hour, and it got as far as it would go by an hour. There are similarities to MDMA, but missing is the benign anti-stress component. I am light-headed, and there just might be a little eye wiggling. And then it dropped right off to nothing within a couple of hours.”

(with 150 mg) “There may have been some visual changes, I’m not sure. But the talking was extremely easy. If there were no other things to use, this would be excellent, but there are other compounds available. This doesn’t have too high a priority.”

(with 150 mg) “Am I enjoying it? Not exactly, but I am in a good mood. There is not the light-filled energy that some other materials can provide. By six hours, pretty much baseline. Strange material, but okay. Final score: body +3, mind +2, barely.”

EXTENSIONS AND COMMENTARY: A most consistent feature with 2C-N was the fact that in every report, somewhere, there is the note that it somehow came up just a little short of expectations. From the esthetic point of view, the pure salt is yellow rather than the usual white color, so the solutions that are to be consumed are by definition also yellow colored. From the structural point of view, the 4-nitro group, like the 4-bromo group of 2C-B, is a dead-end. It cannot be stretched or compressed or lengthened or shortened. This unique aspect demands that you have to live with what you have, as there are no subtle ways of modifying the molecule. With 2C-B, the end product was a total winner; there was no wish to modify it. With 2C-N the end product is something a little less, and there is no way to modify it.

Page updated 30 March 2012 · This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License ·

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. Still others remain to be added.

I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore most of the typographic niceties found in the printed edition. I’ve also made minor changes to some chemical names in line with current nomenclature practice, and in the hope of aligning with more readers’ searches. Typically the change is little more than expanding a prefix and setting it in italics. The errata and changes 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.

Although 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.

Transform Press,
Box 13675
Berkeley, CA 94701

510 · 934 · 4930 (voice)
510 · 934 · 5999 (fax)