PiHKAL

PiHKAL: A Chemical Love Story, also known as Phenethylamines I Have Known and Loved, is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or entactogens. The book has two halves, with the second part containing detailed entries on 179phenethylamines. PiHKAL was followed by TiHKAL: The Continuation (Tryptamines I Have Known and Loved) (1997).

Content

The book is arranged into two parts, the first part being a fictionalized autobiography of the couple and the second part describing 179different psychedelic compounds (most of which Shulgin discovered himself), including detailed synthesis instructions, bioassays, doses, durations, and other commentary.

The second part was made freely available by Shulgin on Erowid while the first part is available only in the printed text. While the reactions described are beyond the ability of people with a basic chemistry education, some tend to emphasize techniques that do not require difficult-to-obtain chemicals. Notable among these are the use of mercury-aluminium amalgam (an unusual but easy to obtain reagent) as a reducing agent and detailed suggestions on legal plant sources of important drug precursors such as safrole.

Members of Shulgin's research who contributed to the experience reports included Shulgin himself, Ann Shulgin, Myron Stolaroff, and Jean Stolaroff, among others.

Response

Through PiHKAL (and later TiHKAL), Shulgin sought to ensure that his discoveries would escape the limits of professional research labs and find their way to the public, a goal consistent with his stated beliefs that psychedelic drugs can be valuable tools for self-exploration. The MDMA ("ecstasy") synthesis published in PiHKAL remains one of the most common clandestine methods of its manufacture to this day. Many countries have banned the major substances for which this book gives directions for synthesis, such as 2C-B, 2C-T-2, and 2C-T-7.

In 1994, two years after PiHKAL was published, the Drug Enforcement Administration (DEA) raided Shulgin's laboratory and requested that he surrender his DEA license. Richard Meyer, spokesman for DEA's San Francisco Field Division, has stated in reference to PiHKAL "It is our opinion that those books are pretty much cookbooks on how to make illegal drugs. Agents tell me that in clandestine labs that they have raided, they have found copies of those books", suggesting that the publication of PiHKAL and the termination of Shulgin's license may have been related.

Notable compounds

Some compounds in PiHKAL, like mescaline, DOM, 2C-B, MDA, and MDMA, are widely known and/or used psychedelics and/or entactogens.

Essential amphetamines

The "essential amphetamines" are what Shulgin describes as ten amphetamines that differ from natural products such as safrole or myristicin by an amine group (). The list consists of:

• PMA (para-methoxyamphetamine)
• 2,4-DMA (2,4-dimethoxyamphetamine)
• 3,4-DMA (3,4-dimethoxyamphetamine)
• MDA (3,4-methylenedioxyamphetamine)
• MMDA (3-methoxy-4,5-methylendioxyamphetamine)
• MMDA-3a (2-methoxy-3,4-methylendioxyamphetamine)
• MMDA-2 (2-methoxy-4,5-methylendioxyamphetamine)
• TMA (3,4,5-trimethoxyamphetamine)
• TMA-2 (2,4,5-trimethoxyamphetamine)
• DMMDA (2,5-dimethoxy-3,4-methylenedioxyamphetamine)
• DMMDA-2 (2,3-dimethoxy-4,5-methylenedioxyamphetamine)
• TeMA (2,3,4,5-tetramethoxyamphetamine)

Not all of these chemicals are bioassayed in PiHKAL; some are merely mentioned.

Magical half-dozen

The so-called "magical half-dozen" refers to Shulgin's self-rated most important phenethylamine compounds, all of which except mescaline he developed and synthesized himself. They are found within the first book of PiHKAL, and are as follows:

• 2C-B (2,5-dimethoxy-4-bromophenethylamine)
• 2C-E (2,5-dimethoxy-4-ethylphenethylamine)
• 2C-T-2 (2,5-dimethoxy-4-ethylthiophenethylamine)
• 2C-T-7 (2,5-dimethoxy-4-propylthiophenethylamine)
• DOM (2,5-dimethoxy-4-methylamphetamine), DOM being short for des-oxy-methyl, referring to the removal of the oxygen atom from the methoxy group on the "4" carbon
• Mescaline (3,4,5-trimethoxyphenethylamine)

All six are now Schedule I controlled substances in the United States.

Ten classic ladies

Shulgin systematically replaced the 10unique hydrogen atoms in DOM with methyl groups in order to explore its activity and named these compounds the "ten classic ladies". The resulting compounds were as follows:

• Ariadne (α-desmethyl-α-ethyl-DOM)
• Beatrice (N-methyl-DOM)
• Charmian (α-methyl-DOM)
• Daphne (threo-β-methyl-DOM)
• Elvira (erythro-β-methyl-DOM)
• Florence (2-desmethoxy-2-ethoxy-DOM; DOM-2-EtO)
• Ganesha (3-methyl-DOM)
• Hecate (DOET; 4-desmethyl-4-ethyl-DOM)
• Iris (5-desmethoxy-5-ethoxy-DOM; DOM-5-EtO)
• Juno (6-methyl-DOM)

As with the essential amphetamines, not all of these compounds have been bioassayed.

Some additional "ladies" have also since been named, including Julia (DOTMA; 3,6-dimethyl-DOM), Jelena (2C-IP), and Selene (2C-P).

Phenethylamines listed

Many additional compounds are also discussed within the individual compound entries of PiHKAL, for instance the 2C TWEETIOs.

In addition to PiHKAL, Shulgin has also described the properties of psychedelic phenethylamines in humans in literature reviews.

Censorship

In December 2025, the Lukashenko regime added the book to the List of printed publications containing information materials, the distribution of which could harm the national interests of Belarus.

See also

• Bibliography of Alexander Shulgin
• TiHKAL (Tryptamines I Have Known and Loved) (1997)
• The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds (2011)
• List of psychedelic literature
• Substituted phenethylamine (PEA)
• Substituted methoxyphenethylamine
• Substituted amphetamine (AMPH)
• Substituted methylenedioxyphenethylamine (MDxx)
• 2C, DOx, 4C, scaline, 3C, Ψ-PEA, 25-NB, FLY

External links

• October 6, 2014, at the Wayback Machine