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.^[1][2][3] The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or entactogens.^[2][3] The book has two halves, with the second part containing detailed entries on 179 phenethylamines.^[2][3] PiHKAL was followed by TiHKAL: The Continuation (Tryptamines I Have Known and Loved) (1997).^[4][5]

Content

The book is arranged into two parts, the first part being a fictionalized autobiography of the couple and the second part describing 179 different psychedelic compounds (most of which Shulgin discovered himself), including detailed synthesis instructions, bioassays, doses, durations, and other commentary.^[2][3]

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.^[3] 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.^[3]

Members of Shulgin's research who contributed to the experience reports included Shulgin himself, Ann Shulgin, Myron Stolaroff, and Jean Stolaroff, among others.^[6][7]

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.^[8]

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.^[9]

Notable compounds

Some compounds in PiHKAL, like mescaline, DOM, 2C-B, MDA, and MDMA, are widely known and/or used psychedelics and/or entactogens.^[3]

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 (PiHKAL Entry #157 TMA).^[3] The list consists of:^[3]

• 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.^[3]

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.^[3] They are found within the first book of PiHKAL, and are as follows:^[3]

• 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.^[10]

Ten classic ladies

Shulgin systematically replaced the 10 unique hydrogen atoms in DOM with methyl groups in order to explore its activity and named these compounds the "ten classic ladies".^[11][3] The resulting compounds were as follows:^[11][3]

• 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.^[3]

Some additional "ladies" have also since been named, including Julia (DOTMA; 3,6-dimethyl-DOM), Jelena (2C-IP), and Selene (2C-P).^[11][12]

Phenethylamines listed

Many additional compounds are also discussed within the individual compound entries of PiHKAL, for instance the 2C TWEETIOs.^[3]

In addition to PiHKAL, Shulgin has also described the properties of psychedelic phenethylamines in humans in literature reviews.^{[13][14][15][16][17][18]}

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.^[19]

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

References

1. ^ Johnson, C. (2018). Magic Medicine: A Trip Through the Intoxicating History and Modern-Day Use of Psychedelic Plants and Substances. Fair Winds Press. pp. 22–24. ISBN 978-1-63159-428-1. Retrieved 30 January 2025.
2. ^ Walker, Scott R.; Pullella, Glenn A.; Piggott, Matthew J.; Duggan, Peter J. (17 July 2023). "Introduction to the chemistry and pharmacology of psychedelic drugs". Australian Journal of Chemistry. 76 (5): 236–257. doi:10.1071/CH23050. ISSN 0004-9425. Retrieved 1 November 2025. Prior to its use being criminalised, mescaline (4) also played a significant role in the development of the synthetic phenethylamines by inspiring the investigations of medicinal chemist Alexander Shulgin. Shulgin synthesised at least 179 phenethylamines, which he then tested either alone on himself or along with his wife and close friends, referred to as the ‘research group’.[85 ] This work established some structure–psychoactivity relationships for phenethylamines in humans and resulted in the discovery of a number of substituted phenethylamines that remain important, such as the ‘classic hallucinogens’ DOM (2,5-dimethoxy-4-methylamphetamine; 40) and 2C-B (2,5-dimethoxy-4-bromophenethylamine; 44, Fig. 10), and entactogens MDEA (3,4-methylenedioxy-N-ethylamphetamine; 38) and MBDB (N-methyl-1-(benzodioxol-5-yl)butan-2-amine; 36, Fig. 9). Alexander (Sasha) and Ann Shulgin’s book Phenethylamines I have known and loved (PiHKAL)[85] is a seminal work that contains frank and detailed descriptions of the subjective effects of phenethylamines and remains extremely valuable to current phenethylamine research.
3. ^ Alexander T. Shulgin & Ann Shulgin (1991). PiHKAL: A Chemical Love Story. 1st ed. Berkeley, CA: Transform Press. ISBN 978-0-9630096-0-9. OCLC 25627628
4. ^ Ben Sessa (2015). "Continuing History of Psychedelics in Medical Practices: The Renaissance of Ps chedelic Medical Research". The Psychedelic Policy Quagmire: Health, Law, Freedom, and Society. Psychology, Religion, and Spirituality. Bloomsbury Publishing. p. 50. ISBN 979-8-216-13356-8. Retrieved 30 January 2025.
5. ^ Alexander T. Shulgin & Ann Shulgin (1997). TiHKAL: The Continuation. 1st ed. Berkeley, CA: Transform Press. ISBN 978-0-9630096-9-2. OCLC 38503252. Retrieved 30 January 2025.
6. ^ Connie Littlefield (director, writer), Siobhan Flanagan, Alexander Shulgin (subject), Ann Shulgin (subject), Paul F. Daley (subject), Myron Stolaroff (subject), Jean Stolaroff (subject), Wendy Perry Tucker (subject), Tania Manning (subject), Greg Manning (subject), Keeper Trout (subject), Earth and Fire Erowid, others (2021). Better Living Through Chemistry (Motion picture). Better Living Through Film, Incorporated. Archived November 19, 2025 at the Wayback Machine. Retrieved November 17, 2025.
7. ^ Passie T, Brandt SD (2018). "Self-Experiments with Psychoactive Substances: A Historical Perspective". Handb Exp Pharmacol. 252: 69–110. doi:10.1007/164_2018_177. PMID 30478735 More ambitious explorations of subjective effects elicited by a series of new psychoactive substances developed by Shulgin were conducted by his close associate and psychologist, Myron Stolaroff. Following SEs with LSD in the mid-1950s, Stolaroff became involved in scientific research on psychedelics. After the control of most psychedelic drugs in the 1970s, Stolaroff conducted SEs with newly synthesized psychedelics 2C-B, 2C-E, 2C-T-2, 2C-T-7, 2C-T4, 2C-T-21, and MEM but also MDMA. Besides Shulgin, Stolaroff was the first who systematically explored the psychological states and their possible uses but under noncontrolled conditions (Stolaroff 1994). He understood his research as an attempt “to make the unconscious conscious” and to give some “guidelines for the proper and safe use of psychedelic drugs in therapy and for spiritual growth” (Stolaroff 1994, pp. 13–14).
8. ^ Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844
9. ^ Bennett, Drake (January 30, 2005). "Dr. Ecstasy". New York Times Magazine
10. ^ "Controlled Substances". Drug Enforcement Administration. February 2016. Archived from the original on April 17, 2016. Retrieved April 13, 2016.
11. ^ Ger A, Ger D. "Triple Goddess of the Night". British Neuroscience Association Bulletin. 63: 28–30.
12. ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function] (in German). Nachtschatten-Science. 1 ed. Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived October 20, 2025 at the Wayback Machine. Retrieved October 31, 2025.
13. ^ Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. Vol. 146. National Institute on Drug Abuse Research Monograph Series. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived 13 July 2025 at the Wayback Machine.
14. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived 13 July 2025 at the Wayback Machine.
15. ^ Shulgin, Alexander T. (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6.
16. ^ Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position". NIDA Res Monogr. ' (22): 27–37. PMID 101882. Archived August 5, 2023 at the Wayback Machine.
17. ^ Shulgin AT (1980). "Hallucinogens". Burger's Medicinal Chemistry. Vol. 3. 4 ed. New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627
18. ^ Shulgin AT (1982). "Chemistry of Psychotomimetics". Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Vol. 55, no. Part 3. Handbook of Experimental Pharmacology. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916
19. ^ "У Беларусі забаранілі навуковую кнігу па гісторыі БНР" (in be). Nasha Niva. 2025-12-29.

External links

• Erowid Online Books: PiHKAL: A Chemical Love Story by Alexander & Ann Shulgin
• PiHKAL • Info: A Visual Index and Map of PiHKAL: A Chemical Love Story by Alexander & Ann Shulgin
• "Shulgin in Spanish" Project – Information on the first complete translation of PiHKAL and TiHKAL into Spanish Archived October 6, 2014 at the Wayback Machine
• Transform Press – Publisher of PiHKAL
• PiHKAL - Wikipedia Massviews Analysis (Wikipedia Page Views of Individual PiHKAL Entries)