PiHKAL

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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.<ref name="Johnson2018">Template:Cite book</ref><ref name="WalkerPullellaPiggott2023">Template:Cite journal</ref><ref name="PiHKAL1991">Template:Cite book</ref> The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or entactogens.<ref name="WalkerPullellaPiggott2023" /><ref name="PiHKAL1991" /> The book has two halves, with the second part containing detailed entries on 179Template:Nbspphenethylamines.<ref name="WalkerPullellaPiggott2023" /><ref name="PiHKAL1991" /> PiHKAL was followed by TiHKAL: The Continuation (Tryptamines I Have Known and Loved) (1997).<ref name="Sessa2015">Template:Cite book</ref><ref name="TiHKAL1997">Template:Cite book</ref>

Content

The book is arranged into two parts, the first part being a fictionalized autobiography of the couple and the second part describing 179Template:Nbspdifferent psychedelic compounds (most of which Shulgin discovered himself), including detailed synthesis instructions, bioassays, doses, durations, and other commentary.<ref name="WalkerPullellaPiggott2023" /><ref name="PiHKAL1991" />

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.<ref name="PiHKAL1991" /> 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.<ref name="PiHKAL1991" />

Members of Shulgin's research who contributed to the experience reports included Shulgin himself, Ann Shulgin, Myron Stolaroff, and Jean Stolaroff, among others.<ref name="BLTC2021">Template:Cite AV media</ref><ref name="PassieBrandt2018">Template:Cite journal</ref>

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.<ref name="DeanStellpflungBurnett2013">Template:Cite journal</ref>

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.<ref name="Dr. Ecstasy">Template:Cite news</ref>

Notable compounds

Some compounds in PiHKAL, like mescaline, DOM, 2C-B, MDA, and MDMA, are widely known and/or used psychedelics and/or entactogens.<ref name="PiHKAL1991" />

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).<ref name="PiHKAL1991" /> The list consists of:<ref name="PiHKAL1991" />

  • PMA (para-methoxy-amphetamine)
  • 2,4-DMA (2,4-dimethoxy-amphetamine)
  • 3,4-DMA (3,4-dimethoxy-amphetamine)
  • MDA (3,4-methylenedioxy-amphetamine)
  • MMDA (3-methoxy-4,5-methylendioxy-amphetamine)
  • 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.<ref name="PiHKAL1991" />

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.<ref name="PiHKAL1991" /> They are found within the first book of PiHKAL, and are as follows:<ref name="PiHKAL1991" />

  • 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 desoxy 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.<ref>Template:Cite web</ref>

Ten classic ladies

Shulgin systematically replaced the 10Template:Nbspunique hydrogen atoms in DOM with methyl groups in order to explore its activity and named these compounds the 10 classic ladies.<ref name="GerGer2011">Template:Cite journal</ref><ref name="PiHKAL1991" /> The resulting compounds were as follows:<ref name="GerGer2011" /><ref name="PiHKAL1991" />

As with the essential amphetamines, not all of these compounds have been bioassayed.<ref name="PiHKAL1991" />

Some additional "ladies" have also since been named, including Julia (DOTMA; 3,6-dimethyl-DOM), Jelena (2C-IP), and Selene (2C-P).<ref name="GerGer2011" /><ref name="TrachselLehmannEnzensperger2013">Template:Cite book</ref>

Phenethylamines listed

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See also

References

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