PiHKAL
Encyclopedia
PiHKAL: A Chemical Love Story is a book
by Dr. Alexander Shulgin
and Ann Shulgin
which was published in 1991. The subject of the work is psychoactive
phenethylamine
chemical derivative
s, notably those that act as psychedelic
s and/or empathogen-entactogen
s. The main title is an acronym that stands for 'Phenethylamines I Have Known and Loved'.
The book is arranged into two parts:
Shulgin's choices of synthesis procedures in the second half of the book are themselves perhaps a small act of subversion: while the reactions 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-aluminum 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
.
), 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 drug
s 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 the United Kingdom
, all but MDOH and Phenethylamine
are illegal.
(US) Drug Enforcement Administration
(DEA) raided Shulgin's chemical lab. They requested that Shulgin turn over his DEA license (which allowed him to work with and possess otherwise illicit substances), claiming to have found problems with his record keeping, and he was fined US$25,000 for the possession of anonymous samples which had been sent to him for quality testing. Shulgin passed commentary of some of these events at the beginning of his second big book, TiHKAL.
Prior to the publication of PiHKAL, during the 15 years in which Shulgin held his license, there were two unannounced reviews of the lab; both failed to find any irregularities. Richard Meyer, spokesman for DEA's San Francisco Field Division, has stated that "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 to many that the publication of PiHKAL and the termination of Shulgin's license were related.
The "Essential Amphetamines" are what Shulgin describes as ten amphetamines that differ from natural products such as safrole
or myristicin
by only a molecule of ammonia.(PiHKAL Entry #157 TMA). The list consists of:
Not all of these chemicals are bioassayed in PiHKAL, some are merely mentioned.
Book
A book is a set or collection of written, printed, illustrated, or blank sheets, made of hot lava, paper, parchment, or other materials, usually fastened together to hinge at one side. A single sheet within a book is called a leaf or leaflet, and each side of a leaf is called a page...
by Dr. Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
and Ann Shulgin
Ann Shulgin
Ann Shulgin is an American author and the wife of chemist Alexander Shulgin.Ann Shulgin grew up in the village Opicina outside the Italian city Trieste where her father was American Consul for six years before World War II. She has worked as a lay therapist with psychedelic substances such as MDMA...
which was published in 1991. The subject of the work is psychoactive
Psychoactive drug
A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...
phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
chemical derivative
Derivative (chemistry)
In chemistry, a derivative is a compound that is derived from a similar compound by some chemical or physical process. In the past it was also used to mean a compound that can be imagined to arise from another compound, if one atom is replaced with another atom or group of atoms, but modern...
s, notably those that act as psychedelic
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
s and/or empathogen-entactogen
Empathogen-entactogen
The terms empathogen and entactogen are used to describe a class of psychoactive drugs that produce distinctive emotional and social effects similar to those of MDMA. Putative members of this class include 2C-B, 2C-I, MDMA, MDA, MDEA, MBDB, 2C-T-7, and 2C-T-2, among others...
s. The main title is an acronym that stands for 'Phenethylamines I Have Known and Loved'.
The book is arranged into two parts:
- A fictionalized autobiography of the couple.
- Detailed synthesis instructions for over 200 psychedelic compounds (most of which Shulgin discovered himself), including bioassays, dosages, and other commentary.
Shulgin's choices of synthesis procedures in the second half of the book are themselves perhaps a small act of subversion: while the reactions 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-aluminum amalgam (an unusual but easy to obtain reagent
Reagent
A reagent is a "substance or compound that is added to a system in order to bring about a chemical reaction, or added to see if a reaction occurs." Although the terms reactant and reagent are often used interchangeably, a reactant is less specifically a "substance that is consumed in the course of...
) as a reducing agent
Reducing agent
A reducing agent is the element or compound in a reduction-oxidation reaction that donates an electron to another species; however, since the reducer loses an electron we say it is "oxidized"...
and detailed suggestions on legal plant sources of important drug precursors such as safrole
Safrole
Safrole, also known as shikimol, is a phenylpropene. It is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil , or synthesized from other related methylenedioxy...
.
Impact & Popularity
Through PiHKAL (and later TiHKALTiHKAL
TiHKAL: The Continuation is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to PiHKAL: A Chemical Love Story, TiHKAL is an acronym that stands for Tryptamines I Have Known and Loved.-Content:TiHKAL, much like its...
), 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 drug
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
s can be valuable tools for self-exploration. The MDMA ("ecstasy") synthesis published in PiHKAL remains one of the most common clandestine
Clandestine chemistry
Clandestine chemistry is chemistry carried out in secret, and particularly in illegal drug laboratories. Larger labs are usually run by gangs or organized crime intending to produce for distribution on the black market...
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-B
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...
, 2C-T-2
2C-T-2
2C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin. The drug has structural and pharmacodynamic properties similar to the drug 2C-T-7 .-Dosage:In Alexander Shulgin's book...
, and 2C-T-7
2C-T-7
2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours...
. In the United Kingdom
United Kingdom
The United Kingdom of Great Britain and Northern IrelandIn the United Kingdom and Dependencies, other languages have been officially recognised as legitimate autochthonous languages under the European Charter for Regional or Minority Languages...
, all but MDOH and Phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
are illegal.
DEA Raid of Shulgin's Lab
In 1994, almost three years after the publication of PiHKAL, the United StatesUnited States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
(US) Drug Enforcement Administration
Drug Enforcement Administration
The Drug Enforcement Administration is a federal law enforcement agency under the United States Department of Justice, tasked with combating drug smuggling and use within the United States...
(DEA) raided Shulgin's chemical lab. They requested that Shulgin turn over his DEA license (which allowed him to work with and possess otherwise illicit substances), claiming to have found problems with his record keeping, and he was fined US$25,000 for the possession of anonymous samples which had been sent to him for quality testing. Shulgin passed commentary of some of these events at the beginning of his second big book, TiHKAL.
Prior to the publication of PiHKAL, during the 15 years in which Shulgin held his license, there were two unannounced reviews of the lab; both failed to find any irregularities. Richard Meyer, spokesman for DEA's San Francisco Field Division, has stated that "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 to many that the publication of PiHKAL and the termination of Shulgin's license were related.
Essential Amphetamines
The "Essential Amphetamines" are what Shulgin describes as ten amphetamines that differ from natural products such as safrole
Safrole
Safrole, also known as shikimol, is a phenylpropene. It is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil , or synthesized from other related methylenedioxy...
or myristicin
Myristicin
Myristicin is a phenylpropene, a natural organic compound present in small amounts in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill.It is insoluble in water, but soluble in ethanol and acetone.-Uses:...
by only a molecule of ammonia.(PiHKAL Entry #157 TMA). The list consists of:
- PMA (para-methoxy-amphetamine)
- 2,4-DMA (2,4-dimethoxy-amphetamine)
- 3,4-DMA (3,4-dimethoxy-amphetamine)
- MDA3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...
(3,4-methylenedioxy-amphetamine) - MMDA3-Methoxy-4,5-methylendioxyamphetamine3-Methoxy-4,5-methylenedioxyamphetamine is a psychedelic and entactogen drug of the amphetamine class. It is an analogue of lophophine, MDA, and MDMA, and also bears resemblance to the essential oil myristicin found in nutmeg....
(3-methoxy-4,5-methylendioxy-amphetamine) - MMDA-3a (2-methoxy-3,4-methylendioxyamphetamine)
- MMDA-2MMDA-22-Methoxy-4,5-methylenedioxyamphetamine is a psychedelic drug of the amphetamine class. It is closely related to MMDA and MDA....
(2-methoxy-4,5-methylendioxyamphetamine) - TMATrimethoxyamphetamineTMAs, also known as trimethoxyamphetamines, are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs of the phenethylamine cactus alkaloid...
(3,4,5-trimethoxyamphetamine) - TMA-2TrimethoxyamphetamineTMAs, also known as trimethoxyamphetamines, are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs of the phenethylamine cactus alkaloid...
(2,4,5-trimethoxyamphetamine) - DMMDADMMDA2,5-Dimethoxy-3,4-methylenedioxyamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin and was described in his book PiHKAL. Shulgin listed the dosage as 30-75 mg and the duration as 6-8 hours...
(2,5-dimethoxy-3,4-methylenedioxyamphetamine) - DMMDA-2DMMDA-2DMMDA-2 is a psychedelic phenethylamine discussed by Alexander Shulgin in his book PiHKAL , however he was not the first to synthesize it.-Further reading:...
(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 were developed and synthesized by himself. They are found within the first book of PiHKAL, and are as follows:- MescalineMescalineMescaline or 3,4,5-trimethoxyphenethylamine is a naturally occurring psychedelic alkaloid of the phenethylamine class used mainly as an entheogen....
(3,4,5-trimethoxyphenethylamine) - DOM2,5-Dimethoxy-4-methylamphetamine2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine...
(2,5-dimethoxy-4-methylamphetamine) - 2C-B2C-B2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...
(2,5-dimethoxy-4-bromophenethylamine) - 2C-E2C-E2C-E is a psychedelic and phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. 2C-E is typically found as a white crystalline powder....
(2,5-dimethoxy-4-ethylphenethylamine) - 2C-T-22C-T-22C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin. The drug has structural and pharmacodynamic properties similar to the drug 2C-T-7 .-Dosage:In Alexander Shulgin's book...
(2,5-dimethoxy-4-ethylthiophenethylamine) - 2C-T-72C-T-72C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours...
(2,5-dimethoxy-4-(N)-propylthiophenethylamine)
See also
- Substituted PhenethylamineSubstituted phenethylamineThe substituted phenethylamines are chemical compounds with the 2-phenethylamine chemical structure modified at the phenyl ring, sidechain, and/or amino group. Some of them are psychoactive drugs, including stimulants, psychedelics, opioids, and entactogens, which exert their effects primarily...
(PEA) - Substituted AmphetamineSubstituted amphetamineSubstituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...
(AMPH) - Substituted Methylenedioxyphenethylamine (MDxx)
- OlivetolOlivetolOlivetol, also known as 5-pentylresorcinol or 5-pentyl-1,3-benzenediol, is an organic compound found in certain species of lichen; it is also a precursor in various syntheses of tetrahydrocannabinol.- Occurrence :...