PIHKAL (Phenethylamines I Have Known And Loved) is a unique book written by renowned psychopharmacologist Alexander Shulgin and his wife Ann Shulgin. This book gives details of their research and investigations into the use of psychedelic drugs for the study of the human mind, and is also a love story.
phen-ethyl-amine \fen-'eth-al-a-,men\ n. [phenyl fr. F. phène, fr. Gk. phainein, to show (from its occurrence in illuminating gas)+ ethyl (+ yl) + amine fr. NL ammonia] 1: A naturally occurring compound found in both the animal and plant kingdoms. It is an endogenous component of the human brain. 2: Any of a series of compounds containing the phenethylamine skeleton, and modified by chemical constituents at appropriate positions in the molecule.
Introduction
Our human bodies and our human brains have evolved in such a way that we cannot see the full scope of what our universe and our reality actually looks like. Instead, we see what we need to survive on the earth and what we need to procreate. That’s it.
Unfortunately, it hampers our development. Not only scientifically, but spiritually as well.
There are techniques on how to “expand” or alter the way our mind interprets the sensory inputs to our brain. Most of which involve various kinds of drugs. These drugs come at a risk, for while they are able to alter the way that the sensory inputs are interpreted, they might give a distorted view of the universe. One that is just as distorted as we normally see in our day to day life.
Alexander Shulgin spent his life as a researcher / scientist for the CIA developing, designing and creating all sorts of drugs that alter the way that the brain interprets senses and works. These drugs were considered a dangerous asset by the United States government, and for the longest time banned the publication of the information.
Here is the free-to-distribute part of his book in conjunction with the Erowid Online Book website.
Disclaimer
I do not advocate the use of any types of drugs in any way other than for medical and therapeutic purposes. This information is provided for study purposes only.
COPYRIGHT NOTICE
The Copyright for Part 1 of PiHKAL has been reserved in all forms and it may not be distributed.
Part 2 of PiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.
CAUTIONARY NOTE: READ BEFORE PROCEEDING
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 herin, 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
ABOUT THIS HTML VERSION OF PiHKAL
This is the online version of the second half of the book “PiHKAL: A Chemical Love Story” by Alexander and Ann Shulgin.
It is presented with the express permission of the authors in order to spread the factual information as widely as possible and make it permanently available in the public domain.
It was originally transcribed into ASCII by Simson Garfinkle and was coverted into HTML by Lamont Granquist.
Any comments or corrections about the HTML version should be sent to Erowid. They can also forward serious and appropriate comments to the author if they are e-mailed.
Bolded entries indicate those substances that have been more popular or more available than others since 1991.
ORDERING INFORMATION
The first half of PiHKAL is an excellent commentary on the Shulgin’s personal experiences with phenethylamines. It is highly recommended and well worth purchasing the book.
Purchasing the book also gets you a far more complete cross-index into the chemicals described in the second half. If you are seriously interested in the chemistry contained in these files, you should order a copy.
The book may be ordered through Transform Press, for $22.95 ($18.95 + $4 p&h U.S., $8 p&h overseas). Box 13675, Berkeley, CA 94701. (510)934-4930 (voice), (510)934-5999 (fax). California residents please add $1.56 State sales tax.
Shulgin Rating Scale
PLUS / MINUS (+/-) The level of effectiveness of a drug that indicates a threshold action. If a higher dosage produces a greater response, then the plus/minus (+/-) was valid. If a higher dosage produces nothing, then this was a false positive.
PLUS ONE (+) The drug is quite certainly active. The chronology can be determined with some accuracy, but the nature of the drug’s effects are not yet apparent.
PLUS TWO (++) Both the chronology and the nature of the action of a drug are unmistakably apparent. But you still have some choice as to whether you will accept the adventure, or rather just continue with your ordinary day’s plans (if you are an experienced researcher, that is). The effects can be allowed a predominant role, or they may be repressed and made secondary to other chosen activities.
PLUS THREE (+++) Not only are the chronology and the nature of a drug’s action quite clear, but ignoring its action is no longer an option. The subject is totally engaged in the experience, for better or worse.
PLUS FOUR (++++) A rare and precious transcendental state, which has been called a ‘peak experience’, a ‘religious experience,’ ‘divine transformation,’ a ‘state of Samadhi’ and many other names in other cultures. It is not connected to the +1, +2, and +3 of the measuring of a drug’s intensity. It is a state of bliss, a participation mystique, a connectedness with both the interior and exterior universes, which has come about after the ingestion of a psychedelic drug, but which is not necessarily repeatable with a subsequent ingestion of that same drug. If a drug (or technique or process) were ever to be discovered which would consistently produce a plus four experience in all human beings, it is conceivable that it would signal the ultimate evolution, and perhaps the end of, the human experiment.
INDEX TO THE PHENETHYLAMINES
| # | SUBSTANCE | CHEMICAL NAME |
| 1 | AEM | alpha-Ethyl-3,4,5-trimethoxy-PEA |
| 2 | AL | 4-Allyloxy-3,5-dimethoxy-PEA |
| 3 | ALEPH | 4-Methylthio-2,5-dimethoxy-A |
| 4 | ALEPH-2 | 4-Ethylthio-2,5-dimethoxy-A |
| 5 | ALEPH-4 | 4-Isopropylthio-2,5-dimethoxy-A |
| 6 | ALEPH-6 | 4-Phenylthio-2,5-dimethoxy-A |
| 7 | ALEPH-7 | 4-Propylthio-2,5-dimethoxy-A |
| 8 | ARIADNE | 2,5-Dimethoxy-alpha-ethyl-4-methyl-PEA |
| 9 | ASB | 3,4-Diethoxy-5-methoxy-PEA |
| 10 | B | 4-Butoxy-3,5-dimethoxy-PEA |
| 11 | BEATRICE | 2,5-Dimethoxy-4,N-dimethyl-A |
| 12 | BIS-TOM | 2,5-Bismethylthio-4-methyl-A |
| 13 | BOB | 4-Bromo-2,5,beta-trimethoxy-PEA |
| 14 | BOD | 2,5,beta-Trimethoxy-4-methyl-PEA |
| 15 | BOH | beta-Methoxy-3,4-methylenedioxy-PEA |
| 16 | BOHD | 2,5-Dimethoxy-beta-hydroxy-4-methyl-PEA |
| 17 | BOM | 3,4,5,beta-Tetramethoxy-PEA |
| 18 | 4-Br-3,5-DMA | 4-Bromo-3,5-dimethoxy-A |
| 19 | 2-Br-4,5-MDA | 2-Bromo-4,5-methylenedioxy-A |
| 20 | 2C-B | 4-Bromo-2,5-dimethoxy-PEA |
| 21 | 3C-BZ | 4-Benzyloxy-3,5-dimethoxy-A |
| 22 | 2C-C | 4-Chloro-2,5-dimethoxy-PEA |
| 23 | 2C-D | 4-Methyl-2,5-dimethoxy-PEA |
| 24 | 2C-E | 4-Ethyl-2,5-dimethoxy-PEA |
| 25 | 3C-E | 4-Ethoxy-3,5-dimethoxy-A |
| 26 | 2C-F | 4-Fluoro-2,5-dimethoxy-PEA |
| 27 | 2C-G | 3,4-Dimethyl-2,5-dimethoxy-PEA |
| 28 | 2C-G-3 | 3,4-Trimethylene-2,5-dimethoxy-PEA |
| 29 | 2C-G-4 | 3,4-Tetramethylene-2,5-dimethoxy-PEA |
| 30 | 2C-G-5 | 3,4-Norbornyl-2,5-dimethoxy-PEA |
| 31 | 2C-G-N | 1,4-Dimethoxynaphthyl-2-ethylamine |
| 32 | 2C-H | 2,5-Dimethoxy-PEA |
| 33 | 2C-I | 4-Iodo-2,5-dimethoxy-PEA |
| 34 | 2C-N | 4-Nitro-2,5-dimethoxy-PEA |
| 35 | 2C-O-4 | 4-Isopropoxy-2,5-dimethoxy-PEA |
| 36 | 2C-P | 4-Propyl-2,5-dimethoxy-PEA |
| 37 | CPM | 4-Cyclopropylmethoxy-3,5-dimethoxy-PEA |
| 38 | 2C-SE | 4-Methylseleno-2,5-dimethoxy-PEA |
| 39 | 2C-T | 4-Methylthio-2,5-dimethoxy-PEA |
| 40 | 2C-T-2 | 4-Ethylthio-2,5-dimethoxy-PEA |
| 41 | 2C-T-4 | 4-Isopropylthio-2,5-dimethoxy-PEA |
| 42 | psi-2C-T-4 | 4-Isopropylthio-2,6-dimethoxy-PEA |
| 43 | 2C-T-7 | 4-Propylthio-2,5-dimethoxy-PEA |
| 44 | 2C-T-8 | 4-Cyclopropylmethylthio-2,5-dimethoxy-PEA |
| 45 | 2C-T-9 | 4-(t)-Butylthio-2,5-dimethoxy-PEA |
| 46 | 2C-T-13 | 4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA |
| 47 | 2C-T-15 | 4-Cyclopropylthio-2,5-dimethoxy-PEA |
| 48 | 2C-T-17 | 4-(s)-Butylthio-2,5-dimethoxy-PEA |
| 49 | 2C-T-21 | 4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA |
| 50 | 4-D | 4-Trideuteromethyl-3,5-dimethoxy-PEA |
| 51 | beta-D | beta,beta-Dideutero-3,4,5-trimethoxy-PEA |
| 52 | DESOXY | 4-Methyl-3,5-Dimethoxy-PEA |
| 53 | 2,4-DMA | 2,4-Dimethoxy-A |
| 54 | 2,5-DMA | 2,5-Dimethoxy-A |
| 55 | 3,4-DMA | 3,4-Dimethoxy-A |
| 56 | DMCPA | 2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine |
| 57 | DME | 3,4-Dimethoxy-beta-hydroxy-PEA |
| 58 | DMMDA | 2,5-Dimethoxy-3,4-methylenedioxy-A |
| 59 | DMMDA-2 | 2,3-Dimethoxy-4,5-methylenedioxy-A |
| 60 | DMPEA | 3,4-Dimethoxy-PEA |
| 61 | DOAM | 4-Amyl-2,5-dimethoxy-A |
| 62 | DOB | 4-Bromo-2,5-dimethoxy-A |
| 63 | DOBU | 4-Butyl-2,5-dimethoxy-A |
| 64 | DOC | 4-Chloro-2,5-dimethoxy-A |
| 65 | DOEF | 4-(2-Fluoroethyl)-2,5-dimethoxy-A |
| 66 | DOET | 4-Ethyl-2,5-dimethoxy-A |
| 67 | DOI | 4-Iodo-2,5-dimethoxy-A |
| 68 | DOM (STP) | 4-Methyl-2,5-dimethoxy-A |
| 69 | psi-DOM | 4-Methyl-2,6-dimethoxy-A |
| 70 | DON | 4-Nitro-2,5-dimethoxy-A |
| 71 | DOPR | 4-Propyl-2,5-dimethoxy-A |
| 72 | E | 4-Ethoxy-3,5-dimethoxy-PEA |
| 73 | EEE | 2,4,5-Triethoxy-A |
| 74 | EEM | 2,4-Diethoxy-5-methoxy-A |
| 75 | EME | 2,5-Diethoxy-4-methoxy-A |
| 76 | EMM | 2-Ethoxy-4,5-dimethoxy-A |
| 77 | ETHYL-J | N,alpha-diethyl-3,4-methylenedioxy-PEA |
| 78 | ETHYL-K | N-Ethyl-alpha-propyl-3,4-methylenedioxy-PEA |
| 79 | F-2 | Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane) |
| 80 | F-22 | Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane) |
| 81 | FLEA | N-Hydroxy-N-methyl-3,4-methylenedioxy-A |
| 82 | G-3 | 3,4-Trimethylene-2,5-dimethoxy-A |
| 83 | G-4 | 3,4-Tetramethylene-2,5-dimethoxy-A |
| 84 | G-5 | 3,4-Norbornyl-2,5-dimethoxy-A |
| 85 | GANESHA | 3,4-Dimethyl-2,5-dimethoxy-A |
| 86 | G-N | 1,4-Dimethoxynaphthyl-2-isopropylamine |
| 87 | HOT-2 | 2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA |
| 88 | HOT-7 | 2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA |
| 89 | HOT-17 | 2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA |
| 90 | IDNNA | 2,5-Dimethoxy-N,N-dimethyl-4-iodo-A |
| 91 | IM | 2,3,4-Trimethoxy-PEA |
| 92 | IP | 3,5-Dimethoxy-4-isopropoxy-PEA |
| 93 | IRIS | 5-Ethoxy-2-methoxy-4-methyl-A |
| 94 | J | alpha-Ethyl-3,4-methylenedioxy-PEA |
| 95 | LOPHOPHINE | 3-Methoxy-4,5-methylenedioxy-PEA |
| 96 | M | 3,4,5-Trimethoxy-PEA |
| 97 | 4-MA | 4-Methoxy-A |
| 98 | MADAM-6 | 2,N-Dimethyl-4,5-methylenedioxy-A |
| 99 | MAL | 3,5-Dimethoxy-4-methallyloxy-PEA |
| 100 | MDA | 3,4-Methylenedioxy-A |
| 101 | MDAL | N-Allyl-3,4-methylenedioxy-A |
| 102 | MDBU | N-Butyl-3,4-methylenedioxy-A |
| 103 | MDBZ | N-Benzyl-3,4-methylenedioxy-A |
| 104 | MDCPM | N-Cyclopropylmethyl-3,4-methylenedioxy-A |
| 105 | MDDM | N,N-Dimethyl-3,4-methylenedioxy-A |
| 106 | MDE | N-Ethyl-3,4-methylenedioxy-A |
| 107 | MDHOET | N-(2-Hydroxyethyl)-3,4-methylenedioxy-A |
| 108 | MDIP | N-Isopropyl-3,4-methylenedioxy-A |
| 109 | MDMA | N-Methyl-3,4-methylenedioxy-A |
| 110 | MDMC | N-Methyl-3,4-ethylenedioxy-A |
| 111 | MDMEO | N-Methoxy-3,4-methylenedioxy-A |
| 112 | MDMEOET | N-(2-Methoxyethyl)-3,4-methylenedioxy-A |
| 113 | MDMP | alpha,alpha,N-Trimethyl-3,4-methylenedioxy-PEA |
| 114 | MDOH | N-Hydroxy-3,4-methylenedioxy-A |
| 115 | MDPEA | 3,4-Methylenedioxy-PEA |
| 116 | MDPH | alpha,alpha-Dimethyl-3,4-methylenedioxy-PEA |
| 117 | MDPL | N-Propargyl-3,4-methylenedioxy-A |
| 118 | MDPR | N-Propyl-3,4-methylenedioxy-A |
| 119 | ME | 3,4-Dimethoxy-5-ethoxy-PEA |
| 120 | MEDA | 3-methoxy-4,5-Ethylenedioxy-A [Erowid corrected] |
| 121 | MEE | 2-Methoxy-4,5-diethoxy-A |
| 122 | MEM | 2,5-Dimethoxy-4-ethoxy-A |
| 123 | MEPEA | 3-Methoxy-4-ethoxy-PEA |
| 124 | META-DOB | 5-Bromo-2,4-dimethoxy-A |
| 125 | META-DOT | 5-Methylthio-2,4-dimethoxy-A |
| 126 | METHYL-DMA | N-Methyl-2,5-dimethoxy-A |
| 127 | METHYL-DOB | 4-Bromo-2,5-dimethoxy-N-methyl-A |
| 128 | METHYL-J | N-Methyl-alpha-ethyl-3,4-methylenedioxy-PEA |
| 129 | METHYL-K | N-Methyl-alpha-propyl-3,4-methylenedioxy-PEA |
| 130 | METHYL-MA | N-Methyl-4-methoxy-A |
| 131 | METHYL-MMDA-2 | N-Methyl-2-methoxy-4,5-methylenedioxy-A |
| 132 | MMDA | 3-Methoxy-4,5-methylenedioxy-A |
| 133 | MMDA-2 | 2-Methoxy-4,5-methylenedioxy-A |
| 134 | MMDA-3a | 2-Methoxy-3,4-methylenedioxy-A |
| 135 | MMDA-3b | 4-Methoxy-2,3-methylenedioxy-A |
| 136 | MME | 2,4-Dimethoxy-5-ethoxy-A |
| 137 | MP | 3,4-Dimethoxy-5-propoxy-PEA |
| 138 | MPM | 2,5-Dimethoxy-4-propoxy-A |
| 139 | ORTHO-DOT | 2-Methylthio-4,5-dimethoxy-A |
| 140 | P | 3,5-Dimethoxy-4-propoxy-PEA |
| 141 | PE | 3,5-Dimethoxy-4-phenethyloxy-PEA |
| 142 | PEA | PEA |
| 143 | PROPYNYL | 4-Propynyloxy-3,5-dimethoxy-PEA |
| 144 | SB | 3,5-Diethoxy-4-methoxy-PEA |
| 145 | TA | 2,3,4,5-Tetramethoxy-A |
| 146 | 3-TASB | 4-Ethoxy-3-ethylthio-5-methoxy-PEA |
| 147 | 4-TASB | 3-Ethoxy-4-ethylthio-5-methoxy-PEA |
| 148 | 5-TASB | 3,4-Diethoxy-5-methylthio-PEA |
| 149 | TB | 4-Thiobutoxy-3,5-dimethoxy-PEA |
| 150 | 3-TE | 4-Ethoxy-5-methoxy-3-methylthio-PEA |
| 151 | 4-TE | 3,5-Dimethoxy-4-ethylthio-PEA |
| 152 | 2-TIM | 2-Methylthio-3,4-dimethoxy-PEA |
| 153 | 3-TIM | 3-Methylthio-2,4-dimethoxy-PEA |
| 154 | 4-TIM | 4-Methylthio-2,3-dimethoxy-PEA |
| 155 | 3-TM | 3-Methylthio-4,5-dimethoxy-PEA |
| 156 | 4-TM | 4-Methylthio-3,5-dimethoxy-PEA |
| 157 | TMA | 3,4,5-Trimethoxy-A |
| 158 | TMA-2 | 2,4,5-Trimethoxy-A |
| 159 | TMA-3 | 2,3,4-Trimethoxy-A |
| 160 | TMA-4 | 2,3,5-Trimethoxy-A |
| 161 | TMA-5 | 2,3,6-Trimethoxy-A |
| 162 | TMA-6 | 2,4,6-Trimethoxy-A |
| 163 | 3-TME | 4,5-Dimethoxy-3-ethylthio-PEA |
| 164 | 4-TME | 3-Ethoxy-5-methoxy-4-methylthio-PEA |
| 165 | 5-TME | 3-Ethoxy-4-methoxy-5-methylthio-PEA |
| 166 | 2T-MMDA-3a | 2-Methylthio-3,4-methylenedioxy-A |
| 167 | 4T-MMDA-2 | 4,5-Thiomethyleneoxy-2-methoxy-A |
| 168 | TMPEA | 2,4,5-Trimethoxy-PEA |
| 169 | 2-TOET | 4-Ethyl-5-methoxy-2-methylthio-A |
| 170 | 5-TOET | 4-Ethyl-2-methoxy-5-methylthio-A |
| 171 | 2-TOM | 5-Methoxy-4-methyl-2-methylthio-A |
| 172 | 5-TOM | 2-Methoxy-4-methyl-5-methylthio-A |
| 173 | TOMSO | 2-Methoxy-4-methyl-5-methylsulfinyl-A |
| 174 | TP | 4-Propylthio-3,5-dimethoxy-PEA |
| 175 | TRIS | 3,4,5-Triethoxy-PEA |
| 176 | 3-TSB | 3-Ethoxy-5-ethylthio-4-methoxy-PEA |
| 177 | 4-TSB | 3,5-Diethoxy-4-methylthio-PEA |
| 178 | 3-T-TRIS | 4,5-Diethoxy-3-ethylthio-PEA |
| 179 | 4-T-TRIS | 3,5-Diethoxy-4-ethylthio-PEA |
| Appendix B: Glossary |
Other PiHKAL related links and files
- Shulgin Rating Scale
- PiHKAL Chemical Legal Status
- Quick Index to 17 of the more important chemicals, by Lamont Granquist
- A Chemical Glossary, by Lamont Granquist
- Printable version (1 page – 1.4 meg ASCII file)
- Printable version (1 page – .5 meg zip of a 1.7 meg MSWord file)
- An ‘Interview’ with Shulgin, by Clifton
- A Bibliography of Shulgin’s work
- Review of PiHKAL, by Tyrone Slothrop Includes notes on PiHKAL and
his list of the 300+ chemicals in Book II — hella impressive (postscript version)
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