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PiHKAL

1991 book by Alexander Shulgin and Ann Shulgin

1991 book by Alexander Shulgin and Ann Shulgin

FieldValue
namePiHKAL: A Chemical Love Story
imagePihkal.jpg
image_size200px
captionCover of *PiHKAL*, 1st ed.
authorAlexander and Ann Shulgin
countryUnited States
subjectPharmacology, Autobiography, Psychoactive drugs
publisherTransform Press
release_date1991
media_typePaperback
isbn0-9630096-0-5
oclc269100404
followed_byTiHKAL (1997)

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 (PiHKAL Entry #157 TMA). 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

#SubstanceChemical nameGroupDoseaDurationLink
1AEM (α-ethylmescaline)α-Ethyl-3,4,5-trimethoxy-PEA[4C-scaline](4c-scaline)220 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal001.shtml](https://erowid.org/library/books_online/pihkal/pihkal001.shtml)
2AL (allylescaline)4-Allyloxy-3,5-dimethoxy-PEAScaline20–35 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal002.shtml](https://erowid.org/library/books_online/pihkal/pihkal002.shtml)
3ALEPH (DOT, para-DOT)4-Methylthio-2,5-dimethoxy-ADOx5–10 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal003.shtml](https://erowid.org/library/books_online/pihkal/pihkal003.shtml)
4ALEPH-24-Ethylthio-2,5-dimethoxy-ADOx4–8 mg8–16 hours[https://erowid.org/library/books_online/pihkal/pihkal004.shtml](https://erowid.org/library/books_online/pihkal/pihkal004.shtml)
5ALEPH-44-Isopropylthio-2,5-dimethoxy-ADOx7–12 mg12–20 hours[https://erowid.org/library/books_online/pihkal/pihkal005.shtml](https://erowid.org/library/books_online/pihkal/pihkal005.shtml)
6ALEPH-64-Phenylthio-2,5-dimethoxy-ADOx40 mg"Probably long"[https://erowid.org/library/books_online/pihkal/pihkal006.shtml](https://erowid.org/library/books_online/pihkal/pihkal006.shtml)
7ALEPH-74-Propylthio-2,5-dimethoxy-ADOx4–7 mg15–30 hours[https://erowid.org/library/books_online/pihkal/pihkal007.shtml](https://erowid.org/library/books_online/pihkal/pihkal007.shtml)
8ARIADNE (4C-D; Dimoxamine)2,5-Dimethoxy-α-ethyl-4-methyl-PEA[4C](4c-psychedelics)UnknownbShort[https://erowid.org/library/books_online/pihkal/pihkal008.shtml](https://erowid.org/library/books_online/pihkal/pihkal008.shtml)
9ASB (asymbescaline)3,4-Diethoxy-5-methoxy-PEAScaline (mod.)200–280 mg10–15 hours[https://erowid.org/library/books_online/pihkal/pihkal009.shtml](https://erowid.org/library/books_online/pihkal/pihkal009.shtml)
10B (buscaline)4-Butoxy-3,5-dimethoxy-PEAScaline150 mg"Several hours"[https://erowid.org/library/books_online/pihkal/pihkal010.shtml](https://erowid.org/library/books_online/pihkal/pihkal010.shtml)
11BEATRICE (*N*-methyl-DOM)2,5-Dimethoxy-4,*N*-dimethyl-ADOx30 mg6–10 hours[https://erowid.org/library/books_online/pihkal/pihkal011.shtml](https://erowid.org/library/books_online/pihkal/pihkal011.shtml)
12Bis-TOM (2,5-dithio-DOM)2,5-Bismethylthio-4-methyl-ADOx (mod.)160 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal012.shtml](https://erowid.org/library/books_online/pihkal/pihkal012.shtml)
13BOB (β-methoxy-2C-B)4-Bromo-2,5,β-trimethoxy-PEABOx, 2C10–20 mg10–20 hours[https://erowid.org/library/books_online/pihkal/pihkal013.shtml](https://erowid.org/library/books_online/pihkal/pihkal013.shtml)
14BOD (β-methoxy-2C-D)2,5,β-Trimethoxy-4-methyl-PEABOx, 2C15–25 mg8–16 hours[https://erowid.org/library/books_online/pihkal/pihkal014.shtml](https://erowid.org/library/books_online/pihkal/pihkal014.shtml)
15BOH (β-methoxy-MDPEA)β-Methoxy-3,4-methylenedioxy-PEABOx, MDxx80–120 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal015.shtml](https://erowid.org/library/books_online/pihkal/pihkal015.shtml)
16BOHD (β-hydroxy-2C-D)2,5-Dimethoxy-β-hydroxy-4-methyl-PEABOx, 2C50 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal016.shtml](https://erowid.org/library/books_online/pihkal/pihkal016.shtml)
17BOM (β-methoxymescaline)3,4,5,β-Tetramethoxy-PEABOx, scaline200 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal017.shtml](https://erowid.org/library/books_online/pihkal/pihkal017.shtml)
18[4-Br-3,5-DMA](4-bromo-3-5-dimethoxyamphetamine)4-Bromo-3,5-dimethoxy-A[3C-scaline](3c-scaline)4–10 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal018.shtml](https://erowid.org/library/books_online/pihkal/pihkal018.shtml)
19[2-Br-4,5-MDA](2-bromo-4-5-methylenedioxyamphetamine)2-Bromo-4,5-methylenedioxy-AMDxx350 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal019.shtml](https://erowid.org/library/books_online/pihkal/pihkal019.shtml)
20[2C-B](2c-b)4-Bromo-2,5-dimethoxy-PEA[2C](2c-psychedelics)12–24 mg4–8 hours[https://erowid.org/library/books_online/pihkal/pihkal020.shtml](https://erowid.org/library/books_online/pihkal/pihkal020.shtml)
21[3C-BZ](3c-bz) (3C-benzscaline)4-Benzyloxy-3,5-dimethoxy-A3C-scaline25–200 mg18–24 hours[https://erowid.org/library/books_online/pihkal/pihkal021.shtml](https://erowid.org/library/books_online/pihkal/pihkal021.shtml)
22[2C-C](2c-c)4-Chloro-2,5-dimethoxy-PEA2C20–40 mg4–8 hours[https://erowid.org/library/books_online/pihkal/pihkal022.shtml](https://erowid.org/library/books_online/pihkal/pihkal022.shtml)
23[2C-D](2c-d)4-Methyl-2,5-dimethoxy-PEA2C20–60 mg4–6 hours[https://erowid.org/library/books_online/pihkal/pihkal023.shtml](https://erowid.org/library/books_online/pihkal/pihkal023.shtml)
24[2C-E](2c-e)4-Ethyl-2,5-dimethoxy-PEA2C10–25 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal024.shtml](https://erowid.org/library/books_online/pihkal/pihkal024.shtml)
25[3C-E](3c-e) (3C-escaline)4-Ethoxy-3,5-dimethoxy-A3C-scaline30–60 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal025.shtml](https://erowid.org/library/books_online/pihkal/pihkal025.shtml)
26[2C-F](2c-f)4-Fluoro-2,5-dimethoxy-PEA2C250 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal026.shtml](https://erowid.org/library/books_online/pihkal/pihkal026.shtml)
27[2C-G](2c-g)3,4-Dimethyl-2,5-dimethoxy-PEA2C20–35 mg18–30 hours[https://erowid.org/library/books_online/pihkal/pihkal027.shtml](https://erowid.org/library/books_online/pihkal/pihkal027.shtml)
28[2C-G-3](2c-g-3)3,4-Trimethylene-2,5-dimethoxy-PEA2C (mod.)16–25 mg12–24 hours[https://erowid.org/library/books_online/pihkal/pihkal028.shtml](https://erowid.org/library/books_online/pihkal/pihkal028.shtml)
29[2C-G-4](2c-g-4)3,4-Tetramethylene-2,5-dimethoxy-PEA2C (mod.)UnknownUnknown[https://erowid.org/library/books_online/pihkal/pihkal029.shtml](https://erowid.org/library/books_online/pihkal/pihkal029.shtml)
30[2C-G-5](2c-g-5)3,4-Norbornyl-2,5-dimethoxy-PEA2C (mod.)10–16 mg32–48 hours[https://erowid.org/library/books_online/pihkal/pihkal030.shtml](https://erowid.org/library/books_online/pihkal/pihkal030.shtml)
31[2C-G-N](2c-g-n)1,4-Dimethoxynaphthyl-2-ethylamine2C (mod.)20–40 mg20–30 hours[https://erowid.org/library/books_online/pihkal/pihkal031.shtml](https://erowid.org/library/books_online/pihkal/pihkal031.shtml)
32[2C-H](2c-h) (2,5-DMPEA)2,5-Dimethoxy-PEA2CUnknownUnknown[https://erowid.org/library/books_online/pihkal/pihkal032.shtml](https://erowid.org/library/books_online/pihkal/pihkal032.shtml)
33[2C-I](2c-i)4-Iodo-2,5-dimethoxy-PEA2C14–22 mg6–10 hours[https://erowid.org/library/books_online/pihkal/pihkal033.shtml](https://erowid.org/library/books_online/pihkal/pihkal033.shtml)
34[2C-N](2c-n)4-Nitro-2,5-dimethoxy-PEA2C100–150 mg4–6 hours[https://erowid.org/library/books_online/pihkal/pihkal034.shtml](https://erowid.org/library/books_online/pihkal/pihkal034.shtml)
35[2C-O-4](2c-o-4)4-Isopropoxy-2,5-dimethoxy-PEA2C60 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal035.shtml](https://erowid.org/library/books_online/pihkal/pihkal035.shtml)
36[2C-P](2c-p)4-Propyl-2,5-dimethoxy-PEA2C6–10 mg10–16 hours[https://erowid.org/library/books_online/pihkal/pihkal036.shtml](https://erowid.org/library/books_online/pihkal/pihkal036.shtml)
37CPM (cyclopropylmescaline)4-Cyclopropylmethoxy-3,5-dimethoxy-PEAScaline60–80 mg12–18 hours[https://erowid.org/library/books_online/pihkal/pihkal037.shtml](https://erowid.org/library/books_online/pihkal/pihkal037.shtml)
38[2C-Se](2c-se)4-Methylseleno-2,5-dimethoxy-PEA2C~100 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal038.shtml](https://erowid.org/library/books_online/pihkal/pihkal038.shtml)
39[2C-T](2c-t)4-Methylthio-2,5-dimethoxy-PEA2C60–100 mg3–5 hours[https://erowid.org/library/books_online/pihkal/pihkal039.shtml](https://erowid.org/library/books_online/pihkal/pihkal039.shtml)
40[2C-T-2](2c-t-2)4-Ethylthio-2,5-dimethoxy-PEA2C12–25 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal040.shtml](https://erowid.org/library/books_online/pihkal/pihkal040.shtml)
41[2C-T-4](2c-t-4)4-Isopropylthio-2,5-dimethoxy-PEA2C8–20 mg12–18 hours[https://erowid.org/library/books_online/pihkal/pihkal041.shtml](https://erowid.org/library/books_online/pihkal/pihkal041.shtml)
42Psi-2C-T-4 (ψ-2C-T-4)4-Isopropylthio-2,6-dimethoxy-PEAψ-PEA12 mg"Probably short"[https://erowid.org/library/books_online/pihkal/pihkal042.shtml](https://erowid.org/library/books_online/pihkal/pihkal042.shtml)
43[2C-T-7](2c-t-7)4-Propylthio-2,5-dimethoxy-PEA2C10–30 mg8–15 hours[https://erowid.org/library/books_online/pihkal/pihkal043.shtml](https://erowid.org/library/books_online/pihkal/pihkal043.shtml)
44[2C-T-8](2c-t-8)4-Cyclopropylmethylthio-2,5-dimethoxy-PEA2C30–50 mg10–15 hours[https://erowid.org/library/books_online/pihkal/pihkal044.shtml](https://erowid.org/library/books_online/pihkal/pihkal044.shtml)
45[2C-T-9](2c-t-9)4-(*t*)-Butylthio-2,5-dimethoxy-PEA2C60–100 mg12–18 hours[https://erowid.org/library/books_online/pihkal/pihkal045.shtml](https://erowid.org/library/books_online/pihkal/pihkal045.shtml)
46[2C-T-13](2c-t-13)4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA2C25–40 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal046.shtml](https://erowid.org/library/books_online/pihkal/pihkal046.shtml)
47[2C-T-15](2c-t-15)4-Cyclopropylthio-2,5-dimethoxy-PEA2C30 mg"Several hours"[https://erowid.org/library/books_online/pihkal/pihkal047.shtml](https://erowid.org/library/books_online/pihkal/pihkal047.shtml)
48[2C-T-17](2c-t-17)4-(*s*)-Butylthio-2,5-dimethoxy-PEA2C60–100 mg10–15 hours[https://erowid.org/library/books_online/pihkal/pihkal048.shtml](https://erowid.org/library/books_online/pihkal/pihkal048.shtml)
49[2C-T-21](2c-t-21)4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA2C8–12 mg7–10 hours[https://erowid.org/library/books_online/pihkal/pihkal049.shtml](https://erowid.org/library/books_online/pihkal/pihkal049.shtml)
50[4-D](4-d-psychedelic) (4-trideuteromescaline)4-Trideuteromethyl-3,5-dimethoxy-PEAScaline~200–400 mgc12 hours[https://erowid.org/library/books_online/pihkal/pihkal050.shtml](https://erowid.org/library/books_online/pihkal/pihkal050.shtml)
51Beta-D (β,β-dideuteromescaline)β,β-Dideutero-3,4,5-trimethoxy-PEAScaline~200–400 mgc12 hours[https://erowid.org/library/books_online/pihkal/pihkal051.shtml](https://erowid.org/library/books_online/pihkal/pihkal051.shtml)
52DESOXY (4-desoxymescaline)4-Methyl-3,5-dimethoxy-PEAScaline (mod.)40–120 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal052.shtml](https://erowid.org/library/books_online/pihkal/pihkal052.shtml)
53[2,4-DMA](2-4-dimethoxyamphetamine)2,4-Dimethoxy-AOther60 mg"Short"[https://erowid.org/library/books_online/pihkal/pihkal053.shtml](https://erowid.org/library/books_online/pihkal/pihkal053.shtml)
54[2,5-DMA](2-5-dimethoxyamphetamine) (DOH)2,5-Dimethoxy-ADOx80–160 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal054.shtml](https://erowid.org/library/books_online/pihkal/pihkal054.shtml)
55[3,4-DMA](3-4-dimethoxyamphetamine) (DMA)3,4-Dimethoxy-AOther"A few [100 mg]"Unknown[https://erowid.org/library/books_online/pihkal/pihkal055.shtml](https://erowid.org/library/books_online/pihkal/pihkal055.shtml)
56[DMCPA](2-5-dimethoxy-4-methylphenylcyclopropylamine)2,5-Dimethoxy-4-methyl-PCPADOx (mod.)15–20 mg4–8 hours[https://erowid.org/library/books_online/pihkal/pihkal056.shtml](https://erowid.org/library/books_online/pihkal/pihkal056.shtml)
57DME (β-hydroxy-3,4-DMPEA)3,4-Dimethoxy-β-hydroxy-PEABOx, other115 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal057.shtml](https://erowid.org/library/books_online/pihkal/pihkal057.shtml)
58DMMDA (2,5-dimethoxy-MDA)2,5-Dimethoxy-3,4-methylenedioxy-AMDxx30–75 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal058.shtml](https://erowid.org/library/books_online/pihkal/pihkal058.shtml)
59DMMDA-2 (5,6-dimethoxy-MDA)2,3-Dimethoxy-4,5-methylenedioxy-AMDxx~50 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal059.shtml](https://erowid.org/library/books_online/pihkal/pihkal059.shtml)
60[DMPEA](3-4-dimethoxyphenethylamine) (3,4-DMPEA)3,4-Dimethoxy-PEAOther1,000 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal060.shtml](https://erowid.org/library/books_online/pihkal/pihkal060.shtml)
61[DOAM](2-5-dimethoxy-4-amylamphetamine)4-Amyl-2,5-dimethoxy-ADOx10 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal061.shtml](https://erowid.org/library/books_online/pihkal/pihkal061.shtml)
62[DOB](2-5-dimethoxy-4-bromoamphetamine)4-Bromo-2,5-dimethoxy-ADOx1–3 mg18–30 hours[https://erowid.org/library/books_online/pihkal/pihkal062.shtml](https://erowid.org/library/books_online/pihkal/pihkal062.shtml)
63[DOBU](2-5-dimethoxy-4-butylamphetamine)4-Butyl-2,5-dimethoxy-ADOxUncertain"Very long"[https://erowid.org/library/books_online/pihkal/pihkal063.shtml](https://erowid.org/library/books_online/pihkal/pihkal063.shtml)
64[DOC](2-5-dimethoxy-4-chloroamphetamine)4-Chloro-2,5-dimethoxy-ADOx1.5–3 mg12–24 hours[https://erowid.org/library/books_online/pihkal/pihkal064.shtml](https://erowid.org/library/books_online/pihkal/pihkal064.shtml)
65[DOEF](2-5-dimethoxy-4-2-fluoroethyl-amphetamine)4-(2-Fluoroethyl)-2,5-dimethoxy-ADOx2–3.5 mg12–16 hours[https://erowid.org/library/books_online/pihkal/pihkal065.shtml](https://erowid.org/library/books_online/pihkal/pihkal065.shtml)
66[DOET](2-5-dimethoxy-4-ethylamphetamine)4-Ethyl-2,5-dimethoxy-ADOx2–6 mg14–20 hours[https://erowid.org/library/books_online/pihkal/pihkal066.shtml](https://erowid.org/library/books_online/pihkal/pihkal066.shtml)
67[DOI](2-5-dimethoxy-4-iodoamphetamine)4-Iodo-2,5-dimethoxy-ADOx1.5–3 mg16–30 hours[https://erowid.org/library/books_online/pihkal/pihkal067.shtml](https://erowid.org/library/books_online/pihkal/pihkal067.shtml)
68[DOM](2-5-dimethoxy-4-methylamphetamine) (STP)4-Methyl-2,5-dimethoxy-ADOx3–10 mg14–20 hours[https://erowid.org/library/books_online/pihkal/pihkal068.shtml](https://erowid.org/library/books_online/pihkal/pihkal068.shtml)
69Psi-DOM (ψ-DOM)4-Methyl-2,6-dimethoxy-Aψ-PEA15–25 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal069.shtml](https://erowid.org/library/books_online/pihkal/pihkal069.shtml)
70[DON](2-5-dimethoxy-4-nitroamphetamine)4-Nitro-2,5-dimethoxy-ADOx3–4.5 mg8–15 hours[https://erowid.org/library/books_online/pihkal/pihkal070.shtml](https://erowid.org/library/books_online/pihkal/pihkal070.shtml)
71[DOPR](2-5-dimethoxy-4-propylamphetamine)4-Propyl-2,5-dimethoxy-ADOx2.5–5 mg20–30 hours[https://erowid.org/library/books_online/pihkal/pihkal071.shtml](https://erowid.org/library/books_online/pihkal/pihkal071.shtml)
72E (escaline)4-Ethoxy-3,5-dimethoxy-PEAScaline40–60 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal072.shtml](https://erowid.org/library/books_online/pihkal/pihkal072.shtml)
73EEE2,4,5-Triethoxy-ADOx (mod.)UnknownUnknown[https://erowid.org/library/books_online/pihkal/pihkal073.shtml](https://erowid.org/library/books_online/pihkal/pihkal073.shtml)
74EEM2,4-Diethoxy-5-methoxy-ADOx (mod.)UnknownUnknown[https://erowid.org/library/books_online/pihkal/pihkal074.shtml](https://erowid.org/library/books_online/pihkal/pihkal074.shtml)
75EME2,5-Diethoxy-4-methoxy-ADOx (mod.)UnknownUnknown[https://erowid.org/library/books_online/pihkal/pihkal075.shtml](https://erowid.org/library/books_online/pihkal/pihkal075.shtml)
76EMM2-Ethoxy-4,5-dimethoxy-ADOx (mod.)50 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal076.shtml](https://erowid.org/library/books_online/pihkal/pihkal076.shtml)
77[ETHYL-J](1-3-benzodioxolyl-n-ethylbutanamine) (EBDB)*N*,α-Diethyl-3,4-methylenedioxy-PEAMDxx90 mg"Probably short"[https://erowid.org/library/books_online/pihkal/pihkal077.shtml](https://erowid.org/library/books_online/pihkal/pihkal077.shtml)
78[ETHYL-K](1-3-benzodioxolyl-n-ethylpentanamine) (EBDP)*N*-Ethyl-α-propyl-3,4-methylenedioxy-PEAMDxx40 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal078.shtml](https://erowid.org/library/books_online/pihkal/pihkal078.shtml)
79F-22-Methyl-5-methoxy-2,3-dihydro-6-APBFBenzofuran15 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal079.shtml](https://erowid.org/library/books_online/pihkal/pihkal079.shtml)
80F-222,2-Dimethyl-5-methoxy-2,3-dihydro-6-APBFBenzofuran15 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal080.shtml](https://erowid.org/library/books_online/pihkal/pihkal080.shtml)
81[FLEA](3-4-methylenedioxy-n-hydroxy-n-methylamphetamine) (MDMOH)*N*-Hydroxy-*N*-methyl-3,4-methylenedioxy-AMDxx100–160 mg4–8 hours[https://erowid.org/library/books_online/pihkal/pihkal081.shtml](https://erowid.org/library/books_online/pihkal/pihkal081.shtml)
82G-33,4-Trimethylene-2,5-dimethoxy-ADOx (mod.)12–18 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal082.shtml](https://erowid.org/library/books_online/pihkal/pihkal082.shtml)
83G-43,4-Tetramethylene-2,5-dimethoxy-ADOx (mod.)UnknownUnknown[https://erowid.org/library/books_online/pihkal/pihkal083.shtml](https://erowid.org/library/books_online/pihkal/pihkal083.shtml)
84G-53,4-Norbornyl-2,5-dimethoxy-ADOx (mod.)14–20 mg16–30 hours[https://erowid.org/library/books_online/pihkal/pihkal084.shtml](https://erowid.org/library/books_online/pihkal/pihkal084.shtml)
85GANESHA (G; 3-methyl-DOM)3,4-Dimethyl-2,5-dimethoxy-ADOx20–32 mg18–24 hours[https://erowid.org/library/books_online/pihkal/pihkal085.shtml](https://erowid.org/library/books_online/pihkal/pihkal085.shtml)
86G-N1,4-Dimethoxynaphthyl-2-isopropylamineDOx (mod.)UnknownUnknown[https://erowid.org/library/books_online/pihkal/pihkal086.shtml](https://erowid.org/library/books_online/pihkal/pihkal086.shtml)
87HOT-2 (*N*-hydroxy-2C-T-2)2,5-Dimethoxy-*N*-hydroxy-4-ethylthio-PEAHOT-x, 2C10–18 mg6–10 hours[https://erowid.org/library/books_online/pihkal/pihkal087.shtml](https://erowid.org/library/books_online/pihkal/pihkal087.shtml)
88HOT-7 (*N*-hydroxy-2C-T-7)2,5-Dimethoxy-*N*-hydroxy-4-(n)-propylthio-PEAHOT-x, 2C15–25 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal088.shtml](https://erowid.org/library/books_online/pihkal/pihkal088.shtml)
89HOT-17 (*N*-hydroxy-2C-T-17)2,5-Dimethoxy-*N*-hydroxy-4-(*s*)-butylthio-PEAHOT-x, 2C70–120 mg12–18 hours[https://erowid.org/library/books_online/pihkal/pihkal089.shtml](https://erowid.org/library/books_online/pihkal/pihkal089.shtml)
90IDNNA (*N*,*N*-dimethyl-DOI)2,5-Dimethoxy-*N*,*N*-dimethyl-4-iodo-ADOx2.6 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal090.shtml](https://erowid.org/library/books_online/pihkal/pihkal090.shtml)
91IM (isomescaline)2,3,4-Trimethoxy-PEAScaline (mod.)400 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal091.shtml](https://erowid.org/library/books_online/pihkal/pihkal091.shtml)
92IP (isoproscaline)3,5-Dimethoxy-4-isopropoxy-PEAScaline (mod.)40–80 mg10–16 hours[https://erowid.org/library/books_online/pihkal/pihkal092.shtml](https://erowid.org/library/books_online/pihkal/pihkal092.shtml)
93IRIS (DOM-5-EtO)5-Ethoxy-2-methoxy-4-methyl-ADOx (mod.)9 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal093.shtml](https://erowid.org/library/books_online/pihkal/pihkal093.shtml)
94[J](1-3-benzodioxolylbutanamine) (BDB)α-Ethyl-3,4-methylenedioxy-PEAMDxx150–230 mg4–8 hours[https://erowid.org/library/books_online/pihkal/pihkal094.shtml](https://erowid.org/library/books_online/pihkal/pihkal094.shtml)
95LOPHOPHINE (MMDPEA)3-Methoxy-4,5-methylenedioxy-PEAMDxx200 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal095.shtml](https://erowid.org/library/books_online/pihkal/pihkal095.shtml)
96M (mescaline; 3,4,5-TMPEA)3,4,5-Trimethoxy-PEAScaline~200–400 mgc10–12 hours[https://erowid.org/library/books_online/pihkal/pihkal096.shtml](https://erowid.org/library/books_online/pihkal/pihkal096.shtml)
974-MA (PMA)4-Methoxy-AOther50–80 mg"Short"[https://erowid.org/library/books_online/pihkal/pihkal097.shtml](https://erowid.org/library/books_online/pihkal/pihkal097.shtml)
98MADAM-6 (6-methyl-MDMA)2,*N*-Dimethyl-4,5-methylenedioxy-AMDxx280 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal098.shtml](https://erowid.org/library/books_online/pihkal/pihkal098.shtml)
99MAL (methallylescaline)3,5-Dimethoxy-4-methallyloxy-PEAScaline40–65 mg12–16 hours[https://erowid.org/library/books_online/pihkal/pihkal099.shtml](https://erowid.org/library/books_online/pihkal/pihkal099.shtml)
100[MDA](3-4-methylenedioxyamphetamine)3,4-Methylenedioxy-AMDxx80–160 mg4–6 hoursd[https://erowid.org/library/books_online/pihkal/pihkal100.shtml](https://erowid.org/library/books_online/pihkal/pihkal100.shtml)
101MDAL*N*-Allyl-3,4-methylenedioxy-AMDxx180 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal101.shtml](https://erowid.org/library/books_online/pihkal/pihkal101.shtml)
102MDBU*N*-Butyl-3,4-methylenedioxy-AMDxx40 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal102.shtml](https://erowid.org/library/books_online/pihkal/pihkal102.shtml)
103MDBZ*N*-Benzyl-3,4-methylenedioxy-AMDxx150 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal103.shtml](https://erowid.org/library/books_online/pihkal/pihkal103.shtml)
104MDCPM*N*-Cyclopropylmethyl-3,4-methylenedioxy-AMDxx10 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal104.shtml](https://erowid.org/library/books_online/pihkal/pihkal104.shtml)
105MDDM*N*,*N*-Dimethyl-3,4-methylenedioxy-AMDxx150 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal105.shtml](https://erowid.org/library/books_online/pihkal/pihkal105.shtml)
106[MDE](3-4-methylenedioxy-n-ethylamphetamine) (MDEA)*N*-Ethyl-3,4-methylenedioxy-AMDxx100–200 mg3–5 hours[https://erowid.org/library/books_online/pihkal/pihkal106.shtml](https://erowid.org/library/books_online/pihkal/pihkal106.shtml)
107MDHOET*N*-(2-Hydroxyethyl)-3,4-methylenedioxy-AMDxx50 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal107.shtml](https://erowid.org/library/books_online/pihkal/pihkal107.shtml)
108[MDIP](3-4-methylenedioxy-n-isopropylamphetamine)*N*-Isopropyl-3,4-methylenedioxy-AMDxx250 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal108.shtml](https://erowid.org/library/books_online/pihkal/pihkal108.shtml)
109MDMA*N*-Methyl-3,4-methylenedioxy-AMDxx80–150 mg4–6 hours[https://erowid.org/library/books_online/pihkal/pihkal109.shtml](https://erowid.org/library/books_online/pihkal/pihkal109.shtml)
110MDMC (EDMA)*N*-Methyl-3,4-ethylenedioxy-AEDxx≥200 mg3–5 hours[https://erowid.org/library/books_online/pihkal/pihkal110.shtml](https://erowid.org/library/books_online/pihkal/pihkal110.shtml)
111[MDMEO](3-4-methylenedioxy-n-methoxyamphetamine)*N*-Methoxy-3,4-methylenedioxy-AMDxx180 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal111.shtml](https://erowid.org/library/books_online/pihkal/pihkal111.shtml)
112MDMEOET*N*-(2-Methoxyethyl)-3,4-methylenedioxy-AMDxx180 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal112.shtml](https://erowid.org/library/books_online/pihkal/pihkal112.shtml)
113[MDMP](3-4-methylenedioxy-n-methylphentermine)α,α,*N*-Trimethyl-3,4-methylenedioxy-PEAMDxx~110 mg~6 hours[https://erowid.org/library/books_online/pihkal/pihkal113.shtml](https://erowid.org/library/books_online/pihkal/pihkal113.shtml)
114[MDOH](3-4-methylenedioxy-n-hydroxyamphetamine)*N*-Hydroxy-3,4-methylenedioxy-AMDxx100–160 mg3–6 hours[https://erowid.org/library/books_online/pihkal/pihkal114.shtml](https://erowid.org/library/books_online/pihkal/pihkal114.shtml)
115[MDPEA](3-4-methylenedioxyphenethylamine)3,4-Methylenedioxy-PEAMDxx300 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal115.shtml](https://erowid.org/library/books_online/pihkal/pihkal115.shtml)
116[MDPH](3-4-methylenedioxyphentermine)α,α-Dimethyl-3,4-methylenedioxy-PEAMDxx160–240 mg3–5 hours[https://erowid.org/library/books_online/pihkal/pihkal116.shtml](https://erowid.org/library/books_online/pihkal/pihkal116.shtml)
117[MDPL](3-4-methylenedioxy-n-propargylamphetamine)*N*-Propargyl-3,4-methylenedioxy-AMDxx150 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal117.shtml](https://erowid.org/library/books_online/pihkal/pihkal117.shtml)
118[MDPR](3-4-methylenedioxy-n-propylamphetamine)*N*-Propyl-3,4-methylenedioxy-AMDxx200 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal118.shtml](https://erowid.org/library/books_online/pihkal/pihkal118.shtml)
119ME (metaescaline)3,4-Dimethoxy-5-ethoxy-PEAScaline (mod.)200–350 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal119.shtml](https://erowid.org/library/books_online/pihkal/pihkal119.shtml)
120MEDA (5-methoxy-EDA)3-Methoxy-4,5-ethylenedioxy-AEDxx200 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal120.shtml](https://erowid.org/library/books_online/pihkal/pihkal120.shtml)
121MEE2-Methoxy-4,5-diethoxy-ADOx (mod.)4.6 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal121.shtml](https://erowid.org/library/books_online/pihkal/pihkal121.shtml)
122[MEM](2-5-dimethoxy-4-ethoxyamphetamine)2,5-Dimethoxy-4-ethoxy-ADOx20–50 mg10–14 hours[https://erowid.org/library/books_online/pihkal/pihkal122.shtml](https://erowid.org/library/books_online/pihkal/pihkal122.shtml)
123[MEPEA](3-methoxy-4-ethoxyphenethylamine)3-Methoxy-4-ethoxy-PEAOther≥300 mg"Short"[https://erowid.org/library/books_online/pihkal/pihkal123.shtml](https://erowid.org/library/books_online/pihkal/pihkal123.shtml)
124Meta-DOB5-Bromo-2,4-dimethoxy-ADOx (mod.)50–100 mg5–6 hours[https://erowid.org/library/books_online/pihkal/pihkal124.shtml](https://erowid.org/library/books_online/pihkal/pihkal124.shtml)
125Meta-DOT (5-thio-TMA-2)5-Methylthio-2,4-dimethoxy-ADOx (mod.)35 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal125.shtml](https://erowid.org/library/books_online/pihkal/pihkal125.shtml)
126Methyl-DMA (*N*-methyl-2,5-DMA)*N*-Methyl-2,5-dimethoxy-ADOx250 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal126.shtml](https://erowid.org/library/books_online/pihkal/pihkal126.shtml)
127Methyl-DOB (*N*-methyl-DOB)4-Bromo-2,5-dimethoxy-*N*-methyl-ADOx8 mg"Probably long"[https://erowid.org/library/books_online/pihkal/pihkal127.shtml](https://erowid.org/library/books_online/pihkal/pihkal127.shtml)
128Methyl-J (MBDB)*N*-Methyl-α-ethyl-3,4-methylenedioxy-PEAMDxx180–210 mg4–6 hours[https://erowid.org/library/books_online/pihkal/pihkal128.shtml](https://erowid.org/library/books_online/pihkal/pihkal128.shtml)
129[Methyl-K](1-3-benzodioxolyl-n-methylpentanamine) (MBDP)*N*-Methyl-α-propyl-3,4-methylenedioxy-PEAMDxx100 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal129.shtml](https://erowid.org/library/books_online/pihkal/pihkal129.shtml)
130Methyl-MA (PMMA)*N*-Methyl-4-methoxy-AOther100 mg"Short"[https://erowid.org/library/books_online/pihkal/pihkal130.shtml](https://erowid.org/library/books_online/pihkal/pihkal130.shtml)
131Methyl-MMDA-2 (6-methoxy-MDMA)*N*-Methyl-2-methoxy-4,5-methylenedioxy-AMDxx70 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal131.shtml](https://erowid.org/library/books_online/pihkal/pihkal131.shtml)
132MMDA (5-methoxy-MDA)3-Methoxy-4,5-methylenedioxy-AMDxx100–250 mg"Moderate"[https://erowid.org/library/books_online/pihkal/pihkal132.shtml](https://erowid.org/library/books_online/pihkal/pihkal132.shtml)
133MMDA-2 (6-methoxy-MDA)2-Methoxy-4,5-methylenedioxy-AMDxx25–50 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal133.shtml](https://erowid.org/library/books_online/pihkal/pihkal133.shtml)
134MMDA-3a (2-methoxy-MDA)2-Methoxy-3,4-methylenedioxy-AMDxx20–80 mg10–16 hours[https://erowid.org/library/books_online/pihkal/pihkal134.shtml](https://erowid.org/library/books_online/pihkal/pihkal134.shtml)
135MMDA-3b (4-methoxy-2,3-MDA)4-Methoxy-2,3-methylenedioxy-AMDxx80 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal135.shtml](https://erowid.org/library/books_online/pihkal/pihkal135.shtml)
136MME2,4-Dimethoxy-5-ethoxy-ADOx (mod.)≥40 mg~6–10 hours[https://erowid.org/library/books_online/pihkal/pihkal136.shtml](https://erowid.org/library/books_online/pihkal/pihkal136.shtml)
137MP (metaproscaline)3,4-Dimethoxy-5-propoxy-PEAScaline (mod.)240 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal137.shtml](https://erowid.org/library/books_online/pihkal/pihkal137.shtml)
138MPM2,5-Dimethoxy-4-propoxy-ADOx≥30 mg"Probably short"[https://erowid.org/library/books_online/pihkal/pihkal138.shtml](https://erowid.org/library/books_online/pihkal/pihkal138.shtml)
139Ortho-DOT (2-thio-TMA-2)2-Methylthio-4,5-dimethoxy-ADOx (mod.)25 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal139.shtml](https://erowid.org/library/books_online/pihkal/pihkal139.shtml)
140P (proscaline)3,5-Dimethoxy-4-propoxy-PEAScaline30–60 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal140.shtml](https://erowid.org/library/books_online/pihkal/pihkal140.shtml)
141PE (phenescaline)3,5-Dimethoxy-4-phenethyloxy-PEAScaline150 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal141.shtml](https://erowid.org/library/books_online/pihkal/pihkal141.shtml)
142PEA (phenethylamine)PEAOther1,600 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal142.shtml](https://erowid.org/library/books_online/pihkal/pihkal142.shtml)
143PROPYNYL (propynylscaline)4-Propynyloxy-3,5-dimethoxy-PEAScaline≥80 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal143.shtml](https://erowid.org/library/books_online/pihkal/pihkal143.shtml)
144SB (symbescaline)3,5-Diethoxy-4-methoxy-PEAScaline (mod.)240 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal144.shtml](https://erowid.org/library/books_online/pihkal/pihkal144.shtml)
145[TA](2-3-4-5-tetramethoxyamphetamine) (TeMA)2,3,4,5-Tetramethoxy-AOther~50 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal145.shtml](https://erowid.org/library/books_online/pihkal/pihkal145.shtml)
146[3-TASB](3-thioasymbescaline) (3-thioasymbescaline)4-Ethoxy-3-ethylthio-5-methoxy-PEAScaline (mod.)~160 mg10–18 hours[https://erowid.org/library/books_online/pihkal/pihkal146.shtml](https://erowid.org/library/books_online/pihkal/pihkal146.shtml)
147[4-TASB](4-thioasymbescaline) (4-thioasymbescaline)3-Ethoxy-4-ethylthio-5-methoxy-PEAScaline (mod.)60–100 mg10–15 hours[https://erowid.org/library/books_online/pihkal/pihkal147.shtml](https://erowid.org/library/books_online/pihkal/pihkal147.shtml)
148[5-TASB](5-thioasymbescaline) (5-thioasymbescaline)3,4-Diethoxy-5-methylthio-PEAScaline (mod.)~160 mg~8 hours[https://erowid.org/library/books_online/pihkal/pihkal148.shtml](https://erowid.org/library/books_online/pihkal/pihkal148.shtml)
149TB (thiobuscaline)4-Thiobutoxy-3,5-dimethoxy-PEAScaline (mod.)60–120 mg~8 hours[https://erowid.org/library/books_online/pihkal/pihkal149.shtml](https://erowid.org/library/books_online/pihkal/pihkal149.shtml)
150[3-TE](3-thioescaline) (3-thioescaline)4-Ethoxy-5-methoxy-3-methylthio-PEAScaline (mod.)60–80 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal150.shtml](https://erowid.org/library/books_online/pihkal/pihkal150.shtml)
151[4-TE](4-thioescaline) (4-thioescaline)3,5-Dimethoxy-4-ethylthio-PEAScaline (mod.)20–30 mg9–12 hours[https://erowid.org/library/books_online/pihkal/pihkal151.shtml](https://erowid.org/library/books_online/pihkal/pihkal151.shtml)
152[2-TIM](2-thioisomescaline) (2-thioisomescaline)2-Methylthio-3,4-dimethoxy-PEAScaline (mod.)240 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal152.shtml](https://erowid.org/library/books_online/pihkal/pihkal152.shtml)
153[3-TIM](3-thioisomescaline) (3-thioisomescaline)3-Methylthio-2,4-dimethoxy-PEAScaline (mod.)240 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal153.shtml](https://erowid.org/library/books_online/pihkal/pihkal153.shtml)
154[4-TIM](4-thioisomescaline) (4-thioisomescaline)4-Methylthio-2,3-dimethoxy-PEAScaline (mod.)160 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal154.shtml](https://erowid.org/library/books_online/pihkal/pihkal154.shtml)
155[3-TM](3-thiomescaline) (3-thiomescaline)3-Methylthio-4,5-dimethoxy-PEAScaline (mod.)60–100 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal155.shtml](https://erowid.org/library/books_online/pihkal/pihkal155.shtml)
156[4-TM](4-thiomescaline) (4-thiomescaline)4-Methylthio-3,5-dimethoxy-PEAScaline (mod.)20–40 mg10–15 hours[https://erowid.org/library/books_online/pihkal/pihkal156.shtml](https://erowid.org/library/books_online/pihkal/pihkal156.shtml)
157[TMA](3-4-5-trimethoxyamphetamine) (α-methylmescaline; 3C-M)3,4,5-Trimethoxy-A3C-scaline100–250 mg6–8 hours[https://erowid.org/library/books_online/pihkal/pihkal157.shtml](https://erowid.org/library/books_online/pihkal/pihkal157.shtml)
158[TMA-2](2-4-5-trimethoxyamphetamine) (DOMeO)2,4,5-Trimethoxy-ADOx20–40 mg8–12 hours[https://erowid.org/library/books_online/pihkal/pihkal158.shtml](https://erowid.org/library/books_online/pihkal/pihkal158.shtml)
159[TMA-3](2-3-4-trimethoxyamphetamine) (α-methylisomescaline)2,3,4-Trimethoxy-AOther100 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal159.shtml](https://erowid.org/library/books_online/pihkal/pihkal159.shtml)
160[TMA-4](2-3-5-trimethoxyamphetamine)2,3,5-Trimethoxy-AOther80 mg~6 hours[https://erowid.org/library/books_online/pihkal/pihkal160.shtml](https://erowid.org/library/books_online/pihkal/pihkal160.shtml)
161[TMA-5](2-3-6-trimethoxyamphetamine)2,3,6-Trimethoxy-AOther≥30 mg8–10 hours[https://erowid.org/library/books_online/pihkal/pihkal161.shtml](https://erowid.org/library/books_online/pihkal/pihkal161.shtml)
162[TMA-6](2-4-6-trimethoxyamphetamine) (ψ-TMA-2)2,4,6-Trimethoxy-Aψ-PEA25–50 mg12–16 hours[https://erowid.org/library/books_online/pihkal/pihkal162.shtml](https://erowid.org/library/books_online/pihkal/pihkal162.shtml)
163[3-TME](3-thiometaescaline) (3-thiometaescaline)4,5-Dimethoxy-3-ethylthio-PEAScaline (mod.)60–100 mg10–15 hours[https://erowid.org/library/books_online/pihkal/pihkal163.shtml](https://erowid.org/library/books_online/pihkal/pihkal163.shtml)
164[4-TME](4-thiometaescaline) (4-thiometaescaline)3-Ethoxy-5-methoxy-4-methylthio-PEAScaline (mod.)60–100 mg10–15 hours[https://erowid.org/library/books_online/pihkal/pihkal164.shtml](https://erowid.org/library/books_online/pihkal/pihkal164.shtml)
165[5-TME](5-thiometaescaline) (5-thiometaescaline)3-Ethoxy-4-methoxy-5-methylthio-PEAScaline (mod.)200 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal165.shtml](https://erowid.org/library/books_online/pihkal/pihkal165.shtml)
166[2T-MMDA-3a](2t-mmda-3a) (2-methylthio-MDA)2-Methylthio-3,4-methylenedioxy-AMDxx12 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal166.shtml](https://erowid.org/library/books_online/pihkal/pihkal166.shtml)
167[4T-MMDA-2](4t-mmda-2) (4-thio-MMDA-2)4,5-Thiomethyleneoxy-2-methoxy-AMDxx (mod.)25 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal167.shtml](https://erowid.org/library/books_online/pihkal/pihkal167.shtml)
168[TMPEA](2-4-5-trimethoxyphenethylamine) (2,4,5-TMPEA; 2C-O)2,4,5-Trimethoxy-PEA2C300 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal168.shtml](https://erowid.org/library/books_online/pihkal/pihkal168.shtml)
169[2-TOET](2-toet) (2-thio-DOET)4-Ethyl-5-methoxy-2-methylthio-ADOx (mod.)65 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal169.shtml](https://erowid.org/library/books_online/pihkal/pihkal169.shtml)
170[5-TOET](5-toet) (5-thio-DOET)4-Ethyl-2-methoxy-5-methylthio-ADOx (mod.)12–25 mg8–24 hours[https://erowid.org/library/books_online/pihkal/pihkal170.shtml](https://erowid.org/library/books_online/pihkal/pihkal170.shtml)
171[2-TOM](2-tom) (2-thio-DOM)5-Methoxy-4-methyl-2-methylthio-ADOx (mod.)60–100 mg8–10 hours[https://erowid.org/library/books_online/pihkal/pihkal171.shtml](https://erowid.org/library/books_online/pihkal/pihkal171.shtml)
172[5-TOM](5-tom) (5-thio-DOM)2-Methoxy-4-methyl-5-methylthio-ADOx (mod.)30–50 mg6–10 hours[https://erowid.org/library/books_online/pihkal/pihkal172.shtml](https://erowid.org/library/books_online/pihkal/pihkal172.shtml)
173TOMSO (5-TOM-sulfoxide)2-Methoxy-4-methyl-5-methylsulfinyl-ADOx (mod.)≥100–150 mge10–16 hours[https://erowid.org/library/books_online/pihkal/pihkal173.shtml](https://erowid.org/library/books_online/pihkal/pihkal173.shtml)
174TP (thioproscaline)4-Propylthio-3,5-dimethoxy-PEAScaline (mod.)20–25 mg10–15 hours[https://erowid.org/library/books_online/pihkal/pihkal174.shtml](https://erowid.org/library/books_online/pihkal/pihkal174.shtml)
175TRIS (trisescaline)3,4,5-Triethoxy-PEAScaline (mod.)240 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal175.shtml](https://erowid.org/library/books_online/pihkal/pihkal175.shtml)
176[3-TSB](3-thiosymbescaline) (3-thiosymbescaline)3-Ethoxy-5-ethylthio-4-methoxy-PEAScaline (mod.)200 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal176.shtml](https://erowid.org/library/books_online/pihkal/pihkal176.shtml)
177[4-TSB](4-thiosymbescaline) (4-thiosymbescaline)3,5-Diethoxy-4-methylthio-PEAScaline (mod.)240 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal177.shtml](https://erowid.org/library/books_online/pihkal/pihkal177.shtml)
178[3-T-TRIS](3-thiotrisescaline) (3-thiotrisescaline)4,5-Diethoxy-3-ethylthio-PEAScaline (mod.)160 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal178.shtml](https://erowid.org/library/books_online/pihkal/pihkal178.shtml)
179[4-T-TRIS](4-thiotrisescaline) (4-thiotrisescaline)3,5-Diethoxy-4-ethylthio-PEAScaline (mod.)200 mgUnknown[https://erowid.org/library/books_online/pihkal/pihkal179.shtml](https://erowid.org/library/books_online/pihkal/pihkal179.shtml)
**Acronyms** (in chemical names)**:** PEA = phenethylamine; A = amphetamine; PCPA = [2-phenylcyclopropylamine](2-phenylcyclopropylamine); 6-APBF = [6-(2-aminopropyl)benzofuran](6-2-aminopropyl-benzofuran). **Footnotes:** a = Dose and duration for compounds are orally unless otherwise specified. b = Ariadne dose is as a psychedelic. Otherwise doses of 12–32mg as the racemate and 25mg as (*R*)-Ariadne were active. c = [4-D](4-d-drug), beta-D, and mescaline doses are 200–400 mg as the sulfate salt and 178–356mg as the hydrochloride salt. d = [MDA](3-4-methylenedioxyamphetamine) duration was originally 8–12hours but was later revised by Shulgin to 4–6hours in September 2001 following the publication of *PiHKAL*. e = TOMSO dose is 150mg alone or 100–150 mg with alcohol.

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.

References

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.
  2. (17 July 2023). "Introduction to the chemistry and pharmacology of psychedelic drugs". Australian Journal of Chemistry.
  3. (1991). "PiHKAL: A Chemical Love Story". [[Transform Press]].
  4. Ben Sessa. (2015). "The Psychedelic Policy Quagmire: Health, Law, Freedom, and Society". Bloomsbury Publishing.
  5. (1997). "TiHKAL: The Continuation". [[Transform Press]].
  6. (2021). "Better Living Through Chemistry". Better Living Through Film, Incorporated.
  7. (2018). "Self-Experiments with Psychoactive Substances: A Historical Perspective". Handb Exp Pharmacol.
  8. (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol.
  9. Bennett, Drake. (January 30, 2005). "Dr. Ecstasy". New York Times Magazine.
  10. (February 2016). "Controlled Substances".
  11. "Triple Goddess of the Night". British Neuroscience Association Bulletin.
  12. (2013). "Phenethylamine: von der Struktur zur Funktion". Nachtschatten-Verlag.
  13. (1994). "Hallucinogens: An Update". National Institute on Drug Abuse.
  14. (2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
  15. Shulgin, Alexander T.. (1978). "Stimulants". Springer US.
  16. (1978). "Mescaline analogs: substitutions at the 4-position". NIDA Res Monogr.
  17. (1980). "Burger's Medicinal Chemistry". Wiley.
  18. (1982). "Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs". Springer Berlin Heidelberg.
  19. (2025-12-29). "У Беларусі забаранілі навуковую кнігу па гісторыі БНР".
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