How PiHKAL · info differs from the printed version of PiHKAL: A Chemical Love Story. Alexander & Ann Shulgin
Paragraphs, where indicated, are numbered sequentially from the top of each page. If the page begins with the continuation of a paragraph that began on the previous page, it is numbered 0. The first paragraph that begins on each page is numbered 1.
  • 453–457 In the short index, I have dropped the abbreviations A (for amphetamine) and PEA (for phenethylamine) in favour of the full names.

    In several cases the short index name does not follow the usual alphabetical ordering of substituents. For instance, 4-Nitro-2,5-dimethoxyphenethylamine might be better named 2,5-Dimethoxy-4-nitrophenethylamine, since methoxy precedes nitro alphabetically (after stripping the multiplicative prefix “di”). I have left these as they are, except where noted below.

  • 454 The short index entry for #46 2C-T-13 is missing a closing parenthesis: 4-(2-Methoxyethylthio)-2,5-dimethoxyphenethylamine.
  • 454 The short index entry for #50 4-D is 4-Trideuteromethyl-3,5-dimethoxyphenethylamine, whereas on page 590 it is named 3,5-Dimethoxy-4-trideuteromethoxyphenethylamine, in agreement with the structural diagram.
  • 454 The short index entry for #52 DESOXY is 4-Me-3,5-dimethoxyphenethylamine instead of 4-Methyl-3,5-dimethoxyphenethylamine.
  • 454 In the short index entry for #56 DMCPA, 2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine, the final hyphen is superfluous.
  • 455 The short index entry for #77 ETHYL-J reads N,α-diethyl-3,4-methylenedioxyphenethylamine. To be consistent with the rest of the short index, it should read N,α-Diethyl-3,4-methylenedioxyphenethylamine.
  • 456, 755 3-Ethoxy-4,5-dimethoxyphenethylamine has been added as an alternative name for #119 ME 3,4-Dimethoxy-5-ethoxyphenethylamine following the principle that (other things being equal) the lower locant is given to the substituent cited earlier.
  • 456, 759 3,4-Ethylenedioxy-5-methoxyamphetamine has been added as an alternative name for #120 MEDA 3-Methoxy-4,5-ethylenedioxyamphetamine following the principle that (other things being equal) the lower locant is given to the substituent cited earlier.
  • 456 Phenethylamine, the unabbreviated name for short index entry #142 PEA, has been added.
  • 457 The short index name for #149 TB, 4-Thiobutoxy-3,5-dimethoxyphenethylamine, is inconsistent with the usual naming conventions used. 4-Butylthio-3,5-dimethoxyphenethylamine has been added as an alternative.
  • 457, 837 4-Ethoxy-3-methoxy-5-methylthiophenethylamine has been added as an alternative name for #150 3-TE 4-Ethoxy-5-methoxy-3-methylthiophenethylamine following the principle that (other things being equal) the lower locant is given to the substituent cited earlier.
  • 457 3,4-Dimethoxy-5-methylthiophenethylamine has been added as an alternative name for #155 3-TM 3-Methylthio-4,5-dimethoxyphenethylamine following the principle that (other things being equal) the lower locant is given to the substituent cited earlier, and to agree with the name given on page 849.
  • 457 3,4-Diethoxy-5-ethylthiophenethylamine has been added as an alternative name for #178 3-T-TRIS 4,5-Diethoxy-3-ethylthiophenethylamine following the principle that (other things being equal) the lower locant is given to the substituent cited earlier, and to agree with the name given on page 918.
  • 472 ¶ 1 For consistency, Aleph-6 has been changed to ALEPH-6 in the first paragraph of the EXTENSIONS AND COMMENTARY section.
  • 485 ¶ 5 In the explanation of why ‘H’ is an imperfect choice as a code name, DMPEA is cited as having a prior claim to the code; it should be MDPEA.
  • 487 ¶ 3 Reader amethyst has pointed out the product of the reaction would be N-cyclopropylmethyl-2,5-dimethoxy-4-methylamphetamine rather than N-cyclopropyl-2,5-dimethoxy-4-methylamphetamine as stated. Changed and noted in the text.
  • 499 The chemical name given for the BOHD analogue BOAD is β-acetoxy-3,4-dimethoxy-4-methylphenthylamine rather than β-acetoxy-2,5-dimethoxy-4-methylphenthylamine.

    The long index lists the correct chemical name for BOAD.

  • 526 In paragraph two of the SYNTHESIS section, the final hyphen in 2-methoxy-3,4-(trimethylene)-benzaldehyde is superfluous.
  • 541 For consistency, 2CI-2EtO has been changed to 2CI-2ETO in the fourth paragraph of the EXTENSIONS AND COMMENTARY section.
  • 551 The section name 2,5-Dimethoxy-4-methylseleneophenethylamine differs from the short index name 2,5-Dimethoxy-4-methylselenophenethylamine.

    This section employs seleneo rather than seleno in several other places. The latter is the IUPAC preferred name in these cases.

  • 558 In paragraph three, the final hyphen in 2,5-dimethoxy-4-(ethylthio)-benzaldehyde is superfluous.
  • 570 To balance the parentheses in the second paragraph of the EXTENSIONS AND COMMENTARY section, a right parenthesis should be inserted following the second benzaldehyde in “The benzaldehyde (2-ethoxy-5-methoxy-4-(i-propylthio)benzaldehyde) had a melting point of …”. At the end the same sentence it reads “…187–189 ” instead of “…187–189 °C”.
  • 581 Superfluous space in “…(2C- T-15)…” near the end of last paragraph of the SYNTHESIS section.
  • 586 ¶ 1 Superfluous space after “…rather fragrant” near the end of second paragraph.
  • 586 ¶ 1 In the last sentence of the print edition, the “S” isomer is compared to itself rather than with the “R” isomer, almost certainly what was intended. Changed and noted in the text. Thanks to RK for reporting this one.
  • 590, 592 The SYNTHESIS section refers to the entry for ESCALINE, though the code used for Escaline in the short index is E.
  • 599 ¶ 2 For the analogy to be sound, the bromo analogue should be 3,5-Dimethoxy-4-bromophenenthylamine rather than 3,5-Dimethoxy-4-bromoamphetamine, and the substituents reordered à la IUPAC, giving 4-Bromo-3,5-dimethoxyphenenthylamine. Changed and noted in the text.
  • 601 In the second paragraph, to be consistent with the description, homologue (3) should be 2-n-decyloxy-N,N-dimethyl-4-methoxyamphetamine rather than 2-n-decyloxy-N,N-dimethylamphetamine
  • 606 ¶ 3 The “factored” name of the two halogenated analogues of 2,6-DNNA has been expanded to allow linking. Changed but not noted in the text.
  • 622 Dosage in first paragraph reads 25 ug/Kg rather than 25 μg/kg.
  • 625, 939 In paragraph three, the final hyphen in 2,5-dimethoxy-4-(2-methylpropyl)-amphetamine and 2,5-dimethoxy-4-(2-methylpropyl)-amphetamine is superfluous. Likewise for the long index entries.
  • 628–631 The final hyphen in 2,5-dimethoxy-4-(2-fluoroethyl)-amphetamine is superfluous.
  • 629 ¶ 3 Changed 1-[2,5-dimethoxy-4-(2-hydroxyethyl)phenyl]-2-(2,2,2-trifluoroacetamido)propane to 1-[2,5-dimethoxy-4-(2-fluoroethyl)phenyl]-2-(2,2,2-trifluoroacetamido)propane. Changed and noted in the text.
  • 650, 938 In the first paragraph, the final hyphen in 2,5-dimethoxy-4-(1-hydroxypropyl)-amphetamine is superfluous. Likewise for the long index entry.
  • 651 ¶ 1 Changed 2,6-dimethoxy-4-dimethylaminophenol to 2,6-dimethoxy-4-dimethylaminomethylphenol. Changed and noted in the text.
  • 681 Paragraph lead reads EXTENTIONS instead of EXTENSIONS.
  • 682 In the last line of the SYNTHESIS section, there is a spurious space in the formula and the analysis appears to be incomplete.
  • 685 The last sentence of the entry for HOT-7 reads “Lets try some other N-hydroxys!” rather than “Let’s try some other N-hydroxys!”.
  • 686 Superfluous space in “DURATION :”.
  • 689 In the third line from the bottom, the substituent 3-(dimethylaminopropyl) should be 3-(dimethylamino)propyl, and homologue should be pluralized. Changed and noted in the text.
  • 692 The SYNTHESIS section refers to the entry for ESCALINE, though the code used for Escaline in the short index is E.
  • 707 ¶ 2 3,4,5-Trimethoxyphenylacetic acid is given the abbreviation TMPEA instead of TMPAA.
  • 707 ¶ 3 An Erowid reader reported the first line of the SYNTHESIS section should read cyclohexylamine—not cyclohexane—a change endorsed by Team Shulgin. Changed and noted in the text.
  • 709 Near the bottom of the first paragraph, a sentence begins “Rrecently…”.
  • 712 The SYNTHESIS section refers to the entry for ESCALINE, though the code used for Escaline in the short index is E.
  • 714, 938 In the first paragraph, the final hyphen in 3,5-dimethoxy-4-(2-methoxyethoxy)-phenethylamine is superfluous. Likewise for the long index entry.
  • 723 Near the middle of the first paragraph, the final hyphen in 3,4-methylenedioxy-N-(4-heptyl)-amphetamine is superfluous.
  • 761 Near the top of the page the compound 3-Methoxy-4,5-trimethylenedioxyamphetamine is given the code MTMA, whereas later in the paragraph the code used is MTDA.

    The latter code is consistent with this series of compounds and appears in the long index.

  • 772 Near the middle of the paragraph that begins “To a stirred and gently refluxing suspension…” I have inserted the presumed units of mL in the fragment 2×200 mL Et2O.
  • 794 ¶ 5 The code name for the 2-carbon homologue of MMDA-2 should be 2C-MMDA-2 rather than 2C-2. Changed and noted in the text.
  • 795 ¶ 0 The code name for the 4-carbon homologue of MMDA-2 should be 4C-MMDA-2 rather than 4C-2. Changed and noted in the text.
  • 806 Not an error per se, but in this case only the lede paragraph reads EXTENSIONS AND EXTRAPOLATIONS rather than EXTENSIONS AND COMMENTARY.
  • 808–809 MAM is said to stand for 4-(n)-Amyl-2,5-dimethoxyamphetamine, but following the logic of the chapter, it ought to be 4-(n)-Amyloxy-2,5-dimethoxyamphetamine. Changed and noted in the text.

    The long index supports this, containing an entry for 4-(n)-Amyloxy-2,5-dimethoxyamphetamine that refers to the parent compound MPM. Also, 4-(n)-Amyl-2,5-dimethoxyamphetamine has its own entry, DOAM.

  • 835 Near the middle of the paragraph that begins “A solution of LAH under N2 …” I have inserted the presumed units of mL in the fragment 3×100 mL CH2Cl2. In the following sentence, a space should follow “dilute.”
  • 846 The heading for 3-TIM reads 3-THIOMESCALINE rather than 3-THIOISOMESCALINE.
  • 853 Paragraph lead reads QUANTITATIVE COMMENTS rather than QUALITATIVE COMMENTS.
  • 859–864 I have inserted paragraph breaks and headings within the multi-page section describing essential oil substitution patterns. The insertions are noted in the text.
  • 896 In the first paragraph of the SYNTHESIS of #170, 5-TOET, the final hyphen in dimethyl-(2-ethyl-4-hydroxyphenyl)-sulfonium chloride is superfluous.
  • 934 Long index entry 2,5-Diethoxy-4-methylthiophenethylamine should probably read 2,5-Diethoxy-4-ethylthiophenethylamine to be consistent with the referral to #40 2C-T-2.
  • 939 The final hyphen in the long index entry for 2,5-dimethoxy-4-(1-morpholinothio)-phenethylamine is superfluous.
  • 943 Long index entry 5-Ethoxy-4-ethylthio-5-methoxyphenethylamine describes an unlikely substance. It should probably read 5-Ethoxy-4-ethylthio-2-methoxyphenethylamine.
  • 950 The long index entry for 3,4-Methylenedioxy-β-hydroxyphenethylamine refers to DMA, #57 rather than DME, #57.
  • 952 The long index entry for ORTHO-DOB refers to META-DOB, #24 rather than META-DOB, #124.
How TiHKAL · info differs from the printed version of TiHKAL: The Continuation. Alexander & Ann Shulgin
Paragraphs are numbered sequentially from the top of each page. If the page begins with the continuation of a paragraph that began on a previous page, it is numbered 0. The first paragraph that begins on each page is numbered 1.
  • 389–390 In the TiHKAL short index on the browse page, alpha has been changed to α throughout.
  • 390 Short index name for #51 PRO-LAD should be N,N-Diethyl-6-propyl-6-norlysergamide rather than 6-Propyl-6-norlysergamide. Changed but not noted in the text.
  • 394 ¶ 1 Spurious space after hyphen in “dihexyl- homologue”. Changed and noted in text.
  • 394 ¶ 2 Should be “indol-3-yl-N,N-diisobutylglyoxylamide” rather than “indo-3-yl-N,N-diisobutylglyoxylamide.” Changed and noted in text.
  • 406 ¶ 3 A homologue of the title compound, “N-Isopropyltryptamine,” is here given the code IPT. However, beginning on page 571 half a recipe is devoted to the same compound under the name NIPT, which follows the N-monosubstituted tryptamine naming convention Sasha details on pages page 395 and page 573. Each of the two sections lists a melting point for this substance, but they do not match. IPT is not listed in the book’s index or anywhere else in the text. Changed and noted in the text,
  • 420 ¶ 2, 3 The order of these paragraphs is reversed in the Erowid online version. The print version ordering is followed here.
  • 421 ¶ 2 The code should read “2-Me-DMT” rather than ”2,Me-DMT”, but in either case this seems at odds with the preceding sentence where this substance is called the “2-Methyl homologue of NMT.”
  • 422 One of the alternative names for 2,α-DMT should be “2,α-Dimethyltryptamine” rather than “2-α;-Dimethyltryptamine.” Changed but not noted in the text.
  • 422 ¶ 2 The name “α,2-dimethyltryptamine,” though correct, is inconsistent. Everywhere else in the book the substance is called “2,α-dimethyltryptamine.” Not changed.
  • 441 ¶ 3 Spurious space and missing capital in “alpha-ethyl tryptamine.” Changed and noted in text.
  • 442 One of the alternative names for ETH-LAD should be “6-Norlysergic acid, 6,N,N-triethylamide” rather than “6-Norlysergic acid, 6-N,N-triethylamide.” The long index entry for this name is correct. Changed but not noted in the text.
  • 454 In the seeds of Syrian rue table, it should be “200-600 mg alkaloids” rather than “200-600 g alkaloids.” On the following line, the capsule size should be “00” rather than “OO.” Both changed and noted in text.
  • 455 One of the alternative names for Harmine should be “β-Carboline, 7-methoxy-1-methyl” rather than “β-Carboline, 7-methoxy.” The long index entry includes both names. Changed but not noted in the text.
  • 455 One of the alternative names for Harmine should be “7-methoxy-1-methyl-β-Carboline” rather than “7-methoxy-β-Carboline.” The long index entry for this name is incorrect also. Changed but not noted in the text.
  • 472 ¶ 3 It should be “accusers” rather than “accusors.” Changed and noted in text.
  • 476–477 I’ve added the structural diagram for each Bufotenine analogue having an individual commentary. Changed but not noted in the text.
  • 477 ¶ 1 The code name for Norbufotenine should be “5-HO-NMT” rather than “5-OH-NMT.” Changed and noted in text.
  • 479 One of the alternative names for 4-HO-DMT should be “N,N-Dipropyl-4-hydroxytryptamine” rather than “N,N-Dipropyl-4-hydroxyaminotryptamine.” Changed but not noted in the text.
  • 480 ¶ 1 Strictly speaking, it should be “(ethyl)(methyl)amine” or “ethyl(methyl)amine” or “N-ethyl-N-methylamine” rather than “methylethyl amine.” Not changed.
  • 481 ¶ 1 I've changed 4-HO-DIPT to 4-HO-MIPT, since the latter is a member of the homologous series beginning with 4-HO-DMT and 4-HO-DET being discussed. It also makes more sense given the discussion of amines in the following paragraph. Changed and noted in the text.
  • 485 ¶ 1 It should read “4-hydroxy-N-methyl-N-propyltryptamine” rather than “4-hydroxy-N-methyl-N-propylindole.” Changed and noted in the text.
  • 493 I’ve added “name,” a column of links to the table of LSD analogues. Noted in the text.
  • 493–495 I’ve added the structural diagram for each LSD analogue having an individual commentary. Changed but not noted in the text.
  • 494 ¶ 2 The name “2-Bromo-N,N-diethyllysergamide” should be in bold to be consistent with the other paragraph heading names in this section. Changed but not noted in the text.
  • 494 ¶ 4 Some substance names in bold have been capitalized for consistency. Changed but not noted in the text.
  • 495 ¶ 1 The name “2-Bromo-N,N-diethyl-1-methyllysergamide” should be in bold to be consistent with the other paragraph heading names in this section. Changed but not noted in the text.
  • 495 A diagram of LSD stereoisomers has been inserted, adapted from Alexander Shulgin, Psychotomimetic Agents, in Pharmacological Agents, v. IV, p. 63, 1976, Academic Press. Noted in the text.
  • 496 In the table, I've added “chemical name,” a column of links to the table of LSD analogues. Noted in the text.
  • 496 In the table, the hyphen preceding each non-bridged substituent has been elided to conserve space. Not noted in the text.
  • 496 In the table, “LMP” another code for the N-methyl-N-propyl analogue has been added, in line with some of Sasha’s earlier publications. I’m not sure if “LAMP” is an alternative code or a misprint. See Alexander Shulgin, Psychotomimetic Agents, in Pharmacological Agents, v. IV, p. 66, 1976, Academic Press. Noted in the text.
  • 497 ¶ 3 Some substance names in bold have been capitalized for consistency. Changed but not noted in the text.
  • 499 In one of the alternative names for MBT, “3-[2-(Butylmethylamino)ethyl]-indole”, the final hyphen is superfluous. The long index entry for this name is correct. Changed but not noted in the text.
  • 500 ¶ 0, 1 The intermediate should be “N-butyl-N-methyl-3-indoleglyoxylamide” rather than “N-butyl-N-methyl-indoleglyoxylamide.” Both changed and noted in the text.
  • 501 ¶ 3 “isopropylalcohol” should be two words. Changed and noted in the text.
  • 502 In a synonym for 4,5-MDO-DIPT, current practice is to elide the terminal “e” in “ethane” when followed by a term beginning with an “a,” forming “ethanamine” rather than “ethaneamine”. Changed but not noted in the text.
  • 503 In a synonym for 5,6-MDO-DIPT, current practice is to elide the terminal “e” in “ethane” when followed by a term beginning with an “a,” forming “ethanamine” rather than “ethaneamine”. Changed but not noted in the text.
  • 505 In a synonym for 4,5-MDO-DMT, current practice is to elide the terminal “e” in “ethane” when followed by a term beginning with an “a,” forming “ethanamine” rather than “ethaneamine”. Changed but not noted in the text.
  • 507 In a synonym for 5,6-MDO-DMT, current practice is to elide the terminal “e” in “ethane” when followed by a term beginning with an “a,” forming “ethanamine” rather than “ethaneamine”. Changed but not noted in the text.
  • 507 ¶ 2, 3 The intermediate should be “N,N-dimethyl-5,6-methylenedioxy-3-indoleglyoxylamide” rather than “N,N-dimethyl-5,6-methylenedioxy-4-indoleglyoxylamide.” Both changed and noted in the text.
  • 508 In a synonym for 5,6-MDO-MIPT, current practice is to elide the terminal “e” in “ethane” when followed by a term beginning with an “a,” forming “ethanamine” rather than “ethaneamine”. Changed but not noted in the text.
  • 508 ¶ 4 IMHO, “sortof” should be two words. Changed and noted in the text.
  • 519 ¶ 2 It should read “heptafluorobutyroyl” rather than “heptofluorobutyroyl.” Changed and noted in the text.
  • 525 ¶ 2 The final sentence lacks a period. Changed and noted in the text.
  • 525 ¶ 3 Not an error per se, but in this case the caption is “CHEMISTRY” rather than “SYNTHESIS.” Not changed.
  • 540 ¶ 3 The Erowid online edition has baeocystine instead of baeocystin, and norbaeocystine instead of norbaeocystin. Changed and noted in the the text.
  • 553 In column one of the table, the final row should read “Ar-7-OMe” rather than “Ar-7-OH.”
  • 553 ¶ 3 The “chemically correct” name for beta-carboline should be “9H-pyrido[3,4-b]indole” rather than “9H-pyrid-[3,4-b]-indole.”
  • 555 ¶ 4 In several places it should read “tryptophan” rather than ”tryptophane” for consistency with the usual spelling and with the rest of the book. All changed and noted in the text.
  • 560 ¶ 3 Not an error per se, but in this case the caption is “CHEMISTRY” rather than “SYNTHESIS.” Not changed.
  • 561 ¶ 7 The long name for 4-MeS-DMT should be N,N-Dimethyl-4-methylthiotryptamine rather than N,N-Dimethyl-4-thiotryptamine. Changed and noted in the text.
  • 573 ¶ 3 Throughout this paragraph I suspect “e/m” should be “m/e”, and “m/e” should be “m/z” to be consistent with the rest of the book and with IUPAC recommendations. Changed and noted in the text.
  • 574 ¶ 1 It should read “Et2O” rather than “diethyl Et2O.”
  • 575 One of the alternative names for PRO-LSD, “6-Norlyseramide, N,N-diethyl-6-propyl”, occurs twice. Changed but not noted in the text.
  • 589 ¶ 0, 2 Single typographic quotes are reversed. Changed but not noted in the text.
Lexical differences between the printed version and this version
  • HCL HCl
  • Kg kg
  • mg. mg
  • ml mL
  • alpha- α-
  • beta- β-
  • psi- Ψ-
  • cis- cis-
  • trans- trans-
  • erythro-erythro-
  • threo- threo-
  • (i)- iso
  • i- iso
  • (n)- n-
  • n- n-
  • (s)- sec-
  • sec- sec-
  • (t)- tert-
  • tert- tert-
  • m- m-
  • o- o-
  • p- p-
  • N- N-
  • N'- N′-
  • O- O-
  • R- R-
  • S- S-
  • ...
  • '…' “…”
  • '…' ‘…’
  • …'… …’…
  • …--… …—…
  • …x… …×…
19 October 2016 · Creative Commons BY-NC-SA ·