• 4 May 2023
    Yes, it’s been an age since I’ve logged any changes. Plenty, plenty has been added though, mostly by my tireless colleague PN. How much? Like, lots!
  • 22 Dec 2022
    Lots more compounds and additional links to Wikipedia and external forensic sites.
    Most tryptamines now have a code name (e.g. 7-Fluoro-EPT) and a trivial name (e.g. 7-Fluoro-N-ethyl-N-propyltryptamine) as well as a IUPAC name. There is some logic to how these names are derived — there has to be. When I'm confident it makes practical sense I'll spell it all out.
  • 21 Sept 2022
    More compounds and additional links to external forensic sites.
  • 12 Aug 2022
    Roughly 1200 new links to Wikidata entries.
    PN has reviewed several patents (thanks to JW for those) and other literature, adding 224 new substances.
  • 4 May 2022
    Structural diagrams have been revisited and many redrawn with an eye to consistency. My thanks to CC for his efforts to date. This is an ongoing project.
    PN has reviewed many dozens of papers and other reference works, affording many new structures and links to the literature.
    The Cactus Alkaloids (2013, upd. 2018) by Keeper Trout (Trout’s Notes) has been indexed. The book has, with the author’s permission, been partioned by compound for easier access.
  • 27 Dec 2021
    All analytical data pdfs previously linked to external websites including Project Response, Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG), and others now link to archived copies of their public data via secure, https protocol. My thanks to these and every legitimate site that provides free and public access finding NPS data.
    I’ve done this just to be on the safe side. Sites do vanish, after all.
  • 28 Nov 2021
    I’ve been very lax updating this log. In fact, hundreds of new compounds and references have been added, largely the work of PN and JW. A few errors have been corrected (thanks to Peter for spotting these), and a few more bugs found and fixed. There is no last bug.
    Data quality is very important; also very challenging. Consider a typical entry in a site like this. It’s usual to find, for any given compound:
    • A structural diagram, sometimes with incomplete or ambiguous stereochemistry,
    • All kinds of names including trivial/historical names like psilocin, code names like 4-HO-DMT, and systematic names having various degrees of conformance with the current standard: Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 (the “Blue Book”), from N,N-Dimethyl-4-hydroxytryptamine (easier to read but not great, formally) to 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol (harder to read but formally correct),
    • Well-known and useful encodings of the structure, e.g. InChI, InChI key, and SMILES, each with its own uses, semantics, and idiosyncrasies, and
    • Links to other sources deemed to be reputable including PubChem, ChemSpider, and Wikipedia.
    Reputable sources tend to self-correct, but it takes work to keep everything accurate and synchronized. So I welcome and encourage readers to report anything that is, or might be, wrong:
  • 18 June 2021
    A few bugs fixed, a few structures corrected, but mostly more content added and organized, thanks to PN and JW.
  • 21 Jan 2021
    The search box was acting weird or downright broken for several weeks. I’m very sorry about that, it was hugely annoying behaviour. I think it’s OK now.
  • 7 Jan 2021
    Gosh, how time flies during a global pandemic. So, how much has been added since my last update? No idea, but a decidely nontrivial number of compounds, links, references etc. With, as always, huge help from my colleagues PN and JW.
    The blotter site has been rewritten completely. It looks much the same but it should load a lot faster.
    This site, meanwhile, is still being rewritten to use Bootstrap 4 and other upgrades. Bear with me, it’ll be ready when it’s ready and better than ever.
  • 26 June 2020
    The late and much-admired website countyourculture.com, has been resurrected (from an Internet Archive snapshot) at: countyourculture: rational exploration of the underground.
  • 22 June 2020
    PN is tearing though the Rhodium drug chemistry archive adding ca. 220 260 new structures and 550 1075 new links. This is an ongoing project. The archive contains an assortment of .html, .pdf, .txt, and .djvu files. The .djvu file format never really caught fire so those are now in .pdf format as well.
  • 3 June 2020
    This history page and all of blotter were missing in action for about a week because of a server configuration error. Really sorry about that.
  • 3 June 2020
    My buddy Richard Apodaca has granted full ChemWriter admission to my other buddy 18F. So structures like this now display just fine. Thanks Rich!
    In another small step towards perfection, the search box now orders matching names from shortest to longest, the idea being the shorter the matching name the closer the match. Seems to work well.
  • 14 May 2020
    Access to the Shulgin notebook transcripts from the explore page has been restored after being lost for some time, likely weeks or even months. Don’t you just hate it when that happens? My sincere thanks to Hamilton Morris for alerting me.
  • 28 Apr 2020
    The search page structure editor modal now accepts a SMILES string as input. This is a ChemWriter feature still under development.
    The site rewrite is proceeding much like past rewrites: by slow, recursive descent into madness a codebase that goes back at least 15 years. Most coders know this mixture of puzzlement, disgust, and fear: “What the fuck was I thinking when I wrote that… and what’s going to break when I fix it?” But it’s coming along.
    Many more structures, references, and links have been added. Thanks as always to PN and JW.
  • 7 Feb 2020
    The site is again having a regularly-scheduled, mid-life crisis and is reinventing itself. Nothing a little Bootstrap 4 and Javascript can’t fix.
    About 80 new structures have been added, comprised of the mid-century friends of the μ-receptor, prohetic frenemies of the cannabinoid receptor, and some novel new AH-style who knows whats. Props to PN and JW for this.
    A few dozen blue-sky, hybrid 2C-fentanyls have also been added, drawn from the catalogue of a splashy, white-market supply house (Ed: No sourcing — but thanks for all the fish!). Who says clandestine chemists have all the fun?
    Many more links (SWGDRUG, Project Response, etc.) to forensic analyses of seized samples have been added. Thanks Pete.
  • 1 Nov 2019
    Almost 300 additional structures have been added, drawn from the literature by content specialists PN and JW.
  • 28 Aug 2019
    Previously on the search page, pressing the ESC key or clicking anywhere outside of the structure editor modal would summarily close the editor, discarding your work. That’s never proper behaviour for software. Now, the editor modal can be closed using either of the buttons at bottom right, or the close icon × at top right, and that’s it.
  • 7 Aug 2019
    I’ve fixed a long-standing design failure on the explore page. Previously, the link between the explore and read pages for book II compounds was quietly buried in the main navigation at the top of the page where it was only too easy to miss — I’ve done it myself, more than a few times. Credit to SB for prompting me to finally fix this by adding a second, explicit link to the read page for all book II compounds.
    Long overdue thanks to Peter for his latest iteration of refinements to the structural diagrams.
  • 22 June 2019
    The site was not fully functional for several hours today following a server upgrade to MySQL. Sorry about that.
    The behaviour of the search page has changed:
    • A snapshot of the most recent search is now linked to the browser’s history, meaning it’s not lost when leaving the page. Navigating back to the search page restores the searched-for structure and the search results without having to redo the search.

      Though an improvement on the old behaviour it falls short of the behaviour seen with static pages. In particular, only the most recent search result is available to the browser history. Thus, search for A; goto page X; search for B; goto page Y; go back (results for search B are shown); back (to page X); and finally back again (results for search B, not search A, are still shown.
    • When a search is bookmarked the results of the search are now saved along with the structure. This allows the results of bookmarked searches to be recalled quickly without having to rerun the search.
    • Search results now include the date and time the search was done. This is intended as a reminder that bookmarked search results may not be current.
    • Bookmarked searches, previously saved as cookies, have migrated to the browser’s local storage. Note: Results were not kept for past bookmarked searches saved as cookies. These will need to be rerun to see the results, and bookmarked again to save the results.
  • 16 June 2019
    Four structures having deuterium atoms are now properly rendered, with 2H instead of D.
  • 10 June 2019
    Pete has further refined, normalized, and tweaked the structural diagrams to afford an appealing, consistent look across the site while respecting the integrity and boundaries all rings, no matter how fused!
  • 20 May 2019
    Pete has redrawn over a thousand tryptamines, indoles, β-carbolines, and friends to better reflect their true geometry, i.e. doesn’t really look like quinoline after a tragic encounter with a riding lawnmower — no matter how often it’s drawn as if pinned to the hexagonal grid by some occult hand. (That still makes me laugh, Arabo :)
    The search page template structures have been dehydrogenated and redrawn and/or replaced. Hydrogenation is now easily done with ChemWriter (see 12 Nov 2018 below). The impetus for adding two β-keto structures (cathinones) was an e-mail from reader Claude earlier this year.
  • 7 May 2019
    The arylcycloalkylamines, cannabinoids, and fentanyls landscape pages are working better. They had been omitting compounds without a trivial or code name. Said compounds are now listed after the named compounds (when sorted by name).
  • 4 May 2019
    About 100 new structures including exotic cannabinoids, prophetic tryptamines, and six degrees of fluorolintane.
    Almost all of the library page links that were broken have been repaired.
    Bluelight has been thoroughly upgraded, with a swell new look! All links to bluelight.org have been updated.
  • 20 Apr 2019
    I’m sorry to say it but… I fucked up.
  • 16 Apr 2019
    Over 125 new compounds have been added, along with their corresponding links to the literature. Credit and thanks to Pete.
    Structures are being redrawn in line with contemporary standards (as much as there are any, in practice.) Significant changes include:
  • 30 Mar 2019
    I cannot seem to quit fussing with the search box, trying to make it better. From systematic chemical names to obscure initialisms, a simplistic “exact match” search algorithm just doesn’t cut it. About a year ago I started using a “fuzzy match” algorithm that ignores certain characters. In this way, search has a better chance of matching names that are, you know, “substantially similiar.”
    As more and more characters were deemed ignorable, the algorithm has gotten incrementally fuzzier. I think the search box is now as fuzzy as it’s going to get using this approach.
    The search box now uses both exact and fuzzy algorithms when searching. The more exact matches are listed first, and things go fuzzily downhill from there. So what’s left, what still matters?

    Only letters, digits, Greek letters, and spaces matter. Everything else is ignored by the fuzzy search algorithm (though ^ and $ can still be used.)

    So this search: ^3 aminoethyl indole$ with match this name 3-(2-Aminoethyl)indole. and more-or-less any name which:
    • begins with 3,
    • contains aminoethyl, and
    • ends with indole.

    For example: 3-[2-(Dipropylamino)ethyl]indole, 3-[2-(Isopropylmethylamino)ethyl]indole, and many others.
  • 17 Mar 2019
    Hundreds of new links to analytical data have been added. Credit and thanks to PN for pulling all this together.
    Roughly 75 novel benzos having specific affinity for the α5 GABAA receptor have been added to aryldiazepines. Thanks to content specialist JW for compiling these, and bringing me up to speed on the nuances of GABAA.
  • 3 Mar 2019
    Loads of new structures from prophetic to forensic, or simply noticed in the wild, have been added.
    Loads of new links to journal references and the analytical data of European Project Response have also been added.
    Fixed a bug in structure search that led to charged substances (i.e. ions or salts) being overlooked. The fault was mine, and not of the third party MOLDB search code. Fortunately, I’ve only about two dozen charged substances. Sorry for any inconvenience.
    Fixed a bug with the name lookup box causing it to crash in some cases.
    Structural diagrams saved as Scalable Vector Graphics (SVG) images now have a white background.
  • 11 Jan 2019
    For coders only: The MySQL database has been converted to use utf8mb4, the one true encoding for Unicode. Previously it used the despicably named, false, and untrue utf8 encoding! Yes, I was shocked, shocked! too. When frigging around with char sets one of two outcomes is likely: i) catastrophic failure or, ii) nothing at all. Cheers, so far, to the latter.
    BTW, that thing to the left that looks like a 55 gallon drum is, presumably, a nostalgic nod to the days when “database” was synonymous with banks of honking big hard drives each the size of a fridge with removable disk packs. Big ones. Good times.
  • 30 Dec 2018
    Over 11,100 IUPAC names have been regenerated, scrutinized, and flagged according to two criteria:
    • Adherence to the Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 (the “Blue Book”), and
    • The overall approach used to construct the name. So, what does that mean? I’m glad you asked that question.
    Chemistry is a vast science with many long-standing traditions, some well-entrenched in the language of chemistry to this day. IUPAC has the vexing problem of devising a well-defined, unambiguous protocol for applying relatively simple, systematic rules to construct a unique name for each and every compound.
    At the same time, they must acknowledge the thousands of so-called trivial or non-systematic names in the quotidian language of chemists. Those names, however capricious and arbitrary, cannot simply be legislated away. That’s not how living languages behave. The only workable solution is to compromise, but at the cost of complexity. The Blue Book has grown from roughly 550 pages in 1979 to over 1550 pages by 2013.
    The software used here to generate IUPAC names has settings directing the approach used in constructing a Preferred IUPAC Name (PIN). Depending on those settings the name may…
    1. Be ruthlessly systematic, adhering as best it can to the IUPAC 2013 rules, eschewing most trivial names.
    2. Embrace the conventions of naming selected alkaloids, steroids, and terpenes.
    3. Embrace the conventions of naming carbohydrates.
    4. Embrace the conventions of naming amino acids and peptides.
    I’ve tried to include IUPAC names constructed using each of these approaches, though practically speaking only the first two find much application to the compounds on this site. I’d like to thank Pete for doing the work that was a prerequisite to regenerating the IUPAC names programmatically.
    Links to Wikidata have been added for the roughly 1670 compounds having a page there. I would suggest taking Wikidata with a grain of salt — I found more than a few mistakes, though of course the same can be said about ChemSpider and PubChem.
  • 28 Nov 2018
    Substance names on the explore page are ordered a bit more rationally then before.
    Names based on a natural product parent name like have been changed to follow IUPAC conventions for such names. It’s mostly about stereochemistry, which is handled differently in these names than in a fully systematic IUPAC name. It’s also pretty simple — For example, the name for changes from (8β)-N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide to N,N-Diethyl-6-methyl-9,10-didehydroergoline-8β-carboxamide.
    Most IUPAC names that incorporate the retained name of a natural product parent, an amino acid, or a carbohydrate, are now flagged like so
  • 12 Nov 2018
    There’s a new tool in the ChemWriter structure editor on the search page. The saturate button
    (tucked in with the selection lasso
    at top left) will saturate an atom or group of atoms with hydrogen. This is invaluable for fine-tuning a substructure search. Many thanks to Richard Apodaca for this wonderful addition to ChemWriter.
    Dozens of designer tropane bicycles have been added alongside the classic prototype model, . Thanks to James and Peter for the assembly and curation of the collection.
    Minor under-the-hood tweaks to the HTML to help speed double-click cut-and-paste operations.
  • 1 Nov 2018
    Structures on the explore page can now be saved as a Scalable Vector Graphics (SVG) image. In the Chrome browser, with the mouse over a structure, the right-click context menu should now include options to Open image in a new tab, Save image as..., etc. I hope to extend this functionality to ChemWriter rendered images throughout the site before long.
  • 17 Oct 2018
    The name search box is a now a bit smarter still, extending the described previously “fuzziness” introduced on 31 May 2018 to all searches. Previously, fuzzy matching was used only for so-called “exact” searches, i.e. with a leading or trailing equals sign (=). Now it’s done in all cases. The minutae are not important. I hope it just works better than before.
    Alternative IUPAC names have been added for about 100 substances (mostly synthetic cannabinoids) that can be viewed as derivatives of amino acids. For example, either of these names is correct for :
    • Methyl (2S)-2-{[1-(5-fluoropentyl)-1H-indole-3-carbonyl]amino}-3-phenylpropanoate
    • Methyl N-[1-(5-fluoropentyl)-1H-indole-3-carbonyl]-L-phenylalaninate
    Viewed as amino acid derivatives, the names are often shorter. The drawback is you have to know the structures of 20-odd amino acids to interpret the names.
  • 4 Oct 2018
    The PiHKAL · info home and TiHKAL · info home pages are updated a bit, drawing your attention to these spectacular new editions from Transform Press!
    The explore pages now include SMILES. Unlike with an InChI where there is only one for a given molecule there are typically many ways to compose SMILES. The SMILES used here are, according to OpenBabel, the “canonical universal” forms. These have some advantages, albeit more theoretical than practical ones.
    Also on the explore pages, pages taken from the Shulgin lab and pharmacology notebooks have been moved to a tab of their own. Previously these were a jumble of offsite links and local image or pdf files, extracted from pharmacology books 1–5 (p1–p5) and chemistry book 8 (c8). Now all the pages link to local pdfs, with many more pages from additional notebooks in the works.
    Subscripts and superscripts in formulae (e.g. C3H8N+) are now written in HTML using <sub> and <sup> tags. In HTML4 this was considered bad form, but since HTML5 that’s all changed and it’s now OK! Just saying. It probably looks the same as before but allows for more intellegent cutting and pasting. Just saying.
  • 31 Aug 2018
    Heaps of new content, so much I’ve mostly lost track. I blame Boom Festival.
    PN has indexed dozens of new and classic papers. Two of Sasha’s are particularly interesting, yielding many novel (if obscure) compounds: The narcotic pepper — The chemistry and pharmacology of Piper methysticum and related species, 1973 and Psychotomimetic agents. In Psychopharmacological Agents, 1976
    The arylcycloalkylamines and cannabinoids landscape pages include new compounds contributed by content specialist JW.
  • 16 July 2018
    My colleague Peter is making short work indexing library page references, both new and historical, adding many new structures and links to the site.
    The arylcycloalkylamines landscape has grown by about 40 compounds. Content specialist-at-large JW very thoughtfully disinterred said compounds from Wikipedia after they had been “scrubbed by the WP:MEDRS Taliban.” Thanks JW.
    The smarter name search box behaviour described on 31 May 2018 below has been tweaked a bit further. It now disregards prime (′), double-prime (″), and triple-prime (‴) characters in addition to spaces and hypens when doing an "exact" search by name. This is particularly helpful with code names for variously substituted three-ring arylcycloalkylamines like .
    The convention adopted here for arylcycloalkylamines is to use:
    Elsewhere though, different conventions are followed with respect to primes. The point being you can find the above three compounds by typing =3-MeO-PCP, =2-Oxo-PCP, and =4-HO-4-Ph-PCP, respectively. For that matter, =3meopcp, =2oxopcp, and =4ho4phpcp works too.
  • 16 July 2018
    All Isomer Design websites were offline for at least eight hours due to a problem at InMotion Hosting. Sorry. I wish they were a bit more on the ball sometimes.
  • 20 June 2018
    Still more new compounds and links thanks to my indefatiguable colleague Peter.
    Bitmapped structural diagrams are now embedded in the page as inline data rather then fetched as individual .png files.
    A search page structure can now be copied to the clipboard in molfile format by clicking the button at the upper left of the structural diagram. This functionality has been available from the explore page for a while.
    Both the explore and search pages now truncate long names with an ellipsis (…) in an attempt to keep the banner contents from overflowing.
  • 5 June 2018
    The explore page banner has new navigation controls, and , for stepping through search page results. Imagine your last search turned up structures x, y, and z. In that case, new controls on the explore page for x, y, or z can be used to step forwards (from x or y) and backwards (from y or z). This behaviour remains in effect until the next search or the browser is closed.
  • 3 June 2018
    Many, many new compounds have been compiled, and links added, by my inimitable colleague Peter. Thanks Pete!
    There’s a new arylcycloalkylamines landscape page containing about 130 compounds sharing, to some degree, the structural motifs of the prototype compound .
  • 31 May 2018
    The name search box is a now a bit smarter about what “exact” means when searching by name, i.e. with a leading or trailing equals sign (=). The thing is, there’s different conventions for names, particularly code names, with regard to spaces and hyphens. Take for example.
    Here, it also goes by 3-FPM and PAL-593, but elsewhere it might be named 3F-PM or PAL 593. Previously those names wouldn’t match using an exact search, but now they will because now spaces and hypens “don’t count,”=3FPM, =3F-PM, =3F PM, even =3-F-P-M will all match 3-FPM. Likewise, =PAL593, In this way, =PAL 593, =PAL-593, etc will match PAL-593. I hope this will reduce “false negatives” when searching.
  • 29 May 2018
    The behaviour of the explore page has changed. Now, clicking on the structural diagram of the title compound leads to the search page for the same compound (as does clicking on search in the top navigation bar. Previously, clicking on the structure opened a new window with two 3D depictions of the structure. That functionality has been moved to its own tab labelled 3D depiction. I hope this new behaviour is more intuitive for readers.
    Further internal cleanup has significantly improved the loading time of the explore page.
  • 22 May 2018
    The top navigation bar is slightly enhanced, providing a visual cue to your location.
    The library page is, I hope, much improved by replacing the unwieldy dropdown lists with auto-complete fields, for author and journal.
  • 8 May 2018
    Fixed the Clear form button on the library page.
  • 2 May 2018
    The URL of the library page now mirrors the settings for Author, Journal, Sort, and so on. Though it looks a bit of a mess this has two happy consequences:
    1. The settings are preserved in the browser’s history. Thus, after navigating to another page and returning using the browser’s back button you really do get back to the same page with the same settings as before. Similarly, the settings are not lost on a page refresh.
    2. With everything in the URL the settings can be saved as a bookmark, e.g. journal articles, S. Brandt, most recent first.
  • 29 Apr 2018
    Hundreds of new links and substances have been compiled by my colleague Peter, many from the EMCDDA annual reports on New Drugs in Europe.
    The search box now recognizes an InChI key (or prefix) and will search for matches. Thus, you can type or paste, for example, OOBHFESNSZDWIU-UHFFFAOYSA-N (or OOBHFESNSZDWIU-UHFFFAOYSA, or OOBHFESNSZDWIU) to search for .
    Two new buttons for InChI searches on the explore page. A bit more functionality and easier to find, inspired by the very clean design of EPA Chemistry Dashboard.
  • 27 Apr 2018
    The library page is back to normal after a few days of not being fully present. Sorry.
  • 26 Apr 2018
    A substantial internal cleanup of the code has been rolled out, ergo There Will Be Bugs. Please bear with me, things ought to stabilize within a few days.
    The explore page no longer attempts to find analogues of the target compound at various substituents. Those results have not been exhaustive since the new structural search page was released quite a while ago. I thought it more misleading than helpful to report just some of the analogues. The page will certainly load faster now.
    The name lookup search box may have seemed intolerably slow lately, and it was. That’s been fixed, as has the “goto” shortcut syntax with names having Greek letters, e.g. alpha-pvp= will now match α-PVP. The home page statistics have been changed.
  • 1 Mar 2018. So, this happened… Too

    PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra

    Stephen J. ChapmanORCID IDhttps://orcid.org/0000-0002-0617-4330. DOI: https://doi.org/10.16889/isomerdesign-5
    1H NMR spectra of 43 alleged psychedelic tryptamines (2-(1H-indol-3-yl)ethan-1-amines) and benzofuran analogues (2-(1-benzofuran-3-yl)ethan-1-amines) from grey-market internet vendors across North America and Europe were acquired and compared. Tryptamines having mono- or di- alkyl, cyclopropyl, or allyl amine substituents and/or substitution of the indole/benzofuran ring by acetyloxy, hydroxy, methoxy, or methyl groups were analysed. 1H NMR spectra for some of these compounds have not been previously reported to my knowledge. The spectrum of each analyte is consistent with the compound as labelled and sold. None of the analytes was found to be unequivocally misrepresented. This collection of experimentally uniform spectra may help forensic and harm-reduction organizations identify these compounds, some of which appear only sporadically. The complete spectra are provided as supplementary data.
  • 17 Feb 2018
    Some cosmetic changes have been made here and there, mostly minor, involving Bootstrap and an 11th-hour, on-the-fly conversion to Font Awesome 5. If you see something that looks like this , that’s a Font Awesome thing I’ve yet to do.
    Links to dozens of Bluelight “Big and Dandy” threads have been added, and more are coming. Big props to the Bluelight crew/mods/admins for maintaining this invaluable history. I get a bit choked up reading old NBOMe threads — why, it seemed like only yesterday they were the Big New Thing! “And then one day you find, ten years have got behind you.”
  • 7 Feb 2018
    Happy Birthday, Jack!
  • 20 Jan 2018
    The rendering of structures in 3D/space-filling form has changed. The energy-minimization calculation has been delegated to the JSmol rendering software, which crunches the numbers in real-time. It takes about 30 seconds and is kind of cool to watch. Try it on any of the above three compounds by clicking on the name, then on View … in 3D.
    On the explore page, clicking on the structural diagram now displays the structure in 3D/space-filling form.
  • 5 Jan 2018
    My thanks to DH for identifying 16 additional links to PsychonautWiki, and for suggestions on URL rationalization—something to think about.
    I’ve added links from several of the newly added and compounds to Compounds related to pethidine--IV. New general chemical methods of increasing the analgesic activity of pethidine. Despite being published almost 60 years ago, it’s still a useful overview of the structure-activity relationships for this group of compounds. Paul Janssen, after all, was the extraordinarily prodigious medicinal chemist who discovered fentanyl, haloperidol, and many other drugs that changed medicine.
  • 31 Dec 2017
    About 40 compounds related to and have been added, drawn from drug law schedules and/or compiled by content specialist JW (Happy New Year, JW!). I’ve tried to follow a consistent style for these guys, and a few pre-existing compounds have been redrawn to match.
  • 25 Nov 2017
    The fentanyls landscape has expanded to 215 substances. Content specialist JW has been surveilling the well-known, white-market research chemical vendor. All you lesser-known, not-so-white-market vendors, pay no attention!
    With so many opportunities for substitution on three rings and two chains, I’ve tried to impose some conventions for the names of these guys. Let’s hope this diagram is truly worth a thousand words, but the gist of it is:
    Generic fentanyl structure
    • Ortho, meta, para, (o-,m-,p-), or single primed numeric locants refer to the amide-attached phenyl ring, shown bracketed in orange,
    • Normal (unprimed) numeric locants refer to the piperidine ring, shown bracketed in green,
    • Double primed numeric locants refer to the tail-attached phenyl ring, show bracketed in violet,
    • Alkyl tail substituents get α and β, and
    • Propanoyl (propionyl) substituents are occasionally referred to using α′.
    Special thanks to my shy correspondent for pointing out an intriguing new approach to the Holy Grail of Med Chem—analgesia without all that other stuff: A nontoxic pain killer designed by modeling of pathological receptor conformations.
  • 15 Nov 2017
    About a hundred benzos have been added to aryldiazepines. Big thanks to content specialist JW for hitting the books to find them. Eight new cannabinoids have also been added: cannabinoids.
  • 9 Nov 2017
    About 20 new substances have been added, mostly drawn from reports by European Project Response. A good chunk of these new cannabinoids and fentanyls appear to have originated from a well-known, white-market, research chemical vendor—not that there’s anything wrong with that.
    Coverage of European Project Response compounds and reports is near total, with links to over 530 analytical reports.
  • 6 Nov 2017
    With 4607 cross-references to 2206 unique substances, the Phenethylamine: Von der Struktur zur Funktion page is now done! Almost all of this massive compilation, transcription, and sequencing job was done by PN.
    Formatting of cross-references to Phenethylamine: Von der Struktur zur Funktion on the explore page is improved.
  • 27 Oct 2017
    Inter-recipe navigation on the read page is improved somewhat.
    About 100 new substances have been added, sifted from the archives by content specialist JW. So remember, if any of these should turn up in future EMCDDA alerts, you saw it here first!
    Silent partner PN wrapped up another batch of cross-references, corrections, and sequencing to the Phenethylamine: Von der Struktur zur Funktion page, with more on the way soon.
    A substance that appears on the essential oils page, the peyote alkaloids page, or one of the newer “collection” pages (e.g. fentanyls) is now also tagged as such on the explore page for the substance, e.g. Tags: Fentanyl.
  • 16 Oct 2017
    Some minor changes to the site design and layout have been made:
    • The (HTML) page titles have been rearranged to put the most pertinent information first.
    • New entries aryldiazepines and fentanyls join cannabinoids in the go drop-down menu of the top navigation bar. The intent of these pages is to provide a quick view of substances having similar pharmacology but lacking a single, easily defined common substructure that can be searched for.
    • All of these pages now sort the structures by name, rather than by substance ID as before.
  • 20 Sept 2017
    About 20 new substances and over 550 more links to Phenethylamine: Von der Struktur zur Funktion have been added. Credit to PN for compiling and sequencing all that, not to mention finding some incorrect structures that had gone unnoticed for a long, long time. Thanks Pete!
  • 16 Sept 2017
    About 60 new substances have been added including many tryptamines from Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT2A-Rezeptors aus der Klasse, a dozen cannabinoids recently observed in the wild, and some of its analogues, and—hot off the pill presses—the latest word in thienotriazolodiazepines: .
  • 5 Sept 2017
    About 50 new substances and 120 new links have been added, most to analytical reports from European Project Response or Wikipedia.
    About a dozen substances listed in chapter 5 part 1 of Phenethylamine: Von der Struktur zur Funktion that were inadvertently skipped have been found and added. Sorry PN, my fault.
  • 28 Aug 2017
    Links to 85 more analytical reports from European Project Response have been added.
    Several papers pertaining to cannabinoids have been added to the library page, and roughly 115 cannabinoids are now linked to their referring paper. Substance pseudo-names modelled after DOIs have been expunged.
  • 20 Aug 2017
    Roughly 135 β-oxo (cathinones) and other β-substituted compounds have been added. Massive thanks to JW for drawing these.
  • 9 Aug 2017
    The 561 structures in chapter 8, parts 0–4 of Phenethylamine: Von der Struktur zur Funktion are now numbered to match the text. Also, a great many pages that I had erroneously listed as part of chapter 9 have been moved to chapter 8 where they belong. Big thanks to PN for his painstaking work and troubleshooting.
  • 6 Aug 2017
    At an intoxicating 10561102 compounds, I do hereby proclaim the JW cannabinoids compilation complete!
    Best IUPAC Name Award goes to compound , both for sheer length (174 characters including Isomer Design Markup Language™) and for employing the “lambda (λ) convention.”
    Compound also deserves special mention for Most Enthusiastic Deployment of Superscripts:
  • 2 Aug 2017
    JW’s cannabinoids compilation now stands at 958 compounds.
    IUPAC name formatting and sorting is improved for compounds with primed stereogenic locants, e.g. (1′R,2′R)-5′-Methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro[1,1′-biphenyl]-2,6-diol. Previously the stereodescriptors of primed locants were not italicized, and the stereodescriptors were not ignored (as they ought to be) with regard to sort order.
  • 22 July 2017
    More cannabinoidsdrawn to perfection by JW—brings the total now to 834 compounds!
  • 17 July 2017
    Further additions and refinements to Phenethylamine: Von der Struktur zur Funktion, thanks to PN. The formatting of this page has been improved, and now includes the number assigned by the text to each compound (this is an ongoing effort and not yet complete). The navigation has also been fixed—an off-by-one error seemed to have crept in there.
    All links to the Drugs-Forum wiki have been pulled, said wiki having been moribund for some years and now, evidently, fully abandoned. On the other hand, a new mechanism is in place to facilitate links to arbitrary webpages of interest, e.g. the link to hyperlab.info on the explore page for .
  • 13 July 2017
    The synthetic qualifier has been dropped from the title of the cannabinoids page, having now grown like a veritable weed to include phytocannabinoids. As always, massive thanks and credit to JW for his meticulous research and industry.
    The search box allows certain Greek letters to be entered by name, and now “Delta” (for Δ) is one of them. For more details about searching by name, mouse over the to the right of the search box.
    Names containing two consecutive Unicode prime characters (′′) have been changed to a single Unicode double-prime character (″) instead. The search box now converts one or two apostrophe (') characters to a single prime or double prime character, respectively.
  • 25 June 2017
    Big thanks to reader W. Snow for providing two prized Fenderson5555 videos: DMT from tryptophan? and Mechanisms and named reactions in 2C-P synthesis. Note: Playback of the latter video in Chrome seems to freeze for me but works fine if downloaded and played locally. Playback in Firefox works for me.
  • 25 June 2017
    Still more synthetic cannabinoid compounds have been added, the total now stands at 640 and you can view them all on the cannabinoids page.
  • 13 June 2017
    Additional synthetic cannabinoid compounds have been added, bringing the current total to 464. Big thanks to content expert JW for drawing the vast majority of these structures.
  • 31 May 2017
    245 Synthetic cannabinoid compounds have been added.
  • 19 May 2017
    My colleague PN has culled dozens of additional structures from Phenethylamine: Von der Struktur zur Funktion. Resequencing of the structures in line with the book also continues apace.
    The background of the button on the explore page is now semi-transparent to avoid obscuring the underlying structural diagram.
    Searching Google for an InChI key () on the explore page is improved by searching for the entire key, i.e. verbatim. This should produce fewer spurious hits by preventing Google from parsing the key.
    With massive help and direction from content specialist JW we’ve embarked on a fantastically ambitious expansion into a vast and unfamiliar landscape: synthetic cannabinoids! It’s a strangely altered chemical space with a distinctive geometry, e.g. indole looks like this:
  • 31 Mar 2017
    The search page has been incrementally improved. The layout is a little more tidy, and some problems with my implementation of substructure searches have been fixed, though others remain. Substructure searching is tricky. Consider aryldiazepines. There are 55 of them included currently, but no single substructure search can find them all simultaneously. In fact, four are required:
    35 of these:
    15 of these:
    4 of these:
    1 of these:
    It would be nice if they could all be fetched in one go, but that’s not as simple as it seems. Something for the future. Anyway, today is International Drug Checking Day. Go on then!
    My thanks to JW (content specialist and QA), Norbert Haider (checkmol/matchmol), and Richard Apodaca (ChemWriter) for their help and enlightening discussion.
  • 23 Mar 2017
    Thanks to PN, my inscrutable colleague, there are now hundreds of new links to almost a hundred new structures from Phenethylamine: Von der Struktur zur Funktion. During the first pass we left out any structures that didn’t meet a certain je ne sais quoi level of PiHKAL-ishness.
    In the book however, Trachsel et al. often meander down interesting side routes, frequently towards compounds that are psychoactive but structurally disparate from phenethylamine, e.g. , (nb. corrected from the book) and .
    We’re aiming to include pretty much the whole nine yards now, as well as improving the order in which structures are presented to more closely follow the book. Aye aye Kirk, that’s indeed a split infinitive.
  • 18 Mar 2017
    More analogues have been added. Some are new, others not so much. None of them are psychedelic as far as I know, but they are much in the news in Canada lately. Pretty damning evidence the Controlled Drugs and Substances Act is working as well as it ever did. Don’t get me started.
    The history of MDMA as an underground drug in the United States, 1960–1979, Passie and Benzenhöfer, is a wonderful read, and spurred me to add almost all their sources to the library.
  • 6 Mar 2017
    Many thanks to reader Jeremy for noticing and reporting (in no small detail) my confusion and disorientation following the recent batch of NMDAR antagonists, in particular , , and . I think it’s sorted now.
    [Note to Jeremy: Regarding , according to The Organic Chemist’s Desk Reference (a really handy thing to have around), propargyl means 2-propynyl or, more properly, prop-2-yn-1-yl. See also Structure activity relationships of phencyclidine derivatives. I suspect the IUPAC name in Morris and Wallach is incorrect and is the intended compound, but who knows? Thanks again, and all the best!]
  • 3 Mar 2017
    More arylcycloalkylamines from Jason Wallach’s thesis are included, but more remain—it’s over 600 pages long.
    About 50 aryldiazepines (e.g. , ) have been added. New ones, or old ones that just never left the lab 50 years ago, keep turning up. There are probably hundreds, even thousands, that were cooked up but left largely unexplored. Just waiting to be mined.
  • 22 Feb 2017
    More N-methyl D-aspartate receptor (NMDAR) antagonists have been added, largely culled from research by Jason Wallach. Arylcycloalkylamines are a whole new wing, really.
    Links to 176 analytical reports from European Project Response have also been added. Hard-core!
  • 15 Feb 2017
    Thanks again to reader Matthew for reporting a mistaken chemical name in the recipe. The recipe has been corrected and the change noted in the text.
  • 13 Feb 2017
    The new search page means this site is no longer constrained as it once was. Still, With Great Power Comes Great Responsibility — and about 40 uncompetitive N-methyl D-aspartate receptor (NMDAR) antagonists recently reviewed by Hamilton Morris and Jason Wallach in From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs.
    The novel behaviour introduced by Google Chrome version 56 (see below) has been resolved.
  • 12 Feb 2017
    Google Chrome version 56 (the current version as of this day) seems to have broken the layout of The Shulgin Index and Phenethylamine: Von der Struktur zur Funktion. At least I think so. All I know is I haven’t touched that code, it worked before the Chrome update and doesn’t work after the Chrome update. So I’m guessing it’s probably the damn Chrome update :/ Sorry, I have to look into this further.
  • 1 Feb 2017
    Added a pile of new substances, more links (Hey Sprites!), and many additions to the library. Three fascinating stories: Addressing the challenges in forensic drug chemistry — Brandt, SD. and Kavanagh, PV, Crystal structure of an LSD-bound human serotonin receptor — Wacker, D. et al., and Sad pink monkey blues by Hamilton Morris.
    Finding isomers on the explore page is now available for every substance; that functionality was lost for a while. Restoring the full former explore-page functionality for every substance will take a while yet. The new search page more than makes up for it, I think.
    Also new on the explore page for 46 substances: links to excerpts from Some Simple Tryptamines by Keeper of the Trout and friends. “More than you need to know.”
  • 9 Jan 2017
    Patched up some title formatting on the library page.
    Note to all authors: Please avoid putting a slash (/) in your titles. My code, you see, doesn’t always handle those properly. Therefore, all of you must change your practice to accommodate this flaw in my design, OK? That’s a trick I learned from the ChemSpider team when I reported their rendering of Muscimol doesn’t align with the names they provide. “That’s just how it works” I was told, apparently without irony.
  • 8 Jan 2017

    The current, the deprecated, and the just plain wrong — A IUPAC sermon (for nomenclature junkies)

    Some of the names commonly used for cathinones, particularly the “latter-day” cathinones that have sprung up this decade, are a ball of mess.
    For instance, butiophenone is not a valid IUPAC name, and probably never was. I suspect it is a recent invention, what linguists call a “back-formation,” patterned after the valid (if deprecated) IUPAC name propiophenone. Propiophenone derives from propionic acid, the older, now-deprecated name for propanoic acid.
    It is easy to see how butiophenone might follow from propiophenone as the name for the four-carbon homologue. In fact, butyrophenone is the analogous name. It derives from butyric acid, the deprecated name for butanoic acid.
    Similarly, pentiophenone is also incorrect. The deprecated name for pentanoic acid, the five-carbon homologue, is valeric acid, from which derives the correct name valerophenone. The trivial name pyrovalerone, for instance, is a contraction of the deprecated (but still valid) name α-Pyrrolidino-p-methylvalerophenone.
    I am indebted to coder extraordinaire Daniel Lowe and his Open Parser for Systematic IUPAC nomenclature (OPSIN) parser, which makes exploring IUPAC nomenclature if not fun, entertaining at least.
    [This sermon has been self-plagiarized (in part) from another website.]
  • 31 Dec 2016
    Added over 225 links to Wikipedia and PsychonautWiki.
  • 15 Dec 2016
    My mate JW keeps feeding me heaps and bounds of new material—the guy’s a psychedelic Merck Index! Look at this for instance Tell me that doesn’t turn you on just looking at it ;)
  • 25 Nov 2016
    Huge thanks to my long-time mate JW for compiling a comprehensive list of exciting avenues for future research. I’m going over it methodically and adding to the collection as I go.
  • 21 Nov 2016
    The search page now retains your last search structure—not the search results, the searched-for structure. You can also “bookmark” up to four search structures using the button. These are all kept in cookies.
  • 19 Nov 2016
    The search page was not returning the complete result set in some cases. It should now. Sorry for any puzzlement this may have caused.
  • 14 Nov 2016
    Two additional phenylethanamine-based “templates” have been added to the search page, replacing the β-carboline and isoquinoline templates for now. These are solely for convenience when composing a search structure, not a constraint—if you can draw it, you can search for it.
    Most of the “explicit” hydrogens have been pruned from the lysergamide search template.
  • 1 Nov 2016
    Almost all of the structures in the Big German Book—Phenethylamine: Von der Struktur zur Funktion by Daniel Trachsel, David Lehmann and Christoph Enzensperger—are now included here. You can view them in the order they are presented in the book here: Phenethylamine: Von der Struktur zur Funktion, and they are linked from the explore pages as well. Full credit goes to my shy colleague PN for painstakingly compiling all this data. PN actually had it done almost a year ago but the great Bootstrapping reinvention put me behind schedule.
    These additional structures can be found using the new search page. However, they will not appear on the legacy search page nor, for the time being, in the analogue tabs of the explore page. I hope to get that sorted out before long.
    A couple hundred new references have been added to the library page.
  • 30 Oct 2016
    The search page has been tweaked a little more, with a button to open the laconic ChemWriter structure editor user guide.
    The results from search and elsewhere where structures are arranged in a grid is now much improved for Firefox and Microsoft Edge.
    The site pretty much demands JavaScript now, there’s no two ways about it. Sorry, old pal :)
  • 19 Oct 2016
    My thanks to sharp-eyed reader Matthew for reporting a mistaken chemical name in the recipe for . The recipe has been corrected and the change noted in the text.
  • 17 Oct 2016
    The library page now lists both the full name and the abbreviated name of journals in the drop-down selection list. The full name of the journals is now displayed when hovering over a journal abbreviation, e.g. N-S. Arch. Pharmacol.
    The problem of 1 Oct 2016 (below) where spurious analogues appeared on some explore pages has been corrected.
  • 7 Oct 2016
    The search page now has eight prototype structures that can be messed with for searching.
  • 5 Oct 2016
    The library page has been reworked a bit and now uses AJAX so the page doesn’t reload for every search.
  • 1 Oct 2016
    Pretty much the whole shebang is now Bootstrapped, the first pass anyway. Yay!
    The search page is completely redone. You can now do full structure and substructure searching, much like ChemSpider and PubChem provide.
    The page uses checkmol and matchmol—free, open-source software from Norbert Haider, University of Vienna—for searching, and ChemWriter for rendering. I’m really quite indebted to Dr. Haider, having used his mol2ps freeware for many years to generate all the png images used on this and my other sites.
  • 1 Oct 2016
    The explore page is showing some some spurious analogues as a result of a hundreds of new structures that are not properly codified in the database. I hope to address this shortly. My apologies for any confusion this may be causing in the mean time.
  • 22 Sept 2016
    Er, I forgot to upload the structures for and . Sorry. Sizing for tall and skinny structures like these has been improved on explore page.
    Pop-up menu spacing on this page is improved.
  • 5 Sept 2016
    Formatting is improved for the DOSAGE paragraph in the entries for DMT, 5-MeO-DMT, 5-MeO-MIPT, and α-MT. It was a bit rough and ragged.
  • 22 Aug 2016
    Thrilling news: Freshly regenerated 2013 Preferred IUPAC Names (PINs), now with even more rigour than before! For the legion of chemistry geeks who care deeply about such minutia (shame on the rest of you), here are the most exciting bits:
  • 20 Aug 2016
    An explore page structure can now be copied to the clipboard in molfile format by clicking the button at the lower right of the structural diagram. It needs JavaScript to work (Sorry, my old pal.)
    The explore page name-search inline form has been Bootstrapped.
  • 12 Aug 2016
    I’ve got rid of the now rather dated “spotlight effect” when hovering on an explore page structural diagram, and structures on this page are now rendered by ChemWriter.
    Chemical names have been fully converted to IDML from HTML and searching by name is improved. Search finds any name that contains all the “pieces” (i.e. any fragment of a name) you type, anywhere within the name. For Greek letters, use either the Greek character itself, or the name of the letter: alpha for α, beta for β, gamma for γ, lambda for λ, xi for ξ, or psi for ψ.
    A caret (^) will match the beginning of a name: ^ethyl will match ethyl ether but not methyl ether. Similarly, a dollar sign ($) will match the end of a name: mescaline$ will match thiomescaline but not mescaline citrimide. To match the whole name, type ^name$, or just =name.
  • 29 July 2016
    Cross-references from the explore page to The Shulgin Index page now link to the corresponding table and page.
  • 24 July 2016
    It seems like only, oh, barely 50 months ago I was just about ready to finish incorporating The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds into PiHKAL · info. Huh. So anyway, it’s ready now: The Shulgin Index.
    The Shulgin Index page is somewhat of a departure from the rest of the site. The structural diagrams are rendered quite differently. Instead of using static raster images individually fetched by the browser, these are rendered as Scalable Vector Graphics (SVG) dynamically generated in the browser using a JavaScript component called ChemWriter. So they look a little different.
    For one thing, the “bond length” is no longer constant and as a result the image expands to fill the space available in the “bounding box.” Also, being vector images lines remain perfectly smooth at any magnification, i.e. diagonal lines do not start looking like a staircase as you zoom in. Still, it takes getting used to and not everyone (cough, cough, JSHater) is going to be thrilled about the gosh dang JavaScript. It’s very fast though, very, very fast. For those who care to, if you look under the hood at the page source you’ll see whence the structures derive: in-line .mol files. Rather neat really.
    The page will render without JavaScript, not perfectly but in some form. The navigation works with or without JavaScript. Also, there are bound to be some discrepancies from the text. If you spot any, I’d be very grateful if you’d fire me a quick alert.
  • 26 June 2016
    Thanks to my friendly ghost for donating to the library page—which has its sort controls back finally.
  • 20 June 2016
    Big thanks to reader AK for discovering and reporting an insidious bug (gasp!) in my code. I was not taking into account deuterium (or tritium) when reporting a chemical formula or calculating a molecular weight, leading to incorrect values for and , for instance. The code now handles isotopes of hydrogen properly. Also, the molecular weight is now rounded to three decimals.
  • 20 June 2016
    The former search page skeletons images for phenylethanamine structures are back, sorry for any WTF inconvenience during their absence.
    Structures and have been assigned the correct skeleton codes for searching.
  • 18 June 2016
    Ten new references and about 120 new links have been added, with many more links to Sasha’s Sprites at PsychonautWiki.
    The under-the-hood conversion of chemical names to IDML (Isomer Design Markup Language™) from HTML is plodding along. This could be the biggest thing since… Esperanto.
  • 28 May 2016
    The PiHKAL · info home and TiHKAL · info home pages have been Bootstrapped.
    The explore page has been much overhauled and Bootstrapped. This is a first pass; let’s see how it works out.
  • 16 May 2016
    My thanks to Tim Cosgrove for noting I had mistakenly been using an en-space (&ensp;) where a non-breaking space (&nbsp;) was called for. “Given enough eyeballs, all bugs are shallow.
  • 10 May 2016
    The peyote alkaloids page has been Bootstrapped.
  • 29 Apr 2016
    The essential oils page has been Bootstrapped.
  • 21 Apr 2016
    Still a few bugs on some read pages, as one reader discovered and reported. Thank you, dear reader; the description of is restored.
  • 20 Apr 2016
    The new read page nav bar seems OK. I’ve refined it a bit. What it lacks in style it makes up for in flexibility and responsiveness. The history, browse, and library pages now use it; other pages will be follow.
    The glossary page has been split off from the read pages. Embedded glossary terms use simple HTML title attribute tags for now; Bootstrap pop-ups may be added later.
    The page footer is now centred properly.
  • 14 Apr 2016
    Aww yeah, the read page has responsive Bootstrap 3 global navigation! It’s nothing fancy, but it seems to work. Page-to-page navigation is back; it still could use a “go to recipe x” control.
    Depending on how this works out, the rest of the site may follow. The pages are styled a bit differently now, we’ll see how that pans out too. Some pages have new “names,” but all URLs remain as before so inbound links should survive. The JavaScript is minimal and there is zero tracking according to Privacy Badger. [Thank you DSR, my friendly ghost, for keeping me in line; I hope you’re well.]
  • 13 Apr 2016
    Oh, yeah? Well, er…, Bootstrap 3 global nav is coming here! Soon…
  • 31 Mar 2016
    Special thanks to one particular looker-on for reporting some dodgy looking blotter. Sheesh, I don’t get away with nothin’ lately!
  • 31 Mar 2016
    This page has a bit less chrome and now works better for the JavaScript-adverse. Big hug to a holy terror , JSHater.
  • 30 Mar 2016
    A much-admired site, countyourculture, now seems inoperative. I noticed this just lately and hoped it might resume, but as one reader reports it does seem gone, gone, gone. Fortunately, the Internet Archive stasis field appears to have caught it. I’ve repointed the links accordingly. My thanks to the reader for the call to action.
  • 24 Mar 2016
    A reader, quite properly, has gently suggested I am Satan’s minion for accepting JavaScript in my site! I have indeed sinned—the site does not degrade gracefully for thee who is without sin and rejects the Dark Lord of inheritance and the prototype chain. I ask forgiveness and will strive to atone. Links on the read pages ought now to work without flirting with evil, it’s a start. I appreciate the reader’s gosh dang generousity of spirit in alerting me.
  • 19 Mar 2016
    Bootstrap has some odd PITA factors I’d not realized—a highly opinionated print stylesheet for one. The read pages ought to print much better now.
  • 16 Mar 2016
    My thanks to wildsnow for reporting an incorrect link on the library page. The repair has the happy side-effect of pushing the previously broken link to the top of the pile along with the erudite Fenderson5555. It also spurred me to finally fix the RETURN TOP thingy at page right. I must have busted it a while back.
    Oh, yes. It’s 2016 now. Has been all year in fact.
  • 12 Feb 2016
    A handful of read pages broken for some weeks have now been repaired.
  • 12 Feb 2016
    Newly recovered Fenderson5555 “Don’t try this at home, kids” video: DOC, DOB, DOI and DOET: Strategic considerations.
  • 29 Dec 2015
    The Boostrapping of PiHKAL • info has come some ways though much remains before even this first pass has stabilized somewhat. After due diligence (a few minutes) to the scope of the project I settled on the tried-and-true DOT.FLY methodology.
    The Great Hazard whenever code, particularly legacy system code, is having work done is the constant lure to fix deeply entrenched design flaws while you’re at it. This is roughly as prudent as getting a haircut and appendectomy the same afternoon but it’s a formidable temptation when confronting some ball of mess from the distant past: What was I thinking?
    Nevertheless, that’s pretty much SOP so I again ask your indulgence during the interesting times ahead. Things that were all but unimaginable 10 years ago are now relatively simple—or so the promise goes. We’ll see. The New! And Responsive! view so far…
    • This history page is much improved, with the content now apportioned as tabs and a bit of loopiness with Font Awesome. May I have a benzene glyph, please?. Both resonance structures? The other three too? Oh, the circley one also, naturally! I’ll be needing those charge-separated forms… What?
    • The PiHKAL read and TiHKAL read pages turned out well, I think. Recipe navigation needs to be put back still.
    • The PiHKAL browse, TiHKAL browse, and SI browse pages look to be in good shape atm.
    • The library page is looking good though you can’t sort the results—that will be put back, it’s only a question of priority.
  • 15 Dec 2015
    My thanks to the shy reader who reported the incorrect name for .
  • 8 Dec 2015
    It appears the hover pop-up menus have, ahem, suddenly stopped working. Sorry about that, further evidence this website may need to be Bootstrapped. Rounded corners are so much easier these days.
  • 8 Dec 2015
    My thanks to the shy reader who reported was masquerading as an amphetamine. I’ve corrected the name—another few bits of entropy banished!
  • 21 Nov 2015
    Home page props to Blotter and PsychonautWiki.
  • 21 Nov 2015
    My thanks to Scientist, M.D. for reporting the depiction of was a methyl short.
  • 7 Oct 2015
    Links are restored I think, with most outbound links now using SSL. Just in passing, Silo42 has moved. If you know what that means, you know what that means. Had to be done.
    My much-virtual colleague PN has for months been going through The Big German Book: Phenethylamine: Von der Struktur zur Funktion by Daniel Trachsel, David Lehmann and Christoph Enzensperger. Apart from the hundreds of new substances and thousands of new links he has compiled (to be added… in the fullness of time…) he found a few balls of mess on this site that have been straightened out. Thanks PN, as always!
    The Comments? Mistakes? button has been busted for a while. Sorry, I think that’s now fixed too. Lurching towards HTML5, without a whole lot of thought really, just glad to be moving away from XHTML <word><letter case="upper">h</letter><letter>e</letter><letter>l</letter><letter>l</letter></word>. It did seem like a good idea at the time; not so much now.
  • 5 Oct 2015
    Some links to external PDFs and such are not working at the moment. They should be restored shortly. Sorry for the inconvenience, it’s only SSL stuff.
  • 27 Sept 2015
    A few dozen links to Blotter and PsychonautWiki have been added. It’s a start…
    DOIs are now displayed according to CrossRef DOI display guidelines. One does strive to follow the rules after all.
  • 14 Sept 2015
    The isomerdesign.com domain is now available via SSL at https://isomerdesign.com. A friendly ghost spurred me on and I’m happy to be so haunted. Still, this was done without a jot of forethought and scarcely more testing. If something suddenly seems broken, it probably is broken. Legacy code, ’nuff said.
    My sincere apologies to Sasha’s Sprites at PsychonautWiki, busily breaking down and describing all things psychonautic. The links are coming my friends.
  • 13 Sept 2015. So, this happened…

    PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra

    Stephen J. ChapmanORCID IDhttps://orcid.org/0000-0002-0617-4330 and Arabo A. AvanesORCID IDhttps://orcid.org/0000-0001-6211-7966. DOI: https://doi.org/10.16889/isomerdesign-1
    1H NMR spectra of 28 alleged psychedelic phenylethanamines from 15 grey-market internet vendors across North America and Europe were acquired and compared. Members from each of the principal phenylethanamine families were analyzed: eleven para-substituted 2,5-dimethoxyphenylethanamines (the 2C and 2C-T series); four para-substituted 3,5-dimethoxyphenylethanamines (mescaline analogues); two β-substituted phenylethanamines; and ten N-substituted phenylethanamines with a 2-methoxybenzyl (NBOMe), 2-hydroxybenzyl (NBOH), or 2,3-methylenedioxybenzyl (NBMD) amine moiety. 1H NMR spectra for some of these compounds have not been previously reported to our knowledge. Others have reported on the composition of "mystery pills," single-dose formulations obtained from retail shops and websites. We believe this is the first published survey of bulk "research chemicals" marketed and sold as such. Only one analyte was unequivocally misrepresented. This collection of experimentally uniform spectra may help forensic and harm-reduction organizations identify these compounds, some of which appear only sporadically. The complete spectra are provided as supplementary data.
  • 1 May 2015
    Some weeks ago I received a kind and engaging e-mail from reader AS. Amid the astute observations and intriguing questions he wondered if I’d ever seen a document he had been seeking? I enjoy the digital gumshoe role and fortunately I was able to track it down. Win-win! (n.b. My initial thought for a Sam Spade × Tim Berners-Lee character simply… couldn’t work.)
    AS then wondered about my “unicorn list,” his clever name for documents believed to exist but stubbornly elusive to find; cited, not seen. Did I have one? I had only two unicorns, really, that I’d pretty much given up ever finding: two articles Sasha co-authored many decades ago, published in the LE-restricted, DEA journal, Microgram.
    I’m especially sore about those because for a brief time in the 1980s, for reasons that made no particular sense, I had “legitimate access” to all of Microgram, as bound, printed journals in the open stacks of the (not public) library of the Ontario Centre of Forensic Sciences (CFS). But I hesitated too long, and the opportunity was lost. OK, I could likely have thrown on a lab coat and bluffed my way back in, but I digress.
    A week or so later I was two unicorns richer. How? How could this happen, as if some occult hand had reached into the CFS library, discreetly scanned Sasha’s work, and to my inbox they fell. I must tell AS about this!
    Turns out many hands were involved, members of a shadowy global alliance reaching into the highest peaks of academia and Contra Costa, including one who remains occult: SC → AS → ? → LK → SB → PD → SC.
    I dare say no more than offer my most sincere thanks to each of you for this gift.
  • 16 Mar 2015
    SB has thoughtfully reported five incorrect dimethylmethcathinone structures, now corrected. Thanks SB, what can I say? It’s… just as you suspected… those damn carrots!
  • 4 Mar 2015
    A handful of exciting new papers from David Nichols, Simon Brandt, and Martin Hansen (and their colleagues) have been added, along with a couple dozen novel N-benzyl phenylethanamines and tryptamines described therein.
    I’ve made some changes to the way names are sorted. It’s a tricky thing because standard database software (e.g. MySQL) will sort these like any other text, i.e. alphabetically. Highly unsatisfactory.
    I’ve tried to follow what I imagine are “best practices,” though I’ve never come across anything remotely like an official standard for sorting. In short, all locants are banished to the end of the name. Nearly everything that is properly set in italics is also banished and punctuation of every kind stripped off.
  • 18 Jan 2015
    Some time ago I managed to get my hands on Sasha’s PhD thesis— The synthesis of several isotopically labelled amino acids —from the library at UC Berkeley. I should note it is not readily accessible; I had pleaded well in advance of my arrival and they graciously agreed to retrieve it from some remote archive so I might have a peek… and hurriedly scan it on-site before handing it back.
    I’ve received permission from Team Shulgin to post it here. As you may have gathered from the title, it has SFA to do with psychedelics; it’s from 1955 after all. Naturally, that’s a bit anticlimactic.
    Still, true to form, Sasha explains on page one the challenges and potential of the then-burgeoning field of radiochemistry. Decades later he would co-author many papers exploring the chemistry and application of radio-labelled psychedelics such as . Research with 11C-labelled DOI analogues continues to this day with the work of Martin Hansen and his colleagues, among others.
    I’ve added a home page badge for Novel Psychoactive Substances: Characteristics, chemistry and pharmacology of all that’s new, an interesting and timely blog. A cut above the norm, in style and substance, I think. Thanks to AA for the tip.
  • 15 Jan 2015
    A former search page bug has been fixed, improving search results involving cyclic amines. Previously, the cyclic amine substituent was not set when using the “search by name” control, leading to overly general search result, e.g. a search for “Phenmetrazine” would return structures having any cyclic amine.
  • 2 Jan 2015
    Happy 2015! Let’s start by getting one thing straight: reader RK thinks there’s a typo in PiHKAL entry for #48 , page 586, second paragraph, last sentence. I think he’s right! Thanks RK.
  • 8 Dec 2014
    Corrected an error in the PiHKAL entry for #97 . Details in the errata section.
    The mistake, in the printed version too, was reported by an Erowid reader to Erowid. They in turn had it vetted before reporting it to me. Thanks to everyone involved.
    This page has been restructered internally. Though it ought to look the same, it will break as a result so my apologies in advance.
  • 1 Oct 2014
    Good news! Reader Billy S. thoughtfully reported finding Total synthesis of lysergic acid one of the breathless drug porn videos from the now defunct Fenderson5555 channel. The resourceful MV quickly responded to my call for help preserving the work. Finally, bestie EV spurred an orgy of activity by donating a dozen more to the collection. Thanks guys! Links to these works have also been restored.
    The core Fenderson5555 oeuvre is now restored and secure but for three works:
    • DOC, DOB, DOI and DOET: Strategic considerations
    • DMT from tryptophan
    • Mechanisms and named reactions in 2C-P synthesis
    As consolation, three additional performances are included. Though somewhat tangential to the main thrust of this site, they’re still porn an important part of the historical record:
  • 26 Sept 2014
    Thanks to ZB who reported a broken link to New Synthetic Drugs Database in an earlier entry on this page. ZB reports the site seems to come and go, and that’s been my experience as well. I’m unsure how actively it is being curated.
  • 23 Sept 2014
    Links to the transcribed pages of Sasha’s Pharmacology Notebook 5 are now up. Thanks once again to PN for his care and diligence.
  • 22 Sept 2014
    My periodic correspondent CC has thoughtfully pointed out an error in my earlier entry on this page about . I am grateful to CC, and to every reader, who finds and reports a mistake, or perhaps suggests a link to a useful resource. Together, we make the site better.
  • 27 Aug 2014
    My thanks to the shy reader who reported an incorrect IUPAC name (now fixed). I do appreciate it, thank you.
  • 26 Aug 2014
    My virtual colleague PN has been indexing the transcripts of Sasha’s pharmacology notebooks as they’ve been completed and published by Team Shulgin and Erowid.
    To mark the release of the Notebook #5, PN’s efforts may now be seen on explore pages at “See also Transcripts:”. The links, listed in {volume}.{page} format, are to transcribed pages in notebooks 1–4. This is a quick-and-dirty implementation; a better one is deserved. But it’s something at least, after too long a wait.
  • 26 Aug 2014
    Links to the sadly vanished Fenderson5555 channel videos have been removed. If anyone managed to save these or knows where to find them, I’d really like to hear from you.
  • 4 Aug 2014
    My thanks to PN for writing up over 40 new references, including the open-access, highly recommended overview and commentary,  The new drug phenomenon by Simon D. Brandt, Leslie A. King, and Michael Evans-Brown, “…dedicated to Dr Alexander Theodore ‘Sasha’ Shulgin and Ann Shulgin, two pioneering explorers and gentle and kind human beings.
    Another addition of particular interest,  Potential psychotomimetics: Bromomethoxyamphetamines and structural congeners of lysergic acid, David E. Nichols’ PhD thesis.
    The library page has a new control, “return top,” to quickly scroll to the top of the page. This was long overdue and since it is so deftly handled by Bill Meyers-Riggs at countyourculture.com… imitation is the sincerest form of flattery.
  • 19 July 2014
    Over 40 new references have been added, including the much sought after notes of an experiment in auto-intoxication—or “trip report”—by Scott Chilton,  The course of an intentional poisoning. My thanks to AA for providing Chilton’s trip report, and to PN for writing all these up.
  • 15 July 2014
    My thanks to Daniel Trachsel for noticing my depiction of was incorrect and I had inadvertently linked it and its α-methyl homologue to his review, Fluorine in psychedelic phenethylamines, instead of the difluoromethoxy analogues and . I’ve also added code names I’d previously overlooked for a couple of the novel compounds in Daniel’s review. I believe it’s all straightened out now.
    Sorting of systematic names containing the symbol ξ (Greek letter ‘xi’) works better now. No doubt many readers have been fuming for years over that.
    IUPAC names have been tightened up in line with Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013. I quoth, chapter and verse:
    P-14.3.3 Citation of locants
    “In preferred IUPAC names (PIN), if any locants are essential for defining the structure of the parent structure or of a unit of structure as defined by its appropriate enclosing marks, then all locants must be cited for the parent structure or that structural unit. For example, the omission of the locant ‘1’ in 2-chloroethanol, while permissible in general usage, is not allowed in preferred IUPAC names, thus the name 2-chloroethan-1-ol is the PIN.”
    Thus we must now write, for example, 2-phenylethan-1-amine whereas before we got away with just 2-phenylethanamine. The rule goes on to list special cases and edge conditions where an implied locant ‘1’ is still the rule. I’ll spare you.
    P-29.6.3 Retained prefixes no longer recommended as approved prefixes
    The contraction phenethyl is now officially passé, along with isobutyl, sec-butyl and several others. Still in good standing: benzyl and isopropyl provided they are unsubstituted. That spells trouble for NBOMe names—adios N-(2-methoxybenzyl)—so I’m circumventing that one for now.
  • 1 July 2014
    I’ve removed the home page link to the Fenderson5555 channel after a shy reader informed me it is no longer available. If anyone managed to save these delightful chemistry lessons or knows where to find them, I’d be happy to host them.
  • 13 June 2014
    Roughly another 50 new references have been added to the library page, with two hundred substance links. Credit and thanks to PN for this.
  • 6 June 2014
    I apologize to anyone who may have been confronted by a blank page lately. I introduced a new bug which I think I’ve now fixed. The former search page was pretty much a write-off; very sorry about that.
  • 4 June 2014
    Rejigged the home page a bit, welcoming a couple of new friends.
  • 3 June 2014
    About 115 new tryptamines culled from (German) theses by Matzdorf, Prainer, and Schumacher have been added. Credit and thanks to PN for his cheminformatic acumen.
    About 50 new references have been added to the library page, again with credit and thanks to PN.
    All articles from the Heffter Review have also been added with links to local copies of the PDFs. Cross references by substance to all this material is planned.
  • 2 June 2014
    Alexander “Sasha” Shulgin began his final trip today. Through his discoveries, his work, his writings, and his teachings, he changed the lives of millions. He, quite simply, changed the world.
    “Think of the things that can change your life,’ asks Dr. David E. Nichols in Science and Sacraments. “You fall in love. Get married. Have children. Maybe, you get a divorce. A child dies. A parent or sibling dies. You take LSD.”
    Meeting Sasha changed my (then) young life. He will forever be, above all else, one of the most generous people I’ve even known.
  • 13 May 2014
    Replaced the busted Facebook button with a simple link. The old button added way too much creepy hidden tracking cruft to the page.
    Fixed still another bug on the library page. And again, 19 May 2014.
  • 4 Apr 2014
    Some poster session abstracts from R. Heim and colleagues have been added.
    Some library page bugs, likely introduced 28 Feb 2014, have been fixed. A textbook example of “If it ain’t broke, don’t fix it.”
  • 7 Mar 2014
    A novel Dimethylaminorex has been added following a report from Interpol and from the EMCDDA. An aside: the two rings conspire to make the nomenclature of compounds especially vexing. The most common convention seen (which is semi-systematic but not pure laine IUPAC ) is to number the oxazole ring using unprimed numerals and the phenyl ring using primed numerals.
  • 6 Mar 2014
    The former search page has been improved, allowing easier searching for structures with cyclic amines. Cyclic amine substituents have been classified according to their core ring structure or size. This simplifies searching for all structures where the nitrogen is, for instance, incorporated into a morpholine ring.
    About 20 structures have been redrawn for consistency.
  • 2 Mar 2014
    Roughly 110 links to 40 new references have been added. Credit and thanks to PN.
  • 1 Mar 2014
    My thanks to reader amethyst for reporting a typo on page 487 of PiHKAL, in the entry for #11 : 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.
  • 28 Feb 2014
    Roughly 90 new substances and 300 links to existing journal references have been added.
    The former search page code name for some Ergoline skeletons has changed and the skeletons reordered. The former system was clumsy, with DH standing for DiHydro or diDeHydro, depending. The new codes use a +/- locant suffix to indicate the addition or removal of hydrogen at the lower of the two locants affected. I hope this will be a little less opaque. Unfortunately this is not “upward compatible;” old search URLs will fail. I concede this would be unforgivable on a commercial website (though it does occur.) I can only ask for your understanding.
    The ordering of authors’ names within the drop-down control on the library page now disregards accents. The result, I hope, is rather more intuitive.
  • 8 Jan 2014
    The former search page bug introduced 6 Jan 2014 has been fixed. I apologize for any frustration this may have caused.
  • 6 Jan 2014
    The entry for has been corrected. My thanks to AA Avanes for reporting the error.
    Entries have been added for a few new substances recently noted in the wild including and .
    Added a new skeleton to “Other” category on the former search page, and rearranged the members somewhat.
    Added over 150 new links to external references. Credit and thanks to PN.
  • 2 Jan 2014
    Added code names for some of the more obscure NBOMe compounds, and also , recently sighted in the wild.
    Corrected the class of a dozen or so substitutents on the former search page.
  • 20 Dec 2013
    Added almost 150 new substances, with links to the literature.
  • 29 Nov 2013
    Corrected the home page layout so it renders properly on very wide screens.
  • 27 Nov 2013
    Over 50 new references and 160 new journal links have been added. A handful of errors are corrected. Thanks to PN, as always, for his ongoing and diligent assistance.
    Nuove sostanze psicoacttive — New Drugs is a very current survey of new drugs in Europe, in Italian, with a strong forensic bent. I’ve partitioned this very large pdf by substance in this index.
    Copyright notices are being replaced by a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License. Go nuts ;)
  • 10 Nov 2013
    Thanks to further help and encouragement from Richard Young, several more incorrect links to PubChem and ChemSpider have been corrected.
  • 9 Nov 2013
    My thanks to Richard Young for spotting and reporting incorrect links from to PubChem and ChemSpider.
  • 25 Oct 2013
    Found an interesting website, New Synthetic Drugs Database, and gave it home page props. Such a lovely clean interface! Nice job, Jan Čermák.
  • 10 Oct 2013
    72 new substances and 90 new references have been added, along with the usual handful of minor corrections. As always, my big thanks to PN for his ongoing and meticulous assistance. If I could keep up with him, this website would be expanding even faster.
  • 20 Sept 2013
    Exciting news, particularly if you read German: Phenethylamine: Von der Struktur zur Funktion by Daniel Trachsel, David Lehmann and Christoph Enzensperger, published by Nachtschatten Science is now in print!
    I’ve revived the links to books listed on the library page; they disappeared for a while. My apologies to anyone inconvenienced by this unfortunate interruption.
    The library page now contains all known issues of the DEA’s Microgram Journal. A bibliographic entry is included for each individual article which links to a local pdf (i.e. not to the DEA website). A link to a local copy of each complete issue of Microgram Journal is also included, these being rather clumsily categorized as an anonymous “book.”
    By 2009, the practice of assembling articles into volumes and issues seems to have gone by the wayside, likely marking the abandonment of the printed edition altogether. I’ll miss those iconic covers with their muscular, ball-and-stick minimalism
  • 1 Sept 2013
    Links have been added to connect some ergolines and related compounds to Lee, The total syntheses of ring-A substituted ergolines, the reference from which they were drawn. My thanks to AA for bringing this to my attention. Note that Lee consistently draws with a 6-methyl substituent, at odds with every other reference I’ve consulted. I’m presuming there is simply a typo in Lee.
    About 100 new links and 20 new substances have been added.
    Codes have been assigned to N-alkyl-2-aminoindanes following the convention Sasha uses for N-alkyltryptamines.
  • 30 Aug 2013
    Links have been added to connect the recent batch of fluorocathinones to the reference(s) from which they were drawn.
    Codes have been assigned to these using a system that is largely an extension of the prevailing practice—for simple ring and N-substituted cathinones only. Bear in mind there is still far too much confusion and disorder in cathinone codes; Sasha and others use a different convention. Please do not treat these names (or indeed any code name) as definitive. Briefly, here’s what I did:
    Several structures with a pyrrolidine cyclic amine have been redrawn in line with the evolving site standard.
  • 26 Aug 2013
    Over one hundred new substances have been added including many ring-monofluorinated phenethylamines and cathinones. These are primarily of interest to the forensic-oriented reader.
    A new phenethylamine-class skeleton, , has been added. Alert readers may recognize the symmetrical depiction breaks with my usual convention and obscures the fact this “new” skeleton is actually just another α-substituted phenethylamine, specifically α-Benzylphenethylamine. I’ve awarded special consideration to this particular structure for aesthetic and practical reasons when, strictly speaking, it might just as well have been folded in with the other phenethylamines.
    A friend has spurred me to revisit—after years of neglect—the “N-bomb” nomenclature mess in an attempt to impose some order on the chaos by following the emerging conventions in journals, Wikipedia and elsewhere. Briefly, here’s what I did:
  • 20 Aug 2013
    I’ve added three new references:
    Some links on this page were repaired.
  • 27 July 2013
    My thanks to the reader who reported a typo on the library page. All the best!
  • 11 July 2013
    My huge thanks to PN for reporting a “fatal error” that has likely existed for weeks. My apologies to every reader who had some idiotic PHP error message splashed on their screen. This time I will fix it.
  • 10 June 2013
    I stumbled across some remarkable documents in quasi- TOR space describing, afaik, four heretofore unknown “eugenoloids” , , and . Not only are these novel materials, the reports look alarmingly like lost chapters from PiHKAL. Be still my heart! Thank you Demonic.
    Added links to all Sasha’s transcribed lab books at Erowid. Super work from a posse of dedicated volunteers.
    E.V., a friend from Psychedelic Science 2013, brought this recording to my attention A Magical Blend—The Shulgins at Home, a lengthy interview with Ann and Sasha. If you want to play it you’ll need something other than iTunes. It’s massive, ca. 750 MB.
  • 27 May 2013
    I’m attaching DOIs to some of the older references. DOIs are a relatively recent innovation but their coverage is expanding as older papers are brought into the fold. Foremost among the newly DOI-ed is the Journal of Psychedelic/Psychoactive Drugs.
  • 17 Apr 2013
    The default sort for references, with the most recently added first, now applies the secondary sort properly.
    Added the structural diagram to the Book II entry for . It has been left off.
  • 28 Mar 2013
    34 new journal articles have been liberated and 62 new substances added, bringing our counts to 1023 and 3057 respectively.
    I’ve taken the liberty of redefining a couple of delightfully silly names coined, as far as I can tell, by Niels Jensen in his thesis: 2CB-FLEA and 2CB-GNAT. I’ve seen these names nowhere else and, pace IUPAC, I think Sasha might easily have named them himself… but for one thing: that pesky α-methyl. So I have rechristened them and and added their 2C and 4-H analogues just because. If you draw them, they may come.
  • 28 Feb 2013
    Flagged a discrepancy between the Erowid and print versions of TiHKAL #23 , spurred by the appearance of this material on the research chemical market.
    3D representations now exist for all substances.
    79 new journal articles have been added, pace. Aaron Swartz.
  • 3 Feb 2013
    Fixed a couple of incorrect references.
    Flagged discrepancies between the Erowid and print versions of TiHKAL #34 , spurred by the appearance of this material on the research chemical market.
  • 23 Jan 2013
    The InChI for each substance has been added and/or verified.
    The InChI key for each substance has also been added and appears on its explore page. InChI keys can be useful for searching with Google etc.
  • 22 Jan 2013
    Fixed a bug on the library page that suppressed results in some cases when filters where used (e.g. author).
    A separate, inscrutable bug on that page seemed soluble only by dropping the period from “Anon.” So I did.
    A reddit button has been added alongside the Facebook button, at the suggestion of a friend and in memory of the late Aaron Swartz and all that he stood for.
  • 29 Dec 2012
    Added about 180 new substances and 50 new references.
    Added Pyrrolidine to the list of frequently used Nc substitutents on the former search page.
    Added Ethyl and n-Propyl to the list of frequently used α substitutents on the former search page.
  • 18 Dec 2012
    Due to unprecedented demand (it was requested in an engaging note from a reader studying cognitive neuroscience), the molecular weight now appears after the molecular formula on the explore page for each substance.
    There are some former search bugs still outstanding; your patience is appreciated while I track these down.
  • 15 Dec 2012
    I’ve added a “badge” to the home page in appreciation of two more sites I quite like:
  • 1 Dec 2012
    Added 100 new tryptamines from Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens, Niels Jensen’s 2004 Ph. D. thesis. The title does not do justice to the wealth of experimental data he reports. Could the N-methyl-N-phenethyl motif be for tryptamines what N-benzyl is for phenethylamines? Space filling (3D) depictions of these new tryptamines, and quite a few other recently added structures, remain to be done.
    Sasha’s lab notebook, excerpts from which recently appeared in Vice courtesy of Paul Daley and Hamilton Morris, is now indexed. I’ve converted the pdf to images for now because, thanks to an acknowledged bug, good ol’ Adobe Reader doesn’t render the pages properly—bravo, Adobe. My thanks to PN for his great work sorting this out.
    My thanks to Daniel Martins for finding Sasha’s 1974 French patent.
    Fixed a former search page bug that erroneously applied the H ⇔ Any button to disabled controls. This led to searches that turned up nada—vexing, if not infuriating! Sorry.
  • 19 Nov 2012
    Fixed some former search page bugs:
    • The grid of individual search structures was sometimes hidden when it should have been visible.
    • The correct “hybrid” structure was not always displayed when multiple search structures were selected.
    • The check boxes used to select locants whose substituents must match was a bit squirrelly in some case.
    Added more lysergamide structures and structure-groups to former search.
    Improved the alignment and names of the β-Carbolines.
    Added ca. 150 new structures and 30 new documents to the library.
  • 26 Oct 2012
    Added some new references, rather less hidebound than usual:
    • Sasha’s 2004 Playboy interview. Huge thanks to my good friend AA who located and donated the pdf! This is a specially redacted edition—all drugs, no sex.
    • Sasha’s 1984 letter to the DEA re MDMA.
    • Several video tutorials by Fenderson5555 on the synthetic chemistry of selected psychedelics.
  • 20 Oct 2012
    Corrected structures 338 and 7188.
    Added two works co-authored by Paul Daley, Hamilton Morris and Ash Smith (1:2:1) to the library.
  • 16 Oct 2012
    Added Sasha’s description of , lifted from a 2004 board posting I just stumbled across! As with , I’ve shoehorned this in as an extra chapter in Book II of TiHKAL when, in fact, neither entry appears in the print edition. The conventional wisdom is both were intended for the Psychedelic Index, that mythical precursor to the radically transformed product, The Shulgin Index.
    Skeleton PEOCA has been renamed CAPE for “consistency.”
    Skeleton BCA has been redrawn to emphasize the inclusion of the α-carbon into the cyclic amine ring.
  • 11 Oct 2012
    The former search page has a new skeleton class, “other,” for structures that just can’t be reasonably lumped in with any of the other skeleton classes. Only limited searching is provided for these extraordinary cases.
    Structures 5217, 5219 and 5221 have been redrawn for consistency.
    I’ve dropped the chapters numbers from names for substances that have a chapter in Book II of PiHKAL or TiHKAL (e.g. #96 M). These names are now set in italics instead. I’m hoping this produces a less cluttered page and avoids confusing chapter numbers with substance numbers. The chapter number is still shown in the mouse-over menu read link for these names.
  • 4 Oct 2012
    Fixed β-Carboline and Isoquinoline former search pages that rendered poorly in Chrome.
  • 20 Sep 2012
    Corrected the name of the sulfinooxy substituent; it had been “carboxy.”
    Corrected the name of the 4-n-butoxybenzo substituent; it had been “4-n-butylbenzo.”
    Corrected the structure of mentioned in the book II entry for DOEF.
    Fixed the alignment of 1237.
  • 17 Sep 2012
    Fixed some bad links to Sasha’s pharmacology notebooks.
    Restored the third (quaternary) nitrogen locant N+ on the former search page. It went missing for a while.
  • 14 Sep 2012
    Restored Facebook chrome.
    Removed PDF icons from library entries. These are little more than visual clutter—and Adobe deserves to be banished, not acknowledged, for their breathtakingly wretched software.
    Corrected the internal representation of structures 2106, 2419, 5210 and 5211.
    The former search pages for tryptamines and lysergamides have been upgraded in line with the improvements for phenylethanamines described previously.
  • 8 Sep 2012
    I’ve added about 165 new substances and over 50 new references.
    On the library page I’ve started to include a link to a Rhodium webpage (HTML) where one exists for the reference, e.g.: Shulgin, AT. Drugs of abuse in the future. Clin. Toxicol., 1 Jan 1975, 8 (4), 405–456. 2507 kB. doi:10.3109/15563657508990076 Rhodium. I hope to clean up these pages in time since many of the external links are long dead.
    The explore pages now includes links to Sasha’s pharmacology notebooks at archive.org, where applicable. Another little bit of synergy thanks to Team Shulgin for publishing the notebooks and to PN, my tireless cyber-associate, for indexing them.
    Substances without a code name or a trivial name now have their “ID” number in the tab in lieu of a proper name. This way the tab’s hover menu is always available.
    Big changes to the former search page for phenylethanamines:
    • I’ve added a score of new skeletons. To keep things manageable I’ve tried to combine skeletons that incorporate cyclic amines (e.g. pyrrolidine, or piperidine) in place of the far more common acyclic nitrogen moiety. These are drawn with a broken circle incorporating or surrounding the amine nitrogen.
    • The substituent drop-down list for cyclic amines, labelled Nc, appears when a cyclic amine skeleton is selected. I’m hoping this approach proves simpler and more intuitive than having to set both N1 and N2 to the same, divalent “bridge;” tetramethylene or butane-1,4-diyl, for instance, to stand for pyrrolidine.
    • To conserve screen space I’ve had to resort to opaque abbreviations of skeleton names. Hover over an abbreviation to see the full name, usually strict IUPAC. Yeah, I know… but I figure it’s past time to suck it up.
    • The names and meanings of the subgroups have been clarified a bit, in particular the meaning of “amine.”
    • I’ve adjusted the depiction of some of the less common skeletons in an effort to keep bonds on the hex grid where practical.
    • The above entailed yet another rewrite of the code. Unfortunately, this ensures two things: 1) your old search URLs won’t work any more and 2) the code is certain to crash even more frequently than before.
    explore page handling of phenylmethanamine (PMA) structures is working properly vis-à-vis the mouse-over “spotlights.”
    In a very, very few cases the explore page may list analogues at locant Rs, i.e. . This is a kind of half-baked measure to distinguish otherwise identical substances that differ in a way too infrequent to implement properly. Translation: it’s a quick kludge.
    Also, on the explore page, cyclic amines that were previously considered N analogues are now considered skeleton analogues.
    Internal changes to the essential oils page, now with, ahem, IUPAC names for the columns (but hover over one to see the old name.)
    Corrected the browse page entry for PK#131 METHYL-MMDA-2.
    Corrected the structure of 5574 and 7177.
    Corrected the internal representation of structures 438, 560, 2456, 5437, 5436 and 5568.
    Deleted/merged duplicate substances including 542, 543, 588, 599, 600, 1201, 1202, 1262, 2423, 5098, 5231, 5234, 5598, 5599, 7222, 7277, 7279, 7280 and 7755.
    Corrected the InChI, InChI keys, PubChem and ChemSpider links for 2442 and 2443.
    Corrected, or let’s say improved, quite a few IUPAC names. In particular, benzodifurans ( and friends) are now named following the style used in The Shulgin Index.
    The InChI and InChI key has been verified for all substances.
  • 16 July 2012
    Links to other pages on the library are working again. They took a week off.
    Added a dozen new references, largely Sasha’s earliest patents but also this intriguing thesis: Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. My thanks to two correspondents for bringing this to my attention.
    My goal is to list all of Sasha’s work here; I mean everything he has published including patents. If you know of something I’ve missed, please tell me.
  • 11 July 2012
    Roughly 140 new structures, 70 new references, and 410 new links have been added.
    library can now be filtered by type (e.g. journal, patent, etc.).
    The most recently added references now appear at the top of the library page. Finally an easy way to see what’s new!
    The former search skeletons Phenylacetic acid and 1-Phenylpropan-2-one have been replaced by 2-Phenylethanal. Coming soon: many more search skeletons including aminorex.
  • 19 June 2012
    Added about 25 new external references including:
    BTW, we’re on Facebook too (I just need to put the buttons back on the banner.)
  • 17 June 2012
    Fixed the browse page—some names from The Shulgin Index had been crammed in by mistake.
    Added 95 new substances and several hundred new links to external references! Note that some of these new substances are sufficiently removed from the current set of structural classes that they cannot be found using the former search page. I’m working on that. My thanks, as always, to my extremely productive colleague for adding the bulk of the new links, among other things.
    Thanks also to my shy correspondent who brought an interesting patent to my attention. I hope to incorporate at least some of that material into the next iteration.
  • 27 May 2012
    Added 45 new references and over 150 new links thereto, again largely thanks to my unassuming foaf who also gently pointed out the difference between EPT and DIBT.
  • 19 May 2012
    Added almost 50 new structures including a few unforgivable omissions such as (something not likely to appear on the RC market any time soon.) Thanks to countyourculture for teaching by example.
    My huge thanks for the prodigious help I’m getting from a very talented (if reticent) friend of a friend.
  • 13 May 2012
    Added about 40 new structures, mostly tryptamines and lysergamides.
    Phenylbutyl is now correctly classed as an arylmethylalkyl rather than an aryl substituent on the former search page.
    Some readers have asked that more attention be given to stereochemistry. I heartily agree and am working towards that, bit by bit.
    Added IUPAC names, and corrected errors in the some existing names, of ergolines.
  • 10 May 2012
    Added over 300 hundred links to dozens of additional journal articles, and much of countyourculture, an outstanding website that’s always a treat.
  • 16 Apr 2012
    Added several new links to Drugs Forum wiki pages.
    Fixed the usual errors and bad links on this page! Sorry.
  • 8 Apr 2012
    I’m making some under-the-hood changes in advance of the (eventual, formal) release of ShulginIndex · info. There may be more than the usual “instability” while I fit everything together. Sorry for any crashes or weirdness you encounter.
    In the mean time, please swan around each and every page of Tables 2–10
    A handful of duplicate structures have been removed, and another handful of incorrect structures have been fixed.
    The newly added structures from The Shulgin Index should now be properly aligned and their space filling (3D) representations available.
  • 27 Mar 2012
    Added about 60 new substances:
    • A series of 5-Ethoxytryptamines from research by Paul Daley et al.
    • A series of 5-Methoxy-2-methyltryptamines, also from Paul Daley et al.
    • Over 30 novel fluorinated phenethylamines from Trachsel.
    Fixed a formatting bug on the explore that may have existed for a very long time.
    The “substance ID” is now displayed in the lower right corner of structural diagrams on the former search page. This can be used instead of a name in the search-by-name boxes when prefixed by “=”, e.g. typing ' =2018’ in the search-by-name box (the substance ID for has the same effect as typing ' =Mephedrone’ in the search box.
  • 22 Mar 2012
    Corrected entry #123 TMePEA in the prototype browse page for The Shulgin Index.
    Changed the chemical names for the B-DFLY, B-FLY, DFLY and FLY entries to match those found in The Shulgin Index.
  • 15 Feb 2012
    Corrected a minor discrepancy, reported by Felix, between the Erowid and printed editions in the chapter.
  • 29 Jan 2012
    Cross references to The Shulgin Index now appear on the explore page for each of the 1374 substances contained therein.
    Note: The alignment of the new images is off a bit. It should be fixed soon.
  • 22 Jan 2012
    I’ve added 803 [sic] new structures to the site, which means everything in The Shulgin Index (SI) is now included! All SI code names are provided as well, as are IUPAC names. Note that the IUPAC names come from ChemSketch and may differ from the chemical names in SI, but in most cases if you can understand one the other should be intelligible too.
    These new structures have no space filling (3D) representations yet. Also, there is at present no cross references linking structures to SI. It’s in the works…
    My sincere thanks to Ron Schwab for painstakingly transcribing SI Tables 2–10, a massive chore I simply couldn’t face.
  • 31 Dec 2011
    The former search page has a new button that toggles substituents between “Hydrogen” and “Any[thing],” the idea being the specification of a search structure can now be approached from either direction.
    The former search page result structures are now ordered by substituent beginning with univalent (ring) locants, followed by divalent (chain) locants, and finally by skeleton. The hope is that similar structures will be grouped closer together than before.
    Sixteen new substances have been added including 11 N-aryl substituted phenylethanamines. I’m indebted to a shy correspondent for bringing these to my attention.
  • 25 Dec 2011
    Corrected the internal representation and structural diagram for .
    The former search page now allows searching for additional classes of substituent:
    • Aryl (Phenyl, Naphthyl, Thienyl etc., including substituted rings, but excluding hydrogenated forms like Tetrahydrofuranyl.)
    • Arylmethyl (Aryl as a substituent of methyl, which may have additional substituents. In practice, it’s usually a 2-substituted Benzyl.)
    • Arylmethylalkyl (Aryl as a substituent of an alkyl higher than methyl, e.g. Phenethyl.)
    • Haloalkyl{oxy|thio} (Halogenated alkyl, alkyloxy or alkylthio. Merry Christmas “FluorinatingAgent!”)
    Note that Alkyl as used here includes cycloalkyl, pace IUPAC.
    2-Methoxybenzyl has been added as a “quick-pick” substituent on the former search page.
    The former search page now tiles result structures to fill the full width of the screen.
    Corrected the spelling of naphthalene everywhere the first h was omitted (hey, even IUPAC gets it wrong sometimes.)
    Printing a read page has been improved, though Firefox behaves strangely, reducing the length of the line with each page!
    Printing a former search page has been improved but it’s still no hell.
  • 4 Dec 2011
    My thanks to Felix for reporting a typo in the chapter, which I’ve now corrected. Sharp eyes, Felix!
  • 27 Oct 2011
    The former search page now allows searching for phenylpiperazines, benzylpiperazines and benzylamines.
    Added , rumoured to be in the RC pipeline (with thanks to Andrew D. for bringing this to my attention.)
    Corrected the internal representation of .
  • 3 Oct 2011
    I have restored the link to the Shulgin book signing which was missing from August Fleishman’s commentary on the home page. The fault is entirely mine and I apologize to August for the error.
    All 23 phenethylamine homologues listed in table 10 of The Shulgin Index have been added, 20 of which are new.
    These, as well as the previously added substances from tables 8 and 9, may appear as skeleton analogues on explore pages. They may also appear within the results when doing the broadest kind of former search, i.e. when the “any phenyl something” option is selected. There remains no way at present to limit the search to phenylpiperazines or benzylpiperazines. However, phenethylamine homologues can be included or excluded using the “3-Phenylpropane-1-amine” radio button
    The internal representation of the two table 10 homologues recently added was incorrect and has been fixed.
  • 24 Sept 2011
    A space filling (3D) rendering is now available for each substance.
  • 18 Sept 2011
    A prototype browse page for the 126 main entry compounds of The Shulgin Index is now available! All 126 compounds are now included in this site, though one cannot yet former search for phenylpiperazines or benzylpiperazines in isolation. Also, the IUPAC names listed here may differ from those in The Shulgin Index, notably those for the “FLY” compounds and friends. Where a discrepancy exists, I hope to eventually list both names.
    Over two dozen ring-substituted cathinones from Osorio-Olivares et al., 2004, have been added.
    A handful of structures from Seggel et al, 1990, have been added.
    The 16 phenylpiperazines listed in table 8 of The Shulgin Index have been added.
    The 22 benzylpiperazines and benzylamines/phenylmethanamines listed in table 9 of The Shulgin Index have been added.
    Two of the homologues listed in table 10 of The Shulgin Index have been added.
    Space filling (3D) renderings remain to be added for almost all the new substances.
    Most of the phenethylamine-class skeleton names on the former search page are now named using IUPAC rules. Slowly but surely…
    My thanks to readers who bring new and interesting substances to my attention. While I fully respect your wish to remain anonymous, I regret that makes it impossible for me to respond directly. Please know I do read and appreciate your comments.
  • 3 Sept 2011
    Fixed the jumbled banners of the essential oils and peyote alkaloids pages.
    About 90 per cent of substances now have their IUPAC name listed on the explore page. The remainder are ergolines and complex natural products.
  • 28 Aug 2011
    The explore page now recognizes stereoisomers of a substance and groups them separately from structural isomers on the explore page. For example, and are now recognized as stereoisomers.
    Fixed the jumbled banners of the browse pages.
    The Standard InChI and IUPAC name for a substance now appear on its explore page. Note: IUPAC coverage is spotty at the moment, but I’m working on it.
    The substance ID is now displayed in the lower right corner of structural diagrams on the explore page. This can be used instead of a name in the search-by-name boxes when prefixed by =>, e.g. typing =2018 in the search-by-name box (the substance ID for has the same effect as typing =Mephedrone in the search box.
    Names that cannot fit in the tab box atop structural diagrams are now truncated. Previously these would wrap, or spill out beyond the tab edge, generally messing up the layout.
    Fixed a long-standing bug which erroneously identified skeletal analogues of lysergamides.
  • 13 Aug 2011
    Adjusted the structural diagram for . It was correct, but the angles were off.
    Spruced up the home page a bit, but pulled the Facebook buttons until they work right.
  • 11 Aug 2011
    Added 180 more links to ChemSpider.
    Added 250 more links to PubChem.
  • 9 Aug 2011
    Added a dozen additional substituted N-benzyl phenethylamines (e.g. ) or their three or four carbon counterparts, from Heim, 2003.
    Added , mentioned in Trachsel, 2003.
    Added two dozen substituted N-arylalkyl phenethylamines and tryptamines (e.g. ) from Glennon et al., 1994.
    Removed a couple of duplicate substances.
    I’ve begun to use IUPAC names instead of/in addition to the familiar, less “rigourous” names used in PiHKAL and TiHKAL. As Sasha et al. point out in The Shulgin Index, under IUPAC rules a seemingly minor change to a substance (e.g. the addition of a hydroxyl group) may radically transform its name. For readers interested in, or repelled by, the arcane details of IUPAC rules, I highly recommend the Open Parser for Systematic IUPAC nomenclature (OPSIN) web service that transforms a IUPAC name into a structural diagram. Let’s hear it for Daniel Lowe and the OPSIN team!
    I intend eventually to flag IUPAC names by some typographic convention, but until then my apologies for having to confront the current mixture of the good, the bad, and the IUPAC.
    My thanks to August Fleishman for his rousing tribute to the Shulgins after attending the Shulgin book signing.
  • 31 July 2011
    Fixed a pervasive and likely long-standing bug in the pop-up menus on read pages: When a pop-up menu linked to a chapter in the “other” book, it cited the wrong one. For example, the F-22 page in PiHKAL mentions LSD, a page in TiHKAL. However, the LSD pop-up menu incorrectly displayed “Read the PiHKAL description of #25 LSD”.
    Full credit for finding and reporting this bug goes to Felix, with my sincere thanks. Let me know when you’re resettled Felix—your chart awaits.
    Fixed a long-standing bug on the library page that prevented a reference from being displayed if it had a DOI containing “<”, “>” or “:”.
    Added more entries to the library page citing some of Sasha’s lesser known writing.
  • 16 July 2011
    On the former search page, an isobutoxy substituent is now properly classified as an alkoxy. It had been incorrectly classified as an alkyl.
    Corrected the name and internal representation of .
  • 5 July 2011
  • 4 June 2011
    A reader has alerted me to an exciting project currently underway: the translation of selected passages from PiHKAL to Castilian ( PiHKAL en castellano):
    I look forward to adding more links as additional passages are translated. My best wishes to the dedicated team of translators.
  • 18 Apr 2011
    and , additions to the “Just because it’s legal doesn’t mean it’s safe!” gallery, and and , their aminoindane counterparts from Cozzi et al, 1998.
    A plethora of “winged” bi-cycles and tri-cycles: