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Shulgins 10 Classic Ladies


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#1 Phlogiston

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Posted 27 October 2018 - 11:43 AM

Deze stofjes zijn nog niet besproken hier op het forum. Dus tijd voor ene topic. :)

 

Wat zijn de Classic Ladies? Shulgin kan dat het beste in zijn eigen woorden vertellen;

Just what is this all about the ten "Classic Ladies?" In the chemical struc-ture of DOM, there is a total of nineteen hydrogen atoms. Some of these are indis-tinguishable from others, such as the three hydrogen atoms on a methyl group. But there are exactly ten "types" of hydrogen atoms present. And, not having much, if any, intuition as to just why DOM was so powerful a psychedelic, I decided to systematically replace each of the ten unique hydrogens, one at a time of course, with a methyl group. And I planned to give the resulting materials the names of famous ladies, alphabetically, as you walk around the molecule.

ARIADNE was the first of these, the methyl for a hydrogen atom on the methyl group of the amphetamine chain. It was Ariadne who gave the long piece of thread to Theseus to guide him through the mazes of the Labyrinth so he could escape after killing the Minotaur. The record is fuzzy as to whether, after the successful killing, she went with him, or let him go on alone. A methyl group on the nitrogen atom produced BEATRICE. There is the legendary Beatrijs of the Dutch religious literature of the 14th century, and there is the Beatrice from Beatrice and Benedict (of Berlioz fame). But the one I had in mind was the lady from Florence whom Dante immortalized in the Divina Commedia, and she is entered under her own name in this footnote. Replacing the alpha-hydrogen of DOM with a methyl group would give the phentermine analogue which is named CHARMIAN. You may be thinking of Cleopatra's favorite attendant, but I was thinking of the sweet wife of a very dear friend of mine, a lady who has been in a state of gentle schizophrenia for some forty years now. The MDA analogue of CHARMIAN has been described in this foornote under the code name of MDPH. CHARMIAN, herself, has been synthesized and is of very much reduced potency in animals, as compared to DOM. It has not been tried in man as far as I know.

The two beta-hydrogen atoms of DOM are distinct in that, upon being replaced with methyl groups, one would produce a threo-isomer, and the other an erythro-isomer. I have named them DAPHNE (who escaped from Apollo by becoming a laurel tree which was, incidentally, named for her) and ELVIRA (who might not be too well known classically, but whose name has been attached to Mozart's 21st piano concerto as its slow movement was used as theme music for the movie Elvira Madigan). I don't know if either of this pair has been made--I started and got as far as the cis-trans mixture of adducts betweeen nitroethane and 2,5-dimethoxy-4-methylacetophenone. Whoever finally makes them gets to assign the names. I had made and tested the corresponding homologues of DMMDA that correspond to these two ladies.

And there are five positions (2,3,4,5 and 6) around the aromatic ring, each of which either carries a hydrogen atom or a methyl group that has a hydrogen atom. There is the 2-methoxy group which can become a 2-ethoxy group to produce a compound called FLORENCE. Her name is the English translation of the Italian Firenze, a city that, although having a female name, has always seemed thoroughly masculine to me. There is the 3-hydrogen atom which can become a 3-methyl group to produce a compound called GANESHA. This is a fine elephant-headed Indian God who is the symbol of worldly wisdom and also has been seen as the creator of obstacles. Here I really blew it; the Classic Lady turned out to be a Classic Gentle-man; not even the name is feminine. There is the 4-methyl group which can become a 4-ethyl group to produce a compound called HECATE who presided over magic arts and spells. There is the 5-methoxy group which can become a 5-ethoxy group to produce a compound called IRIS, who is the Goddess of the rainbow. And there is the 6-hydrogen atom which can become a 6-methyl group to produce a compound called JUNO, who is pretty much a lady's lady, or should I say a woman's woman.

 

800px-Shulgin_Classic_Ladies.png

 

 

Niet alle Ladies hebben een entry in PiHKAL, maar zijn linkjes naar degene die dat het wel hebben;

PiHKAL #8: ARIADNE - Wikipedia: ARIADNE

PiHKAL #11: BEATRICE - Wikipedia: BEATRICE

PiHKAL # 85: GANESHA - Wikipedia: GANESHA

PiHKAL #66: HECATE (DOET) - Wikipedia: DOET

PiHKAL #93: IRIS

 

De hoofdzakelijk om het topic nu aan te maken is dat ik onlangs Ariadne aangeboden zag (onder de naam 4C-D). Nu lijkt mij deze totaal niet de moeite waard. Mocht iemand ervarig hebben, ben desondanks heel erg benieuwd. In de Shulgin Index staat dat deze bij 270mg nog steeds geen psychedelische effecten te weeg bracht.

 

De 3 dames die mij het meest aanspreken zijn Ganesha, Hecate en Juno. De eerste twee hebben hun eigen pagina in PiHKAL en jullie kunnen zelf wel lezen waarom die interessant lijken. Over Juno kan ik niet meer infor vinden dan wat in de pagina van Ariadne is beschreven. Shulgin heeft deze wel ooit is gemaakt, maar blijkbaar nooit geproefd. Mij zou het niks verbazen als deze een vergelijkbare activiteit heeft als Ganesha. Misschien zullen we het ooit zien, misschien nooit.


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#2 dreamer

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Posted 27 October 2018 - 01:36 PM

Ganesha is helemaal geen dame joh :P

Deze compounts heb ik in pihkal wel langs zien komen. En inderdaad de 3 die je noemt lijken de meeste potentie als psychedelica te hebben.
Zelf heb ik totaal geen ervaring met de DOx-en dus ik vind het wat moeilijk om dieper op de te verwachten effecten in te gaan.

Een compound als Ariadne is wel apart dat die aangeboden wordt, gezien het gebrek aan activiteit. Misschien vanwege een gesimplificeerde synthese route?
Daar kan jij misschien op commenten :)

#3 Phlogiston

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Posted 27 October 2018 - 02:17 PM

Ganesha is helemaal geen dame joh :P

 
Gelukkig had Shulgin dat zelf ook door;

Here I really blew it; the Classic Lady turned out to be a Classic Gentle-man; not even the name is feminine

 
 
Synthese van Ariadne is net zo moeilijk/makkelijk als alle andere DOx's.
 
Het is geen inactieve stof, het is echter geen psychedelicum. Op wikipedia staat dat het een MDMA vervanger zou kunnen zijn.
 
(R)-Ariadne heeft "increased mental alertness and feelings of well-being" bij een dosis van 25-50mg in gezonde testpersonen, aldus de Shulgin Index. Als we ervan uitgaan dat de (S) inactief is, zou dat op een dosis van 50-100mg zijn voor het racemisch materiaal dat online wordt aangeboden.

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