Author Topic: Lysergic amides to monohydrate?  (Read 439 times)

Wizard X

  • Lord of the Realms
  • Foundress Queen
  • *****
  • Posts: 1,224
Re: Lysergic amides to monohydrate?
« Reply #20 on: October 05, 2011, 01:56:43 AM »
ok, and that stuff matters how?

Well for starters, the actual date & time the picture was taken. IPhone & software version.

As you all know, cameras attach exif metadata to photos. The exif contains mostly innocent details such as exposure program and lens focal length, but also potentially privacy compromising info such as the camera serial number, and in cameras whit built-in GPS, such as the iPhone, also the location. To remove exif in Windows Vista and Windows 7 you can right click on a file and select Properties, and in the Details tab click on Remove Properties and Personal Information. You will than be able to remove all possible properties, or selectively remove few of them. Windows XP users can use this freeware to remove exif metadata.

http://www.dpug.org/forums/f7/how-remove-metadata-photos-2033/
Albert Einstein - "Great ideas often receive violent opposition from mediocre minds."

aniracetam

  • bioanalytical chemist
  • Subordinate Wasp
  • ***
  • Posts: 123
Re: Lysergic amides to monohydrate?
« Reply #21 on: October 05, 2011, 02:05:07 AM »
hmm,  ok. good to know. I am ignorant with regards to metadata,
and I use fedora 15 on my comp. opened that prog in wine
« Last Edit: October 05, 2011, 02:08:27 AM by aniracetam »
"Experiments are the only means of knowledge at our disposal. The rest is poetry, imagination." - Max Planck

aniracetam

  • bioanalytical chemist
  • Subordinate Wasp
  • ***
  • Posts: 123
Re: Lysergic amides to monohydrate?
« Reply #22 on: October 05, 2011, 03:10:09 AM »
$ exiftool IMG_0086.JPG
ExifTool Version Number         : 8.60
File Name                       : IMG_0086.JPG
Directory                       : .
File Size                       : 555 kB
File Modification Date/Time     : 2011:10:04 06:15:59-05:00
File Permissions                : rw-rw-r--
File Type                       : JPEG
MIME Type                       : image/jpeg
Image Width                     : 1600
Image Height                    : 1200
Encoding Process                : Baseline DCT, Huffman coding
Bits Per Sample                 : 8
Color Components                : 3
Y Cb Cr Sub Sampling            : YCbCr4:2:0 (2 2)
Image Size                      : 1600x1200


 ::)
"Experiments are the only means of knowledge at our disposal. The rest is poetry, imagination." - Max Planck

Sol Invictus

  • Larvae
  • *
  • Posts: 29
Re: Lysergic amides to monohydrate?
« Reply #23 on: October 05, 2011, 08:10:25 AM »
 The Chao paper I have is this one: Ergoline Alkaloidal Constituents of Hawaiian Baby Wood Rose, _Argyreia
nervosa_ (Burm. f.) Bojer. Jew-Ming Chao and Ara H. Der Marderosian.
Journal of Pharmaceutical Sciences 62(4):588-91. 1973.

Can you provide the ref for the other one from 1973? I wasn't aware he'd done another relevant paper on this particular subject.

And thanks for the other refs!

   --Sol

letters

  • Subordinate Wasp
  • ***
  • Posts: 138
Re: Lysergic amides to monohydrate?
« Reply #24 on: October 09, 2011, 10:51:49 PM »
IDENTIFICATION OF ERGOLINE ALKALOIDS IN THE GENUS ARGYREIA AND RELATED GENERA AND THEIR CHEMOTAXONOMIC IMPLICATIONS IN THE CONVOLVULACEAE. Jew-Ming Chao and Ara H. DerMarderosian, Phytochemistry, 1973, vol 12, pp. 2435 to 2440.

StonedOwlsley

  • Larvae
  • *
  • Posts: 7
Re: Lysergic amides to monohydrate?
« Reply #25 on: October 12, 2011, 11:44:31 PM »
@Sol Invictus: Hey man, that's why I'm here: to learn. I assure you that I have done many more forgiving synthesis, extensive acid base nonsense, and am doing some college chemistry classes at my community college. I know that this hypothetical tek is not "kitchen chemistry," but buddy has a dog who wants to take it to the next level, and this is a great place to get some questions answered that one can't ask in chem class. I'm not going to embark on this without the proper equipment, or in a country in which it is illegal; I assure you that I'm not diving into anything over my head, This is what it looks like to learn how to swim.
@letters, @akcom: thanks a million for the refs, they are under my close investigation. I really appreciate your clean concise information on this subject.

overunity33

  • Subordinate Wasp
  • ***
  • Posts: 218
Re: Lysergic amides to monohydrate?
« Reply #26 on: October 14, 2011, 04:31:14 AM »
So Im pretty sure I was right about lysergic acid forming a zwitterion instead of a traditional salt.. The ph is adjusted similar to salting or freebasing but instead of the amine group bonding to the salt it bonds to the lysergic acid's carboxylic acid group, which is what is responsible for the solubility change.  I have never heard of lysergic acid hcl, tartrate, whatever.

letters

  • Subordinate Wasp
  • ***
  • Posts: 138
Re: Lysergic amides to monohydrate?
« Reply #27 on: October 15, 2011, 01:25:42 PM »
So Im pretty sure I was right about lysergic acid forming a zwitterion instead of a traditional salt.. The ph is adjusted similar to salting or freebasing but instead of the amine group bonding to the salt it bonds to the lysergic acid's carboxylic acid group, which is what is responsible for the solubility change.  I have never heard of lysergic acid hcl, tartrate, whatever.
the fact that you "have never heard of lysergic acid hcl, tartrate, whatever", only means you have not researched properly. as i have stated before, lysergic acid does produce a salt with common acids, as is evident by the numerous publications on ergot alkaloids from the 1930s. some examples :
"The Alkaloids of Ergot. Part V. The Nature of Ergine". Smith and Timmis.  J.Chem.Soc., 1934, 674-674 (page 675) reads :
"Lysergic acid sulphate was prepared by dissolving the acid in 0.2N-sulphuric acid by heating on a water-bath ; on cooling, the sulphate separated in clusters of thin plates, which blackened and frothed at 245C (Found : C, 60.6,60.4; H, 5.4, 5.3; N, 8.8, 8.8; S, 5.2. C16H16O2N2,0.5H2SO4. requires C, 60.5; H, 5.4; N, 8.8; S, 5.1%)."

also, "The Alkuloids of Ergot. Part VII. isoErgine and isoLysergic Acids", Smith and Timmis. J.Chem.Soc., 1936, 1440-1444 (page 1443) reads :
"isoLysergic acid nitrate was deposited in well-formed needles when 10% aqueous nitric acid was added to an aqueous solution of isolysergic acid. It melted and decomposed at about 185C. (Found for material dried at 80C in a vacuum : C, 55.0 ; H, 5.3 ; N, 11.7. C16H16O2N2,HNO3,H2O requires C, 55.0; H, 5.5; N, 12.0%)."

and from "The Ergot Alkaloids. III. On Lysergic Acid." by Jacbos and Craig., J.Biol.Chem., 106, 393 reads also :
"Lysergic Acid Hydrochloride-100 mg. of lysergic acid were dissolved in 4 cc. of dilute hydrochloric acid. After cooling the crystals which separated were collected with dilute HCl. When recrystallized from methyl alcohol the product melted with decomposition at 208-210C, depending somewhat on the rate of heating.
It was dried for analysis at 120” and 2 mm. C16H16O2N2.HCl. Calculated C63.03, H5.63, N9.19. Cl11.62. Found C62.93, H5.48, N9.31, Cl11.15".

there are other examples, look them up.

overunity33

  • Subordinate Wasp
  • ***
  • Posts: 218
Re: Lysergic amides to monohydrate?
« Reply #28 on: October 16, 2011, 06:07:43 PM »
i was mistaken, thanks letters

Sol Invictus

  • Larvae
  • *
  • Posts: 29
Re: Lysergic amides to monohydrate?
« Reply #29 on: October 20, 2011, 04:43:48 AM »

 Yeah I was pretty sure that LA formed a sulfate, as per "The Ergot Alkaloids" refs that I mentioned earlier when discussing the hydrolysis of ergine. Pretty sure it was in the vol. called "A New Derivative of Lysergic Acid".

 Wow-- I've never seen "The Alkaloids of Ergot" series by Smith and Timmis. Looks like a real gem! Gonna have to start archiving those. The stuff from the 1930's is excellent. I only wish that there was more accessible translations of Arthur Stoll's work.

 Learning more every day! Thanks guys!

    --Sol

letters

  • Subordinate Wasp
  • ***
  • Posts: 138
Re: Lysergic amides to monohydrate?
« Reply #30 on: October 20, 2011, 08:09:27 AM »
your best bet would be to use a machine translation on the german articles, or study german yourself. if you are a non native english speaking, it is pretty easy.

Sol Invictus

  • Larvae
  • *
  • Posts: 29
Re: Lysergic amides to monohydrate?
« Reply #31 on: October 20, 2011, 09:39:02 AM »

 Not to go off topic but I have tried both of your suggestions Letters, and while such efforts do bring about a greater understanding of the material, in the end I am able to glean only disjointed chunks of data within a foggy gist of the overall content. I can make out some German and the mechanical translations do help, but there are still technical terms or certain unique descriptive mechanisms within the articles that often render even earnest attempts at translation too vague for me to feel comfortable.

 Thank you for your suggestions nonetheless  :)  Something tells me that there might be versions out there that were translated by actual chemists who verified the details therein for the benefit of other researchers who might be in need of such an article in an English-language scientific publication.

  --Sol